Furan-functional and isocyanate-functional compounds and reversibly curable compositions

Abstract

Disclosed are compounds comprising: a furan functional group; an isocyanate functional group; and a urethane linkage, a urea linkage, and / or a thiourethane linkage. Also disclosed herein are compositions comprising a first component comprising any of the compounds disclosed herein, and a second component comprising a dienophile-containing compound. Also disclosed are coatings and articles formed from the compositions. Also disclosed are methods of coating a substrate with a hot melt formed from the compositions.

Description

FURAN-FUNCTIONAL AND ISOCYANATE-FUNCTIONAL COMPOUNDSANDREVERSIBLY CURABLE COMPOSITIONSGOVERNMENT CONTRACT

[0001] This material is based upon work supported by the CCDC Ground Vehicle Systems Center under Government Contract No. 201830-140914 entitled “Reversible Adhesives Phase II.” The United States Government has certain rights in this invention.CROSS-REFERENCE

[0002] This application claims the benefit of U.S. Provisional Patent Application Serial No. 63 / 557,664 filed on February 26, 2024, and U.S. Provisional Patent Application Serial No. 63 / 691,207 filed on September 5, 2024, both entitled “Furan-Functional and Isocyanate- Functional Compounds and Reversibly Curable Compositions”, both of which are incorporated herein by reference in their entirety.FIELD

[0003] The present disclosure relates to furan-functional and isocyanate-functional compounds and reversibly curable compositions, for example coating 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] Disclosed herein are compounds comprising: a furan functional group; an isocyanate functional group; and a urethane linkage, a urea linkage, and / or a thiourethane linkage.

[0006] Also disclosed herein are compositions comprising: a first component comprising any of the compounds disclosed herein; and a second component comprising a dienophile-containing compound.

[0007] Also disclosed herein are methods for coating a substrate comprising contacting a portion of a surface of the substrate with any of the compositions disclosed herein.

[0008] Also disclosed herein are methods of forming an article comprising extruding any of the compositions disclosed herein.

[0009] Also disclosed herein are hot melts formed from any of the compositions disclosed herein.

[0010] Also disclosed herein are substrates comprising a coating formed from any of the hot melts disclosed herein on a portion of a surface of the substrate.

[0011] Also disclosed herein are batteries comprising any of the battery cells disclosed herein.

[0012] Also disclosed herein are free-standing films formed from any of the compositions disclosed herein.BRIEF DESCRIPTION OF THE FIGURES

[0013] FIG. 1 is a schematic of a top-down view of cylindrical battery cells.

[0014] FIG. 2 is a schematic of an exploded isometric view of an array of prismatic battery cells.

[0015] FIG. 3 is a schematic of a front view of an array of pouch battery cells.

[0016] FIG. 4 is a schematic of an isometric view of cylindrical cells positioned in a battery module.

[0017] FIG. 5 is a schematic of an exploded perspective view of a battery pack comprising multiple battery cells.

[0018] FIG. 6 is a schematic of an isometric view of (A) a battery cell, (B) a battery module, and (C) a battery pack.

[0019] FIG. 7 is a schematic of a perspective view of a battery pack.

[0020] FIG. 8 is a schematic of a cell to battery pack configuration.

[0021] FIG. 9 is a schematic of an isometric cut-out view of a cell to chassis battery assembly.

[0022] FIG. 10 is a picture of ground and reprocessed (A) Composition XII, (B) Composition XIII, and (C) Composition XIV.

[0023] FIG. 11 shows optical macroscopy images of a damaged cured coating of Composition XII (A) prior to heating and (B) after heating at 130°C for one hour.

[0024] FIG. 12 is a bar graph of the lap shear strength of Compositions VIII to XII measured at room temperature.

[0025] FIG. 13 is a bar graph of the lap shear strength of Compositions VIII, IX, XI, and XII measured at 50°C.

[0026] FIG. 14 is a bar graph of the lap shear strength of Compositions VIII to XII measured at 150°C.

[0027] FIG. 15 is a graph of the viscosity of Compositions I to VII as a function of shear rate.DETAILED DESCRIPTION

[0028] For purposes of this detailed description, it is to be understood that the disclosure may assume alternative variations and step sequences, except where expressly specified to the contrary.

[0029] The numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard variation found in their respective testing measurements.

[0030] 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.

[0031] 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, or ingredients or method steps “and those that do not materially affect the basic and novel characteristic(s)” of what is being described. As used herein, open- ended terms include closed terms such as consisting essentially of and consisting of.

[0032] 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.

[0033] As used herein, the terms “on,” “onto,” “applied on,” “applied onto,” “formed on,” “deposited on,” “deposited onto,” and the like mean formed, overlaid, deposited, orprovided on, but not necessarily in contact with, a substrate surface. For example, a composition “applied onto” a substrate surface docs not preclude the presence of one or more other intervening coatings of the same or different composition located between the composition and the substrate surface.

[0034] As used herein, a “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.

[0035] As used herein, a “solid” means a material having a viscosity of at least 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.

[0036] As used herein, “moiety” refers to a part of the chemical structure of a molecule or compound that may include a substructure, such as a functional group or a linkage.

[0037] As used herein, a “composition” or a “coating composition” refers to a solution, mixture, or a dispersion that is capable of producing a coating on a substrate surface.

[0038] As used herein, “coating” refers to a coating composition applied to a substrate and cured.

[0039] As used herein, a “free-standing film” refers to a coating composition that may be extruded or a coating that may be delaminated from the substrate following cure. As used herein, an “article” refers to the cured composition as a formed or fabricated solid.

[0040] As used herein, a “sealant composition” refers to a coating composition that forms a sealant in its cured state.

[0041] As used herein, a “sealant” refers to a coating or a free-standing film that can provide a protective barrier against moisture, chemicals, and other environmental factors, preventing corrosion and extending the lifespan of components.

[0042] As used herein, an “adhesive composition” refers to a coating composition that forms an adhesive in its cured state.

[0043] As used herein, an “adhesive” refers to a cured coating or a free-standing film that forms a load-bearing joint having a lap shear strength of at least 0.5 MPa and less than 5 MPa, as determined according to ASTM D 1002- 10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute at room temperature.

[0044] As used herein, a “structural adhesive composition” refers to a coating composition that, in a cured state, produces a structural adhesive.

[0045] As used herein, a “structural adhesive” refers to a cured coating or a freestanding film that forms a load bearing joint having a lap shear strength of at least 5 MPa measured according to ASTM D 1002- 10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute at room temperature.

[0046] As further defined herein, “ambient conditions” generally refer to room temperature (e.g., 25°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 conditions, such as greater than 40°C to 60°C.

[0047] 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.

[0048] As used herein, the term “hot melt” refers to a composition that (i) cures under ambient conditions to form a solid, (ii) begins to reflow upon exposure to the reflow onset temperature to form a liquid, (iii) begins to reform a solid upon cooling below the reflow onset temperature, and (iv) reforms a solid at ambient conditions.

[0049] As used herein, the term “reflow onset temperature” means the temperature at which the storage modulus of the composition drops below 20,000,000 Pa as may be determined by performing Dynamic Mechanical Analysis (DMA) at a frequency of 1.0 Hz and a temperature ramp rate of 3°C / min. The reflow onset temperature may be the result of dynamic covalent chemistry, softening (i.e., heating beyond the glass transition temperature of the composition), and / or melting (i.e., converting from a solid to a liquid).

[0050] As used herein, the term “glass transition temperature” (“Tg”) refers to the temperature at which an amorphous material, such as glass or a polymer, changes from a brittle vitreous state to a plastic state or from a plastic state to a brittle vitreous state.

[0051] As used herein, the term “hot melt application” means application of a hot melt to a substrate surface under thermal conditions. As used herein, “thermal conditions” include (i) heat extrusion, (ii) heating the composition to a temperature greater than the reflow onset temperature of the composition, and / or (iii) heating of the substrate comprising the composition to a temperature greater than the reflow onset temperature of the composition.

[0052] As used herein, the terms “cure,” “cured,” and similar terms, means that the reactive components that form the composition interact, react, and / or are crosslinked to form a coating, a free-standing film, 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 and / or physical interaction of the reactive components of the composition. As used herein, “curing” of a composition refers to subjecting the composition to curing conditions that result in cure of the composition. As used herein, a “curable” composition refers to a composition that may be cured. As used herein, a curable composition may be considered “cured” if it has a lap shear- strength of at least 0.5 MPa (measured according to ASTM DI 002- 10) and a tensile strength of at least 0.5 MPa at ambient conditions (measured according to ISO-37 TYPE 2 using an Instron 4443 machine in tensile mode with a pull rate of 10 mm per minutes). “Complete” cure is obtained when a curable composition is subjected to curing conditions without any significant increase in lap shear strength.

[0053] As used herein, the term “furan equivalent weight” is the theoretical molecular weight of a compound comprising a furan functional group divided by the theoretical number of furan functional groups.

[0054] As used herein, the term “isocyanate equivalent weight” is the theoretical molecular weight of a compound comprising an isocyanate functional group divided by the theoretical number of isocyanate functional groups.

[0055] As used herein, the term “maleimide equivalent weight” is the theoretical molecular weight of a compound comprising a maleimide functional group divided by the theoretical number of maleimide functional groups.

[0056] As used herein, the term “accelerator” means 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 the accelerator. An accelerator may be either a “catalyst” (that is, without itselfundergoing any permanent chemical change) or may be reactive (that is, undergoing a permanent chemical change).

[0057] As used herein, a “latent” accelerator refers to a molecule or a compound that is activated by an external energy source prior to reacting (i.e., crosslinking) or having a catalytic effect, as the case may be. The latent accelerator may be in the form of a solid at room temperature and has no accelerator effect until it is heated and melts. The latent accelerator may be blocked or encapsulated. A “blocked” accelerator means an accelerator that may be reversibly reacted with a second compound that prevents any accelerator effect until the reversible reaction is reversed by the application of heat and the second compound is removed, freeing the accelerator to increase the rate or decrease the activation energy of a chemical reaction. An “encapsulated” accelerator may be encapsulated within a thermoplastic material which melts upon heating, releasing the accelerator to increase the rate or decrease the activation energy of chemical reactions.

[0058] As used herein, the term “urethane linkage” means a bond formed between two molecules forming the linkage RNHC(O)OR.

[0059] As used herein, the term “urea linkage” means a bond formed between two molecules forming the linkage RNHC(O)NHR.

[0060] As used herein, the term “thiourethane linkage” means a bond formed between molecules forming the linkage RNHC(O)SR.

[0061] As used herein, “reprocessability” means that the composition is capable of undergoing reprocessing, wherein an article comprising the cured composition is mechanically or chemically processed into a different article. In some cases, “reprocessing” may refer to a mechanical process wherein an article comprising the cured composition is ground, chopped, pulverized, or processed by a mechanical means, then the composition is molded into a new article via a process such as compression molding, extrusion, or the like (i.e., the material is recycled). The reprocessing may further comprise heating.

[0062] As used herein, “reprocessing efficiency” means the ratio of a mechanical property of the material after reprocessing relative to the mechanical property of the original material, typically defined as a percentage. Reprocessing efficiency may refer to the efficiency of recovery of properties such as tensile strength, Young’s modulus, strain at break, lap shear strength, or the like, following reprocessing.

[0063] As used herein, “reshaping” means a material that was previously molded into a fixed physical form or shape is capable of being molded into a different fixed physical form or shape. In some cases, reshaping will involve heating the material to above a reflow onset temperature of the material to make the new shape permanent.

[0064] As used herein, “self-healing” means that a material is capable of repairing itself, for example, healing cracks, scratches, or marring in the material. The self-healing process may comprise heating the material above the material’s reflow onset temperature.

[0065] As used herein, “monosubstituted” refers to a compound or functional group in which one hydrogen is substituted by a different atom or functional group.

[0066] As used herein, “terminal,” when used with respect to a functional group, refers to a functional group that is at the end of a polymer backbone or a prepolymer backbone or mono substituted with respect to a monomer or non-polymerizable molecules.

[0067] As used herein, “monomer” refers to a molecule which can undergo polymerization, thereby contributing repeat units to the structure of a prepolymer or a polymer, as defined in Pure and Applied Chemistry, 1996, 68, 2287 (2289), “Glossary of basic terms in polymer science (IUPAC Recommendations 1996).”

[0068] As used herein, “prepolymer” refers to a molecule comprising a reaction product of two or more molecules that can be further polymerized or crosslinked.

[0069] As used herein, “polymer” refers to a molecule having more than one repeating unit and includes oligomers and homopolymers.

[0070] As used herein, unless indicated otherwise, the term “substantially free” means that a particular material is not purposefully added to a mixture or composition, respectively, and is present only as an impurity in a trace amount of less than 0.05% by weight based on a total weight of the mixture or composition, respectively. As used herein, unless indicated otherwise, the term “essentially free” means that a particular- material is present only in an amount of less than 0.01% by weight based on a total weight of the mixture or composition, respectively. As used herein, unless indicated otherwise, the term “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.

[0071] The present disclosure is directed to a compound comprising, consisting essentially of, or consisting of: a furan functional group; an isocyanate functional group; and aurethane linkage, a urea linkage, and / or a thiourethane linkage. The compound may comprise the general structure:wherein X comprises O, N, or S; m > 1; n > 1; the sum of m+n > 2; Ri comprises a substituted or unsubstituted alkyl group, an alkylene group, a (cyclo)alkyl group, an aromatic group, an isocyanurate moiety, a biuret moiety, an allophonate moiety, a glycoluril moiety, a benzoguanamine moiety, an iminooxadiazinedione moiety, or a polymeric moiety different from the urethane linkage, the urea linkage, and / or a thiourethane linkage; and R2 comprises a substituted or unsubstituted alkyl group, an ester moiety, an ether moiety, or a urethane moiety. Optionally, m < 12; n < 12; and / or m+n < 13.

[0072] The compound may comprise a reaction product of reactants comprising a furan-containing compound comprising an active hydrogen-containing functional group and a polyisocyanate-containing compound. As used herein, a “furan-containing compound” refers to a compound comprising a furan functional group. As used herein, a “polyisocyanate-containing compound” refers to a compound comprising more than one isocyanate functional groups, including diisocyanates, triisocyanates, or higher. The active hydrogen-containing functional group on the furan-containing compound may comprise a hydroxyl functional group, an amine functional group, and / or a thiol functional group. The active hydrogen-containing functional group of the furan-containing compound may react with an isocyanate group of the polyisocyanate. The compound comprises at least one unreacted isocyanate group, providing the compound with isocyanate functionality.

[0073] A sub-stoichiometric amount of the active hydrogen-containing functional group on the furan-containing compound may be reacted with the isocyanate functional groups on the polyisocyanate-containing compound. For example, the active hydrogen-containing functional group of the furan-containing compound and the isocyanate groups on the polyisocyanate-containing compound may be reacted at an equivalence ratio of less than 1:1,such as no more than 1 :2, such as no more than 1 :3, such as no more than 1 :5. As used herein, “sub- stoichiometric” means that the number of active hydrogcn-containing functional groups from the furan-containing compound is lower than the number required to react with all of the isocyanate groups on the polyisocyanate-containing compoud, so that the reaction product comprises isocyanate functionality from the polyisocyanate.

[0074] Suitable furan-containing compounds useful in forming the compounds disclosed herein include but are not limited to furfuryl alcohol, furfuryl amine, furfuryl mercaptan, furfuryl glycidyl ether, bis(hydroxymethyl)furan, derivatives thereof, and / or combinations thereof.

[0075] Suitable polyisocyanate-containing compounds useful in forming the compounds disclosed herein can be polymeric containing two or more isocyanate functional groups. For example, the polyisocyanates may comprise 2 to 20 carbon atoms and may be linear, cyclic, aliphatic, and / or aromatic polyisocyanates, or mixtures thereof.

[0076] Suitable aliphatic polyisocyanates may include alkylene isocyanates, such as: trimethylene diisocyanate, tetramethylene diisocyanate, such as 1 ,4-tetramethylene 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, and 1,3-butylene diisocyanate; ethylene diisocyanate; decamethylene diisocyanate, such as 1,10-decamethylene diisocyanate; ethylidene diisocyanate; and butylidene diisocyanate. Aliphatic polyisocyanates may also include 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) (“HMD1”); polymeric methylene diphenyl diisocyanate (“MD1”); and mixed aralkyl diisocyanates such as tetramethylxylyl diisocyanates, such as meta- tetramethylxylylene diisocyanate (commercially available as TMXDI® from Allnex SA).

[0077] Suitable aromatic polyisocyanates may include arylene isocyanates, such as: phenylene diisocyanate, such as m-phenylene diisocyanate, p-phenylene diisocyanate, andchlorophenylene 2,4-diisocyanate; naphthalene diisocyanate, such as 1 ,5-naphthalene diisocyanatc and 1 ,4-naphthalcnc diisocyanatc. Aromatic polyisocyanatcs may also include alkarylene isocyanates, such as: methylene-interrupted aromatic diisocyanates, such as 4,4’ - diphenylene methane diisocyanate (“MDI”), and alkylated analogs such as 3,3’-dimethyl-4,4’- 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.

[0078] Suitable polyisocyanates include dimers, trimers, oligomers, or prepolymers comprising any of the isocyanates listed herein.

[0079] The compound may comprise, consist essentially of, or consist of a monomer, a prepolymer, or a polymer.

[0080] The compound may comprise one, two, three, or more furan functional groups. The furan functional group may be linked to the compound by a urethane linkage, a urea linkage, and / or a thiourethane linkage.

[0081] The compound of the present disclosure may be substantially free, essentially free, or completely free of an ether linkage.

[0082] The compound may comprise a furan equivalent weight of at least 100 g / eq, such as at least 200 g / eq. The compound may comprise a furan equivalent weight of no more than 3,000 g / eq, such as no more than 1,500 g / eq. The compound may comprise a furan equivalent weight of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0083] The compound may comprise an isocyanate equivalent weight of at least 100 g / eq, such as at least 200 g / eq. The compound may comprise an isocyanate equivalent weight of no more than 3,000 g / eq, such as no more than 1,500 g / eq, such as no more than 850 g / eq. The compound may comprise an isocyanate equivalent weight of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0084] The compound may comprise the furan functional group and the isocyanate functional group in an equivalence ratio of at least 1:5, such as at least 1:4, such as at least 1:2. The compound may comprise the furan functional group and the isocyanate functional group in an equivalence ratio of no more than 5:1, such as no more than 4:1, such as no more than 2:1.The compound may comprise the furan functional group and the isocyanate functional group in an equivalence ratio of 1:5 to 5:1, such as 1:4 to 4:1, such as 1:2 to 2:1.

[0085] The present disclosure is further directed to a composition comprising a first component comprising any of the compounds disclosed herein and a second component comprising a dienophile-containing compound.

[0086] The second component may comprise, consist essentially of, or consist of a dienophile-containing compound. As used herein, a dienophile means any unsaturated functional group capable of undergoing a Diels-Alder [4+2] cycloaddition with a conjugated diene. As used herein, a “conjugated diene” refers to a compound containing two double bonds separated by a single covalent bond.

[0087] Suitable dienophiles may comprise a maleimide functional group, a maleate functional group, and / or a fumarate functional group.

[0088] The dienophile-containing compound may comprise a maleimide functional group. The general structure of the dienophile-containing compound comprising a maleimide functional group comprises:wherein R3 may comprise a hydrogen, an alkyl, a (cyclo)alkyl, an aryl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane).

[0089] Suitable maleimide-containing compounds can be prepared by the reaction of maleic anhydride with di- or polyfunctional amine-containing compounds. The amine- containing compound may be selected such that the maleimide-containing compound or mixture of maleimide-containing compounds does not crystallize. Examples of suitable maleimide- containing compounds include the reaction products of maleic anhydride with dimer fatty acid diamines, such as BMI-689, commercially available from Designer Molecules, Inc. Additional maleimide-containing compounds include the reaction products of amine-terminated polyethers or polysiloxanes with maleic anhydride. Further suitable maleimide-containing compounds include maleimide-terminated poly imides, available from Designer Molecules, Inc., or reactionproducts of maleimide-functional carboxylic acids with epoxy, hydroxy, or other carboxylic acid-reactive functional groups.

[0090] The dienophile may comprise a maleate functional group. The general structure of the dienophile-containing compound comprising a maleate functional group comprises:wherein each X independently comprises O, N, or S; R4 comprises a hydrogen, an alkyl, a (cyclo)alkyl, an aryl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane); and R5 comprises a hydrogen, an alkyl, a (cyclo)alkyl, an aryl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane). The dienophile-containing compound comprising a maleate functional group may comprise an unsaturated polyester comprising the reaction product of maleic acid (or an anhydride or ester thereof) with a polyol. Suitable polyols include any of those described below. The dienophile-containing compound comprising a maleate functional group may also comprise an unsaturated polyester comprising a maleate functional group synthesized by other methods, such as copolymerization of an epoxide and maleic anhydride. The unsaturated polyester may further comprise other functional groups, such as a hydroxyl group. The unsaturated polyester may comprise a liquid.

[0091] The dienophile-containing compound may comprise a fumarate functional group. The general structure of the dienophile-containing compound comprising a fumarate functional group comprises:wherein each X independently comprises O, N, or S; Re comprises a hydrogen, an alkyl, a (cyclo)alkyl, an aryl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane); and R7 comprises a hydrogen, an alkyl, a (cyclo)alkyl, an aryl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane). The dienophile-containing compound comprising a fumarate functional group may comprise an unsaturated polyester comprising the reaction product of fumaric acid (or an anhydride or ester thereof) with a polyol. Suitable polyols include any of those described below. The dienophile-containing compound comprising a fumarate functional group may also comprise an unsaturated polyester comprising a fumarate functional group synthesized by other methods, such as copolymerization of an epoxide and maleic anhydride. The unsaturated polyester may further comprise other functional groups, such as a hydroxyl group. The unsaturated polyester may comprise a liquid.

[0092] The dienophile-containing compound may comprise a dienophile equivalent weight of at least 100 g / eq, such as at least 200 g / eq. The dienophile-containing compound may comprise a dienophile equivalent weight of no more than 3,000 g / eq, such as no more than 1,500 g / eq. The dienophile-containing compound may comprise a dienophile equivalent weight of 100 g / eq to 3,000 g / eq, such as 100 g / eq to 1 ,500 g / eq.

[0093] The composition may comprise the furan functional groups on the first compound and the dienophile functional groups on the dienophile-containing compound in an equivalence ratio of at least 0.5:1, such as at least 0.6:1. The composition may comprise the furan functional groups on the first compound and the dienophile functional groups on the dienophile-containing compound at a molar ratio of no more than 2:1, such as no more than 1.5:1. The composition may comprise the furan functional groups on the first compound and the dienophile functional groups on the dienophile-containing compound at a molar ratio of 0.5:1 to 2:1, such as 0.6:1 to 1.5:1.

[0094] The composition may further comprise a third compound that is reactive with the isocyanate functional group. The third compound may be present in the second component and / or a third or more component. The third compound may comprise a hydroxyl functional group, such as a polyol.

[0095] Suitable polyols include diols, triols, tetraols and higher functional polyols. Combinations of such polyols may also be used. The polyol may comprise polyhydric alcoholssuch as ethylene glycol, propanediol, neopentyl glycol, butanediol, pentanediol, hexanediol, cyclohcxancdimcthanol, cyclohcxancdiol, bcnzcncdimcthanol, 4,4’isopropylidenedicyclohexanol, 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, polysiloxane polyols, and combinations thereof.

[0096] 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.

[0097] 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, or 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. The polyol may comprise amine-containing polyols such as Quadrol PM, commercially available from BASF.

[0098] The composition may comprise the isocyanate functional group on the compound and the hydroxyl functional group on the third compound in an equivalence ratio of at least 0.2:1, such as at least 0.4:1. The composition may comprise the isocyanate functional group on the compound and the hydroxyl functional group on the third compound in an equivalence ratio of no more than 3:1, such as no more than 2:1. The composition may comprise the isocyanate functional group on the compound and the hydroxyl functional group on the third compound in an equivalence ratio of 0.2:1 to 3:1, such as 0.4:1 to 2:1.

[0099] The composition may further comprise a fourth compound comprising a furan functional group that is different from the compounds disclosed herein. The fourth compound may be present in the first component and / or a third or more component. The fourth compound may comprise a furan equivalent weight of at least 68 g / eq, such as at least 80 g / eq. The fourth compound may comprise a furan equivalent weight of no more than 1,500 g / eq, such as no more than 1,000 g / eq. The fourth compound may comprise a furan equivalent weight of 68 g / eq to 1,500 g / eq, such as 80 g / eq to 1,000 g / eq.

[0100] As used herein with respect to the compounds, reference to “first,” “second,” “third,” “fourth,” etc. is for convenience only and does not refer to order of addition to the 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 two compounds comprising a furan functional group, such as three compounds, such as four compounds.Filler

[0101] The composition of the present disclosure may further comprise a filler. The filler may be present in the first component, the second component, and / or a third component. The filler may comprise particles of a single type of filler material or may comprise particles of two or more types of filler materials. That is, the filler may comprise particles of a first filler material and may further comprise particles of a second (and a third, a fourth, etc.) filler material that is different from the first filler material. As used herein with respect to types of filler material, reference to “first,” “second,” etc. is for convenience only and does not refer to order of addition to the composition or the like.

[0102] The composition may comprise the filler in an amount of at least 1% by weight based on total weight of the composition, such as no more than 50% by weight. The composition may comprise the filler in an amount of at least 50% by weight based on total weight of the composition, such as no more than 90% by weight. The composition may comprise the filler in an amount up to 90% by weight based on total weight of the composition, such as 1 % to no more than 50% by weight, or such as 50% to 90% by weight.

[0103] When the disclosed compositions are highly loaded compositions (i.e., containing filler in an amount of 50% by weight to 90% by weight based on total weight of the composition), the compositions were found to be pumpable (i.e., each component having a viscosity of no more than 106Pa-s at a shear stress of 1 Hz measured by an Anton Paar MCR 301rotational rheometer at 25°C using a parallel plate with a diameter of 25 mm (1 mm gap)). This was a surprising result.

[0104] The filler may comprise thermally conductive filler material, such as a thermally conductive, electrically insulative filler material (referred to herein as “TC / EI filler material” and described below in more detail) and / or a thermally conductive, electrically conductive filler (referred to herein as “TC / EC filler” and described in more detail below). The TC / EI and / or TC / EC filler (referred to collectively as “thermally conductive fillers”) may be present in the first component, the second component, and / or a third component. The thermally conductive fillers 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 TC / EI fillers and / or two or more types of TC / EC fillers. That is, the filler may comprise a first TC / EI filler and may further comprise at least a second (i.e., a second, a third, a fourth, etc.) TC / EI filler in addition to the first TC / EI filler. Likewise, the filler may comprise a first TC / EC filler and may further comprise at least a second (i.e., a second, a third, a fourth, etc.) TC / EC filler in addition to the first TC / EC filler. As used herein with respect to types of filler, reference to “first,” “second,” etc. is for convenience only and does not refer to order of addition to the composition or the like.

[0105] The thermally conductive filler (i.e., TC / EI and / or TC / EC 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, and may have a thermal conductivity of no more than 3,000 W / mK at 25°C, such as no more than 1,400 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 D7984-21), such as 18 W / m K to 1,400 W / m K.

[0106] The filler (TC / EI and / or NTC / EI) may be electrically insulative. The electrically insulative filler may have a volume resistivity of at least 1 Q-m, such as at least 10 Q-m, such as at least 100 Qin. Electrical insulation may be measured according to ASTM D257- 19.

[0107] The filler may be electrically conductive. The electrically conductive filler may have a volume resistivity of less than 1 Q-m (measured according to ASTM D257-19), such as less than 0.1 Q-m.

[0108] Suitable TC / EI fillers include boron nitride (for example, commercially available as CarboTherm from Saint-Gobain, 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 from Nabaltec, as Aeroxide from Evonik, and as Alodur from Imerys), magnesium oxide, beryllium oxide, titanium oxide, zinc oxide, nickel oxide, copper oxide, or tin oxide, metal hydroxides such as 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. The TC / EI filler may also be ferromagnetic, ferrimagnetic, and / or superparamagnetic.

[0109] Suitable TC / EC fillers include metals such as silver, zinc, copper, gold, or metal coated hollow particles, carbon compounds, such as graphite (such as Timrex commercially available from Imerys or ThermoCarb commercially available from Asbury Carbons), carbon black (for example, commercially available as Vulcan from Cabot Corporation), carbon fibers (for example, commercially available as milled carbon fiber from Zoltek), graphene and grapheme carbon particles (for example, xGnP graphene nanoplatelets commercially available from XG Sciences, and / or, for example, the graphene particles described below), carbonyl iron, copper (such as spheroidal powder commercially available from Sigma Aldrich), zinc (such as Ultrapure commercially available from Purity Zinc Metals and Zinc Dust XL and XLP available from US Zinc), and the like. Examples of “grapheme carbon particles” include carbon particles having structures comprising one or more layers of one-atom-thick planar sheets of sp2-bonded carbon atoms that are densely packed in a honeycomb crystal lattice. The average number of stacked layers may be less than 100, for example, less than 50. The average number of stacked layers may be 30 or less, such as 20 or less, such as 10 or less, such as 5 or less. The grapheme carbon particles may be substantially flat; however, at least a portion of the planar sheets may be substantially curved, curled, creased, or buckled. The particlestypically do not have a spheroidal or equiaxed morphology. Suitable graphenic carbon particles arc described in U.S. Publication No. 2012 / 0129980, at paragraphs

[0059] -

[0065] , the cited portion of which is incorporated herein by reference. Other suitable graphenic carbon particles are described in U.S. Pat. No. 9,562,175, at 6:6 to 9:52, the cited portion of which are incorporated herein by reference. As used herein, the term “substantially flat” means planar; “curved” or “curled” materials deviate from planarity by having a non-zero curvature; and “creased” or “buckled” indicates that at least a portion of the area is thicker than one sheet, such that the plane is doubled or folded upon itself. The TC / EC filler may also be ferromagnetic, ferrimagnetic, and / or superparamagnetic.

[0110] The composition may comprise the thermally conductive filler material in an amount of 100% by volume based on total volume of the filler. The composition may comprise the thermally conductive filler in an amount of no more than 90% by volume, such as no more than 80% by volume. The composition may comprise the thermally conductive filler material in an amount of at least 20% by volume based on total volume of the filler, such as at least 50% by volume. The composition may comprise the thermally conductive filler material in an amount of 20% to 90% by volume based on total volume of the filler, such as 50% by volume to 80% by volume.

[0111] The filler may comprise non-thermally conductive filler material, such as non- thermally conductive, electrically insulative filler (referred to herein as “NTC / EI” filler). As used herein, the 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 a second (i.e., a second, a third, a fourth, etc.) NTC / EI filler in addition to the first NTC / EI filler.

[0112] The non-thermally conductive filler may have a thermal conductivity of less than 5 W / m K at 25°C (measured according to ASTM D7984-21), such no more than 3 W / mK, such as no more than 1 W / m K, such as no more than 0.1 W / mK, 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.

[0113] 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 D257-19), such as at least 10 Q-m, such as at least 100 Q-m.

[0114] Suitable NTC / EI fillers include but are not limited to mica, wollastonite, calcium carbonate, glass microspheres, clay, silicon dioxide, or combinations thereof.

[0115] 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(AlSiaOio)(F,OH)2 or (KF)2(AhO3)3(SiO2)6(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 (CaSiCh) that may contain small amounts of iron, aluminum, magnesium, manganese, titanium and / or potassium. Non-limiting examples of commercially available wollastonite include NY AD 400 available from NYCO Minerals, Inc.

[0116] The calcium carbonate (CaCCb ) 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, such as Socal® 312, commercially available from IMERYS. 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.

[0117] Useful clay minerals include a non-ionic platy filler such as talc, pyrophyllite, chlorite, vermiculite, or combinations thereof.

[0118] 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.

[0119] The NTC / EI filler particles, if present at all, may be present in an amount of at least 10% by volume based on total volume of the filler, such as at least 20% by volume. The NTC / EI filler particles, if present at all, may be present in a positive amount up to 100% byvolume based on total volume of the filler, such as no more than 80% by volume, such as no more than 50% by volume. The NTC / EI filler particles may be present in an amount of 10% by volume to 80% by volume based on total volume of the filler, such as 20% by volume to 50% by volume.

[0120] Optionally, the filler may comprise a surface coating. The surface coating may comprise a silane, an amino-silane, and / or a polymer with multiple functional groups that can bind to or interact with the filler.

[0121] The filler may have an average particle size in at least one dimension of at least 0.01 m, as reported by the manufacturer or determined as described below, such as at least 2 pm, and may have an average particle size in at least one dimension of no more than 500 pm as reported by the manufacturer or determined as described below, such as no more than 300 pm. The filler may have an average particle size in at least one dimension of 0.01 pm to 500 pm as reported by the manufacturer or determined as described below, such as 2 pm to 300 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 lOkV and spot size 3.0), measuring 30 particles from three different areas to provide an average particle size for each sample. 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.

[0122] The filler may comprise particles each having, for example, a platy, spherical, or acicular shape, and agglomerates thereof. As used herein, “platy” refers to a two-dimensional material having a substantially flat surface and that has a thickness in one direction that is less than 25% of the largest dimension.Additional Components

[0123] The composition may optionally comprise one or more additives. As used herein, an “additive” refers to a rheology modifier, a tackifier, a thermoplastic polymer, a surface-active agent, 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 silane terminated polymer, and / or a moisture scavenger.

[0124] Compositions provided by the present disclosure can comprise a flame retardant or combination of flame retardants. Certain thermally conductive materials such as aluminum hydroxide and magnesium hydroxide, for example, also may be flame retardants; for purposes of calculating weight percentages herein, such materials are counted as thermally conductive materials. 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.

[0125] The composition may comprise the additive in an amount of at least 0.01% by weight based on total weight of the composition, such as at least 0.1% by weight. The composition may comprise the additive in an amount of no more than 15% by weight based on total weight of the composition, such as no more than 10% by weight. The composition may comprise the additive in an amount of 0.01% to 15% by weight based on total weight of the composition, such as 0.1% to 10% by weight.

[0126] The composition of the present disclosure may further comprise elastomeric particles. As used herein, “elastomeric particles” refers to particles comprising one or more materials having a glass transition temperature (Tg) of greater than -150°C and less than 30°C, calculated, for example, using the Fox Equation.

[0127] The elastomeric particles may have a core / shell structure. Suitable core-shell elastomeric particles may be comprised of an acrylic shell and an elastomeric core. The core may comprise natural or synthetic rubbers, polybutadiene, styrene-butadiene, polyisoprene, chloroprene, acrylonitrile butadiene, butyl rubber, polysiloxane, polysulfide, ethylene-vinyl acetate, fluoroelastomer, polyolefin, or combinations thereof. The elastomeric particles may comprise a polybutadiene core, a styrene butadiene core, and / or a poly siloxane core.

[0128] An exemplary non-limiting commercial core-shell elastomeric particle product using poly(butadiene) rubber particles that may be utilized in the composition of the present disclosure include core-shell poly(butadiene) rubber powder (commercially available as PARALOID™ EXL 2650A from Dow Chemical).

[0129] Exemplary non-limiting commercial core- shell elastomeric particle products using styrene-butadiene rubber particles that may be utilized in the composition include a coreshell styrene-butadiene rubber powder (commercially available as CLEARSTRENGTH® XT100 from Arkema or as PARALOID™ EXL 2650J), and a core-shell styrene-butadiene rubber dispersion (25% core- shell rubber by weight) in polypropylene glycol (MW 400) (commercially available as Kane Ace MX 715 from Kaneka Texas Corporation).

[0130] Exemplary non-limiting commercial core- shell elastomeric particle products using polysiloxane rubber particles that may be utilized in the composition of the present disclosure include a core-shell polysiloxane rubber powder (commercially available as GENIOPERL® P52 from Wacker).

[0131] The composition may comprise the elastomeric particles in an amount of at least 0.1% by weight based on total weight of the composition, such as at least 1% by weight. The composition may comprise the elastomeric particles in an amount of no more than 50% by weight based on total weight of the composition, such as no more than 20% by weight. The composition may comprise the elastomeric particles in a positive amount up to 25% by weight based on total weight of the composition, such as 0.1% to 50% by weight, such as 1% to 20% by weight.

[0132] The composition may further comprise an accelerator. The accelerator may be present in the first component, the second component, and / or a third or higher component. The accelerator may comprise an amine or nitrogen-based catalyst. The accelerator may comprise a tertiary amine, an A-heterocyclic carbene, or an amidine / guanidine. Suitable accelerators that may be used in the present disclosure include A,A-dimethylcyclohexylamine, A,A-dimethylethanolamine, A- methyl morpholine, 2,2’ -dimorpholinodiethylether, dimethylaminoethoxyethanol, triethylenediamine, bis(2-dimethylaminoethyl)ether, A,A,A’- trimethylaminoethylethanolamine, A,A,A’,A’-tetramethyl- 1 ,6-hexanediamine, 1,3,5- tris(dimethylaminopropyl)-hexahydro-s-triazine, 1 ,8-diazabicyclo[5.4.0]undec-7-ene, A-(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. In some cases, the accelerator may comprise an organic acid, such as diphenyl phosphate, methanesulfonic acid, or triflic acid. The accelerator may comprise an organometallic complex. Suitable organometallic complexes comprise titanates, such as tetrabutyl titanate or tetrapropyl titanate, tin compounds, such as dibutyltindilaurate, dibutyltin diacetate, tin octoate, or dibutyl tin oxide, or other metal compounds, such as chelates of bismuth, zirconium, titanium, aluminum, or iron, such as zirconium acctylacctonatc or iron acetylacetonate. In examples, the accelerator may be latent, blocked, and / or encapsulated.

[0133] The composition may comprise the accelerator 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% to 2% by weight based on total weight of the composition, such as 0.01% to 1% by weight. The composition may comprise the accelerator in an amount up to 2% by weight based on total weight of the composition, such as in an amount up to 1% by weight.Compositions, Hot Melts, Methods and Systems

[0134] The first component and the second component may be liquid at ambient conditions, may be mixable at ambient temperature, and may be capable of curing at ambient temperature. The composition may be formulated as a two-component composition.

[0135] The compositions according to the present disclosure may form a hot melt. The hot melt may be used to form a free-standing film, an adhesive, a structural adhesive, a sealant, a pottant, a gap filler, a pre-preg, an embedding material, an encapsulant or the like. The solid- state hot melt may be heated above its reflow onset temperature and may be used to surround a substrate or assembly to substantially exclude air, water, and / or moisture from the substrate and / or to add strength or stiffness to the substrate or assembly. Additionally, the composition may be brought into contact with a surface or assembly as a pre-formed film, and the system may be heated above the reflow onset temperature of the composition, then cooled to yield a bonded or embedded system.

[0136] The composition may have a reflow onset temperature of at least 50°C, such as at least 60°C. The composition may have a reflow onset temperature of less than 150°C, such as less than 140°C. The composition may have a reflow onset temperature of 50°C to 150°C, such as 60°C to 140°C.

[0137] The reflow onset temperature may be achieved, for example, by heating the coating comprising the coatings disclosed herein and / or heating the substrate on which thecoating is formed. The coating and / or the substrate may be heated by direct thermal exposure and / or, in substrates containing ferromagnetic materials, ferrimagnetic materials, and / or superparamagnetic materials or in coatings formed from compositions containing ferromagnetic materials, ferrimagnetic materials, and / or superparamagnetic materials, by indirect heating through the application of a magnetic field resulting in ferromagnetic heating, ferrimagnetic heating, and / or superparamagnetic heating.

[0138] Disclosed herein are methods of making a hot melt. The method may comprise, or consist essentially of, or consist of mixing the first component and the second component under ambient conditions to form one of the hot melts disclosed herein.

[0139] The compositions and hot melts disclosed herein may be applied alone or as pail of a coating system. The compositions and hot melts disclosed herein may be applied directly onto the surface of a substrate or over an underlayer by any suitable coating process, such as by manual pressure, mechanical pressure, and / or extrusion at or above the reflow onset temperature to cause the hot melt to flow and form a liquid. As the hot melt cools below the reflow onset temperature towards ambient temperatures, the hot melt forms a solid. The system may comprise a number of the same or different layers and may further comprise additional coating compositions such as pretreatment compositions, primers, and the like. A coating may be formed when a composition disclosed herein is deposited onto the substrate and is cured by methods known to those of ordinary skill in the art (e.g., under ambient conditions and may further cure through the use of an external energy source such as an oven or other thermal means or through the use of actinic radiation) to form a coating. The composition may cured at ambient or slightly thermal temperature. When cured at room temperature, a coating provided by the present disclosure can cure to a tack free surface, for example, within 24 hours, within 20 hours, within 16 hours, within 12 hours, within 6 hours, or within 3 hours, from the time of mixing. The skilled person understands, however, that time of curing varies with temperature and humidity.

[0140] The solid-state hot melt may be applied to a surface of a first substrate as described above.

[0141] Also disclosed are methods for forming a bond between two substrates for a wide variety of potential applications in which the bond between the substrates provides mechanical properties. The method may comprise contacting a surface of a first substrate asdescribed above with the hot melt or composition; contacting a surface of a second substrate to the hot melt or composition such that the hot melt or composition is located between the surface of the first substrate and the surface of the second substrate; applying sufficient pressure for the hot melt or composition to intimately contact both substrates; and cooling the hot melt or composition to below the reflow onset temperature. For example, the hot melt or 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 may be aligned and pressure and / or spacers may be added to control bond thickness. As described above, an external energy source, such as heat, may be applied to the cured hot melt or composition, which may reverse the crosslinking and allow for separation of the bonded substrates.

[0142] The composition may have a reduction in lap shear strength from >5 MPa at ambient temperature to <0.5 MPa at a temperature greater than 50°C, such as greater than 60°C.

[0143] The composition may have a Tg of at least -120°C (measured using a TA Instruments Q800 DMA V21 .3 in single cantilever mode). The composition may have a Tg of no more than 150°C, such as no more than 100°C, such as up to 90°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode). The composition may have a Tg of - 120°C to 150°C, such as -120°C to 100°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode).

[0144] The hot melt or composition may be applied to cleaned or uncleaned (i.e., including oily or oiled) substrate surfaces. The hot melt or composition also may be applied to a substrate that has been pretreated, coated with an electrodepositable coating, and / or coated with additional layers such as a primer, basecoat, or topcoat.

[0145] The present disclosure is also directed to a method of repairing a joint upon failure or damage to the joint, wherein the bond between the two substrates is broken. The bond between the two substrates may be reformed by the method of bonding two substrates described herein above, heating the assembly above the reflow onset temperature of the hot melt, then cooling the assembly, as described herein above.

[0146] The present disclosure is also directed to a method of repairing an article, coating, or film formed from one of the hot melts or compositions disclosed herein.

[0147] The composition may be injected or otherwise placed in a die caster or a mold and cured under ambient conditions to form a pail or a member and optionally may be machined to a particular configuration.Dielectric Coating Compositions and Dielectric Coatings and Dielectric Systems and Kits

[0148] Also disclosed herein are dielectric coating systems. The dielectric coating system may comprise: a first composition for application to a first portion of a substrate surface, the first composition comprising a dielectric coating composition; and a second composition for application to a second portion of a substrate surface, the second composition comprising any of the compositions disclosed above that, in a cured state, may form a second coating. The first portion and the second portion may be on a single substrate or may be on a first substrate and a second substrate, respectively.

[0149] Also disclosed herein are dielectric coating kits. The dielectric coating kit may comprise: a first composition for application to a first portion of a substrate surface, the first composition comprising a dielectric coating composition; and a second composition for application to a second portion of a substrate surface, the second composition comprising any of the compositions disclosed above that, in a cured state, may form a second coating. The first portion and the second portion may be on a single substrate or may be on a first substrate and a second substrate, respectively. The kit optionally may comprise instructions for applying the first composition and the second composition to the first portion and the second portion of the substrate surface, respectively.

[0150] When used with respect to the dielectric coating systems and kits disclosed herein, the first portion and the second portion may be the same or different, provided that the first portion and the second portion overlap to form a coating stack, e.g., a second coating on a dielectric coating. 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 between the dielectric coating and the second coating. Optionally, the coating stack may be formed between two substrates.

[0151] The dielectric coating may be formed on a first portion of a surface of a first substrate and the second coating may be formed on a second portion of a surface of a second substrate and the substrates may be positioned such that the first portion and the second portion overlap to form a coating stack as described above.

[0152] As used herein, “dielectric” refers to a coating composition or coating comprising a dielectric strength of at least 10 kV / mm measured using a Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as at least 12 kV / mm, such as at least 15 kV / mm.

[0153] 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, polyolefin, polysiloxane, amine-aldehydes, resinous polyols, phosphatized polyepoxides, phosphatized acrylic polymers, and / or aminoplasts.

[0154] 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, poly isocyanates, including blocked polyisocyanates, polyepoxides, beta-hydroxyalkylamides, polyacids, organometallic acid-functional materials, polyamines, polyamides, polysulfides, polythiols, polyenes such as polyacrylates, polyols, polysilanes and the like, or combinations thereof.

[0155] The dielectric coating composition may optionally further comprise colorants, pigments, additives, and / or fillers. Suitable fillers that may be used in the dielectric coating composition includeTC / EI filler materials, TC / EC filler materials, and / or NTC / ET filler materials.

[0156] 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 maycomprise 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.

[0157] 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.

[0158] Suitable liquid coating compositions include but are not limited to electrodepositable coating compositions, one-component coating compositions, and / or multicomponent coating compositions.

[0159] 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.

[0160] 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 film-forming 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.

[0161] 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 applicationof the coating composition and may optionally cure under ambient conditions without any external energy source.

[0162] 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 filmforming resins useful in dielectric powder coating compositions include those discussed in PCT Publ. No. WO 2021 / 173941A1, par’s.

[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.

[0163] 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 ait, such as baking, induction heating, infrared heating, and / or exposure to actinic radiation such as UV.

[0164] A dielectric coating may be formed from the dielectric coating compositions described herein.

[0165] The dielectric coating may comprise a dielectric strength of at least 10 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 12 kV / min, such as at least 15 kV / mm. The dielectric coating may comprise a dielectric strength of no more than 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 D 149-09, such as no more than 100 kV / mm. The dielectric coating may comprise a dielectric strength of 10 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, 19sec ramp, 20 sec dwell, 2 sec fall) according to ASTM DI 49-09, such as 12 kV / mm to 100 kV / mm, such as 15 kV / mm to 100 kV / mm.

[0166] The dielectric coating may be formulated as a hot-melt or a free-standing film. As used herein, a “free-standing film” refers to a sheet comprising a cured composition that may be formed independent of a substrate surface. The free-standing film may optionally comprise an adhesive layer, such as a pressure sensitive adhesive layer.

[0167] Compositions of the present disclosure may be applied or deposited using any suitable method, including those aforementioned. Using the methods provided by the present disclosure articles may be formed from one of the compositions disclosed herein. The articles may be formed through extrusion, casting, molding, additive manufacturing, such as 3D-printing, subtractive manufacturing, and / or machining.Additive Manufacturing

[0168] The compositions disclosed herein may be used in any suitable additive manufacturing technology, such as three-dimensional (3D) printing, extrusion, jetting, and binder jetting. Additive manufacturing refers to a process of producing a part or member by constructing it in layers, such as one layer at a time.

[0169] The present disclosure is also directed to the production of structural articles, such as by way of a non-limiting example, sound damping pads, 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 pail 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.

[0170] It will be appreciate 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.

[0171] Compositions as disclosed herein may be applied or deposited by any suitable 3D printing method as known to those skilled in the art. The first component and the second component of the compositions disclosed herein may be mixed and then deposited, or the first component and the second component may be deposited separately, such as simultaneously or sequentially.

[0172] The first component and the second component may be premixed, i.e., mixed together, prior to application, and then deposited. The mixture may be partially 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.

[0173] In a non-limiting example, the first component and the second component 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 the materials 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 aim 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.

[0174] 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 component and the second component may be deposited in any pattern such that the first component and the second component 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.

[0175] Methods provided by the present disclosure include printing the composition on a fabricated part. Methods provided by the present disclosure include directly printing parts.Use of the Compositions and Hot Melts

[0176] The compositions disclosed herein demonstrate ambient temperature curability. The hot melts formed from the compositions disclosed herein may be used to form coatings and / or free-standing films. The coatings and / or free-standing films surprisingly may be used as structural adhesives.

[0177] The coatings and / or free-standing films disclosed herein demonstrate high lap shear strength at room temperature and 50°C, determined according to ASTM D 1002- 10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute, but a low lap shear strength at 150°C, determined according to ASTM D1002-10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute. This was a surprising and unexpected result.

[0178] Additionally, the articles formed from the compositions disclosed herein surprisingly exhibit high reprocessability, reshaping, and / or self-sealing. The coatings and / or free-standing films disclosed herein surprisingly also exhibit self-healing.

[0179] The hot melts disclosed herein may be used to repair a joint between two substrates.

[0180] The hot melts formed from the compositions disclosed herein may be used to make a coating and / or a free-standing film having:(a) a lap shear strength of at least 5 MPa, such as 5 MPa to 40 MPa at 25 °C measured according to ASTM D1002-10 using 2024 T3 aluminum substrate of 0.063 inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute;(b) a lap shear strength of 1 MPa to 20 MPa, such as 2 MPa to 20 MPa, such as 2 MPa to 15 MPa, at 50°C measured according to ASTM D1002-10 using 2024 T3 aluminum substrate of 0.063 inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute;(c) a lap shear strength of up to 2 MPa at 150°C measured according to ASTM D1002-10 using 2024 T3 aluminum substrate of 0.063 inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute; and / or(d) a glass transition temperature of 35°C to 55°C as measured by Dynamic Chemical Analysis (DMA) at a frequency of 1.0 Hz and a temperature ramp rate of 3°C / min.Substrates

[0181] Hot melts and 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.

[0182] 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 AZ31B, AZ91C, AM60B, or EV31A 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.

[0183] It will also be understood that the substrate may comprise a bare substrate or the substrate may be pretreated or pre-coated 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, 3:5 to 5:8 and 5:64 to 11:50, incorporated herein by reference, and 5,588,989, 1:65 to 10:40, incorporated herein by reference, or a zirconium containing pretreatment solution such as, for example, those described in U.S. Pat. Nos. 7,749,368, 1:55 to 2:12 and 2:53-14:60, incorporated herein by reference, and 8,673,091, 1:53 to 2:11, 3:26 to 15:45, and 16:51 to 18:26, incorporated herein by reference.

[0184] 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. Hot melts formed from compositions comprising the materials disclosed herein may be used to coat a substrate, such as by depositing, applying, or contacting the hot melt to a substrate surface.

[0185] 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 one surface comprised of a first metal and one surface comprised of a second metal that is different from the first metal, (2) a first article that has one surface comprised of a first metal and a second article that has one surface comprised of a second metal that is different from the first metal, or (3) both (1) and (2).

[0186] 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 pails, 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.

[0187] 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 a cured state, may be used to form pads, adhesives, structural 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, compositions disclosed 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 (FIG. 8), and cell to chassis battery assemblies (FIG. 9). Such battery assemblies may be used in, but not limited to, any aforementioned application.

[0188] Battery assemblies may be any combination of one or more battery cells, the interconnection of 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 busbar’s, battery management systems, battery thermal management systems, chargers, inverters and converters).

[0189] 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.

[0190] 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 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.

[0191] 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 a cured state, may be positioned between the cells 10, cooling tubes 3 and / or e-paper 4.

[0192] 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 a cured state, may be positioned between surfaces of cell walls 13 of adjacent cells 10.

[0193] FIG. 3 illustrates a cut-out front view of an array of pouch battery cells 10 in a module 100. The module walls 120 partially or fully encase the cells 10. As shown, materials, such as pads 8 formed from the compositions disclosed herein in a cured state, may be positioned between surfaces of cells 10.

[0194] 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 coating compositions disclosed herein may be positioned within the space to consume 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 one or more of the walls 120 of the module 100.

[0195] 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 a cured state, may be positioned between cells 10. Additional pads 8 may be positioned between the 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 to an exterior surface of the walls 120.

[0196] 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.

[0197] 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 a 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 a cured state, may be positioned between cells 10 within modules 100.

[0198] 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).

[0199] 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.

[0200] 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.

[0201] The substrate may comprise a coating formed from a hot melt formed by one of the compositions disclosed herein on a portion of a surface of the substrate that, in a cured state, has: (a) a lap shear strength of at least 15 MPa at 25°C measured according to ASTM D1002-10 using 2024 T3 aluminum substrate of 0.063 inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute; (b) a lap shear strength of at least 5 MPa at 50°C measured according to ASTM DI 002- 10 using 2024 T3 aluminum substrate of 0.063 inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute; (c) a lap shear strength of no more than 2 MPa at 150°C measured according to ASTM D1002-10 using 2024 T3 aluminum substrate of 0.063 inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute; and / or (d) a glass transition temperature of 35°C to 55°C as measured by Dynamic Chemical Analysis (DMA) at a frequency of 1.0 Hz and a temperature ramp rate of 3°C / min.Aspects

[0202] 1. A compound comprising: a furan functional group; an isocyanate functional group; and a urethane linkage, a urea linkage, and / or a thiourethane linkage.

[0203] 2. The compound of aspect 1, wherein the urethane linkage, the urea linkage, and / or the thiourethane linkage is between the furan functional group and the isocyanate functional group.

[0204] 3. The compound of aspect 1 or aspect 2, wherein the compound comprisesStructure I:wherein X comprises O, N, or S, m > 1, n > 1, the sum of m+n > 2, Ri comprises a substituted or unsubstituted alkyl group, an alkylene group, a (cyclo)alkyl group, an aromatic group, an isocyanurate moiety, a biuret moiety, an allophonate moiety, a glycoluril moiety, a benzoguanamine moiety, an iminooxadiazinedione moiety, or a polymeric moiety different from the urethane linkage, the urea linkage, and / or the thiourethane linkage; and Ro comprises a substituted or unsubstituted alkyl group, an ester moiety, an ether moiety, and / or a urethane moiety.

[0205] 4. The compound of aspect 3, wherein R2 comprises one carbon.

[0206] 5. The compound of aspect 3 or aspect 4, wherein Ri comprises isocyanurate or allophonate, or iminooxadiazinedione, R2 comprises CH2, and X comprises O.

[0207] 6. The compound of any of aspects 3 to 5, wherein m < 12, n < 12, and / or m+n < 13.

[0208] 7. The compound of any of aspects 3 to 6, wherein m+n >2.

[0209] 8. The compound of any of the preceding aspects, wherein the compound is substantially free of an ether linkage.

[0210] 9. The compound of any of the preceding aspects, wherein the compound comprises a monomer, prepolymer, or polymer.

[0211] 10. The compound of any of the preceding aspects, wherein the compound comprises a furan equivalent weight of at least 100 g / eq, such as at least 200 g / eq.

[0212] 11. The compound of any of the preceding aspects, wherein the compound comprises a furan equivalent weight of no more than 3,000 g / eq, such as no more than 1,500 g / eq.

[0213] 12. The compound of any of the preceding aspects, wherein the compound comprises a furan equivalent weight of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0214] 13. The compound of any of the preceding aspects, wherein the compound comprises an isocyanate equivalent weight of at least 100 g / eq, such as at least 200 g / eq.

[0215] 14. The compound of any of the preceding aspects, wherein the compound comprises an isocyanate equivalent weight of no more than 3,000 g / eq, such as no more than 1,500 g / eq.

[0216] 15. The compound of any of the preceding aspects, wherein the compound comprises an isocyanate equivalent weight of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0217] 16. The compound of any of the preceding aspects, wherein the compound comprises a reaction product of reactants comprising:(a) a furan-containing compound comprising an active hydrogen-containing functional group; and(b) a polyisocyanate-containing compound.

[0218] 17. The compound of aspect 16, wherein the active hydrogen-containing functional group comprises a hydroxyl functional group, an amine functional group, and / or a mercapto functional group.

[0219] 18. The compound of aspect 16 or aspect 17, wherein the isocyanate functional group comprises an isocyanate functional group from the polyisocyanate.

[0220] 19. The compound of any of aspects 16 to 18, wherein the active hydrogencontaining functional group is present in a sub-stoichiometric amount relative to the isocyanate functional groups.

[0221] 20. The compound of any of aspects 16 to 19, wherein the equivalence ratio of the active hydrogen-containing functional group and the isocyanate functional groups is less than 1:1, such as no more than 1:2, such as no more than 1:3, such as no more than 1:5.

[0222] 21. The compound of any of aspects 16 to 20, wherein the furan functional group is monosubstituted and / or terminal.

[0223] 22. A composition comprising: a first component comprising the compound of any of the preceding aspects; and a second component comprising a dienophile-containing compound.

[0224] 23. The composition of aspect 22, wherein the furan functional group of the compound and the dienophile of the dienophile-containing compound are present in an equivalence ratio of at least 0.5:1, such as at least 0.6:1.

[0225] 24. The composition of aspect 22 or aspect 23, wherein the furan functional group of the compound and the dienophile of the dienophile-containing compound are present in an equivalence ratio of no more than 2:1, such as no more than 1.5:1.

[0226] 25. The composition of any of aspects 22 to 24, wherein the furan functional group of the compound and the dienophile of the dienophile-containing compound are present in an equivalence ratio of 0.5:1 to 2:1, such as 0.6:1 to 1.5:1.

[0227] 26. The composition of any of aspects 22 to 25, wherein the dienophile- containing compound comprises a dienophile equivalent weight of at least 100 g / eq, such as at least 200 g / eq.

[0228] 27. The composition of any of aspects 22 to 26, wherein the dienophile- containing compound comprises a dienophile equivalent weight of no more than 3,000 g / eq, such as no more than 1,500 g / eq.

[0229] 28. The composition of any of aspects 22 to 27, wherein the dienophile- containing compound comprises a dienophile equivalent weight of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0230] 29. The composition of any of aspects 22 to 28, wherein the furan functional group and the dienophile are reactive under ambient conditions.

[0231] 30. The composition of any of aspects 22 to 29, wherein the dienophile comprises a maleimide functional group, a maleate functional group, and / or a fumarate functional group.

[0232] 31. The composition of any of aspects 22 to 30, wherein the second component comprises a third compound that is reactive with the isocyanate functional group.

[0233] 32. The composition of aspect 31, wherein the third compound comprises a hydroxyl functional group.

[0234] 33. The composition of aspect 32, comprising the isocyanate functional group on the compound and the hydroxyl functional group on the third compound at an equivalence ratio of at least 0.2:1, such as at least 0.4:1.

[0235] 34. The composition of aspect 32 or aspect 33, comprising the isocyanate functional group on the compound and the hydroxyl functional group on the third compound at an equivalence ratio of no more than 3:1, such as no more than 2:1.

[0236] 35. The composition of any of aspects 32 to 34, comprising the isocyanate functional group on the compound and the hydroxyl functional group on the third compound at an equivalence ratio of 0.2:1 to 3:1, such as 0.4:1 to 2:1.

[0237] 36. The composition of any of aspects 22 to 35, wherein the first component further comprises a fourth compound comprising a furan functional group.

[0238] 37. The composition of aspect 36, wherein the fourth compound comprises a furan equivalent weight of at least 68 g / eq, such as at least 80 g / eq.

[0239] 38. The composition of aspect 36 or aspect 37, wherein the fourth compound comprises a furan equivalent weight of no more than 1,500 g / eq, such as no more than 1,000 g / eq.

[0240] 39. The composition of any of aspects 36 to 38, wherein the fourth compound comprises a furan equivalent weight of 68 g / eq to 1,500 g / eq, such as 80 g / eq to 1,000 g / eq.

[0241] 40. The composition of any of aspects 22 to 39, further comprising a filler, an additive, elastomeric particles, and / or an accelerator.

[0242] 41. The composition of aspect 40, wherein the first component, the second component and / or a third component comprises the filler, the additive, the elastomeric particles, and / or the accelerator.

[0243] 42. The composition of aspect 40 or aspect 41, wherein the composition comprises the filler in an amount of at least 0.5% by weight based on total weight of the composition, such as at least 1% by weight.

[0244] 43. The composition of any of aspects 40 to 42, wherein the composition comprises the filler in an amount of no more than 90% by weight based on total weight of the composition, such as no more than 30% by weight.

[0245] 44. The composition of any of aspects 40 to 43, wherein the composition comprises the filler in an amount of 0.5% by weight to 90% by weight based on total weight of the composition, such as 1% by weight to 30% by weight.

[0246] 45. The composition of any of aspects 40 to 44, wherein the composition comprises the additive in an amount of at least 0.01% by weight based on total weight of the composition, such as at least 0.1% by weight.

[0247] 46. The composition of any of aspects 40 to 45, wherein the composition comprises the additive in an amount of no more than 15% by weight based on total weight of the composition, such as no more than 10% by weight.

[0248] 47. The composition of any of aspects 40 to 46, wherein the composition comprises the additive in an amount of 0.01% by weight to 15% by weight based on total weight of the composition, such as 0.1% by weight to 10% by weight.

[0249] 48. The composition of any of aspects 40 to 47, comprising the elastomeric particles in an amount of at least 0.1% by weight based on total weight of the composition, such as at least 1% by weight.

[0250] 49. The composition of any of aspects 40 to 48, comprising the elastomeric particles in an amount of no more than 50% by weight based on total weight of the composition, such as no more than 20% by weight.

[0251] 50. The composition of any of aspects 40 to 49, comprising the elastomeric particles in an amount of 0.1% by weight to 50% by weight based on total weight of the composition, such as 1% by weight to 20% by weight.

[0252] 51 . The composition of any of aspects 40 to 50, comprising the accelerator 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.

[0253] 52. The composition of any of aspects 40 to 51, comprising the accelerator 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.

[0254] 53. The composition of any of aspects 40 to 52, 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% by weight to 1% by weight.

[0255] 54. The composition of any of aspects 40 to 53, wherein:(a) the filler comprises a thermally conductive filler such as boron nitride, aluminum trihydrate, and / or aluminum oxide and / or a non-thermally conductive filler such as fumed silica, wollastonite, calcium carbonate, micaceous iron oxide, carbon fibers, or combinations thereof;(b) the additive comprises a rheology modifier, a tackifier, a thermoplastic polymer, a surface-active agent, 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 silane terminated polymer, a moisture scavenger, a thixotrope, and / or a sag control agent;(c) the elastomeric particles comprise a core-shell structure, such as comprising an acrylic shell and an elastomeric core; and / or(d) the accelerator comprises an amine-based catalyst and / or an organometallic complex.

[0256] 55. The composition of aspect 54, wherein the thermally conductive filler comprises a thermally stable filler, a thermally unstable filler, a ferromagnetic material, a ferrimagnetic material, and / or a superparamagnetic material; and wherein the non-thermally conductive filler comprises a ferromagnetic material, a ferrimagnetic material, and / or a superparamagnetic material.

[0257] 56. The composition of any of aspects 40 to 55, wherein the composition comprises the filler in an amount of 50% by weight to 90% by weight based on total weight of the composition, and has a viscosity of no more than 106Pa-s at a shear stress of 1Hz measured by an Anton Paar MCR 301 rotational rheometer at 25 °C using a parallel plate with a diameter of 25 mm (1 mm gap)).

[0258] 57. The composition of any of aspects 22 to 56, having a Tg of at least -120°C(measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode).

[0259] 58. The composition of any of aspects 22 to 57, having a Tg of no more than150°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode), such as no more than 100°C, such as up to 90°C.

[0260] 59. The composition of any of aspects 22 to 58, having a Tg of -120°C to150°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode), such as -120°C to 100°C.

[0261] 60. The composition of any of aspects 22 to 59, wherein the composition is formulated as a two-component composition.

[0262] 61. The composition of any of aspects 22 to 60, wherein the composition is formulated to cure at ambient conditions.

[0263] 62. A method of coating a substrate comprising: contacting a portion of a surface of the substrate with the composition of any of aspects 22 to 61.

[0264] 63. The method of aspect 58, further comprising mixing the first component and the second component to form the composition of any of aspects 22 to 61; and optionally heating the composition following the contacting.

[0265] 64. The method of aspect 62 or aspect 63, further comprising contacting a surface of a second substrate to the composition such that the composition is between the first substrate and the second substrate.

[0266] 65. The method of aspect 64, wherein a joint between the first substrate and the second substrate is broken prior to the contacting and wherein the contacting forms a repair joint.

[0267] 66. A method of forming an article comprising extruding the composition of any of aspects 22 to 61.

[0268] 67. The method of aspect 66, wherein the extruding comprises three- dimensional printing.

[0269] 68. The article formed by the method of aspect 66 or aspect 67.

[0270] 69. The article of any of aspects 66 to 68, wherein the article exhibits reshaping, reprocessability, and / or self-healing.

[0271] 70. A substrate comprising a coating formed from the composition of any of aspects 22 to 61 on a portion of a surface of the substrate.

[0272] 71. The substrate of aspect 70, coated according to the method of any of aspects 62 to 65.

[0273] 72. The substrate of aspect 70 or aspect 71, wherein the coating comprises a sealant, an adhesive, a gap filler, a pottant, an encapsulant such as a solid or a gel, and / or a pad, such as a pre-formed pad, a pre-manufactured pad, or a pad formed in situ.

[0274] 73. The substrate of any of aspects 70 to 72, wherein the substrate comprises an article, a pail, or combinations thereof.

[0275] 74. The substrate of aspect 73, wherein the article comprises a vehicle, an appliance, a personal electronic device, a circuit board, a battery cell, a multi-metal substrate, or combinations thereof.

[0276] 75. The substrate of aspect 73, wherein the part comprises a vehicular part.

[0277] 76. The substrate of aspect 74, wherein the vehicle comprises a land vehicle or an aircraft.

[0278] 77. The substrate of aspect 76, wherein the land vehicle comprises a bicycle, such as an electric bicycle.

[0279] 78. A pre-formed film comprising the composition of any of aspects 22 to 61.

[0280] 79. A use of the composition of any of aspects 22 to 57, comprising repairing a joint between two substrates.

[0281] 80. The use of aspect 79 for making a coating having a lap shear strength of at least 15 MPa at 25 °C measured according to ASTM DI 002- 10 using 2024 T3 aluminum substrate of 0.063-inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0282] 81. The use of aspect 79 or aspect 80 for making a coating having a lap shear strength of at least 5 MPa at 50°C measured according to ASTM D 1002- 10 using 2024 T3 aluminum substrate of 0.063-inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0283] 82. The use of any of aspects 79 to 81 for making a coating having a lap shear strength of no more than 2 MPa at 150°C measured according to ASTM D1002-10 using 2024 T3 aluminum substrate of 0.063-inch thickness, as measured by an INSTON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0284] 83. The use of any of aspects 79 to 82 for making a coating having a glass transition temperature of 35°C to 55°C as measured by Dynamic Chemical Analysis (DMA) at a frequency of 1.0 Hz and a temperature ramp rate of 3°C / min.

[0285] 84. A battery, comprising a battery cell and the composition of any of aspects22 to 61 in a cured state and optionally further comprising a battery component.

[0286] 85. The battery of aspect 80, wherein the battery cell and the composition are housed in a module and / or a pack and / or wherein the battery cell and composition are adjacent to a vehicle chassis.

[0287] 86. The battery of aspect 85, wherein the module is housed in a pack.

[0288] 87. A system comprising: a first composition for application to a portion of a substrate surface comprising a dielectric coating composition; and a second composition for application to the portion of the substrate surface having the first composition thereon, comprising the composition of any of aspects 22 to 61.

[0289] 88. A kit comprising: a first composition for application to a portion of a substrate surface comprising a dielectric coating composition; and a second composition for application to the portion having the first composition thereon, comprising the composition of any of aspects 22 to 61.

[0290] 89. The kit of aspect 88, further comprising instructions for applying the first composition and the second composition.

[0291] 90. The system or kit of any of aspects 87 to 89, wherein the dielectric coating composition comprises: a binder comprising a film- forming resin such as a polyester, alkyd, urethane, isocyanate, polyurea, epoxy, acrylic, polyether, polysulfide, polyamine, polyamide, polyvinyl chloride, polyolefin, polyvinylidene fluoride, polyvinyl chloride, polyolefin, polysiloxane, aminealdehydes, resinous polyols, phosphatized polyepoxides, phosphatized acrylic polymers, aminoplasts, or combinations thereof; and / or a curing agent and / or crosslinker capable of crosslinking with the film-forming resin to cure the dielectric coating composition, such as an amine, aminoplast, phenoplast, polyisocyanate, including blocked polyisocyanate, polyepoxide, beta-hydroxyalkylamide,polyacid, organometallic acid-functional material, polyamine, polyamide, polysulfide, polythiol, polyene such as poly aery late, polyol, poly silane and the like, or combinations thereof.

[0292] 91. The system or kit of any of aspects 87 to 90, wherein the dielectric coating composition comprises a powder coating composition and / or a liquid coating composition such as an electrodepositable coating composition, a UV-curable coating composition, and / or a solvent-based coating composition.

[0293] 92. A substrate comprising: a dielectric coating formed from a dielectric coating composition on a portion of a surface of the substrate; and a second coating and / or a free-standing film formed from the composition of any of aspects 22 to 61 on the portion of the surface.

[0294] 93. The substrate of aspect 92, wherein the dielectric coating composition comprises: a binder comprising a film-forming resin such as a polyester, alkyl, urethane, isocyanate, polyurea, epoxy, acrylic, polyether, polysulfide, polyamine, polyamide, polyvinyl chloride, polyolefin, polyvinylidene fluoride, polyvinyl chloride, polyolefin, polysiloxane, aminealdehydes, resinous polyols, phosphatized polyepoxides, phosphatized acrylic polymers, aminoplasts, or combinations thereof; and / or a curing agent and / or crosslinker capable of crosslinking with the film-forming resin to cure the dielectric coating composition, such as an amine, aminoplast, phenoplast, polyisocyanate, including blocked isocyanate, polyepoxide, beta-hydroxyalkylamide, polyacid, organometallic acid-functional material, polyamine, polyamide, polysulfide, polythiol, polyene such as polyacrylate, polyol, polysilane and the like, or combinations thereof.

[0295] 94. The substrate of aspect 92 or aspect 93, wherein the dielectric coating composition comprises a powder coating composition and / or a liquid coating composition such as an electrodepositable coating composition, a UV-curable coating composition, and / or a solvent-based coating composition.

[0296] 95. A free-standing film formed from the composition of any of aspects 22 to61.

[0297] Illustrating the disclosed subject matter are the following examples that are not to be considered as limiting the disclosure to their details. All pails and percentages in the examples, as well as throughout the specification, are by weight unless otherwise indicated.Examples

[0298] All quantities in the following tables are measured in terms of weight in grams unless otherwise noted.

[0299] Compositions I to V were prepared using the materials and quantities listed in Table 1. Desmodur N33OO or Desmodur N3900 was charged to an appropriately sized flask and blanketed with nitrogen to avoid interaction with moisture. Dibutyltin dilaurate was added as a catalyst and this mixture was heated to 60°C. Furfuryl alcohol was then added at a rate such that the temperature of the mixture did not exceed 80°C. After all of the furfuryl alcohol was added, the reaction was held at 80°C until the isocyanate equivalent weight was stalled by titration (determined using a Metrohm 888 Titrando; titration by dissolving a sample (-2.00 g) of the mixture in 30 mL of a solution comprising 20 mL of dibutylamine and 980 mL of N-methyl pyrrolidone, followed by titration with 0.2 N HC1 solution in isopropanol titration agent).

[0300] Composition VI (a blend of furan-functional and isocyanate prepolymer) was prepared by adding Desmodur N3900 and Composition V to an appropriately sized flask at the amounts set forth in Table 1, such that the theoretical furan equivalents and the theoreticalisocyanate equivalents are equal to that of Composition IV. Composition V (139 g) was blanketed with nitrogen and heated to 60°C. Desmodur N3900 (44.9 g) was then added. The solution was stirred for 90 minutes at 60°C. The isocyanate equivalent weight was stalled by titration using the method set forth above.Example 1 - 3D Printing & Reprocessing Efficiency Testing

[0301] In this example, a two-component formulation was tested for applicability of extrusion-based 3D-printing and reprocessability. The materials in Components A and B of Compositions VII to IX, provided in Table 2, were weighed into separate Dual Asymmetric Centrifugal (DAC) cups and mixed via Speedmixer procedure for 3 min at 1200 RPM at room temperature until homogeneous.

[0302] Components A and B of Compositions VII through IX were transferred from the DAC cup to an Optimum cartridge to be suitable for 3D printing by ambient reactive extrusion via Viscotec 2K extruders mounted to a gantry such as the Lulzbot Taz 6. The B and A Components were printed at a volume mix ratio of 1 .4: 1 .0 for Compositions VII and IX.Table 2: Compositions VII-IX

[0303] The reprocessability of Composition VII, Composition VIII andComposition IX were tested by compression molding. To reprocess the material, the printed part was broken into pieces and placed into a rectangular' aluminum mold (40 mm x 30 mm x 15 mm). The mold with the material was placed in a 110°C preheated compression press for 15minutes for temperature equilibration. The temperature of the mold was monitored by a Barnat 100 thermocouple. Pressure was then applied at 2 tons and kept constant for 15 minutes. After reprocessing, the sample was removed from the mold while still warm. Pictures of ground and reprocessed materials of Compositions VII to IX are shown in FIGS. 10A to 10C, respectively. Only Composition VII, containing the compound of the present disclosure, was found to be reprocessable under these conditions.

[0304] Mechanical properties of the reprocessed Composition VII via compression molding were determined using a rectangular sample (40 mm x 7 mm x 0.8 mm, approximate dimensions) tested in the Instron Model 5567 at a 50 mm / min pull rate. Prior to tensile testing, the reprocessed material was placed in a hot room at 71 °C for 24 h. The mechanical properties after each reprocessing cycle were tested and compared to the original material. Results are reported in Table 3. Compositions VIII and IX were not tested because they were unable to be reprocessed into suitable samples.Table 3. Tensile properties of Composition VII after multiple reprocessing cycles.

[0305] This example demonstrates that the compositions disclosed herein can retain mechanical properties and modulus upon repeated reprocessing.

[0306] Self-healing properties of Composition VII were tested by making a slight cut in a cured coating made with Composition VII with scissors, creating a small fissure or defect area. FIG. 11 A shows the cured coating with the defect. The coating was then heated in an oven at 130°C for 1 hour. FIG. 11B shows the cured coating after heating. The self-healing efficiency of the material was calculated using Equation 1 by measuring the dimensions of the cut before (wo, 98.76 pm) and after thermal healing ( f, 59.25 pm) using optical macroscopy. The self- healing efficiency was calculated to be 40%. This demonstrates that the compositions disclosed herein are capable of self-healing.(w0- v ) self — healing efficiency (%) = - x 100 w0(1)Example 2 - Lap Shear Testing

[0307] A deoxidizing composition (DEOX-1) was prepared using 18.2 liters of deionized water, 180.5 g of fluorosilicic acid (23% solution), 80 g of fhiorozirconic acid (45% solution), 1 1 .61 g of potassium bifluoride, and 31 .6 g of Chemfil Buffer (commercially available from PPG Industries, Inc.).

[0308] Compositions X to XIV were prepared by blending the components set forth in Table 4 and mixed for 2 minutes at 2350 RPM using a Dual-Asymmetric Mixer (SpeedMixer®). Lap shear specimen (dimensions of 17.5 mm x 12.8 mm x 0.52 mm) were prepared using 0.063” 2024 T3 Aluminum. The panels were cleaned of oils with acetone and methyl-ethyl ketone and treated with DEOX- 1. These panels were then primed by drawing down the two-component epoxy adhesive composition Corabond® CB8111 (commercially available from PPG) to form a primer layer over the panels at 0.005” thickness and baking at 140°C for 5 minutes. One of Compositions X to XIV was applied to one side of a panel and overlapped with a second panel (overlap dimensions 1” x z”). The two panels were held together using binder clips and excess composition was removed from the joint using a metal spatula. Samples were cured at ambient conditions for at least 7 days before testing. Lap shear strength (LSS) was then measured at room temperature (RT, 25°C), 50°C, and 150°C and a pull rate of 1.3 mm / minute using Instron Model 5567 with 30kN load cell. Results are provided in FIGS. 12 to 14, respectively. Tgdata was obtained using a TA Instruments Q800 DMA V21.3 in single cantilever mode. The frequency was set at 1 Hz and the temperature ramped from 0 to 150°C at a rate of 3°C / minute.

[0309] Compositions X through XIV all demonstrate high lap shear strength at room temperature. By varying the ratio of isocyanate functional groups to furan functional groups, the lap shear strength at 50°C can be adjusted, while maintaining reversibility at 150°C, as defined by having a lap shear strength of no more than 2 MPa.Example 3. Viscosity Measurements

[0310] The viscosity of Compositions 1 to VI were determined by rheology and recorded in Table 5. The measurements were conducted at 25°C using a 25 mm parallel plate set-up and a gap height of 0.2-0.3 mm. The viscosity of the compositions was measured across a shear rate of at least 0.1 to 10 s'1. The viscosity as a function of shear rate is shown in FIG. 15 and the viscosity of all reagents at a shear rate of 1 s'1are listed in Table 5.Table 5Example 4, Synthesis Examples

[0311] The following Examples A and B provide descriptions of the synthesis of a furan / isocyanate-functional polymer.Table 61DESMODUR N3900 is commercially available from Covestro.2Dibutyl tin dilaurate is commercially available from Evonik Industries.3Furfuryl alcohol is commercially available from Sigma Aldrich.

[0312] Part #1 was added to a 2000-mililiter, 4-necked round flask equipped with a motor driven stainless steel stir blade, a water-cooled condenser, a nitrogen blanket, and a heating mantle with a thermometer connected through a temperature feedback control device. The reaction mixture was heated to 60°C. Then part #2 was added at a rate such that the temperature of the mixture did not exceed 80°C. After part #2 was added, the reaction was held at 80°C until the isocyanate equivalent weight was stalled. The isocyanate equivalent weight was determined by titration of a sample. The sample was prepared by dissolving 1 g of the isocyanate per 420 g / eq of predicted isocyanate equivalent weight in 30 mL of a solution comprising 20 mL of dibutylamine and 980 mL of N-methyl-2-pyrrolidone. The sample was then titrated with 0.2 N HC1 solution in isopropanol titration agent using a Metrohm 808 or 888 Titrando. The reaction mixture was maintained at 80°C until the isocyanate equivalent weight was stalled. Then the reaction mixture was poured out at 40°C with a N2 blanket.

[0313] The following Example C provides descriptions of the synthesis of alternative dienophile prepolymers.Table 71Dipropylene glycol is commercially available from Sigma Aldrich.2Maleic Anhydride is commercially available from TCI America.3IONOL is 2,6-di-tert-Butyl-4-methylphenol and commercially available from Sasol Chemicals (USA) LLC.4Monobutyltin oxide is commercially available from ARKEMA INC.32-ethylhexyl glycidyl ether is commercially available from Negase America LLC.

[0314] Part #1 was added to a 1000-mililiter, 4-necked round flask equipped with a motor driven stainless steel stir blade, a water-cooled condenser, and a heating mantle with a thermometer connected through a temperature feedback control device. The mixture was heated to 220°C and held until the acid value was stalled around 150 mg KOH / g by titration. Then the mixture was cooled to 120°C and Part #2 was added. The mixture was heated to 140°C and held until the acid value was less than 2 mg KOH / g by titration. The mixture was then cooled to 80°C and poured into an appropriately sized container. The final OH equivalent weight was 302 g / eq, determined by titration. The hydroxyl number was determined by esterification of the same with excess acetic anhydride at elevated temperatures using imidazole as a catalyst. The excess acetic anhydride was converted to acetic acid by hydrolysis and titrated potentiometrically with standard potassium hydroxide.Example 5. Lap Shear Testing

[0315] DEOX-1 was prepared as described above.

[0316] Composition XV was formed by blending the components in Table 8 at the ratios described and mixed for 4 minutes at 2350 RPM using a Dual-Asymmetric Mixer (SpeedMixer®). Lap shear specimens (dimensions of 25.6 mm x 12.8 mm) were prepared using 0.063” 2024 T3 Aluminum. The panels were cleaned of oils with acetone and methyl-ethyl ketone and treated with DEOX-1. Lap shear specimens were prepared by applying Composition XV to one side of a primed panel, then overlapping with a second panel (overlap dimensions 1” x W). The two panels were held together using binder clips and excess composition was removed from the joint using a metal spatula. Samples were allowed to cure at ambient conditions for at least 7 days before testing. Lap shear strength was measured at room temperature (25°C), and 150°C (pull rate of 1.3 mm / min using Instron Model 5567 with 30 kN load cell). After testing, the samples were rejoined and held together with binder clips. The samples were then heated to 120°C for 2 hours, allowed to cool overnight, and retested at 25°C. The retest measurement is recorded as Rebond Lapshear Strength. Results are provided in Table 8.Table 8

[0317] This example demonstrates that compositions disclosed herein form coatings that exhibit good mechanical properties and rebondability.

[0318] 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 compound comprising: a furan functional group; an isocyanate functional group; and a urethane linkage, a urea linkage, and / or a thiourethane linkage.

2. The compound of claim 1, wherein the urethane linkage, the urea linkage, and / or the thiourethane linkage is between the furan functional group and the isocyanate functional group.

3. The compound of claim 1 or claim 2, comprising Structure I:wherein X comprises O, N, or S, m > 1, n > 1, the sum of m+n > 2, Ri comprises a substituted or unsubstituted alkyl group, an alkylene group, a (cyclo)alkyl group, an aromatic group, an isocyanurate moiety, an iminooxadiazinedione moiety, a biuret moiety, an allophonate moiety, a glycoluril moiety, a benzoguanamine moiety, or a polymeric moiety different from the urethane linkage or the urea linkage, and R2 comprises a substituted or unsubstituted alkyl group, an ester moiety, an ether moiety, or a urethane moiety.

4. The compound of any of the preceding claims, wherein the compound is substantially free of an ether linkage.

5. The compound of any of the preceding claims, comprising a furan equivalent weight of 250 g / eq to 3,000 g / eq and / or an isocyanate equivalent weight of 250 g / eq to 3,000 g / eq.

6. A composition comprising: a first component comprising the compound of any of the preceding claims; and a second component comprising a dienophile-containing compound.

7. The composition of claim 6, wherein the dienophile comprises a malcimidc functional group, a maleate functional group, and / or a fumarate functional group.

8. The composition of claim 7, comprising the furan functional group and the maleimide functional group in an equivalence ratio of 0.5:1 to 1:5:1.

9. The composition of any of claims 6 to 8, wherein the dienophile-containing compound comprises a maleimide equivalent weight of 100 g / eq to 3,000 g / eq.

10. The composition of any of claims 6 to 9, wherein the second component comprises a third compound that is reactive with the isocyanate functional group.

11. The composition of claim 10, wherein the third compound comprises a hydroxyl functional group.

12. A method for coating a substrate comprising: contacting a portion of a surface of the substrate with the composition of any of claims 6 to 11.

13. A method of forming an article comprising extruding the composition of any of claims 6 to 11.

14. A hot melt formed from the composition of any of claims 6 to 11.

15. A substrate comprising a coating formed from the hot melt of claim 1 on a portion of a surface of the substrate.

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

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

18. A battery comprising the battery cell of claim 17.

19. A free-standing film formed from the composition of any of claims 6 to 11.

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