Curable compositions

Abstract

Disclosed are compositions comprising a first component comprising an isocyanate-functional prepolymer; a second component comprising a polyurethane polyol; an aromatic diamine; and a filler in an amount of greater than 50% by weight to 88% by weight based on total weight of the composition. Also disclosed are methods for treating a substrate with any of the compositions disclosed herein. Also disclosed are substrates comprising a coating formed from any of the compositions disclosed herein on a substrate surface, and optionally a dielectric coating on the substrate surface. Also disclosed are systems and kits comprising a dielectric coating composition and any of the coating compositions disclosed herein.

Description

CURABLE COMPOSITIONSGOVERNMENT CONTRACT

[0001] This disclosure was made with Government support under Government Contract No. NCMS FY2020 Ambient Temperature Adhesive Contract Number 2021007-142040 awarded by GVSC. The United States Government may have certain rights in this disclosure.CROSS-REFERENCE TO RELATED APPLICATION

[0002] This application claims priority to U.S. Provisional Application No. 63 / 600,720, filed on November 19, 2023, and entitled “Curable Compositions,” incorporated herein in its entirety.FIELD

[0003] The present disclosure relates to curable compositions.BACKGROUND

[0004] Coating compositions, including sealants and adhesives, are utilized in a wide variety of applications to treat a variety of substrates or to bond together two or more substrate materials.SUMMARY

[0005] The present disclosure is directed to compositions comprising: a first component comprising an isocyanate-functional prepolymer; a second component comprising a polyurethane polyol; an aromatic diamine; and a filler in an amount of greater than 50% by weight to 88% by weight based on total weight of the composition.

[0006] Also disclosed are methods for treating a substrate comprising contacting a surface of the substrate with any of the compositions disclosed herein.

[0007] Also disclosed are substrates comprising a coating on a surface thereof, the coating formed from any of the compositions disclosed herein.

[0008] Also disclosed are batteries comprising a battery cell comprising a coating on a surface thereof, the coating formed from any of the compositions disclosed herein, and optionally a battery component.

[0009] Also disclosed are batteries comprising a battery cell comprising a coating on a surface thereof, the coating formed from any of the compositions disclosed herein, and optionally a battery component.

[0010] Also disclosed are vehicles comprising any of the batteries disclosed herein.BRIEF DESCRIPTION OF THE DRAWINGS

[0011] FIG. 1 is a schematic of a top-down view of cylindrical battery cells.

[0012] FIG. 2 is a schematic of an exploded isometric view of an array of prismatic battery cells.

[0013] FIG. 3 is a schematic of a front view of an array of pouch battery cells.

[0014] FIG. 4 is a schematic of an isometric view of cylindrical cells positioned in a battery module.

[0015] FIG. 5 is a schematic of an exploded perspective view of a battery pack comprising multiple battery cells.

[0016] FIG. 6 is a schematic of an isometric view of (A) a battery cell, (B) a battery module, and (C) a battery pack.

[0017] FIG. 7 is a schematic of a perspective view of a battery pack.

[0018] FIG. 8 is a schematic of a cell to battery pack configuration.

[0019] FIG. 9 is a schematic of an isometric cut-out view of a cell to chassis battery assembly.DETAILED DESCRIPTION

[0020] For purposes of this detailed description, it is to be understood that the disclosure may assume various alternative variations and step sequences, except where expressly specified to the contrary. Moreover, other than in any operating examples, or where otherwise indicated, all numbers expressing, for example, quantities of ingredients used in the specification and claims, are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties to be obtained in the present disclosure. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0021] Notwithstanding that the numerical ranges and parameters set forth the broad scope of the disclosure are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherentlycontains certain errors necessarily resulting from the standard variation found in their respective testing measurements.[00221 Also, any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of “1 to 10” is intended to include all sub-ranges between (and including) the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10.

[0023] As used herein, “including,” “containing,” and like terms are understood in the context of this application to be synonymous with “comprising” and are therefore open-ended and do not exclude the presence of additional undescribed or unrecited elements, materials, ingredients, or method steps. As used herein, “consisting of’ is understood in the context of this application to exclude the presence of any unspecified element, ingredient, or method step. As used herein, “consisting essentially of’ is understood in the context of this application to include the specified elements, materials, ingredients, or method steps “and those that do not materially affect the basic and novel “ character! stic(s)” of what is being described. As used herein, open- ended terms include closed terms such as consisting essentially of and consisting of.

[0024] In this application, the use of the singular includes the plural and plural encompasses singular, unless specifically stated otherwise. For example, although reference is made herein to “an” isocyanate and “a” polyol, a combination (i.e., a plurality) of these components may be used.

[0025] In addition, in this application, the use of “or” means “and / or” unless specifically stated otherwise, even though “and / or” may be explicitly used in certain instances.

[0026] As used herein, the terms “on,” “onto,” “applied on,” “applied onto,” “formed on,” “deposited on,” “deposited onto,” “injected on,” “injected onto” and the like mean formed, overlaid, deposited, or provided on, but not necessarily in contact with, a substrate surface. For example, a composition “applied onto” a substrate surface does not preclude the presence of one or more other intervening coating layers or films of the same or different composition located between the composition and the substrate surface.

[0027] As used herein, a “composition” or “coating composition” refers to a solution, mixture, or a dispersion that is capable of producing a coating on a surface of a substrate. “Coating” as used herein includes films, layers, and the like.

[0028] As used herein, a “sealant composition” refers to a curable composition that, when cured, forms a seal.

[0029] As used herein, a “seal” refers to a cured coating that has the ability to resist atmospheric conditions such as temperature and moisture gradients and particulate matter, such as moisture and temperature, and block transmission of materials, such as particulates, water, fuel, and other liquids and gasses.

[0030] As used herein, an “adhesive composition” refers to a curable composition that, when cured, forms an adhesive or a structural adhesive.

[0031] As used herein, an “adhesive” refers to a cured coating that produces a loadbearing joint.

[0032] As used herein, a “structural adhesive” refers to a cured coating that produces a load-bearing joint having a lap shear strength of at least 5 MPa measured according to ASTM D1002-10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0033] As used herein, a “gap filler composition” refers to a curable composition that, when cured, forms a gap filler.

[0034] As used herein, a “gap filler” refers to a coating that fills a gap.

[0035] As used herein, a “pottant composition” refers to a curable composition that, when cured, forms a pottant.

[0036] As used herein, a “pottant” refers to an encapsulant.

[0037] As used herein, a “pre-preg” refers to a composition pre-impregnating reinforcement fibers prior to cure.

[0038] As used herein, a “liquid shim composition” refers to a curable composition that, when cured, forms a liquid shim.

[0039] As used herein, a “liquid shim” refers to a coating that eliminates gaps between substrate surfaces.

[0040] As further defined herein, ambient conditions generally refer to room temperature (e.g., 23 °C) and humidity conditions or temperature and humidity conditions that are typically found in the area in which the composition is applied to a substrate, e.g., at 10°C to 40°C and 5% to 80% relative humidity, while slightly thermal conditions are temperatures that are slightly above ambient temperature, but are generally below the curing temperature for the composition (i.e., in other words, at temperatures and humidity conditions below which the reactivecomponents will readily react and cure, e ., > 40°C and less than 220°C at 20% to 80% relative humidity).[00411 As used herein, the term “two-component” or “2K” refers to a composition in which the reactive components readily associate to form an interaction or react to form a bond (physically or chemically), i.e., cure without activation from an external energy source, such as at ambient or slightly thermal conditions, when mixed. One of skill in the art understands that the two components of the composition are stored separately from each other and mixed just prior to application of the composition. Two-component compositions may optionally be heated or baked, as described below.

[0042] As used herein, the terms “cure,” “cured,” “curing,” means that the components that form the composition are crosslinked (i.e., interact and / or react) to form a coating or a bond. In the case of a 2K composition, the composition begins to cure when the components of the composition are mixed resulting in the reaction of the reactive functional groups of the components of the composition.

[0043] The term “curable,” as used in connection with a coating composition, means that the composition is able to be cured under ambient and / or slightly thermal conditions.

[0044] As used herein, “dielectric” refers to a coating or composition having a dielectric strength of at least 50 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC- DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM DI 49-09.

[0045] As used herein, “Mn” refers to the number average molecular weight, for example the theoretical value as determined by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector), polystyrene standards, using tetrahydrofuran (THF) as the eluent at a flow rate of 1 mL min'1and two PL Gel Mixed C columns for separation.

[0046] As used herein, “isocyanate equivalent weight” or “NCO equivalent weight” refers to the total weight of isocyanate-containing components divided by the molar equivalents of isocyanate functionality. The value may be determined from the isocyanate content as measured in accordance with ASTM D2572-19.

[0047] As used herein, “active hydrogens” refer to hydrogens that can be displaced when a nitrogen-containing functional group, an oxygen-containing functional group, and / or a sulfur-containing functional group reacts as a nucleophile with an appropriate electrophile and can be determined, for example, by the Zerewitinoff test. Examples of active hydrogen groups include amines, hydroxyls, and thiols.

[0048] As used herein, “active hydrogen equivalent weight” refers to the total weight of active hydrogen-containing components divided by the molar equivalents of active hydrogen functionality. The active hydrogen equivalent weight may be determined from the amine equivalent weight and the hydroxyl equivalent weight. “Amine equivalent weight” refers to the total weight of amine-containing components divided by the molar equivalents of amine functionality, which can be determined in accordance with ASTM D6979-03. “Hydroxyl equivalent weight” refers to the total weight of hydroxyl-containing component divided by the molar equivalents of hydroxyl functionality, which may be determined, for example, in accordance with ASTM D4247-23.

[0049] As used herein, “aromatic,” when referring to a compound, means that the compound comprises at least one aromatic ring.

[0050] As used herein, “accelerator” refers to a substance that increases the rate or decreases the activation energy of a chemical reaction in comparison to the same reaction in the absence of an accelerator. An accelerator may be either a “catalyst,” that is, without itself undergoing any permanent chemical change, or may be reactive, that is, capable of chemical reactions and includes any level of reaction from partial to complete reaction of a reactant.

[0051] As used herein, the term “thermally conductive filler” or “TC” filler means a pigment, filler, or inorganic powder that has a thermal conductivity of at least 5 W / m-K at 25 "C measured according to ASTM D7984.

[0052] As used herein, the term “non-thermally conductive filler” or “NTC filler” means a pigment, filler, or inorganic powder that has a thermal conductivity of less than 5 W / m-K at 25SC measured according to ASTM D7984.

[0053] As used herein, the term “electrically insulative filler” or “El filler” means a pigment, filler, or inorganic powder that has a volume resistivity of at least 1 Q m measured according to ASTM D257.

[0054] As used herein, the term “electrically conductive filler” or “EC filler” means a pigment, filler, or inorganic powder that has a volume resistivity of less than 1 £lm measured according to ASTM D257.

[0055] As used herein, the term “thermally stable” means a pigment, filler, or inorganic powder that, when tested using the TGA test under air according to ASTM El 131, has no more than 5% weight loss of the total weight of the pigment, filler, or powder occurring before 600 °C.

[0056] As used herein, the term “thermally unstable” means a pigment, filler, or inorganic powder that, when tested using the TGA test under air according to ASTM El 131, has a weight loss of the total weight of the pigment of more than 5% occurring before 600 'C.

[0057] As used herein, unless indicated otherwise, “substantially free” refers to a particular material that is not purposefully added to a mixture or composition, respectively, and is present only as an impurity in a trace amount of less than 5% by weight based on total weight of the mixture or composition, respectively. As used herein, unless indicated otherwise, “essentially free” means that a particular material is not purposefully added to a mixture or composition and is present only as an impurity in a trace amount of less than 2% by weight based on total weight of the mixture or composition, respectively. As used herein, unless indicated otherwise, “completely free” means that a mixture or composition, respectively, does not comprise a particular material, i.e., the mixture or composition comprises 0% by weight of such material based on total weight of the mixture or composition.

[0058] Disclosed herein is a composition comprising, or consisting essentially of, or consisting of: a first component comprising, or consisting essentially of, or consisting of an isocyanate-functional prepolymer; a second component comprising, or consisting essentially of, or consisting of a polyurethane polyol; an aromatic diamine; and a filler in an amount of greater than 50% by weight to 88% percent by weight based on total weight of the composition.Isocyanate-Functional Prepolymer

[0059] The first component may comprise, or consist essentially of, or consist of an isocyanate-functional prepolymer. The isocyanate-functional prepolymer may comprise a reaction product of reactants comprising a polyol and a polyisocyanate. As used herein “isocyanate-functional prepolymer” refers to the reaction product of a polyisocyanate with a polyol. The isocyanate-functional prepolymer has one or more free isocyanate functional groups (NCO). The free isocyanate functional group may be terminal and / or pendant. Combinations of isocyanate functional prepolymers can be used. The isocyanate-functional prepolymer may be pre-formed or may be formed in situ.

[0060] Suitable polyols useful in forming the isocyanate-functional prepolymer include diols, triols, tetraols and higher functional polyols. Combinations of such polyols may also be used. The polyol may include polyhydric alcohols such as ethylene glycol, propanediol, neopentyl glycol, butanediol, pentanediol, hexanediol, cyclohexanedimethanol, cyclohexanediol, benzenedimethanol, 4,4’ -isopropylidenedi cyclohexanol, glycerol, trimethylolpropane, pentaerythritol, di(trimethylolpronane) or di (pentaerythritol). Suitable polyols may also include polyether polyols, polyester polyols, acrylic polyols, polybutadiene polyols, hydrogenated polybutadiene polyols, polycarbonate polyols, and / or polysiloxane polyols. Polyamines corresponding to polyols may also be used, and in this case, urea linkages will be formed with the isocyanates.

[0061] The polyol may comprise a polycaprolactone-based polyol. The polycaprolactone-based polyols may comprise diols terminated with primary hydroxyl groups. Commercially available polycaprolactone-based polyols include those sold under the trade name Capa™ from Perstorp Group, such as, for example, Capa 2054, Capa 2077A, Capa 2085, Capa 2205, Capa 3031, Capa 3050, Capa 3091, and Capa 4101.

[0062] The polyol may comprise a polyether polyol. The polyols may be based on a polyether chain derived from ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and the like, and mixtures thereof. The polyol may comprise a tetrahydrofuran-based polyol. The polytetrahydrofuran-based polyols may comprise diols, triols, or tetraols terminated with primary hydroxyl groups. Commercially available polytetrahydrofuran-based polyols include those sold under the trade name Terathane®, such as Terathane® PTMEG 250, Terathane® PTMEG 650, and Terathane® PTMEG 1000 which are blends of linear diols in which the hydroxyl groups are separated by repeating tetramethylene ether groups, available from Invista. In addition, polyols based on dimer diols sold under the trade names Pripol®, Solvermol™ and Empol®, available from Cognis Corporation, or bio-based polyols, such as the tetrafunctional polyol Agrol 4.0, available from BioBased Technologies, may also be utilized.

[0063] The polyol may comprise a combination of any of the polyols disclosed herein.

[0064] In examples, the polyol used to make the isocyanate-functional prepolymer may have an Mn of at least 60 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, andtwo PL Gel Mixed C columns used for separation, such as at least 90 g / mol, and may have an Mn of no more than 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as no more than 2,000 g / mol. The polyol may have an Mn of 60 g / mol to 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 90 g / mol to 2,000 g / mol.

[0065] Suitable polyisocyanates useful in forming the isocyanate-functional prepolymer can be polymeric, i.e., containing two or more isocyanate functional groups. For example, the polyisocyanates may comprise Ci to C20 linear, cyclic, aliphatic, and / or aromatic polyisocyanates, or mixtures thereof.

[0066] Aliphatic polyisocyanates may include (i) alkylene isocyanates, such as: trimethylene diisocyanate, tetramethylene diisocyanate, such as 1,4-tetram ethylene diisocyanate; pentamethylene diisocyanate, such as 1,5 -pentamethylene diisocyanate and 2-methyl-l,5- pentamethylene diisocyanate; hexamethylene diisocyanate (“HDI”), such as 1,6-hexamethylene diisocyanate and 2,2,4- and 2,4,4-trimethylhexamethylene diisocyanate, or mixtures thereof; heptamethylene diisocyanate, such as 1,7-heptamethylene diisocyanate; propylene diisocyanate, such as 1,2-propylene diisocyanate; butylene diisocyanate, such as 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, and 1,4-butylene diisocyanate; ethylene diisocyanate; decamethylene diisocyanate, such as 1,10-decam ethylene diisocyanate; ethylidene diisocyanate; butylidene diisocyanate; and hexamethylene diisocyanate (“HDI”). Aliphatic polyisocyanates may also include (ii) cycloalkylene isocyanates, such as: cyclopentane diisocyanate, such as 1,3 -cyclopentane diisocyanate; cyclohexane diisocyanate, such as 1,4- cyclohexane diisocyanate, 1,2-cyclohexane diisocyanate, isophorone diisocyanate (“IPDI”), IPDI trimer (commercially available as Desmodur® Z 4470 SN); methylene bis(4- cyclohexylisocyanate) (“HMDI”); polymeric methylene diphenyl diisocyanate (“MDI”); and mixed aralkyl diisocyanates such as tetramethylxylyl diisocyanates, such as meta- tetram ethylxylyl ene diisocyanate (commercially available as TMXDI® from Allnex SA).

[0067] Aromatic polyisocyanates may include (i) arylene isocyanates, such as: phenylene diisocyanate, such as m-phenylene diisocyanate, p-phenylene diisocyanate, and chlorophenylene 2,4-diisocyanate; naphthalene diisocyanate, such as 1,5-naphthalene diisocyanate and 1,4- naphthalene diisocyanate. Aromatic polyisocyanates may also include (ii) alkarylene isocyanates, such as: methylene-interrupted aromatic diisocyanates, such as 4,4’ -diphenylene methane diisocyanate (“MDI”), and alkylated analogs such as 3,3 ’-dimethyl-4, d’diphenylmethane diisocyanate, and polymeric methylenediphenyl diisocyanate; toluene diisocyanate (“TDI”), such as 2,4-tolylene or 2,6-tolylene diisocyanate, or mixtures thereof, bitoluene diisocyanates; and 4,4-toluidine diisocyanate; xylene diisocyanate; dianisidine diisocyanate; xylylene diisocyanate; and other alkylated benzene diisocyanates.

[0068] The isocyanate-functional prepolymer may comprise an aliphatic isocyanate, such as cyclic aliphatic isocyanate, and / or an aromatic isocyanate-functional prepolymer.

[0069] The isocyanate-functional prepolymer may comprise a difunctional isocyanate- functional prepolymer. As used herein, “difunctional isocyanate-functional prepolymer” refers to an isocyanate-functional prepolymer containing two isocyanate functional groups.

[0070] The isocyanate-functional prepolymer may comprise the diisocyanate functional prepolymer in an amount of at least 50% by weight based on total weight of the isocyanate- functional prepolymer, such as at least 60% by weight, such as at least 70% by weight, such as at least 80% by weight, such as at least 90% by weight, such as 100% by weight, such as 60% by weight to 90% by weight.

[0071] The isocyanate-functional prepolymer may comprise a monofunctional isocyanate-functional prepolymer and / or a polyfunctional isocyanate-functional prepolymer. As used herein, “monofunctional isocyanate-functional prepolymer” refers to an isocyanate- functional prepolymer containing one isocyanate functional group. As used herein, “polyfunctional isocyanate-functional prepolymer” refers to an isocyanate-functional prepolymer containing more than two isocyanate functional groups.

[0072] The isocyanate-functional prepolymer may comprise the monofunctional isocyanate-functional prepolymer and / or polyfunctional isocyanate-functional prepolymer in an amount of 50% by weight or less based on total weight of the isocyanate-functional pre-polymer, such as 40% by weight or less, such as 30% by weight or less, such as 20% by weight or less, such as 10% by weight or less, such as 10% by weight to 40% by weight.

[0073] The composition may be substantially free, essentially free, or completely free of the monofunctional isocyanate-functional prepolymer and / or the polyfunctional isocyanate- functional prepolymer.

[0074] Commercially available isocyanate-functional prepolymers that may be used in the present disclosure include isocyanate-functional prepolymers available under the Desmodur® trade name from Covestro AG, prepolymers available under the Adiprene® trade name from Lanxess, and prepolymers available under the Lupranat® trade name from BASF.

[0075] The isocyanate-functional prepolymer may comprise an Mn of at least 500 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min1, and two PL Gel Mixed C columns used for separation, such as at least 750 g / mol. The isocyanate-functional prepolymer may comprise an Mn of no more than 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as no more than 2,500 g / mol. The isocyanate-functional prepolymer may comprise an Mn of 500 g / mol to 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 750 g / mol to 2,500 g / mol.

[0076] The isocyanate-functional prepolymer may comprise an NCO equivalent weight of at least 250 g / eq, such as at least 300 g / eq. The isocyanate-functional prepolymer may comprise an NCO equivalent weight of no more than 2,500 g / eq, such as no more than 1,250 g / eq. The isocyanate-functional prepolymer may comprise an NCO equivalent weight of 250 g / eq to 2,500 g / eq, such as 300 g / eq to 1,250 g / eq.

[0077] The composition may comprise the isocyanate-functional prepolymer in an amount of at least 10% by weight based on total weight of the composition, such as at least 12% by weight, such as at least 15% by weight, such as at least 20% by weight. The composition may comprise the isocyanate-functional prepolymer in an amount of no more than 48% by weight based on total weight of the composition, such as no more than 40% by weight, such as no morethan 35% by weight, such as no more than 30% by weight. The composition may comprise the isocyanate-functional prepolymer in an amount of 10% to 48% by weight based on total weight of the composition, such as 12% to 40% by weight, such as 15% to 35% by weight, such as 20% to 30% by weight.Polyurethane Polyol

[0078] The second component may comprise, consist essentially of, or consist of a polyurethane polyol. The polyurethane polyol may comprise a polyurethane backbone and at least one hydroxyl functional group. The hydroxyl functional group may be terminal and / or pendant. The polyurethane polyol may comprise an aromatic polyurethane polyol.

[0079] The polyurethane polyol may comprise a difunctional polyurethane polyol. The polyurethane polyol may comprise the difunctional polyurethane polyol in an amount of at least 50% by weight based on total weight of the polyurethane polyol, such as at least 60% by weight, such as at least 70% by weight, such as at least 80% by weight, such as at least 90% by weight, such as 100% by weight, such as 60% by weight to 90% by weight. As used herein, “difunctional polyurethane polyol” refers to a polyurethane polyol comprising two hydroxyl functional groups.

[0080] The polyurethane polyol may further comprise a monofunctional and / or polyfunctional polyurethane polyol. As used herein, “monofunctional polyurethane polyol” refers to a polyurethane polyol comprising one hydroxyl functional group. As used herein, “polyfunctional polyurethane polyol” refers to a polyurethane polyol comprising more than two hydroxyl functional groups.

[0081] The polyurethane polyol may comprise a monofunctional and / or polyfunctional polyurethane polyol in an amount of 50% by weight or less based on total weight of the polyurethane polyol, such as 40% by weight or less, such as 30% by weight or less, such as 20% by weight or less, such as 10% by weight or less, such as 10% by weight to 40% by weight. Alternatively, the composition may be substantially free, essentially free, or completely free of a monofunctional and / or polyfunctional polyurethane polyol.

[0082] Suitable polyurethane polyols that may be used in the present disclosure include polyurethane polyols comprising a reaction product of any of the isocyanate-functional compounds and polyols described herein above, or any combinations thereof.

[0083] The polyurethane polyol may comprise an Mn of at least 1,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as at least 1,500 g / mol, such as at least 2,000 g / mol. The polyurethane polyol may comprise an Mn of no more than 6,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as no more than 5,500 g / mol, such as no more than 5,000 g / mol, such as no more than 4,000 g / mol, such as no more than 3,500 g / mol, such as no more than 3,000 g / mol. The polyurethane polyol may comprise an Mn of 1,000 g / mol to 6,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 1,500 g / mol to 5,500 g / mol, such as 2,000 g / mol to 5,000 g / mol, such as 1,000 g / mol to 4,000 g / mol, such as 1,500 g / mol to 3,500 g / mol, such as 2,000 g / mol to 3,000 g / mol.

[0084] The composition may comprise the polyurethane polyol in an amount of at least 1% by weight based on total weight of the composition, such as at least 3% by weight, such as at least 4% by weight, such as at least 5% by weight. The composition may comprise the polyurethane polyol in an amount of no more than 20% by weight based on total weight of the composition, such as no more than 15% by weight, such as no more than 12% by weight, such as no more than 10% by weight. The composition may comprise the polyurethane polyol in an amount of 1% to 20% by weight based on total weight of the composition, such as 3% to 15% by weight, such as 4% to 12% by weight, such as 5% to 10% by weight.Aromatic Diamine

[0085] The composition may comprise an aromatic diamine. As used herein, “aromatic diamine” refers to a compound comprising an aromatic ring and two amine functional groups bonded to the aromatic ring. The aromatic diamine may be present in the second component, a third component, or higher component. As used herein with respect to components, reference to “first,” “second,” “third,” etc., is for convenience only and does not refer to order of addition tothe composition or the like. Furthermore, this language is not intended to be limiting and does not exclude the possibility of the composition comprising more than three components.[00861 The aromatic diamine may be a sterically hindered aromatic diamine. As used herein, a “sterically hindered aromatic diamine” refers to an aromatic diamine that comprises a substituent, usually a C1-C4 alkyl, C1-C4 alkoxy, or C1-C4 alkylthio group, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n- butylthio, or isobutylthio, wherein the substituent is in at least one position ortho to each amino group. Sterically hindered aromatic diamine may also refer to an aromatic diamine in which the amine nitrogen additionally comprises a substituent such as an alkyl substituent. The aromatic diamine may comprise a liquid.

[0087] Suitable aromatic diamines that may be used in the present disclosure include phenylene diamine, diaminodiphenylmethane, 2,4-diaminomesitylene, l,3,5-triethyl-2,6- diaminobenzene, l-methyl-3,5-diethyl-2,4-diaminobenzene, isobutyl 4-chloro-3,5- di ami nobenzoate, methylene bis(methylanthranilate), trimethylene glycol di-p-aminobenzoate, dimethylthiotoluenediamine, available as Ethacure 300, di ethyltoluenediamine, available as Ethacure 100, 4,4’-bis(5ec-butylamino)diphenyl methane, available as Ethacure 420, or combinations thereof.

[0088] The aromatic diamine may comprise an Mn of at least 100 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min1, and two PL Gel Mixed C columns used for separation, such as at least 125 g / mol. The aromatic diamine may comprise an Mn of no more than 750 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as no more than 500 g / mol. The aromatic diamine may comprise an Mn of 100 g / mol to 750 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 125 g / mol to 500 g / mol.

[0089] The composition may comprise the aromatic diamine in an amount of at least 1% by weight based on total weight of the composition, such as at least 5% by weight. The composition may comprise the aromatic diamine in an amount of no more than 20% by weight based on total weight of the composition, such as no more than 10% by weight. The composition may comprise the aromatic diamine in an amount of 1% to 20% by weight based on total weight of the composition, such as 5% to 10% by weight.Filler

[0090] The composition may comprise a filler in an amount greater than 50% by weight to 88% by weight based on total weight of the composition. The fillers may comprise thermally conductive fillers. The fillers may comprise a thermally conductive, electrically insulative filler (referred to herein as “TC / EI filler” and described in more detail below).

[0091] Optionally, any of the fillers may comprise a surface coating. The surface coating may comprise a silane, an amino-silane, a polysiloxane, and / or a multidendate polymer.

[0092] The fillers may have an average particle size in a dimension of at least 0.01 pm, as reported by the manufacturer, such as at least 2 pm, such as at least 10 pm, and may have an average particle size in at least one dimension of no more than 500 pm as reported by the manufacturer, such as no more than 400 pm, such as no more than 300 pm, such as no more than 100 pm. The fillers may have an average particle size in a dimension of 0.01 pm to 500 pm as reported by the manufacturer, such as 0.1 pm to 400 pm, such as 2 pm to 300 pm, such as 10 pm to 100 pm. Particle sizes may be measured by methods known to those skilled in the art, for example, using a scanning electron microscope (SEM), such as a Quanta 250 FEG SEM or an equivalent instrument. For example, powders may be dispersed on segments of carbon tape attached to aluminum stubs and coated with Au / Pd for 20 seconds. Samples then may be analyzed in an SEM under high vacuum (accelerating voltage 10 kV and spot size 3.0), measuring 30 particles from the different areas to provide an average particle size for each sample. The particle size may be reported by the manufacturer. One skilled in the art will recognize that there can be variations in this procedure that retain the essential elements of microscopic imaging and averaging of representative size.

[0093] Thermally conductive filler may comprise particles each having, for example, a platy, spherical, or acicular shape, and agglomerates thereof. As used herein, “platy” refers to atwo-dimensional material having a substantially flat surface and that has a thickness in one direction that is less than 25% of the largest dimension.[00941 The thermally conductive filler, including the TC / EI fillers, may have a thermal conductivity of at least 5 W / m-K at 25°C (measured according to ASTM D7984-21), such as at least 18 W / m-K, such as at least 55 W / m-K, and may have a thermal conductivity of no more than 3,000 W / m-K at 25°C, such as no more than 1,400 W / m-K, such as no more than 450 W / m-K. The thermally conductive filler may have a thermal conductivity of 5 W / m-K to 3,000 W / m-K at 25°C (measured according to ASTM D7984), such as 18 W / m-K to 1,400 W / m-K, such as 55 W / m-K to 450 W / m-K.

[0095] The thermally conductive filler may comprise a thermally stable filler and / or a thermally unstable filler. That is, a portion of the TC / EI filler may be thermally stable and / or thermally unstable.

[0096] Suitable thermally stable TC / EI fillers include boron nitride, silicon nitride, or aluminum nitride, arsenides such as boron arsenide, metal oxides such as aluminum oxide, magnesium oxide, beryllium oxide, silicon dioxide, titanium oxide, zinc oxide, nickel oxide, copper oxide, or tin oxide, carbides such as silicon carbide, minerals such as agate and emery, ceramics such as ceramic microspheres, and diamond. These thermally stable, TC / EI fillers may be used alone or in a combination of two or more.

[0097] Suitable thermally unstable TC / EI filler materials include metal hydroxides such as aluminum trihydrate, aluminum hydroxide or magnesium hydroxide. These fillers can also be surface modified, such as Hymod® M9400 SF available from J.M. Huber Corporation. These thermally unstable, TC / EI fillers may be used alone or in a combination of two or more.

[0098] The filler may be electrically insulative. The electrically insulative filler may have a volume resistivity of at least 10 Q-m (measured according to ASTM D257-07), such as at least 100 Q-m.

[0099] Suitable TC / EI fillers include boron nitride (for example, commercially available as CarboTherm from Saint-Gorbain, as CoolFlow and PolarTherm from Momentive, and as hexagonal boron nitride powder available from Panadyne), silicon nitride, or aluminum nitride (for example, commercially available as aluminum nitride powder available from Micron Metals Inc., and as Toyalnite from Toyal), metal oxides such as Boehmite, Pseudo Boehmite, aluminum oxide (for example, commercially available as Microgrit from Micro Abrasives, as Nabalox fromNabaltec, as Aeroxide from Evonik, and as Alodur from Imerys), magnesium oxide, beryllium oxide, silicon dioxide, titanium oxide, zinc oxide, nickel oxide, copper oxide, or tin oxide, metal hydroxides such as aluminum trihydrate, aluminum hydroxide, or magnesium hydroxide, arsenides such as boron arsenide, carbides such as silicon carbide, minerals such as agate and emery, ceramics such as ceramic microspheres (for example, commercially available from Zeeospheres Ceramics or 3M), silicon carbide, and diamond. These fillers can also be surface modified, such as PYROKISUMA 5301K available from Kyowa Chemical Industry Co., Ltd. These thermally conductive fillers may be used alone or in a combination of two or more.

[0100] The filler may further comprise glass microspheres, such as hollow borosilicate glass. Non-limiting examples of commercially available glass microspheres include 3M Glass bubbles type VS, K series, and S series available from 3M.

[0101] The filler may be present in the first component, the second component, a third component, and / or higher component.

[0102] The composition may comprise the filler in an amount greater than 50% by weight based on total weight of the composition, such as at least 55% by weight, such as at least 65% by weight. The composition may comprise the filler in an amount of no more than 88% by weight based on total weight of the composition, such as no more than 80% by weight. The composition may comprise the filler in an amount of greater than 50% to 88% by weight based on total weight of the composition, such as 55% to 88% by weight, such as 55% by weight to 80% by weight, such as such as 65% to 88% by weight, such as 65% to 80% by weight.

[0103] The filler may comprise a thermally conductive filler. As used herein, “thermally conductive filler” or “TC filler” refers to a pigment, filler, or inorganic powder that has a thermal conductivity of at least 5 W / mK at 25°C (measured according to ASTM D7984-21). The filler may comprise an electrically insulative filler. As used herein, “electrically insulative filler” or “El filler” means a pigment, filler, or inorganic powder that has a volume resistivity of at least 10 Q-m (measured according to ASTM D25707). The filler may comprise, consist essentially of, or consist of thermally conductive, electrically insulative filler material (referred to herein as “TC / EI filler material” and described in more detail below).Non-thermally Conductive Filler

[0104] The filler may comprise a non-thermally conductive filler. That is, the compositions disclosed herein also may comprise non-thermally conductive, electricallyinsulative filler (referred to herein as “NTC / EI” filler). NTC / EI filler may be present in the first component, the second component and / or a third component. The NTC / EI filler may comprise an organic or inorganic material and may comprise particles of a single type of filler material or may comprise particles of two or more types of NTC / EI filler. That is, the composition may comprise a first NTC / EI filler and may further comprise at least a second (i.e., a second, a third, a fourth, etc.) NTC / EI filler in addition to the first NTC / EI filler.

[0105] The NTC / EI filler may comprise any of the surface coatings and may be the particle sizes described above with respect to the thermally conductive fillers. The NTC / EI filler may comprise particles each having, for example, a platy, spherical, or acicular shape, and agglomerates thereof, as described above with respect to the thermally conductive fillers.

[0106] The non-thermally conductive filler may have a thermal conductivity of less than 5 W / m-K at 25°C (measured according to ASTM D7984), such no more than 3 W / m-K, such as no more than W / m-K, such as no more than 0.1 W / m-K, such as no more than 0.05 W / m-K, such as 0.02 W / m-K at 25°C to 5 W / m-K at 25°C. Thermal conductivity may be measured as described above.

[0107] The non-thermally conductive filler may be electrically insulative. The electrically insulative filler may have a volume resistivity of at least 1 Q-m (measured according to ASTM D257), such as at least 10 Q-m, such as at least 100 Q-m.

[0108] Suitable NTC / EI fillers include but are not limited to mica, wollastonite, calcium carbonate, glass microspheres, clay, silicon dioxide, or combinations thereof.

[0109] As used herein, the term “mica” generally refers to sheet silicate (phyllosilicate) minerals. The mica may comprise muscovite mica. Muscovite mica comprises a phyllosilicate mineral of aluminum and potassium with the formula KA12(AlSi30io)(F,OH)2 or (KF)2(A12O3)3(SiO2)e(H2O). Exemplary non-limiting commercially available muscovite mica include products sold under the trade name DakotaPURE™, such as DakotaPURE™ 700, DakotaPURE™ 1500, DakotaPURE™ 2400, DakotaPURE™ 3000, DakotaPURE™ 3500 and DakotaPURE™ 4000, available from Pacer Minerals. Wollastonite comprises a calcium inosilicate mineral (CaSiCE) that may contain small amounts of iron, aluminum, magnesium, manganese, titanium and / or potassium. The wollastonite may have a B E T. surface area of 1.5 to 2.1 m2 / g, such as 1.8 m2 / g and a median particle size of 6 microns to 10 microns, such as 8microns. Non-limiting examples of commercially available wollastonite include NY AD 400 available from NYCO Minerals, Inc.[01101 The calcium carbonate (CaCCh) may comprise a precipitated calcium carbonate or a ground calcium carbonate. The calcium carbonate may or may not be surface treated, such as treated with stearic acid. Non-limiting examples of commercially available precipitated calcium carbonate include Ultra-Pflex®, Albafil®, and Albacar HO® available from Specialty Minerals and Winnofil® SPT available from Solvay. Non-limiting examples of commercially available ground calcium carbonate include Duramite™ available from IMERYS and Marblewhite® available from Specialty Minerals.

[0111] Useful clay minerals include a non-ionic platy filler such as talc, pyrophyllite, chlorite, vermiculite, or combinations thereof.

[0112] The glass microspheres may be hollow borosilicate glass. Non-limiting examples of commercially available glass microspheres include 3M Glass bubbles type VS, K series, and S series available from 3M.

[0113] As discussed above, NTC / EI filler may be present in the first component, the second component and / or the third component or higher component. The compositions disclosed herein may comprise NTC / EI filler in an amount of at least 0.5 percent by weight based on total weight of the composition, such as at least 1 percent by weight, such as at least 1.5 percent by weight. The compositions disclosed herein may comprise NTC / EI filler in an amount of no more than 30 percent by weight based on total weight of the composition, such as no more than 20 percent by weight, such as no more than 10 percent by weight. The compositions disclosed herein may comprise NTC / EI filler in an amount of up to 30 percent by weight based on total weight of the composition, such as 0.5 percent by weight to 30 percent by weight, such as 1 percent by weight to 20 percent by weight, such as 1.5 percent by weight to 10 percent by weight.Accelerator

[0114] The disclosed compositions optionally may comprise an accelerator. The accelerator may comprise a nitrogen-based catalyst, such as an amine catalyst. The accelerator may comprise a tertiary amine, an V-heterocyclic carbene, or an amidine / guanidine. Suitable accelerators that may be used in the present disclosure include / V,V-dimethylcyclohexylamine, V,V-dimethylethanolamine, V-m ethyl morpholine, 2,2’-dimorpholinodiethylether,dimethylaminoethoxyethanol, triethylenediamine, bis(2-dimethylaminoethyl)ether, N,N,N’~ trimethylaminoethylethanolamine, N,N,N’,N ’-tetramethyl-l,6-hexanediamine, 1,3,5- tris(dimethylaminopropyl)-hexahydro-s-triazine, l,8-diazabicyclo[5.4.0]undec-7-ene, N-(3- aminopropyl)imidazole, 1,2-dimethylimidazole, l,5,7-triazabicyclo[4.4.0]dec-5-ene, or 7- methyl-l,5,7-triazabicyclo[4.4.0]dec-5-ene.

[0115] In some cases, the accelerator may be an organic acid, such as diphenyl phosphate, methanesulfonic acid, or triflic acid.

[0116] The accelerator may be an inorganic accelerator, such as an organometallic complex. Suitable inorganic accelerators include titanates, such as tetrabutyl titanate or tetrapropyl titanate, tin compounds, such as dibutyltin dilaurate, dibutyltin diacetate, tin octoate, or dibutyl tin oxide, or other metal compounds, such as bismuth, zirconium, titanium, aluminum, or iron, or chelates thereof, such as zirconium acetylacetonate or iron acetylacetonate.

[0117] The accelerator may be present in the composition in an amount of at least 0.001% by weight based on total weight of the composition, such as at least 0.01% by weight, and may be present in an amount of no more than 2% by weight based on total weight of the composition, such as no more than 1% by weight. The accelerator may be present in the composition in an amount of 0.001% by weight to 2% by weight based on total weight of the composition, such as 0.01% by weight to 1% by weight. The composition may comprise the accelerator in a positive amount of up to 2% by weight based on total weight of the composition, such as in a positive amount up to 1% by weight. As used herein, “a positive amount” when referring to the amount of a component means that the component is present in an amount greater than 0 up to the recited upper limit.Second Polyol

[0118] The composition may further comprise a second polyol in addition to and different than the polyurethane polyol. The second polyol may be present in the second component, a third component, or a higher component.

[0119] The composition may comprise the second polyol in an amount up to 10% by weight based on total weight of the composition, such as no more than 7.5% by weight. The composition may comprise the second polyol in an amount of at least 0.5% by weight based on total weight of the composition. The composition may comprise the second polyol in an amountof 0.5% by weight to 10% by weight based on total weight of the composition, such as 0.5% by weight to 7.5% by weight.[01201 The second polyol may comprise an Mn of at least 60 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min’1, and two PL Gel Mixed C columns used for separation, such as at least 90 g / mol. The second polyol may comprise an Mn of no more than 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min’1, and two PL Gel Mixed C columns used for separation, such as no more than 2,000 g / mol. The second polyol may comprise an Mn of 60 g / mol to 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min’1, and two PL Gel Mixed C columns used for separation, such as 90 g / mol to 2,000 g / mol.Additive

[0121] The composition may optionally comprise an additive. Additives may be present in the first component, the second component, and / or a third or higher components. As used herein, an “additive” refers to a rheology modifier including a thixotrope, a tackifier, a thermoplastic polymer, a surfactant, a dispersant, a flame retardant, a corrosion inhibitor, a UV stabilizer, a colorant, a tint, a solvent, a plasticizer, an adhesion promoter, an antioxidant, a silane, a stabilizer, an oil, a moisture scavenger, and / or a blowing agent. Certain thermally conductive materials such as aluminum hydroxide and magnesium hydroxide, for example, also may be flame retardants. As used herein, “flame retardant” refers to a material that slows down or stops the spread of fire or reduces its intensity. Flame retardants may be available as a powder that may be mixed with a composition, a foam, or a gel. In examples, when the compositions disclosed herein include a flame retardant, such compositions may form a coating on a substrate surface and such coating may function as a flame retardant. A flame retardant can include a mineral, an organic compound, an organohalogen compound, an organophosphorous compound, or a combination thereof.

[0122] Additives, if present at all, may be present in the composition in an amount of at least 0.1% by weight based on total weight of the composition, such as at least 0.5% by weight, such as at least 1.0% by weight. Such additives, if present at all, may be present in the composition in an amount of no more than 5% by weight based on total weight of the composition, such as no more than 4% by weight, such as no more than 3% by weight. If present at all, the composition may comprise the additives in an amount of 0.1% to 5% by weight based on total weight of the composition, such as 0.5% by weight to 4% by weight, such as 1% to 3% by weight.Compositions

[0123] The composition may comprise an isocyanate equivalent weight of at least 500 g / eq, such as at least 750 g / eq based on total weight of all isocyanate-containing components. The composition may comprise an isocyanate equivalent weight of no more than 5,000 g / eq, such as no more than 3,000 g / eq, based on total weight of all isocyanate-containing components. The composition may comprise an isocyanate equivalent weight of 500 g / eq to 5,000 g / eq, such as 750 g / eq to 3,000 g / eq, based on total weight of all isocyanate-based components.

[0124] The composition may comprise an active hydrogen equivalent weight of at least 500 g / eq, such as at least 750 g / eq, based on total weight of all amine- and polyol-containing components. The composition may comprise an active hydrogen equivalent weight of no more than 6,000 g / eq, such as no more than 4,000 g / eq, based on total weight of all amine- and polyol- containing components. The composition may comprise an active hydrogen equivalent weight of 500 g / eq to 6,000 g / eq, such as 750 g / eq to 4,000 g / eq, based on total weight of all amine- and polyol-containing components.

[0125] The composition may comprise a ratio of NCO OH of at least 0.7: 1, such as at least 0.9: l. The composition may comprise a ratio of NCO:OH of no more than 1.7:1, such as no more than 1.5: 1. The composition may comprise a ratio of NCO:OH of 0.7: 1 to 1.7: 1, such as 0.9:1 to 1.5: 1.

[0126] The composition may comprise a ratio of active hydrogens from the aromatic amine to active hydrogens of the polyurethane polyol of at least 1 : 10, such as at least 1 :5. The composition may comprise a ratio of active hydrogens from the aromatic amine to active hydrogens of the polyurethane polyol of no more than 10: 1, such as no more than 5: 1. Thecomposition may comprise a ratio of active hydrogens from the aromatic amine to active hydrogens of the polyurethane polyol of 1 : 10 to 10:1, such as 1 :5 to 5: 1.[01271 The compositions disclosed herein may be formulated as a coating composition, for example, an adhesive composition such as a structural adhesive composition, a pottant composition, a pre-preg, a liquid shim composition, a sealant composition, or a gap fdler composition.Methods

[0128] The compositions described above may be applied alone or as part of a system that can be deposited in a number of different ways onto a number of different substrates. Accordingly, disclosed herein are methods for treating a substrate comprising, or consisting essentially of, or consisting of, contacting a surface of the substrate with any of the compositions disclosed herein. Optionally, the method may comprise mixing the first component and second component to form the composition. The composition can be applied to the surface of a substrate in any number of different ways, non-limiting examples of which include brushes, rollers, films, pellets, trowels, spatulas, dips, spray guns, and applicator guns to form a coating on the substrate surface.

[0129] After application to the substrate(s), the composition may be cured. For example, the composition may be allowed to cure at room temperature or slightly thermal conditions, and for any desired time period (e.g., from 5 minutes to 1 hour) sufficient to cure the composition on the substrate(s). Optionally, the composition may be further cured by heating at an elevated temperature following the contacting of the substrate surface with the composition, such as at a temperature of less than 90°C, such as less than 80°C, such as less than 70°C, such as less than 60°C, but greater than ambient, such as greater than 40°C, such as greater than 50°C, and for any desired time period (e.g., from 5 minutes to 1 hour) sufficient to cure the composition on the substrate(s). Upon cure, the composition may form a coating on the substrate surface. The coating may be, for example, an adhesive such as a structural adhesive, a pottant, a pre-preg, a liquid shim, a seal, or a gap filler.

[0130] The method optionally may further comprise contacting a surface of a second substrate to the composition such that the composition is between the first substrate and the second substrate. For example, the composition may be applied to either one or both of the substrate materials being bonded to form an adhesive bond there between and the substrates maybe aligned and pressure and / or spacers may be added to control bond thickness. The composition may be applied to cleaned or uncleaned (i.e., including oil or oiled) substrate surfaces.

[0131] The compositions disclosed herein may also be applied to a substrate that has been pretreated, coated with an electrodepositable coating, and / or coated with additional coatings such as a primer, basecoat, or topcoat. That is, “contacting a surface of the substrate” encompasses contacting a surface of a substrate that has been treated with other coatings, as described herein.

[0132] The system may comprise a number of the same or different coatings. A coating is typically formed when a composition that is deposited onto the substrate surface is cured by methods known to those of ordinary skill in the art (e.g., under ambient conditions).

[0133] As stated above, the composition of the present disclosure also may form a coating on a substrate or a substrate surface. The coating composition may be applied to substrate surfaces, including, by way of non-limiting example, a vehicle body or components of an automobile frame or an airplane. The coating composition may be applied to cleaned or uncleaned (i.e., including oily or oiled) substrate surfaces. The coating composition may dry or cure at ambient conditions once applied to a substrate or substrates coated with coating compositions and may optionally subsequently be baked in an oven to cure the coating composition.

[0134] The composition may be injected or otherwise placed in a die caster or a mould and dried or cured under ambient conditions or by exposure to an external energy source, for example, such as by heating to a temperature of less than 180°C, such as less than 130°C, such as less than 90°C to form a part or a member and optionally may be machined to a particular configuration.3-D Printing

[0135] Compositions of the present disclosure may be applied or deposited using any suitable method, including those aforementioned. Alternatively, the composition may be casted, extruded, molded, or machined to form a part or a member in a cured state.

[0136] The compositions disclosed herein may be used in any suitable additive manufacturing technology, such as three-dimensional (3D) printing, extrusionjetting, and binderjetting. Additive manufacturing refers to a process of producing a part or member by constructing it in layers, such as one layer at a time.[01371 The present disclosure is also directed to the production of structural articles, such as by way of a non-limiting example, sound damping pads, print gaskets, or seals, using an additive manufacturing process, such as 3D printing. 3D printing refers to a computerized process, optionally including artificial intelligence modulation, by which materials are printed or deposited in successive layers to produce a 3D part or member, such as, by way of a non-limiting example, sound damping pads in a battery assembly. A 3D part or member may be produced by depositing successive portions or layers over a base of any spatial configuration and thereafter depositing additional portions or layers over the underlying deposited portion or layer and / or adjacent to the previously deposited portion or layer to produce the 3D printed part or member.

[0138] It will be appreciated that the configuration of the 3D printing process, including the selection of suitable deposition equipment, depends on a number of factors such as the deposition volume, the viscosity of the composition and the complexity of the part being fabricated. Any suitable mixing, delivery, and 3D printing equipment as known to those skilled in the art, may be used. Compositions may be printed or deposited in any size and / or shape of droplets or extrudate, and in any patterns to produce the 3D structure.

[0139] Compositions as disclosed herein may be applied or deposited by any suitable 3D printing method as known to those skilled in the art. First and second components of 2K compositions may be mixed and then deposited, or the first and second components may be deposited separately, such as simultaneously and / or sequentially.

[0140] The first component and the second component may be premixed, i.e., mixed together, prior to application, and then deposited. The mixture may be reacted or thermoset when the material is deposited; the deposited reaction mixture may react after deposition and may also react with previously deposited portions and / or subsequently deposited portions of the article such as underlying layers or overlying layers of the article.

[0141] In a non-limiting example, the first and second components may be released from their individual storage containers and pushed, such as pumped through conduits, such as hoses, to a mixer, such as a static or dynamic mixer, wherein the composition may be mixed for a time sufficient to homogenize the composition, wherein the composition may then be released through an outlet. The outlet may be a deposition device, such as a printing head, and / or thematerials may exit the mixing unit and be pushed, such as by a pump, through a conduit, such as a hose, to the printing head. The printing head may optionally be mounted on a 3D rotational robotic arm to allow delivery of 3D print compositions to any base in any spatial configuration and / or the base may be manipulated in any spatial configuration during the 3D printing process.

[0142] Alternatively, the first component and the second component may be deposited independently from different printing heads. The first component may be deposited from one printing head and the second component may be deposited from a second printing head. The first and second components may be deposited in any pattern such that the first and second components comprising any deposited layer can react together as well as react with underlying and / or overlying layers to produce the 3D printed part or member.

[0143] Methods provided by the present disclosure include printing the composition on a fabricated part. Methods provided by the present disclosure include directly printing parts.

[0144] Using the methods provided by the present disclosure parts can be fabricated. The entire part can be formed from one of the compositions disclosed herein, one or more portions of a part can be formed from one of the compositions disclosed herein, one or more different portions of a part can be formed using the compositions disclosed herein, and / or one or more surfaces of a part can be formed from a composition provided by the present disclosure. In addition, internal regions of a part can be formed from a composition provided by the present disclosure.Dielectric Coatings and Dielectric Systems and Kits

[0145] Any of the substrates disclosed herein may comprise a dielectric coating in addition to the coating formed from any of the compositions described above. The substrate may comprise the dielectric coating on a first substrate surface and a second coating formed from any of the compositions described above on a second substrate surface. The second coating may be an adhesive, such as a structural adhesive, a seal, a gap filler, a pottant, a pre-preg, or a liquid shim.

[0146] Also disclosed herein are coating systems. The coating system may comprise: a dielectric coating composition; and any of the coating compositions. In a cured state, the dielectric coating composition may form a dielectric coating. In a cured state, coating composition may form a coating such as an adhesive, such as a structural adhesive, a seal, a gap filler, a pottant, a pre-preg, or a liquid shim.

[0147] Also disclosed herein are coating kits. The coating kit may comprise: a dielectric coating composition; and any of the coating compositions disclosed. The kit optionally may comprise instructions for applying the dielectric composition to a first substrate surface and the coating composition to a second substrate surface.

[0148] As used herein with respect to dielectric coatings and thermally expandable coatings, and systems and kits comprising compositions for forming the same, the first substrate surface and the second substrate surface may be on a single substrate or may be on a first substrate and a second substrate, respectively.

[0149] The dielectric coating composition and the thermally expandable coating composition may form continuous or discontinuous coatings, provided that the coatings overlap to form a coating stack, e.g., a thermally expandable coating formed from the thermally expandable coating composition on a dielectric coating formed from the dielectric coating composition. Such a coating stack does not preclude the possibility of coatings in addition to the dielectric coating and the second coating, wherein such additional coatings may or may not be positioned between the dielectric coating and the second coating. Optionally, the coating stack may be formed between two substrates.

[0150] Also disclosed herein are articles comprising, consisting essentially of, or consisting of, a dielectric coating on a first portion of a substrate surface, a coating, such as an adhesive, a structural adhesive, a seal, a gap filler, a pottant, a pre-preg, or a liquid shim, formed from any of the compositions disclosed herein in contact with the dielectric coating, and a second substrate comprising a surface adjacent to the coating.

[0151] As described in more detail below, the dielectric coating may be deposited from a powder dielectric coating composition or a liquid dielectric coating composition, such as, for example, a UV dielectric coating composition or an electrodepositable dielectric coating composition.

[0152] Additional coatings may be present between the surface, the dielectric coating and / or the coating.

[0153] The dielectric coating may comprise a dielectric strength of at least 50 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as at least 60 kV / mm. The dielectric coating may comprise a dielectric strength of no more than120 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as no more than 100 kV / mm. The dielectric coating may comprise a dielectric strength of 50 kV / mm to 120 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as 60 kV / mm to 100 kV / mm.

[0154] The dielectric coating may comprise a thermal conductivity of at least 0.3 W / K-m measured using a TIM Thermal Resistance and Conductivity Measurement Apparatus (model LW-9389) according to ASTM D5470-17 (steady-state methods), such as at least 0.35 W / K-m. The dielectric coating may comprise a thermal conductivity of no more than 0.5 W / K-m measured using a TIM Thermal Resistance and Conductivity Measurement Apparatus (model LW-9389) according to ASTM D5470-17 (steady-state methods), such as no more than 0.45 W / K-m. The dielectric coating may comprise a thermal conductivity of 0.3 W / K-m to 0.5 W / K-m measured using a TIM Thermal Resistance and Conductivity Measurement Apparatus (model LW-9389) according to ASTM D5470-17 (steady-state methods), such as 0.35 W / K-m to 0.45 W / K-m.

[0155] The dielectric coating may comprise a dielectric breakdown of at least 12 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as at least 15 kV / mm, such as at least 20 kV / mm, such as at least 25 kV / mm, such as at least 30 kV / mm.

[0156] The dielectric coating can be applied at any desired dry fdm thickness. For example, the dry film thickness may be at least 50 microns, such as at least 75 microns, such as at least 100 microns. For example, the dry film thickness may be no more than 300 microns, such as no more than 250 microns, such as no more than 200 microns. The dry film thickness may be 50 microns to 300 microns, such as 75 microns to 250 microns, such as 100 microns to 200 microns, such as 100 microns to 220 microns. It is appreciated that, when multiple dielectric coating compositions are applied, each composition can be applied to separately provide any of the previously described dry film thicknesses. For instance, when two separate dielectric coating compositions are applied, each individual dielectric coating composition can be applied at any of the previously described dry film thicknesses.

[0157] The adhesive may comprise a thermal conductivity of at least 0.7 W / K-m measured using a TIM Thermal Resistance and Conductivity Measurement Apparatus (model LW-9389) according to ASTM D5470-17 (steady-state methods), such as at least 0.8 W / K-m, such as at least 0.9 W / K-m, such as at least 1.0 W / K-m, such as at least 1.5 W / K-m. The coating layer may comprise a thermal conductivity of no more than 2.5 W / K-m measured using a TIM Thermal Resistance and Conductivity Measurement Apparatus (model LW-9389) according to ASTM D5470-17 (steady-state methods), such as no more than 2.0 W / K-m. The coating layer may comprise a thermal conductivity of 0.7 W / K-m to 2.5 W / K-m measured using a TIM Thermal Resistance and Conductivity Measurement Apparatus (model LW-9389) according to ASTM D5470-17 (steady-state methods), such as 0.8 W / K-m to 2.5 W / K-m, such as 0.9 W / K-m to 2.5 W / K-m, such as 1.0 W / K-m to 2.5 W / K-m, such as 1.5 W / K-m to 2.5 W / K-m, such as 0.7 W / K-m to 2.0 W / K-m such as 0.8 W / K-m to 2.0 W / K-m, such as 0.9 W / K-m to 2.0 W / K-m, such as 1.0 W / K-m to 2.0 W / K-m, such as 1.5 W / K-m to 2.0 W / K-m.

[0158] The adhesive may comprise a dielectric breakdown of at least 6 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as at least 10 kV / mm. The adhesive may comprise a dielectric breakdown of no more than 20 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as no more than 17 kV / mm. The adhesive may comprise a dielectric breakdown of 6 kV / mm to 20 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as 10 kV / mm to 17 kV / mm.

[0159] The compositions disclosed herein may be applied by any methods disclosed herein to form the adhesive.Dielectric Coating Compositions

[0160] As previously stated, the dielectric coating may be formed from a dielectric coating composition. Any suitable dielectric coating composition known in the art may be used, such as a powder coating composition or a liquid coating composition, such as a UV cured coating composition or an electrodepositable dielectric coating composition.

[0161] The dielectric coating composition may comprise a binder comprising a filmforming resin. As used herein, “film-forming resin” refers to one or more monomers, oligomers, prepolymers and / or polymers, such as homopolymers and / or copolymers, that can form a coating upon reaction with a curing agent or crosslinker, upon evaporation of a solvent, and / or upon photo or thermal activation. The dielectric coating composition may comprise any suitable filmforming resin, including organic film-forming resins and / or inorganic film-forming resins, such as silicon-based film-forming resins. Examples of suitable film-forming resins include but are not limited to polyester, alkyd, urethane, isocyanate, polyurea, epoxy, acrylic, polyether, polysulfide, polyamine, polyamide, polyvinyl chloride, polyolefin, polyvinylidene fluoride, polyvinyl chloride, polyolefin, polysiloxane, amine-aldehydes, resinous polyols, phosphatized polyepoxides, phosphatized acrylic polymers, aminoplasts, or combinations thereof.

[0162] The dielectric coating composition may optionally comprise a curing agent and / or crosslinker that is capable of crosslinking with the film-forming resin to cure the dielectric coating composition. Any suitable curing agent and / or crosslinker that is capable of crosslinking with the film-forming resin may be used. Examples of suitable curing agents include but are not limited to amines, aminoplasts, phenoplasts, polyisocyanates, including blocked isocyanates, polyepoxides, beta-hydroxyalkylamides, polyacids, organometallic acid-functional materials, polyamines, polyamides, polysulfides, polythiols, polyenes such as polyacrylates, polyols, polysilanes and the like, or combinations thereof.

[0163] The dielectric coating composition may optionally further comprise colorants, pigments, additives, flame retardants, and / or fillers. Suitable fillers that may be used in the dielectric coating composition include thermally conductive, electrically insulative filler materials, thermally conductive, electrically conductive filler materials, and / or thermally insulative, electrically insulative filler materials.

[0164] The dielectric coating composition may comprise a thermoset coating composition, wherein the coating composition is cured upon crosslinking of a film-forming resin and a curing agent and / or crosslinker. Alternatively, the dielectric coating composition may comprise a thermoplastic coating composition, wherein the coating composition comprises a film-forming resin that cures upon evaporation of water and / or solvent. Alternatively, the dielectric coating composition may comprise a thermoset or thermoplastic coating composition that cures upon exposure to actinic radiation, such as ultraviolet light.

[0165] As previously stated, the dielectric coating composition may comprise a liquid coating composition or a powder coating composition. As used herein, when referring to a dielectric coating composition, “liquid” means a material having a viscosity less than 100,000 Pa-s at 25°C as measured by parallel plate rheology with a plate diameter of 25 mm, a gap of 0.5 mm, and a shear rate of 1 s'1.

[0166] Suitable liquid coating compositions include but are not limited to electrodepositable coating compositions, one-component coating compositions, and / or multicomponent coating compositions.

[0167] For example, the liquid dielectric coating composition may comprise an electrodepositable coating composition. The electrodepositable coating composition may comprise one or more cationic or anionic salt group-containing film-forming resins that may be deposited onto a metal or other conductive substrate under the influence of an applied electrical potential, i.e., by electrodeposition.

[0168] In other examples, the liquid dielectric coating composition may comprise a UV- curable coating composition comprising film-forming resins capable of curing upon exposure to UV radiation. Any suitable UV-curable film-forming resin may be used, such as free radical polymerizable resins containing ethylenic unsaturation or olefinic double bonds and / or filmforming resins that may react through a cationic photopolymerization mechanism. Examples of suitable UV-curable coating compositions that may be used include but are not limited to the RAYCRON line of UV-curable coatings, commercially available from PPG Industries, Inc.

[0169] Other suitable liquid dielectric coating compositions include but are not limited to the SPECTRACRON line of solvent-based coating compositions and the AQUACRON line of water-based coating compositions, all commercially available from PPG Industries, Inc. The liquid dielectric coating may also be applied as a two-component composition where the filmforming resins and the reactive curing agent and / or crosslinker are mixed just before application of the coating composition and may optionally cure under ambient conditions without any external energy source.

[0170] Alternatively, the dielectric coating composition may comprise a powder coating composition. “Powder coating composition” as used herein refers to any dielectric coating composition in the form of a co-reactable solid in particulate form which may be substantially free, essentially free, or completely free of water and / or solvent. Suitable film-forming resinsuseful in dielectric powder coating compositions include those discussed in PCT Publ. No. WO 2021 / 173941A1, pars.

[0006] to

[0042] ,

[0057] to

[0068] ,

[0088] to

[0105] and

[0128] to

[0139] , incorporated herein by reference. Non-limiting examples of suitable powder compositions that may be used in the present disclosure include the polyester-based ENVIROCRON line of powder coating compositions (commercially available from PPG Industries, Inc.), silicon modified polyester compositions, epoxy-polyester hybrid compositions, and / or UV-curable powder compositions.

[0171] The dielectric coating composition may be applied to a substrate by any suitable method known in the art, including but not limited to electrodeposition, coil coating, spraying, such as electrostatic spraying, flow coating, spin coating, curtain coating, brushing, dipping, hot- melt extrusion, application of a free-standing film, and / or by the use of a fluidized bed. Once applied to the substrate, the dielectric coating composition may be cured by any method known in the art, such as baking, induction heating, infrared heating, and / or exposure to actinic radiation such as UV.

[0172] The powder dielectric coating compositions can be applied by any means standard in the art, such as spraying, electrostatic spraying, a fluidized bed process, and the like. The powder dielectric coating compositions can also be applied in multiple applications over a substrate (a “multi-application process”). For instance, a first dielectric powder coating composition can be applied over at least a substrate surface. A second dielectric powder coating composition can be applied over the first dielectric powder coating composition. The first and second dielectric powder coating compositions can then be cured together at the same time.

[0173] It is appreciated that the dielectric powder coating composition can be cured with multiple types of heat sources such as both convection heating and infrared radiation. For example, the dielectric powder coating composition can be partially cured with convection heating or infrared radiation, and then completely cured with a different heat source chosen from convection heating and infrared radiation.

[0174] In some examples, the dielectric powder coating composition can be cured with heat, such as convection heating within a range of 120°C to 260°C, such as 160°C to 240°C, such as 180°C to 200°C, for 1 minute to 40 minutes. The dielectric powder coating composition can also be cured with infrared radiation in which peak metal temperatures can reach 200°C to 260°C in about 10 seconds. The elevated heat ramping with infrared radiation allows for fastcure times. In some examples, the dielectric powder coating composition is cured with infrared radiation to heat the composition within a range of from 140°C to 180°C for 1 to 20 minutes.Substrates

[0175] Compositions described herein may be coated or deposited on, or otherwise contacted with, any substrate or surface, such as, but not limited to, metals or metal alloys, polymeric materials, such as plastics including filled and unfilled thermoplastic or thermoset materials, and / or composite materials. Other suitable substrates include, but are not limited to, glass or natural materials such as wood. Substrates may include two or more of any different materials in any combination, such as, but not limited to, two different metals, or a metal and a metal alloy, or a metal and a metal alloy and one or more composite materials.

[0176] Suitable substrates may include, but are not limited to, both flexible and rigid metal substrates such as ferrous metals, aluminum, aluminum alloys, magnesium, titanium, copper, and other metal and alloy substrates. The ferrous metal substrates may include, for example, iron, steel, and alloys thereof. Non-limiting examples of useful steel materials include cold rolled steel, nickel plated cold rolled steel, galvanized (zinc coated) steel, electrogalvanized steel, stainless steel, pickled steel, zinc-iron alloy such as GALV ANNEAL, and combinations thereof. Aluminum alloys, such as those, for example, of the 1XXX, 2XXX, 3XXX, 4XXX, 5XXX, 6XXX, 7XXX, or 8XXX series as well as clad aluminum alloys and cast aluminum alloys, such as those, for example, of the A356, 1XX.X, 2XX.X, 3XX.X, 4XX.X, 5XX.X, 6XX.X, 7XX.X, or 8XX.X series also may be used as the substrate. The substrate also may comprise, for example, magnesium, such as magnesium alloys of the AZ3 IB, AZ91C, AM60B, or EV31 A series, titanium and / or titanium alloys, such as those of grades 1-36 including H grade variants, copper and copper alloys, or other non-ferrous metals, as well as alloys of these materials. The substrate may comprise a composite material such as a plastic, fiberglass and / or carbon fiber composite.

[0177] It will also be understood that the substrate may comprise a bare substrate or the substrate may be pretreated or pre-coated, at least in part, with one or more layers. Suitable pretreatment solutions may include but are not limited to a zinc phosphate pretreatment solution such as, for example, those described in U.S. Pat. Nos. 4,793,867 and 5,588,989, or a zirconium containing pretreatment solution such as, for example, those described in U.S. Pat. Nos. 7,749,368 and 8,673,091, all of which are incorporated herein by reference.

[0178] The substrate may be in any form, such as, without limitation, a sheet, a foil, a laminate foil, a pad, a fabricated part, a component, or an article. Compositions comprising the materials disclosed herein may be used to coat a substrate, such as by depositing, applying, or contacting the compositions to a substrate surface. The compositions, in an at least partially cured state, may be used in any form, such as but not limited to, a coating, a sealant, an adhesive, a pottant, or an encapsulant, such as a solid or gel, such as a pad formed in-situ or a discrete premanufactured or pre-formed pad.

[0179] In examples, the substrate may be a multi-metal article. As used herein, the term “multi-metal article” refers to (1) an article that has at least one surface comprised of a first metal and at least one surface comprised of a second metal that is different from the first metal, (2) a first article that has at least one surface comprised of a first metal and a second article that has at least one surface comprised of a second metal that is different from the first metal, or (3) both (1) and (2).

[0180] The compositions disclosed herein are not limited and may be particularly suitable for use in various industrial or transportation applications including automotive applications, commercial applications, rail locomotive, marine applications, and / or aerospace applications. Suitable substrates for use in the present disclosure include those that are used in the assembly of vehicular bodies (for example, without limitation, door, body panel, trunk deck lid, roof panel, hood, roof, and / or stringers, rivets, landing gear components, and / or skins used on an aircraft), vehicular frames, vehicular parts, motorcycles, wheels, and industrial structures and components. As used herein, “vehicle” or variations thereof includes, but is not limited to, civilian vehicles, light and heavy commercial vehicles, civilian and military aircraft, and / or land vehicles such as cars, motorcycles, and / or trucks.

[0181] FIGS. 1 to 9 illustrate non-limiting examples of battery assembly components and constructions as well as non-limiting applications or use of compositions as disclosed herein in said battery assemblies. Although FIGS. 1 to 9 illustrate specific examples of cell shapes and cell arrangements, cells may be arranged in any configuration known to those skilled in the art. Additionally, the compositions disclosed herein, in an at least partially cured state, may be used to form pads, adhesives, coatings, pottants and the like, to provide thermal protection between battery cells, within battery modules and / or within battery packs. These materials may be used on any surface or in any space within such battery assemblies. For example, compositionsdisclosed herein also may be useful in battery assemblies including, but not limited to, cell to module (FIGS. 3, 4, 6B), module to pack (FIGS. 6C, 7), cell to pack (FIGS. 8), and cell to chassis battery assemblies (FIG. 9). Such battery assemblies may be used in, but not limited to, any aforementioned application.

[0182] Battery assemblies may be any combination of one or more battery cells, the interconnects which provide electrical conductivity between them, as well as ancillary components such as, in non-limiting examples, control electronics and components that ensure the necessary structural mechanical and environmental requirements for the operation of a specific battery (for example, without limitation, cell interconnectors such as wires, battery pack enclosures including trays and lids, module enclosures, module frames and frame plates, module racking, cooling and heating components including cooling plates, cooling fins, and cooling tubes, electrical busbars, battery management systems, battery thermal management systems, chargers, inverters and converters).

[0183] Battery cells 10 are generally single unit energy storage containers that may be connected in series or in parallel. Battery cells may be any suitable size or shape known to those skilled in the art, such as but not limited to, cylindrical (FIGS. 1, 4 and 9), prismatic (FIGS. 2, 5- 8) and / or pouch (FIG. 3). Battery cells 10 are enclosed to provide desired mechanical protection and environmental isolation of the cell. For example, cylindrical and prismatic cells may be encased in metal cans, cases, and lids, while pouch cells may be enclosed in multilayer laminate foils. Battery terminals 1 connect the electrodes inside the battery cell to the electrical circuit outside the battery cell, with one being a positive terminal and the other being a negative terminal. As illustrated in FIG. 4, battery cells 10 may be connected by interconnector wires 5 with other battery cells 10 in series or in parallel to enable an electric current to flow between cells 10.

[0184] As illustrated in FIGS. 3 and 4, battery cells 10 may be arranged in modules 100 comprising multiple cells 10 connected in series or in parallel. The modules 100 may include an at least partial enclosure of the arranged cells 10. Ancillary components, such as those aforementioned, may be included. Spaces of any dimensions may be located between the plurality of cells, ancillary components, base, and / or any interior surface of the module wall or other enclosure 120.

[0185] FIG. 1 illustrates a top-down view of cylindrical battery cells 10 having terminals 1. As shown, the cells are arranged in rows with either cooling tubes 3 or dielectric insulation paper (e-paper) 4 between them. As shown, materials, such as adhesive 6 and / or pottants 7 optionally formed from the compositions disclosed herein in an at least partially cured state, may be positioned between the cells 10, cooling tubes 3 and / or e-paper 4.

[0186] FIG. 2 illustrates an exploded isometric view of an array of prismatic battery cells 10. As shown, each prismatic cell 10 may comprise a top 11, a bottom, and walls 13 positioned between the top and bottom and each having a surface. As shown, materials, such as pads 8 formed from the compositions disclosed herein in an at least partially cured state, may be positioned between surfaces of cell walls 13 of adjacent cells 10.

[0187] FIG. 3 illustrates a cut-out front view of an array of pouch battery cells 10 in a module 100. The module walls 120 at least partially encase the cells 10. As shown, materials, such as pads 8 formed from the compositions disclosed herein in an at least partially cured state, may be positioned between surfaces of cells 10.

[0188] FIG. 4 illustrates an isometric view of cylindrical cells 10 in a battery module 100. Each cell may comprise a top 11, a bottom 12, and walls 13 positioned between the top and bottom and each having a surface. The top 11 and the bottom 12 may be oppositely charged terminals with one being a positive terminal 1 and the other being a negative terminal (not shown). The battery cells may be connected at their terminals by interconnectors such as wires 5 and the like to enable an electric current to flow between the electric cells. The module 100 or module walls 120 may form a space having a volume. The cells 10 may be positioned within the space to consume a portion of the volume. The material, such as a pottant 7 formed from the compositions disclosed herein in an at least partially cured state, may be positioned, formed from the coating compositions disclosed herein may be positioned within the space to consume at least a portion of the volume such that the material is adjacent to a surface of a cell wall 13 and / or an interior surface of at least one of the walls 120 of the module 100.

[0189] FIG. 5 illustrates an exploded perspective view of a battery module 100 comprised of one or more arrays of battery cells 10, a cooling fin 230, and a cooling plate 240. Materials, such as pads 8 formed from the compositions disclosed herein in an at least partially cured state, may be positioned between cells 10. Additional pads 8 may be positioned betweenthe cells 10, the cooling fin 230, the cooling plate 240, and / or an interior surface of walls 120. Other pads 8 may be positioned adjacent an exterior surface of the walls 120.[01901 FIG. 6 illustrates an isometric view of a battery cell 10 (FIG. 6A) to battery module 100 (FIG. 6B) to battery pack 200 (FIG. 6C) battery assembly. The battery module 100 comprises a plurality of battery cells 10 and the battery pack 200 comprises a plurality of battery modules 100.

[0191] FIG. 7 illustrates a perspective view of a battery pack 200 cutout. The battery pack includes a plurality of battery modules 100 and cells 10 within each module 100. The base of the battery pack 200 comprises a cooling plate 240. Materials, such as adhesives, 9 formed from the compositions disclosed herein in an at least partially cured state, may be positioned between the cooling plate 240 and interior surface of a wall of the battery pack 200. Materials, such as pads 8 formed from the compositions disclosed herein in an at least partially cured state, may be positioned between cells 10 within modules 100.

[0192] FIG. 8 illustrates an isometric view of a cell 10 to pack battery 200 assembly. Cells 10 are arranged within the pack 200 (without being in separate modules).

[0193] In other cases, the battery cells may be arranged on or within an article such as, but not limited to, a cell to chassis battery assembly, as illustrated in FIG. 9, wherein one or more cells is used to construct the battery assembly without prior assembly of the cells into modules and / or packs. FIG. 9 illustrates an isometric cut-out view of a cell to chassis battery assembly 300. Cells 10 are arranged on a base comprising the undercarriage 55 and supported by the vehicle frame 45 and under the vehicle interior floor 35.

[0194] Any battery assembly may further comprise a thermal management system comprising air or fluid circuits which may be liquid based (for example glycol solutions) or direct refrigerant based.

[0195] The substrate may comprise a film formed by one of the compositions disclosed herein on the surface of the substrate that, when cured, may have at least one of the following:(a) a lap shear strength of at least 5 MPa at failure, such as at least 6 MPa, such as at least 7 MPa, such as at least 8 MPa, wherein the lap shear displacement and the lap shear strength are measured according to ASTM D1002-10 using 3003 H24 aluminum substrate of 0.063 in. thickness, as measured by an INSTRON 5567 machine in tensile mode with a pull rate of 10 mm per minute;(b) a tensile strength at ambient conditions of greater than 1 .8 MPa measured according to ASTM D412-16(2021) using an INSTRON 5567 machine;(c) an elongation at break at ambient conditions of greater than 24% measured according to ASTM D412-16(2021) using an INSTRON 5567 machine;(d) a tensile strength at -35°C of greater than 7.4 MPa measured according to ASTM D412-16(2021) using an INSTRON 5567 machine;(e) an elongation at break at 35°C of greater than 14% measured according to ASTM D412-16(2021) using an INSTRON 5567 machine; and / or(f) a thermal conductivity of greater than 0.78 W / mK measured according to ASTM D7984-21 using a C-Therm TCi Thermal Conductivity Analyzer with Modified Transient Plane Source method.

[0196] The present disclosure is further directed to a part comprising any of the compositions disclosed herein coated on the surface of the part.

[0197] The present disclosure is further directed to an article comprising a first substrate, a second substrate, and any of the compositions disclosed herein positioned between the first substrate and the second substrate.

[0198] In view of the foregoing description the present disclosure thus relates in particular to the following Aspects 1 to 82 without being limited thereto.Aspects

[0199] 1 A composition comprising: a first component comprising an isocyanate-functional prepolymer; a second component comprising a polyurethane polyol; an aromatic diamine; and a filler in an amount of greater than 50% by weight to 88% by weight based on total weight of the composition.

[0200] 2 The composition of aspect 1, comprising the filler in an amount of 55% by weight to 88% by weight based on total weight of the composition, such as 55% by weight to 80% by weight.

[0201] 3 The composition of aspect 1 or aspect 2, comprising the filler in an amount of 65% by weight to 88% by weight based on total weight of the composition, such as 65% by weight to 80% by weight.

[0202] 4 The composition of any of the preceding aspects, wherein the composition further comprises an isocyanate-functional compound in addition to the isocyanate functional prepolymer.

[0203] 5. The composition of any of the preceding aspects, wherein the isocyanate- functional prepolymer comprises a reaction product of reactants comprising a polyol and a polyisocyanate.

[0204] 6 The composition of aspect 5, wherein the polyol comprises an Mn of 60 g / mol to 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 90 g / mol to 2,000 g / mol.

[0205] 7 The composition of any of the preceding aspects, wherein the isocyanate- functional prepolymer comprises an Mn of 500 g / mol to 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 750 g / mol to 2,500 g / mol.

[0206] 8. The composition of any of the preceding aspects, wherein the isocyanate- functional prepolymer comprises:(a) an aromatic isocyanate-functional prepolymer;(b) a difunctional isocyanate-functional prepolymer;(c) a monofunctional isocyanate-functional prepolymer; and / or(d) a polyfunctional isocyanate-functional prepolymer.

[0207] 9. The composition of aspect 8, wherein the isocyanate-functional prepolymer comprises the difunctional isocyanate-functional prepolymer in an amount of 50% by weight to 100% by weight based on total weight of the isocyanate-functional prepolymer, such as 60% by weight to 90% by weight.

[0208] 10. The composition of aspect 8 or aspect 9, wherein the isocyanate-functional prepolymer comprises the monofunctional isocyanate-functional prepolymer and / or the polyfunctional isocyanate-functional prepolymer in an amount of 50% by weight or less basedon total weight of the isocyanate-functional prepolymer, such as 10% by weight to 40% by weight.[02091 11 • The composition of any of the preceding aspects, wherein the isocyanate- functional prepolymer comprises an NCO equivalent weight of at least 250 g / eq, such as at least 300 g / eq.

[0210] 12. The composition of any of the preceding aspects, wherein the isocyanate functional prepolymer comprises an NCO equivalent weight of no more than 2,500 g / eq, such as no more than 1,250 g / eq.

[0211] 13 The composition of any of the preceding aspects, wherein the isocyanate functional prepolymer comprises an NCO equivalent weight of 250 g / eq to 2,500 g / eq, such as 300 g / eq to 1,250 g / eq.

[0212] 14. The composition of any of the preceding aspects, comprising the isocyanate-functional prepolymer in an amount of at least 10% by weight based on total weight of the composition, such as at least 12% by weight.

[0213] 15. The composition of any of the preceding aspects, comprising the isocyanate-functional prepolymer in an amount of at least 15% by weight based on total weight of the composition, such as at least 20% by weight.

[0214] 16. The composition of any of the preceding aspects, comprising the isocyanate-functional prepolymer in an amount of no more than 48% by weight based on total weight of the composition, such as no more than 40% by weight.

[0215] 17. The composition of any of the preceding aspects, comprising the isocyanate-functional prepolymer in an amount of no more than 35% by weight based on total weight of the composition, such as no more than 30% by weight.

[0216] 18. The composition of any of the preceding aspects, comprising the isocyanate-functional prepolymer in an amount of 10% by weight to 48% by weight based on total weight of the composition, such as 12% by weight to 40% by weight.

[0217] 19. The composition of any of the preceding claims, comprising the isocyanate-functional prepolymer in an amount of 15% by weight to 35% by weight based on total weight of the composition, such as 20% by weight to 30% by weight.

[0218] 20. The composition of any of the preceding aspects, wherein the polyurethane polyol comprises an Mn of 1,000 g / mol to 6,000 g / mol as measured by GelPermeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min1, and two PL Gel Mixed C columns used for separation, such as 2,000 g / mol to 3,000 g / mol.

[0219] 21. The composition of any of the preceding aspects, wherein the polyurethane polyol comprises:(a) an aromatic polyurethane polyol;(b) a difunctional polyurethane polyol;(c)a monofunctional polyurethane polyol; and / or(d) a polyfunctional polyurethane polyol.

[0220] 22. The composition of aspect 21, wherein the polyurethane polyol comprises the difunctional polyurethane polyol in an amount of 50% by weight to 100% by weight based on total weight of the polyurethane polyol, such as 60% by weight to 90% by weight.

[0221] 23. The composition of aspect 21 or aspect 22, wherein the polyurethane polyol comprises the monofunctional polyurethane polyol and / or the polyfunctional polyurethane polyol in an amount of 50% by weight or less based on total weight of the polyurethane polyol, such as 10% by weight to 40% by weight.

[0222] 24. The composition of any of the preceding aspects, comprising the polyurethane polyol in an amount of at least 1% by weight based on total weight of the composition, such as at least 3% by weight.

[0223] 25. The composition of any of the preceding aspects, comprising the polyurethane polyol in an amount of at least 4% by weight based on total weight of the composition, such as at least 5% by weight.

[0224] 26. The composition of any of the preceding aspects, comprising the polyurethane polyol in an amount of no more than 20% by weight based on total weight of the composition., such as no more than 15% by weight.

[0225] 27. The composition of any of the preceding aspects, comprising the polyurethane polyol in an amount of no more than 12% by weight based on total weight of the composition, such as no more than 10% by weight.

[0226] 28. The composition of any of the preceding aspects, comprising the polyurethane polyol in an amount of 1% by weight to 20% by weight based on total weight of the composition, such as 3% by weight to 15% by weight.

[0227] 29. The composition of any of the preceding aspects, comprising the polyurethane polyol in an amount of 4% by weight to 12% by weight based on total weight of the composition, such as 5% by weight to 10% by weight.

[0228] 30. The composition of any of the preceding aspects, comprising an isocyanate equivalent weight of at least 500 g / eq based on total weight of isocyanate-containing components, such as at least 750 g / eq.

[0229] 31. The composition of any of the preceding aspects, comprising an isocyanate equivalent weight of no more than 5,000 g / eq based on total weight of isocyanate- containing components, such as no more than 3,000 g / eq.

[0230] 32. The composition of any of the preceding aspects, comprising an isocyanate equivalent weight of 500 g / eq to 5,000 g / eq based on total weight of isocyanate- containing components, such as 750 g / eq to 3,000 g / eq.

[0231] 33. The composition of any of the preceding aspects, comprising an active hydrogen equivalent weight of at least 500 g / eq based on total weight of all amine- and polyol- containing components, such as at least 750 g / eq.

[0232] 34. The composition of any of the preceding aspects, comprising an active hydrogen equivalent weight of no more than 6,000 g / eq based on total weight of all amine- and polyol-containing components, such as no more than 4,000 g / eq.

[0233] 35. The composition of any of the preceding aspects, comprising an active hydrogen equivalent weight of 500 g / eq to 6,000 g / eq based on total weight of all amine- and polyol-containing components, such as 750 g / eq to 4,000 g / eq.

[0234] 36. The composition of any of the preceding aspects, wherein the aromatic diamine comprises a liquid aromatic diamine and / or a sterically hindered aromatic diamine.

[0235] 37. The composition of any of the preceding aspects, wherein the aromatic diamine comprises dimethyltoluenediamine, diethyltoluenediamine, 4,4’-bis( ec- butylamino)diphenylmethane, or combinations thereof.

[0236] 38. The composition of any of the preceding aspects, wherein the aromatic diamine comprises an Mn of 100 g / mol to 750 g / mol calculated by Gel PermeationChromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min1, and two PL Gel Mixed C columns used for separation, such as 125 g / mol to 500 g / mol.

[0237] 39. The composition of any of the preceding aspects, comprising the aromatic diamine in an amount of at least 1% by weight based on total weight of the composition, such as at least 5% by weight.

[0238] 40. The composition of any of the preceding aspects, comprising the aromatic diamine in an amount of no more than 20% by weight based on total weight of the composition, such as no more than 10% by weight.

[0239] 41. The composition of any of the preceding aspects, comprising the aromatic diamine in an amount of 1% by weight to 20% by weight based on total weight of the composition, such as 5% by weight to 10% by weight.

[0240] 42. The composition of any of the preceding aspects, wherein the fdler comprises a thermally conductive, electrically insulative filler.

[0241] 43. The composition of aspect 42, wherein the thermally conductive, electrically insulative filler comprises a thermally stable filler and / or a thermally unstable filler.

[0242] 44. The composition of aspect 43, comprising the thermally stable filler in an amount of at least 90% by volume based on total volume of the thermally conductive, electrically insulative filler.

[0243] 45. The composition of aspect 43 or aspect 44, comprising the thermally unstable filler in an amount of no more than 10% by volume based on total volume of the thermally conductive, electrically insulative filler.

[0244] 46. The composition of any of aspects 42 to 45, wherein the thermally conductive, electrically insulative filler comprises aluminum oxide, aluminum hydroxide, or combinations thereof.

[0245] 47. The composition of any of the preceding aspects, further comprising an accelerator, a second polyol, and / or an additive.

[0246] 48. The composition of aspect 47, wherein the accelerator comprises a nitrogen-based catalyst, such as an amine-based catalyst.

[0247] 49. The composition of aspect 48, wherein the amine-based catalyst comprises tri ethylenediamine.

[0248] 50. The composition of any of aspects 47 to 49, comprising the accelerator in an amount of 0.001% by weight to 2% by weight based on total weight of the composition, such as 0.01% to 1% by weight.

[0249] 51. The composition of any of aspects 47 to 50, comprising the second polyol in an amount up of 0.5% by weight to 10% by weight based on total weight of the composition, such as 0.5% to 7.5% by weight.

[0250] 52. The composition of any of aspects 47 to 51, wherein the second polyol comprises a number average molecular weight of at least 60 g / mol to 5,000 g / mol as measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'1, and two PL Gel Mixed C columns used for separation, such as 90 g / mol to 2,000 g / mol.

[0251] 53. The composition of any of the preceding aspects, wherein the composition is substantially free of castor oil.

[0252] 54. The composition of any of the preceding aspects, comprising a ratio ofNCO:OH of 0.7:1 to 1.7: 1, such as 0.9: 1 to 1.5: 1.

[0253] 55. The composition of any of the preceding aspects, comprising a ratio of active hydrogens from the aromatic amine to active hydrogens from the polyurethane polyol of 1 : 10 to 10: 1, such as 1:5 to 5:1.

[0254] 56. A substrate comprising a coating formed from the composition of any of the preceding claims on a surface thereof.

[0255] 57. The substrate of aspect 56, further comprising a dielectric coating on the surface.

[0256] 58. A battery comprising the substrate of aspect 56 or aspect 57.

[0257] 59. A use of the composition of any of aspects 1 to 55 for form a coating having at least one of the following:(a) a lap shear strength of at least 5 MPa at failure, such as at least 6 MPa, such as at least 7 MPa, such as at least 8 MPa, wherein the lap shear displacement and the lap shear strength are measured according to ASTM D1002-10 using 3003 H24 aluminum substrate of 0.063 in.thickness, as measured by an INSTR ON 5567 machine in tensile mode with a pull rate of 10 mm per minute;(b) a tensile strength at ambient conditions of greater than 1.8 MPa measured according to ASTM D412-16(2021) using an INSTRON 5567 machine;(c) an elongation at break at ambient conditions of greater than 24% measured according to ASTM D412-16(2021) using an INSTRON 5567 machine;(d) a tensile strength at -35°C of greater than 7.4 MPa measured according to ASTM D412-16(2021) using an INSTRON 5567 machine;(e) an elongation at break at 35°C of greater than 14% measured according to ASTM D412-16(2021) using an INSTRON 5567 machine; and / or(I) a thermal conductivity of greater than 0.78 W / mK measured according to ASTM D7984-21 using a C-Therm TCi Thermal Conductivity Analyzer with Modified Transient Plane Source method.

[0258] Illustrating the disclosed subject matter are the following examples that are not to be considered as limiting the disclosure to their details. All parts and percentages in the examples, as well as throughout the specification, are by weight unless otherwise indicated.ExamplesExample 1: Synthesis of Isocyanate-Terminated Prepolymer

[0259] To a round-bottom flask was added Mondur TD Grade 80 A (mixture of 2,4- and 2,6-toluenediisocyanate, 107.0 g, 0.410 eq. NCO) and heated to 70°C. In a separate flask, Polymeg 1000 (polytetrahydrofuran-based diol, Mw = 1000 g / mol, 124.2 g, 0.0828 eq. OH) and Arcol PPG-1025 (polypropylene oxide-based diol, Mw = 1000 g / mol, 57.3 g, 0.0382 eq. OH) were mixed. The mixture of polyols was added over approximately 1 hour, ensuring that the temperature of the mixture did not exceed 90°C. The mixture was held at 70°C for about 1 hour, until the mixture measured an isocyanate equivalent weight of 333 g / eq. 1,4-Butanediol (11.4 g, 0.084 eq. OH) was added to the mixture over approximately 1 hour, ensuring that the temperature of the mixture did not exceed 90°C. The mixture was held at 70°C for about 1 hour, until the mixture measured an isocyanate equivalent weight of 504 g / eq determined by titration. The titration was performed by dissolving the isocyanate sample in a solution of n-dibutylamine in the appropriate solvent (e.g., toluene) and the mixture was stirred for 20 minutes, followed by dilution with isopropanol. The excess n-dibutylamine was back-titrated with HC1 solution.Example 2: Synthesis of Polyurethane Polyol

[0260] To a round-bottom flask was added Polymeg 1000 (90.67 g, 0.181 eq. OH) and heated to 70°C Mondur TD Grade 80 A (9.33 g, 0.107 mol of NCO) was added over approximately 1 h, ensuring that the temperature of the mixture did not exceed 90°C. The mixture was held at 70°C until the isocyanate was consumed, yielding a material with a measured OH equivalent weight of 1350 g / eq.Example 3: Preparation of Compositions

[0261] All quantities in the following tables are measured in terms of weight in grams unless otherwise noted. Compositions I-V were prepared using the materials and quantities listed in Table 1. Part A and Part B of each composition was formed by blending the liquid components in Table 1 at the ratios described and mixing for 1 minute at 2500 RPM using a Dual-Asymmetric Mixer (SpeedMixer®) then adding portions of the solid components and mixing for 1 minute at 2500 RPM between each addition. The individual parts were mixed for 2 minutes at 2500 RPM for a final mix. Part A and Part B were then combined and mixed for 1 minute at 2350 RPM using a SpeedMixer®. Lap shears were prepared on 0.063”xl”x4” pieces of aluminum which had been de-greased in Ultrax 98D (commercially available from PPG Industries, Inc.) according to manufacturer instructions. Wet adhesive was applied to approximately3" to the end of one piece of substrate and 0.02” diameter glass beads were lightly applied on top. A second piece of substrate was applied over ! " of the adhesive and pressed together. A binder clip was clipped on the joint during cure. The joints were cured for seven days at 25 °C and 50% relative humidity. Lap shear was tested according to ASTM D1002-10 using 3003 H24 aluminum substrate of 0.063 in. thickness, as measured by an INSTRON 5567 machine in tensile mode with a pull rate of 10 mm per minute. Tensile samples were prepared by pressing wet adhesive between two sheets of polyethylene plastic to 1 / 8” thickness then cut with an ISO 37-C die after curing for 7 days at 25°C and 50% humidity according to ISO 37:2017. The tensile samples were tested on an Instron 5567 frame using a pull rate of 10 mm / min. Tensile strength and elongation at break were measured according to ASTM D412-16 (2021) by an INSTRON 5567 machine. Thermal conductivity was measured according to ASTM D7984-21 using a C-Therm TCi Thermal Conductivity Analyzer with Modified Transient Plane Source.

[0262] Samples for thermal conductivity testing were prepared in molds with a 2.25” diameter and a thickness of at least 0.2”. Thermal conductivity testing was conducted in accordance with ASTM D7984-21 using a C-Therm Thermal Conductivity Instrument (TCI) with the Modified Transient Plane Source (MTPS) method.

[0263] Results for lap shear, tensile strength, elongation at break, and thermal conductivity are provided in Table 1.Table 1

[0264] The examples illustrate that when polyurethane polyol is added to a highly filled composition, the composition exhibits improvement in tensile strength and elongation at break both at room temperature and at -35 °C compared to a composition that does not contain polyurethane polyol, while also maintaining thermal conductivity.

[0265] Whereas aspects of the disclosure have been described in detail, it will be appreciated by those skilled in the art that various modifications and alternatives to those details could be developed in light of the overall teachings of the disclosure. Accordingly, the particular arrangements disclosed are meant to be illustrative only and not limited as to the scope of the disclosure, which is to be given the full breadth of the claims and aspects appended and any and all equivalents thereof.

Claims

We claim:

1. A composition comprising: a first component comprising an isocyanate-functional prepolymer; a second component comprising a polyurethane polyol; an aromatic diamine; and a filler in an amount of greater than 50% by weight to 88% by weight based on total weight of the composition.

2. The composition of claim 1, wherein the isocyanate-functional prepolymer comprises a reaction product of reactants comprising a polyol and a polyisocyanate.

3. The composition of claim 2, wherein the polyol comprises an Mn of 60 g / mol to 5,000 g / mol measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min’1, and two PL Gel Mixed C columns used for separation.

4. The composition of any of the preceding claims, wherein:(a) the isocyanate functional prepolymer comprises an Mn of 500 g / mol to 5,000 g / mol;(b) the polyurethane polyol comprises an Mn of 1,000 g / mol to 6,000 g / mol; and / or(c) the aromatic diamine comprises an Mn of 100 g / mol to 750 g / mol; wherein Mn is measured by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min’1, and two PL Gel Mixed C columns used for separation.

5. The composition of any of the preceding claims, wherein the isocyanate-functional prepolymer comprises a difunctional isocyanate-functional prepolymer.

6. The composition of any of the preceding claims, wherein the isocyanate-functional prepolymer comprises an NCO equivalent weight of 250 g / eq to 2,500 g / eq.

7. The composition of any of the preceding claims, wherein the composition comprises:(a) the isocyanate-functional prepolymer in an amount of 10% by weight to 48% by weight based on total weight of the composition;(b) the polyurethane polyol in an amount of 1% by weight to 20% by weight based on total weight of the composition; and / or(c) the aromatic diamine in an amount of 1% by weight to 20% by weight based on total weight of the composition.

8. The composition of any of the preceding claims, wherein the polyurethane polyol comprises a difunctional polyurethane polyol.

9. The composition of any of the preceding claims, wherein the composition comprises:(a) an isocyanate equivalent weight of 500 g / eq to 5,000 g / eq based on total weight of all isocyanate-containing components; and / or(b) an active hydrogen equivalent weight of 500 g / eq to 6,000 g / eq based on total weight of amine- and polyol -containing components.

10. The composition of any of the preceding claims, wherein the aromatic diamine comprises a liquid aromatic diamine and / or a sterically hindered aromatic diamine.

11. The composition of any of the preceding aspects, wherein the filler comprises a thermally conductive, electrically insulative filler.

12. The composition of any of the preceding claims, further comprising an accelerator and / or a second polyol.

13. The composition of any of the preceding claims, wherein the composition comprises a ratio ofNCO:OH of 0.7: 1 to 1.7: 1.

14. A method for treating a substrate comprising: contacting a surface of the substrate with the composition of any of the preceding claims.

15. A substrate comprising a coating on a surface thereof, the coating formed from the composition of any of claims 1 to 13.

16. The surface of claim 15, further comprising a dielectric coating on the surface.

17. The substrate of claim 15 or claim 16, wherein the substrate comprises a battery cell.

18. A battery comprising the battery cell of claim 17, and optionally a battery component.

19. A vehicle comprising the battery of claim 18.

20. The vehicle of claim 19, comprising a land vehicle or an aircraft.

Images