Reversibly curable compositions

Abstract

Disclosed are compositions comprising a first component comprising a furan-containing compound comprising (i) a furan functional group, (ii) an isocyanate functional group, and (iii) a urethane linkage; a second component comprising a dienophile-containing compound; and a polar organic solvent in an amount greater than 15% by weight based on total weight of the composition, wherein the solvent is not reactive with the furan-containing compound or the dienophile-containing compound at ambient conditions. Also disclosed are films formed from the compositions disclosed herein. Also disclosed are substrates comprising a surface coated with or embedded in a composition disclosed herein. Also disclosed are methods of separating two substrates bonded by a coating formed from one of the compositions disclosed herein. Also disclosed are substrates comprising an adhesive and a reversible coating formed on a portion of the adhesive, wherein the reversible coating is formed from any of the compositions disclosed herein.

Description

REVERSIBLY CURABLE COMPOSITIONSCROSS-REFERENCE TO RELATED APPLICATION

[0001] This application claims priority to U.S. Provisional Application No. 63 / 775,523, filed on March 21, 2025, and U.S. Provisional Application No. 63 / 875,215, filed on September 3, 2025, both entitled “Furan-Functional and Isocyanate-Functional Compounds and Reversibly Curable Compositions,” and both of which are incorporated herein in their entirety.FIELD

[0002] The present disclosure relates to reversibly curable compositions.BACKGROUND

[0003] 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

[0004] Disclosed herein are compositions comprising: a first component comprising a furan-containing compound comprising (i) a furan functional group, (ii) an isocyanate functional group, and (iii) a urethane linkage; a second component comprising a dienophile-containing compound; and a polar organic solvent in an amount greater than 15% by weight based on total weight of the composition, wherein the solvent is not reactive with the furan-containing compound or the dienophile-containing compound.

[0005] Also disclosed herein are substrates comprising a surface coated with or embedded in any of the compositions disclosed herein.

[0006] Also disclosed herein are films formed from any of the compositions disclosed herein.

[0007] Also disclosed herein are batteries comprising: a battery cell; a battery component; and a coating formed from any of the compositions disclosed herein positioned between the battery cell and the battery component.

[0008] Also disclosed herein are methods of separating two substrates bonded by a coating formed from one of the compositions disclosed herein comprising heating the coating above a reflow onset temperature of the coating and separating the substrates.

[0009] Also disclosed herein are substrates comprising an adhesive and a reversible coating formed on a portion of the adhesive, wherein the reversible coating is formed from any of the compositions disclosed herein.

[0010] Also disclosed herein are kits comprising (a) any of the compositions disclosed herein and (b) a thermally conductive adhesive composition.BRIEF DESCRIPTION OF THE DRAWINGS

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

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

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

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

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

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

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

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

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

[0020] FIG. 10 is a legend of the failure modes used to categorize the examples.DETAILED DESCRIPTION

[0021] The present disclosure is directed to a composition comprising, consisting essentially of, or consisting of a first component; a second component; and a polar organic solvent in an amount greater than 15% by weight based on total weight of the composition. The first component may comprise, consist essentially of, or consist of a furan-containing compound comprising (i) a furan functional group, (ii) an isocyanate functional group, and (iii) a urethane linkage. The second component may comprise, consist essentially of, or consist of a dienophile-containing compound. The solvent may not be reactive with the furan-containing compound or the dienophile-containing compound.

[0022] As used herein with respect to the components, 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.Furan-Containing Compound

[0023] The furan-containing compound comprises (i) a furan functional group, (ii) an isocyanate functional group, and (iii) a urethane linkage.

[0024] The furan-containing compound may comprise the general structure:- -*m u "*n(i)wherein X comprises O, N, or S; m > 1; n > 1; m+n > 2; Ri comprises a substituted or unsubstituted alkyl group, an alkylene group, a (cyclo)alkyl group, an aromatic group, an allophonate moiety, a benzoguanamine moiety, an iminooxadiazinedione moiety, or a polymeric moiety different from the urethane linkage; and R2 comprises a substituted or unsubstituted alkyl group, an ester moiety, an ether moiety, or a urethane moiety. Optionally, l < m < 12; l < n < 12; and 2 < m+n < 13.

[0025] The furan-containing compound may comprise, consist essentially of, or consist of a monomer, a prepolymer, or a polymer.

[0026] The furan-containing compound may comprise one, two, three, or more furan functional groups. The furan functional group of the furan-containing compound may be linked to the backbone of the furan-containing compound by the urethane linkage.

[0027] The furan-containing compound of the present disclosure may be substantially free, essentially free, or completely free of an ether linkage.

[0028] The furan-containing compound may comprise a furan equivalent weight of at least 180 g / eq, such as at least 200 g / eq. The furan-containing compound may comprise a furan equivalent weight of no more than 1,000 g / eq, such as no more than 800 g / eq. The furan-containing compound may comprise a furan equivalent weight of 180 g / eq to 1,000 g / eq, such as200 g / eq to 800 g / eq. 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 of the compound.

[0029] The furan-containing compound may comprise an isocyanate equivalent weight of at least 200 g / eq. The furan-containing compound may comprise an isocyanate equivalent weight of no more than 1,000 g / eq, such as no more than 800 g / eq. The furan-containing compound may comprise an isocyanate equivalent weight of 200 g / eq to 1,000 g / eq, such as 200 g / eq to 800 g / eq. 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 of the compound.

[0030] The furan-containing compound may comprise the furan functional group and the isocyanate functional group in a molar ratio of at least 0.15: 1, such as at least 0.2:1, such as at least 0.3: 1. The furan-containing compound may comprise the furan functional group and the isocyanate functional group in a molar ratio of no more than 5:1, such as no more than 4:1, such as no more than 2:1. The furan-containing compound may comprise the furan functional group and the isocyanate functional group in a molar ratio of 0.15: 1 to 5: 1, such as 0.2: 1 to 4:1, such as 0.3:1 to 2:1.

[0031] The furan-containing compound may comprise a reaction product of reactants comprising (i) a furan-containing reactant comprising an active hydrogen-containing functional group and a furan functional group and (ii) a poly isocyanate-containing reactant. As used herein, a “poly isocyanate-containing reactant” refers to a compound comprising more than one isocyanate functional group, including diisocyanates, triisocyanates, or higher. The active hydrogen-containing functional group may comprise, for example, a hydroxyl functional group, an amine functional group, and / or a thiol functional group. The active hydrogen-containing functional group of the furan-containing reactant may react with an isocyanate functional group of the polyisocyanate-containing reactant.

[0032] A sub -stoichiometric amount of the active hydrogen-containing functional group on the furan-containing reactant may be reacted with the isocyanate functional groups on the polyisocyanate-containing reactant. For example, the active hydrogen-containing functional group of the furan-containing reactant and the isocyanate functional groups on the polyisocyanate-containing reactant may be reacted at a molar ratio of less than 1:1, such as nomore than 0.3:1, such as no more than 0.25:1, such as no more than 0.2:1. As used herein, “sub-stoichiometric” means that the number of active hydrogen-containing functional groups on the furan-containing reactant is lower than the number of active hydrogen-containing functional groups required to react with all of the isocyanate functional groups on the polyisocyanate-containing reactant, so that the reaction product comprises isocyanate functionality from the polyisocyanate-containing reactant.

[0033] The furan functional group of the furan-containing reactant may be monosubstituted and / or terminal.

[0034] Suitable furan-containing reactants include but are not limited to furfuryl alcohol, furfuryl amine, furfuryl thiol, furfuryl glycidyl ether, bis(hydroxymethyl)furan, and / or derivatives thereof.

[0035] Suitable polyisocyanate-containing reactants may be polymeric and may contain two or more isocyanate functional groups. For example, the polyisocyanate may be linear, cyclic, such as cycloaliphatic, aliphatic, and / or aromatic.

[0036] Suitable aliphatic polyisocyanates may include alkylene isocyanates, such as: trimethylene diisocyanate, tetramethylene diisocyanate, such as 1,4-tetram ethylene diisocyanate; pentamethylene diisocyanate, such as 1,5-pentamethylene diisocyanate and 2-methyl-l,5-pentamethylene diisocyanate; hexamethylene diisocyanate (“HDI”), such as 1,6-hexam ethylene diisocyanate and 2,2,4- and / or 2,4,4-trimethylhexamethylene diisocyanate; 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-decam ethylene diisocyanate; ethylidene diisocyanate; and / or 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”), TPDI trimer (commercially available as Desmodur® Z 4470 SN); methylene bis(4-cyclohexylisocyanate) (“HMDI”); polymeric methylene diphenyl diisocyanate (“MDI”); and mixed aralkyl diisocyanates such as tetramethylxylyl diisocyanates, such as meta-tetram ethylxylyl ene diisocyanate (commercially available as TMXDI® from Allnex SA).

[0037] Suitable aromatic polyisocyanates may include arylene isocyanates, such as: phenylene diisocyanate, such as m-phenylene diisocyanate, p-phenylene diisocyanate, and chlorophenylene 2,4-diisocyanate; naphthalene diisocyanate, such as 1,5-naphthalene diisocyanate and 1,4-naphthalene diisocyanate. Aromatic polyisocyanates may also include alkarylene isocyanates, such as: methylene-interrupted aromatic diisocyanates, such as 4, d’diphenylene methane diisocyanate (“MDI”), and alkylated analogs such as 3,3 ’-dimethyl-4, d’diphenylmethane diisocyanate, and polymeric methylenediphenyl diisocyanate; toluene diisocyanate (“TDI”), such as 2,4-tolylene, 2,6-tolylene diisocyanate, and / or bitoluene diisocyanates; and 4,4-toluidine diisocyanate; xylene diisocyanate; dianisidine diisocyanate; xylylene diisocyanate; and other alkylated benzene diisocyanates.

[0038] Suitable polyisocyanates include dimers, trimers, oligomers, or prepolymers comprising any of the isocyanates listed herein.Dienophile-Containing Compound

[0039] A “dienophile” refers to a fumarate-containing compound, a maleate-containing compound, and / or a maleimide-containing compound. As used herein, a “diene” refers to a compound containing two unsaturated bonds separated by a single covalent bond.

[0040] The dienophile-containing compound may comprise a maleimide functional group (a “maleimide-containing compound”). The general structure of the dienophile-containing compound comprising a maleimide functional group comprises:(II)wherein R3 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).

[0041] The maleimide-containing compound may comprise a reaction product of reactants comprising maleic anhydride and a di- or polyfunctional amine-containing compound. The amine-containing compound may be selected such that the maleimide-containing compound does not crystallize. The maleimide-containing compound may comprise the reaction product ofreactants comprising a maleic anhydride and a dimer fatty acid diamine, such as BMT-689, commercially available from Designer Molecules, Inc. The maleimide-containing compound may comprise the reaction product of reactants comprising an amine-terminated polyether or a polysiloxane and maleic anhydride. Additionally, the maleimide-containing compound may comprise a maleimide-terminated polyimide, available from Designer Molecules, Inc., or a reaction product of a maleimide-functional carboxylic acid and a compound comprising an epoxide functional group, hydroxyl functional group, and / or other carboxylic acid-reactive functional group.

[0042] The dienophile may comprise a maleate functional group (“maleate-containing compound”). The general structure of the maleate-containing compound comprises:o o(III)wherein each X independently comprises O, N, or S; and R4 and R5 each independently 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 maleate-containing compound may comprise an unsaturated polyester comprising a maleate functional group. In an example, the maleate-containing compound may comprise an unsaturated polyester comprising the reaction product of reactants comprising maleic acid (or an anhydride or ester thereof) and a polyol. Suitable polyols include any of those described below. In another example, the maleate-containing compound may comprise a reaction product of reactants comprising an epoxide and a maleic anhydride. The unsaturated polyester may further comprise an additional functional group, such as a hydroxyl functional group. The unsaturated polyester may comprise a liquid.

[0043] The dienophile-containing compound may comprise a fumarate functional group (a “fumarate-containing compound”). The general structure of the fumarate-containing compound comprises:(IV)wherein each X independently comprises O, N, or S; and Re and R7 each independently comprises a hydrogen, an alkyl, a (cyclo)alkyl, an aryl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a poly ether, an acrylic, or a siloxane). The fumarate-containing compound may comprise an unsaturated polyester comprising a fumarate functional group. In an example, the fumarate-containing compound may comprise an unsaturated polyester comprising the reaction product of reactants comprising fumaric acid (or an anhydride or ester thereof) and a polyol. Suitable polyols include any of those described below. In another example, the fumarate-containing compound may comprise a reaction product of an epoxide and fumaric acid anhydride. The unsaturated polyester may further comprise an additional functional group, such as a hydroxyl functional group. The unsaturated polyester may comprise a liquid.

[0044] The dienophile-containing compound may comprise a dienophile equivalent weight of at least 150 g / eq, such as no more than 800 g / eq, such as 150 g / eq to 800 g / eq. As used herein, “dienophile equivalent weight” refers to the theoretical molecular weight of a compound comprising a dienophile divided by the theoretical number of dienophiles of the compound.

[0045] The composition may have a molar ratio of the furan functional groups on the furan-containing compound to the dienophiles on the dienophile-containing compound of at least 0.5:1, such as at least 0.6:1. The composition may have a molar ratio of the furan functional groups on the furan-containing compound to the dienophiles on the dienophile-containing compound of no more than 2:1, such as no more than 1.5:1. The composition may have a molar ratio of the furan functional groups on the furan-containing compound to the dienophiles on the dienophile-containing compound of 0.5:1 to 2:1, such as 0.6:1 to 1.5:1.

[0046] The composition may further comprise a third compound in addition to the furan-containing compound and the dienophile-containing compound. The third compound may be reactive with the isocyanate functional group on the furan-containing compound. The thirdcompound may be present in the second component and / or a third or higher component. The third compound may comprise a hydroxyl functional group. For example, the third compound may comprise a polyol.

[0047] Suitable polyols include diols, triols, tetraols and higher functional polyols. The polyol may comprise a polyhydric alcohol such as ethylene glycol, propanediol, neopentyl glycol, butanediol, pentanediol, hexanediol, cyclohexanedimethanol, cyclohexanediol, benzenedimethanol, 4,4’isopropylidenedicyclohexanol, glycerol, trimethylolpropane, pentaerythritol, di(trimethylolpropane), and / or di(pentaerythritol). The polyol may also include a polyether polyol, a polyester polyol, an acrylic polyol, a polybutadiene polyol, a hydrogenated polybutadiene polyol, a polycarbonate polyols, and / or a polysiloxane polyol.

[0048] The polyol may comprise a polycaprolactone-based polyol. The polycaprolactone-based polyol may comprise a diol 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.

[0049] The polyol may comprise a polyether polyol. The polyol may be based on a polyether chain derived from ethylene glycol, propylene glycol, butylene glycol, and / or hexylene glycol, and the like. The polyol may comprise a tetrahydrofuran-based polyol. The polytetrahydrofuran-based polyol may comprise a diol, a triol, and / or a tetraol 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 an amine-containing polyol, such as Quadrol PM commercially available from BASF.

[0050] The composition may have a molar ratio of the isocyanate functional groups on the furan-containing compound to the hydroxyl functional groups on the third compound of at least 0.2:1, such as at least 0.4: 1. The composition may have a molar ratio of the isocyanate functional group on the furan-containing compound to the hydroxyl functional group on the thirdcompound of no more than 3:1, such as no more than 2: 1. The composition may have a molar ratio of the isocyanate functional group on the furan-containing compound to the hydroxyl functional group on the third compound in a molar ratio of 0.2: 1 to 3: 1, such as 0.4:1 to 2: 1.

[0051] The composition may further comprise a second furan-containing compound comprising a furan functional group in addition to the furan-containing compound described above, wherein the second furan-containing compound is different from the furan-containing compound. The second furan-containing compound may be present in the first component and / or a third or higher component. The second furan-containing compound may comprise a furan equivalent weight of at least 68 g / eq, such as at least 80 g / eq. The second furan-containing 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 second furan-containing 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.Polar Organic Solvent

[0052] The composition comprises a polar organic solvent. As used herein, “polar organic solvent” refers to an organic solvent having a dipole moment of one or more. Dipole moments of various organic solvents can be found in The Prelude of Green Syntheses of Drugs and Natural Products, Greener Synthesis of Organic Compounds. As used herein, an “organic solvent” refers to carbon-based substances capable of dissolving or dispersing other substances at ambient conditions. The polar organic solvent is non-reactive with the furan-containing compound and the dienophile-containing compound at ambient conditions. The polar organic solvent may be non-reactive with other components of the composition. The polar organic solvent may be present in the first component, the second component, and / or a third component.

[0053] The polar organic solvent may comprise a ketone, an ester, an amide, a nitrile, a haloalkane, a haloarene, an alcohol, and / or a nitroalkane functionality.

[0054] The polar organic solvent may have a boiling point of no more than 180°C at 1 atm.

[0055] The composition may comprise the polar organic solvent in an amount of greater than 15% by weight based on total weight of the composition, such as at least 20% by weight. The composition may comprise the polar organic solvent in an amount of no more than 90% by weight based on total weight of the composition, such as no more than 85% by weight. The composition may comprise the polar organic solvent in an amount of greater than 15% byweight to 90% by weight based on total weight of the composition, such as 20% by weight to 85% by weight.Filler

[0056] 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. For purposes of this disclosure, fillers that function as thermally expandable materials or elastomeric particles are included in the amounts disclosed with respect to the thermally expandable material or elastomeric particles, respectively.

[0057] The filler may comprise a thermally conductive filler and / or a non-thermally conductive filler.

[0058] The thermally conductive (“TC”) filler may have a thermal conductivity of at least 5 W / m·K at 25ºC 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 / m·K at 25ºC, 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 25ºC measured according to ASTM D7984-21, such as 18 W / m·K to 1,400 W / m·K.

[0059] The non-thermally conductive (“NTC”) filler may have a thermal conductivity of less than 5 W / m·K at 25ºC measured according to ASTM D7984-21, such no more than 3 W / m·K, such as no more than 1 W / m·K, such as no more than 0.1 W / m·K, such as no more than 0.05 W / m·K, such as 0.02 W / m·K to 5 W / m·K at 25ºC.

[0060] The filler may be electrically insulative. The electrically insulative filler may have a volume resistivity of at least 1 Ω·m measured according to ASTM D257-19, such as at least 10 Ω·m, such as at least 100 Ω·m.

[0061] The filler may be electrically conductive. The electrically conductive filler may have a volume resistivity of less than 1 Ω·m measured according to ASTM D257-19, such as less than 0.1 Ω·m.

[0062] 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.

[0063] The TC / EI filler may also be ferromagnetic, ferrimagnetic, and / or superparamagnetic. As used herein, a “ferromagnetic” material is one in which the magnetic moments of individual atoms align parallel to one another, resulting in a strong net magnetic moment. As used herein, a “ferrimagnetic” material is one in which the magnetic moments of individual atoms partially align antiparallel to one another, leading to a net magnetic moment smaller than that of the individual magnetic moments. As used herein, a “superparamagnetic” material is one in which magnetization can flip direction as a response to thermal fluctuations. Superparamagnetic materials may comprise ferromagnetic nanoparticles and / or ferrimagnetic nanoparticles.

[0064] 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 DustXL 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 graphenic carbon particles may be substantially flat; however, at least a portion of the planar sheets may be substantially curved, curled, creased, or buckled. The particles typically do not have a spheroidal or equiaxed morphology. Suitable graphenic carbon particles are 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. Patent No. 9,562,175, at 6:6 to 9:52, the cited portion of which is 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 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.

[0065] Suitable NTC / EI fillers include but are not limited to mica, wollastonite, calcium carbonate, glass microspheres, clay, and / or silicon dioxide.

[0066] 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 KAl2(AlSi3O10)(F,OH)2or (KF)2(Al2O3)3(SiO2)6(H2O). Exemplary non-limiting commercially available muscovite mica includes 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 (CaSiO3) that may contain small amounts of iron, aluminum, magnesium, manganese, titanium, and / or potassium. Wollastonite is commercially available as NYAD 400 available from NYCO Minerals, Inc.

[0067] The calcium carbonate (CaCCh) may comprise a precipitated calcium carbonate or a ground calcium carbonate. The calcium carbonate may or may not be surface treated, such as treated with stearic acid, such as Socal® 312, commercially available fromIMERYS. 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.

[0068] Useful clay minerals include non-ionic platy fillers such as talc, pyrophyllite, chlorite, and / or vermiculite.

[0069] The glass microspheres may comprise 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.

[0070] The filler may comprise a lightweight filler. The lightweight filler may be organic and / or inorganic. As used herein, the term “lightweight” when used with reference to particles of the present disclosure means that the particles have a specific gravity of no more than 1.0 measured according to ASTM D5965-19, with “specific gravity” being the ratio of a mass of a solid or liquid (e.g., a mass of particles) to a mass of an equal volume of distilled water at the same temperature (e.g., 25°C). The lightweight fillers may have a specific gravity of at least 0.01 measured according to ASTM D5965-19, such as at least 0.02, such as at least 0.1. The lightweight fillers may have a specific gravity of no more than 1.0 measured according to ASTM D5965-19, such as no more than 0.7. The lightweight fillers may have a specific gravity of 0.01 to 1.0 measured according to ASTM D5965-19, such as 0.02 to 0.7.

[0071] Suitable lightweight fillers may comprise microspheres. Useful examples of lightweight fillers include polystyrene foam, microspheres of polyacrylates and polyolefins, and silica microspheres having a number average particle size of 5 to 100 microns and a specific gravity of 0.25 (ECCOSPHERES®, Trelleborg Applied Technologies). Other examples include alumina / silica microspheres having a number average particle size of 5 to 300 microns and a specific gravity of 0.7 (FILLITE®, Pluess-Stauffer International), aluminum silicate microspheres having a specific gravity of 0.45 to 0.7 (Z-LIGHT®), and calcium carbonate-coated poly vinylidene copolymer microspheres having a specific gravity of 0.13 (DU ALITE 6001AE®, Pierce & Stevens Corp.). Other suitable lightweight fillers include, for example, expanded hollow microspheres, such as Expancel® expanded microspheres, such as Expancel® 920 DET 40 d25, Expancel® 043 DET 80 d20, and Expancel® 920 DE 80 d30 (all availablefrom Nouryon) Dualite® low density polymer microspheres (available from Henkel) or hollow borosilicate glass, such as 3M Glass bubbles type VS, K series and S series available from 3M. Compositions provided by the present disclosure may include lightweight filler particles comprising an exterior surface coated with a thin coating, such as those described in U. S.Publication No. 2010 / 0041839 at paragraphs

[0016] -

[0052] , the cited portion of which is incorporated herein by reference. It will be appreciated that these particle sizes refer to the particle size of the lightweight filler at the time of incorporation into the composition. Particle size may be measured by methods known to those skilled in the art, for example, using a scanning electron microscope (SEM).

[0072] Suitable lightweight fillers include, for example, those described in U. S. Patent No. 6,525,168, column 4, lines 14-55 and U. S. Patent No. 8,816,023, column 3, line 18 to column 9, line 44, the cited portions of which are incorporated herein by reference.

[0073] The composition may comprise the filler in an amount of at least 1% by volume based on total solids volume of the composition, such as at least 5% by volume, such as at least 40% by volume. The composition may comprise the filler in an amount of no more than 90% by volume based on total solids volume of the composition, such as no more than 85% by volume, such as no more than 20% by volume. The composition may comprise the filler in an amount of 1% by volume to 90% by volume based on total solids volume of the composition, such as 40% by volume to 85% by volume, such as 5% by volume to 20% by volume. As used herein, “total solids” refers to the non-volatile content of the composition, i.e., materials which will not volatilize when heated to 110°C and standard atmospheric pressure (1 atm) for 60 minutes.Thermally Expandable Material

[0074] The composition may further comprise a thermally expandable material. The thermally expandable material may be present in the first component, the second component, and / or a third component. As used herein, the term “thermally expandable material” means a pigment, filler, encapsulant, thermoplastic, inorganic powder, capsule, microcapsule, or the like that, upon heating, undergoes an increase in volume.

[0075] Suitable examples of thermally expandable materials include inorganic salts and / or thermally expandable graphite, such as thermally expandable graphite available from ACS Material.

[0076] The thermally expandable material may comprise thermally expandable capsules. The thermally expandable capsules may comprise thermally expandable hollow capsules. The thermally expandable capsules may comprise a thermoplastic resin and / or a volatile material, such as a volatile hydrocarbon and / or a volatile gas. The thermally expandable capsules may comprise a thermoplastic resin shell with a volatile material core. Suitable thermally expandable materials include Expancel® unexpanded microspheres, such as Expancel® 920 DU 20 and Expancel® 980 MB 100 (both commercially available from Nouryon) and / or Advancell (commercially available from Sekisui).

[0077] The thermally expandable material may have an average initial (i.e., preexpansion) particle size of at least 0.5 pm, such as at least 1 pm, such as at least 2 pm, such as at least 3 pm, such as at least 5 pm, such as at least 10 pm. The thermally expandable material may have an average initial particle size of no more than 100 pm, such as no more than 80 pm, such as no more than 60 pm, such as no more than 50 pm. The thermally expandable material may have an average initial particle size of 0.5 pm to 100 pm, such as 1 pm to 80 pm, such as 2 pm to 60 pm, such as 3 pm to 50 pm, such as 5 pm to 50 pm, such as 10 pm to 50 pm. Initial particle size of the thermally expandable material may be measured by methods known to those skilled in the art, such as laser diffraction.

[0078] The thermally expandable material may have an expansion temperature of at least 60°C, such as at least 70°C, such as at least 80°C, such as at least 90°C, such as at least 100°C, such as at least 110°C, such as at least 120°C, such as at least 130°C, such as at least 140°C, such as at least 150°C, such as at least 160°C, such as at least 170°C, such as at least 180°C, such as at least 190°C, such as at least 200°C, such as no more than 250°C. As used herein, the term “expansion temperature,” when used with respect to the thermally expandable material, means the temperature at which the particle size begins to increase due to an increase in volume in at least one dimension. In the case of thermally expandable capsules, the increase in particle size may be, for example, the result of the volatile material beginning to expand while the thermoplastic resin shell softens. Expansion temperature may be achieved, for example, by heating the coating comprising the thermally expandable material and / or heating the substrate on which the coating is formed. The coating and / or the substrate may be heated by direct thermal exposure and / or, in substrates containing ferromagnetic materials, superparamagnetic materials, and / or ferrimagnetic materials or in coatings formed from compositions containingferromagnetic materials, superparamagnetic materials and / or ferrimagnetic materials, by indirect heating through the application of a magnetic field resulting in ferromagnetic heating, superparamagnetic heating, or ferrimagnetic heating.

[0079] Under thermal conditions of at least the expansion temperature of the thermally expandable material, the thermally expandable material may have an expansion volume ratio (i.e., post-expansion volume / pre-expansion volume) of at least 5, such as at least 10, such as at least 20, such as at least 25, such as at least 50, such as at least 75, such as at least 100, such as at least 125, such as at least 175, such as at least 200. Under thermal conditions of at least the expansion temperature of the thermally expandable material, the thermally expandable material may have an expansion volume ratio (i.e., post-expansion volume / preexpansion volume) of no more than 250. Under thermal conditions of at least the expansion temperature of the thermally expandable material, the thermally expandable material may have an expansion volume ratio (i.e., post-expansion volume / pre-expansion volume) of 5 to 250, such as 10 to 250, such as 20 to 250, such as 25 to 250, such as 50 to 250, such as 75 to 250, such as 100 to 250, such as 125 to 250, such as 175 to 250, such as 200 to 250. The postexpansion volume and the pre-expansion volume of the thermally expandable material may be measured by methods known to those skilled in the art, such as laser diffraction.

[0080] The composition may comprise the thermally expandable material in an amount of at least 0.5 percent by weight based on total weight of the composition, such as at least 1 percent by weight. The composition may comprise the thermally expandable material in an amount of no more than 20 percent by weight based on total weight of the composition, such as no more than 10 percent by weight. The composition may comprise the thermally expandable material in an amount of 0.5 percent by weight to 20 percent by weight based on total weight of the composition, such as 1 percent by weight to 10 percent by weight.Blowing Agent

[0081] The composition may further comprise a blowing agent. As used herein, “blowing agent” refers to a pigment, filler, encapsulant, thermoplastic, inorganic powder, microcapsule, or the like that, upon heating, releases gas by virtue of chemical decomposition or phase change. The blowing agent may be present in the first component, the second component, and / or a third or higher component.

[0082] The blowing agent may comprise a chemical blowing agent and / or a physical blowing agent.

[0083] Suitable physical blowing agents include compounds with boiling points of -80°C to 50°C at 1 atm and which are vaporized during the exothermic polymerization reaction. Physical blowing agents typically do not decompose or react during the polymerization reaction. Suitable examples of physical blowing agents include carbon dioxide, a hydrocarbon, a chlorofluorocarbon (CFC), a hydrofluorocarbon (HFC) such as 1,1, 1,3, 3, 3-pentafluoropropane (commercially available as Genetron® 245fa from Honeywell) and (1,2-bis(trifluoromethyl)ethene (commercially available as Opteon™ 1100 or Formacel®l 100 from Honeywell and The Chemours Company, respectively), a hydrochlorofluorocarbon (HCFC) such as trans-l-chloro-3,3,3-trifluoropropene (commercially available as Solstice ® LBA from Honeywell), a fluoroolefin (FO), a chlorofluoroolefin (CFO), a hydrofluoroolefin (HFO), a hydrochlorofluoroolefin (HCFO), acetone, and / or a low-boiling hydrocarbon such as cyclopentane, isopentane, and / or n-pentane. As used herein, a “low-boiling hydrocarbon” refers to a hydrocarbon having a boiling point of -80°C to 50°C at 1 atm.

[0084] A chemical blowing agent may comprise a compound, for example water, that reacts with an isocyanate compound to produce a gas.

[0085] The composition may comprise the blowing agent in an amount of at least 0.5 percent by weight based on total weight of the composition, such as at least 1 percent by weight. The composition may comprise the blowing agent in an amount of no more than 20 percent by weight based on total weight of the composition, such as no more than 10 percent by weight. The composition may comprise the blowing agent in an amount of 0.5 percent by weight to 20 percent by weight based on total weight of the composition, such as 1 percent by weight to 10 percent by weight.Additives

[0086] The composition may optionally comprise an additive. 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 plasticizer, an adhesion promoter, an antioxidant, a silane, and / or a moisture scavenger. The additive(s) may be present in the first component, the second component, and / or a third or higher component so long as the additive is not reactive with any of the other ingredients in such components.

[0087] The composition disclosed herein may comprise a flame retardant. 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 in a composition or coating that makes the composition or coating capable of slowing down or stopping the spread of fire or reducing its intensity compared to a composition or coating that does not contain the material. A flame retardant may be available as a powder that may be mixed with a composition, a foam, or a gel. In examples, when the composition disclosed herein comprises a flame retardant, the composition may form a coating comprising a flame retardant on a substrate surface.

[0088] A flame retardant can include a mineral, an organic compound, an organohalogen compound, and / or an organophosphorous compound. Suitable examples of minerals include huntite, hydromagnesite, a hydrate, red phosphorous, a boron compound such as a borate, and / or a carbonate such as magnesium carbonate. Suitable examples of organohalogen compounds include an organochlorine such as a chlorendic acid derivative and a chlorinated paraffin; an organobromine such as decabromodiphenyl ether (decaBDE), decabromodiphenyl ethane (a replacement for decaBDE), a polymeric brominated compound such as a brominated polystyrene, a brominated carbonate oligomer (BCO), a brominated epoxy oligomer (BEO), tetrabromophthalic anyhydride, tetrabromobisphenol A (TBBPA) and / or hexabromocyclododecane (HBCD). Such halogenated flame retardants may be used in conjunction with a synergist to enhance their efficiency. Other suitable examples include antimony trioxide, antimony pentaoxide, and / or sodium antimonate. Suitable examples of organophosphorous compounds include triphenyl phosphate (TPP), resorcinol bis(diphenylphosphate) (RDP), bisphenol A diphenyl phosphate (BADP), and tricresyl phosphate (TCP); phosphonates such as dimethyl methylphosphonate (DMMP); and phosphinates such as aluminum diethyl phosphinate. In one class of flame retardants, compounds contain both phosphorus and a halogen. Such compounds include tris(2,3-dibromopropyl) phosphate (brominated tris) and a chlorinated organophosphate such as tris(l,3 -dichloro-2-propyl)phosphate (chlorinated tris or TDCPP) and tetrakis(2-chlorethyljdichloroisopentyldiphosphate (V6). Suitable examples of organic compounds includecarboxylic acids, dicarboxylic acid, melamine, and / or an organonitrogen compound. Other suitable flame retardants include ammonium polyphosphate and barium sulfate.

[0089] Additive(s), if present at all, may be present in the composition in a combined amount of at least 0.01 percent by weight based on total weight of the composition, such as at least 0.1 percent by weight. Additive(s), if present at all, may be present in the composition in a combined amount of no more than 15 percent by weight based on total weight of the composition, such as no more than 10 percent by weight. Additive(s), if present at all, may be present in the composition in a combined amount of 0.01 percent by weight to 15 percent by weight based on total weight of the composition, such as 0.1 percent by weight to 10 percent by weight.Elastomeric Particles

[0090] The composition of the present disclosure may further comprise elastomeric particles. As used herein, the term “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 by the method of Fox on the basis of monomer composition of the monomer charge according to T. G. Fox, Bull. Am. Phys. Soc. (Ser. II) 1, 123 (1956). 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.

[0091] The elastomeric particles may be present in the first component, the second component, and / or a third or higher component.

[0092] The elastomeric particles may have a core / shell structure. Suitable core-shell elastomeric particles may comprise an acrylic shell and an elastomeric core. The core may comprise a natural or a synthetic rubber, polybutadiene, styrene-butadiene, polyisoprene, chloroprene, acrylonitrile butadiene, butyl rubber, polysiloxane, polysulfide, ethylene-vinyl acetate, fluoroelastomer, and / or polyolefin.

[0093] An exemplary non-limiting commercial core-shell elastomeric particle product using polybutadiene rubber particles that may be utilized in the composition of the present disclosure include core-shell polybutadiene rubber powder (commercially available as PARALOID™ EXL 2650A from Dow Chemical).

[0094] Exemplary non-limiting commercial core-shell elastomeric particle products using styrene-butadiene rubber particles that may be utilized in the composition include a core-shell 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).

[0095] Exemplary non-limiting commercial core-shell elastomeric particle products using poly siloxane 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).

[0096] The composition may comprise the elastomeric particles in an amount of at least 0.1 percent by weight based on total weight of the composition, such as at least 1 percent by weight. The composition may comprise the elastomeric particles in an amount of no more than 35 percent by weight based on total weight of the composition, such as no more than 20 percent by weight. The composition may comprise the elastomeric particles in an amount of 0.1 percent by weight to 35 percent by weight, such as 1 percent by weight to 20 percent by weight.Accelerator

[0097] The composition may further comprise an accelerator. As used herein, the term “accelerator” refers to a substance that increases the rate or decreases the activation energy of a chemical reaction between the furan-containing compound and the dienophile-containing compound in comparison to the same reaction in the absence of the accelerator. An accelerator may be either a “catalyst” (that is, without itself undergoing any permanent chemical change) or may be reactive (that is, undergoing a permanent chemical change).

[0098] 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 N-heterocyclic carbene, or an amidine / guanidine. Suitable accelerators that may be used in the present disclosure include N, N-dimethylcyclohexylamine, N,N'-dimethylethanolamine, N-methyl morpholine, 2,2’-dimorpholinodiethylether, dimethylaminoethoxyethanol, triethylenediamine, bis(2-dimethylaminoethyl)ether, N, N, N" -trimethylaminoethylethanolamine, N, N, N ’, N ’-tetramethyl- 1,6-hexanediamine, l,3,5-tris(dimethylaminopropyl)-hexahydro-s-triazine, 1,8-diazabicyclo[5.4.0]undec-7-ene, N-(3-aminopropyl)imidazole, 1,2-dimethylimidazole, 1,5,7-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.

[0099] The accelerator may comprise an organometallic complex. Suitable organometallic complexes comprise titanates, such as tetrabutyl titanate or tetrapropyl titanate, tin compounds, such as dibutyltin dilaurate, dibutyltin diacetate, tin octoate, or dibutyl tin oxide, or other metal compounds, such as chelates of bismuth, zirconium, titanium, aluminum, or iron, such as zirconium acetylacetonate or iron acetylacetonate.

[0100] In examples, the accelerator may comprise a latent accelerator. 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. 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.

[0101] The composition may comprise the accelerator in an amount of at least 0.001 percent by weight based on total weight of the composition, such as at least 0.01 percent by weight, and may be present in an amount of no more than 5 percent by weight based on total weight of the composition, such as no more than 2 percent by weight. The accelerator may be present in the composition in an amount of 0.001 percent by weight to 5 percent by weight based on total weight of the composition, such as 0.01 percent by weight to 2 percent by weight.Compositions

[0102] The first component and the second component may be liquid at ambient conditions and may be mixable at ambient conditions. The compositions disclosed herein may be capable of curing at ambient conditions. As used herein, “mixable” means that the first component and the second component are capable of being blended into a single homogenouscomposition. The furan functional group of the furan-containing compound and the dienophile of the dienophile-containing compound may be reactive under ambient conditions. The composition may be formulated as a two-component composition.

[0103] The compositions disclosed herein may be formulated, for example, as a coating composition such as an adhesive composition, such as a structural adhesive composition, a sealant composition, a pottant composition, a foam, a pre-preg, a liquid shim composition, a sealant composition, or a gap filler composition.

[0104] The compositions disclosed herein may be substantially free, essentially free, or completely free of an oxanorbornene moiety before mixing the first component and the second component. As used herein, an “oxanorbomene moiety” refers to a moiety formed from a compound having the general structure:(V)wherein R8, R9, R10, and R11each independently comprise a substituted or unsubstituted alkyl group, alkylene group, (cyclo)alkyl group, an aromatic group, a hydrogen, a carbamate group, and / or a heteroatom.

[0105] Additionally, the composition may be brought into contact with a surface or assembly as a film, and the system may be heated above the reflow onset temperature of the composition, then cooled to yield a bonded or embedded system. As used herein, “reflow onset temperature” refers to the temperature at which a coating formed from the composition has an average pull-off strength of no more than 1.8 MPa, as measured by PosiTest AT-A Automatic Adhesion Tester, available from DeFelsko. If thermally expandable material is present, the reflow onset temperature must fall below the expansion temperature. The reflow onsettemperature 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).

[0106] The reflow onset temperature may be achieved, for example, by heating the coating disclosed herein and / or heating the substrate on which the coating is formed. The coating and / or the substrate may be heated by direct thermal exposure. 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, the coating and / or the substrate may be heated by indirect heating through the application of a magnetic field resulting in ferromagnetic heating, ferrimagnetic heating, and / or superparamagnetic heating.Systems and Methods

[0107] The compositions and / or films disclosed herein may be applied alone or as part of a system that can be deposited in different ways onto different substrates. As used herein, the terms “system” and “kit” may be used interchangeably. The compositions and / or films 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. When applied by film, the film may be heated to at least the reflow onset temperature to form a liquid. As the liquid cools below the reflow onset temperature toward ambient conditions, a solid forms.

[0108] The system may comprise the same or different compositions and may further comprise additional compositions such as a pretreatment composition, a primer, an adhesive composition, such as a thermally conductive adhesive composition, and the like. The compositions may be packaged individually or together. Optionally, the system may comprise instructions for applying the compositions of the system onto a substrate.

[0109] 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). The composition may be cured at ambient or slightly thermal conditions. When cured at ambient conditions, 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. “Tackiness” may be evaluated using the fingerprint test, which may consist of touching the composition with a gloved finger and assessing the tackiness or stickiness of the formed coating. If the gloved finger does not stick to the coating, then the coating may be called “tack-free” at that time point, and if the gloved finger sticks to the coating, was sticky, and / or left a residue on the glove, then the coating may be called “tacky.” The skilled person understands, however, that time of curing varies with temperature and humidity.

[0110] The coating may be, for example, an adhesive such as a structural adhesive, a sealant, a pottant, a pre-preg, a liquid shim, a seal, or a gap filler.

[0111] The compositions and / or films disclosed herein may form 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 as described above with the film and / or composition; contacting a surface of a second substrate to the film and / or composition such that the film and / or composition is located between the surface of the first substrate and the surface of the second substrate; applying sufficient pressure for the film and / or composition to intimately contact both substrate surfaces; and cooling the film and / or composition. For example, the film and / or composition may be applied to either one or both substrate materials being bonded to form an adhesive bond there between, the substrates may be aligned, and pressure and / or spacers may be added to control bond thickness.

[0112] The film and / or composition may be applied to cleaned or uncleaned (i.e., including oily or oiled) substrate surfaces. The film and / 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.

[0113] The present disclosure is also directed to a method of separating two substrates bonded by a coating formed from any of the compositions and / or films disclosed herein comprising heating the coating above the reflow onset temperature. As described above, an external energy source, such as heat, may be applied to the cured film and / or composition, which may reverse the crosslinking and allow for separation of the bonded substrates.

[0114] The compositions and / or films disclosed herein may be used to repair a joint upon failure or damage to the joint, wherein the bond between the two substrates, formed fromone of the compositions and / or films disclosed herein, 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, then cooling the assembly, as described herein above.Dielectric Coating Compositions, Dielectric Coatings, and Dielectric Kits

[0115] 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.

[0116] When used with respect to the dielectric coating 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.

[0117] 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.

[0118] As used herein, a “dielectric coating” refers to a 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 Hipot test, such as at least 12 kV / mm, such as at least 15 kV / mm.

[0119] As used herein, a “dielectric coating composition” refers to a coating composition that upon cure forms a dielectric coating.

[0120] 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.

[0121] The dielectric coating composition may optionally comprise a curing agent and / or crosslinker that can crosslink with the film-forming resin to cure the dielectric coating composition. Any suitable curing agent and / or crosslinker that can crosslink with the filmforming resin may be used. Examples of suitable curing agents include but are not limited to amines, aminoplasts, phenoplasts, polyisocyanates, including blocked polyisocyanates, polyepoxides, beta-hydroxyalkylamides, polyacids, organometallic acid-functional materials, polyamines, polyamides, polysulfides, polythiols, polyenes such as polyacrylates, polyols, and / or polysilanes and the like.

[0122] The dielectric coating composition may optionally further comprise a colorant, a pigment, an additive, and / or a filler. Suitable fillers that may be used in the dielectric coating composition include a TC / E1 filler, a TC / EC filler, and / or an NTC / E1 filler material, as described herein above.

[0123] The dielectric coating composition may comprise a thermoset coating composition, wherein the coating composition is cured upon crosslinking of a film-forming resin and a curing agent and / or crosslinker. Alternatively, the dielectric coating composition may comprise a thermoplastic coating composition, wherein the coating composition comprises a film-forming resin that cures upon evaporation of water and / or solvent. Alternatively, thedielectric coating composition may comprise a thermoset or thermoplastic coating composition that cures upon exposure to actinic radiation, such as ultraviolet light.

[0124] The dielectric coating composition may comprise a liquid coating composition or a powder coating composition.

[0125] A suitable liquid coating composition includes but is not limited to an electrodepositable coating composition, a one-component coating composition, and / or a multicomponent coating composition.

[0126] For example, the liquid dielectric coating composition may comprise an electrodepositable coating composition. The electrodepositable coating composition may comprise a cationic salt group-containing film-forming resin or an anionic salt group-containing film-forming resin that may be deposited onto a metal or other conductive substrate under the influence of an applied electrical potential, i.e., by electrodeposition.

[0127] In other examples, the liquid dielectric coating composition may comprise a UV-curable coating composition comprising a film-forming resin capable of curing upon exposure to UV radiation. Any suitable UV-curable film-forming resin may be used, such as a free radical polymerizable resin containing ethylenic unsaturation or an olefinic double bond and / or a film-forming resin 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.

[0128] 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 film-forming resin and the reactive curing agent and / or crosslinker are mixed just before application of the coating composition and may optionally cure under ambient conditions without any external energy source.

[0129] Alternatively, the dielectric coating composition may comprise a powder coating composition. “Powder coating composition” as used herein refers to any dielectric coating composition in the form of a co-reactable solid in particulate form which may be substantially free, essentially free, or completely free of water and / or solvent. Suitable film-forming resins useful in dielectric powder coating compositions include those discussed in PCT Publ. No. WO 2021 / 173941A1, pars.

[0006] to

[0042] ,

[0057] to

[0068] ,

[0088] to

[0105] and

[0128] to

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

[0130] 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 film, and / or by the use of a fluidized bed. Once applied to the substrate, the dielectric coating composition may be cured by any method known in the art, such as baking, induction heating, infrared heating, and / or exposure to actinic radiation such as UV.

[0131] A dielectric coating may be formed from the dielectric coating compositions described herein.

[0132] 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 / mm, 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 kVDC, Imax Limit 0.1 mA, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as no more than 100 kV / mm. The dielectric coating may comprise a dielectric strength of 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, 19 sec ramp, 20 sec dwell, 2 sec fall) according to ASTM D149-09, such as 12 kV / mm to 100 kV / mm, such as 15 kV / mm to 100 kV / mm.

[0133] The dielectric coating may be formulated as a hot-melt or a film. The film may optionally comprise an adhesive layer, such as a pressure sensitive adhesive layer.

[0134] Compositions of the present disclosure may be applied or deposited using any suitable method, including those discussed above. Using the methods provided by the present disclosure articles may be formed from one of the compositions disclosed herein.Use of the Compositions

[0135] The compositions disclosed herein demonstrate ambient conditions curability. The compositions disclosed herein are “cured” when they demonstrate a pull-off strength of at least 0.5 MPa at ambient conditions (measured by PATTI adhesion testing using a PosiTest AT-A automatic adhesion tester available from DeFelsko® at a pull rate of 4.0 MPa / s) and / or 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).

[0136] The coatings disclosed herein surprisingly may be used as structural adhesives. The coatings formed from the compositions or films disclosed herein demonstrate: (a) an average pull-off strength of no more than 1.8 MPa at 90°C as measured by PosiTest AT-A Automatic Adhesion Tester, available from DeFelsko; and / or (b) an average pull-off strength of at least 1.0 MPa at ambient conditions as measured by PosiTest AT-A Automatic Adhesion Tester, available from DeFelsko.

[0137] The compositions disclosed herein demonstrate reversible cure at an elevated temperature (i.e., a temperature greater than ambient temperature), such as at a temperature of at least 50°C, such as at least 60°C, such as at least 70°C, such as at least 80°C, such as at least 90°C. A composition is “reversibly curable” if a coating formed from the composition exhibits reversibility. A coating demonstrates “reversibility” at an elevated temperature if a joint (i.e., a bond between two substrates formed from the coating and an adhesive) demonstrates, at the elevated temperature, a reduction in pull-off strength of at least 50% and a failure mode of cohesive failure in coating or adhesive failure between adhesive and coating. As used herein, “pull-off strength” is measured using a universal testing machine at a pull rate of 4.0 MPa / s. As used herein, “cohesive failure in coating” means that the joint between the bonded substrates breaks in the coating formed from the compositions disclosed herein. As used herein, “adhesive failure between adhesive and coating” means that the joint between the bonded substrates breaks between the adhesive and the coating formed from one of the compositions disclosed herein. A schematic of failure modes in an assembly comprising a coating formed from one of the compositions disclosed herein and a thermally conductive adhesive can be found in FIG. 10.

[0138] Additionally, an article and / or coating formed from one of the compositions or films disclosed herein surprisingly exhibit high reprocessability, reshaping, and / or self-sealing.Substrates

[0139] Compositions described herein may be coated or deposited on, or otherwise contacted with, any substrate or surface, such as, but not limited to, a metal or metal alloy, a polymeric material, such as a plastic including a filled or unfilled thermoplastic or thermoset material, and / or a composite material. The substrate may comprise glass or a natural material 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, a metal alloy, and one or more composite materials.

[0140] Suitable substrates may include, but are not limited to, both flexible and rigid metal substrates such as a ferrous metal, aluminum, an aluminum alloy, magnesium, titanium, copper, and other metal and alloy substrates. The ferrous metal substrate may include, for example, iron, steel, and / or an alloy 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, and / or zinc-iron alloy such as galvanneal steel. An aluminum alloy, such as, for example, an aluminum alloy of the 1XXX, 2XXX, 3XXX, 4XXX, 5XXX, 6XXX, 7XXX, or 8XXX series as well as a clad aluminum alloy and a cast aluminum alloy, 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 EV31 A series, titanium and / or titanium alloys, such as those of grades 1-36 including H grade variants, copper and copper alloys, or other non-ferrous metals, as well as alloys of these materials. The substrate may comprise a composite material such as a plastic, fiberglass and / or carbon fiber composite.

[0141] 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. Patent No. 4,793,867, 3:5 to 5:8 and 5:64 to 11:50, incorporated herein by reference, and U.S. Patent No. 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. Patent No. 7,749,368, 1:55 to2:12 and 2:53-14:60, incorporated herein by reference, and U.S. Patent No. 8,673,091, 1:53 to 2:11, 3:26 to 15:45, and 16:51 to 18:26, incorporated herein by reference.

[0142] 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.

[0143] In examples, the substrate may be a multi-metal substrate. As used herein, the term “multi-metal substrate” refers to (1) a substrate that has one surface comprising a first metal and one surface comprising a second metal that is different from the first metal, (2) a first substrate that has one surface comprising a first metal and a second substrate that has one surface comprising a second metal that is different from the first metal, or (3) both (1) and (2).

[0144] The compositions disclosed herein may be used in various industrial or transportation applications including automotive applications, commercial applications, rail locomotive applications, marine applications, and / or aerospace applications. Suitable substrates for use in the present disclosure include those that are used in the assembly of vehicular bodies (for example, without limitation, door, body panel, trunk deck lid, roof panel, hood, roof, and / or stringers, rivets, landing gear components, and / or skins used on an aircraft), vehicular frames, vehicular parts, motorcycles, wheels, and industrial structures and components. As used herein, “vehicle” or variations thereof includes, but is not limited to, civilian vehicles, light and heavy commercial vehicles, civilian and military aircraft, and / or land vehicles such as cars, motorcycles, and / or trucks.

[0145] The present disclosure is further directed to a battery comprising a battery cell; a battery component in addition to the battery cell; and a coating or film formed from any of the compositions disclosed herein positioned between the battery cell and the battery component.

[0146] 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 composition disclosed herein, in a cured state, may be used to form a pad, an adhesive, a structural adhesive, a coating, a pottant 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, the composition disclosed herein also may be useful in battery assemblies including, but not limitedto, 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.

[0147] A battery assembly 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 busbars, battery management systems, battery thermal management systems, chargers, inverters and converters).

[0148] 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.

[0149] 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.

[0150] 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 dielectricinsulation 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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 100comprises a plurality of battery cells 10 and the battery pack 200 comprises a plurality of battery modules 100.

[0156] 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. A material, such as an adhesive, 9 formed from any of 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. A material, such as a pad 8 formed from one of the compositions disclosed herein in a cured state, may be positioned between cells 10 within a module 100.

[0157] 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).

[0158] In other cases, the battery cells may be arranged on or within an assembly 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.

[0159] 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.Definitions

[0160] 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.

[0161] 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.

[0162] 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.

[0163] As used herein, “including,” “containing” and like terms are understood in the context of this application to be synonymous with “comprising” and are therefore open-ended and do not exclude the presence of additional undescribed or unrecited elements, materials, ingredients or method steps. As used herein, “consisting of’ is understood in the context of this application to exclude the presence of any unspecified element, ingredient, or method step. As used herein, “consisting essentially of’ is understood in the context of this application to include the specified elements, materials, ingredients, or method steps “and those that do not materially affect the basic and novel characteristic(s)” of what is being described.

[0164] 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.

[0165] As used herein, the terms “on,” “onto,” “applied on,” “applied onto,” “formed on,” “deposited on,” “deposited onto,” and the like mean formed, overlaid, deposited, or provided on, but not necessarily in contact with, a substrate surface. For example, a composition “applied onto” a substrate surface does not preclude the presence of one or more other intervening coatings of the same or different composition located between the composition and the substrate surface.

[0166] As used herein, a “liquid” means a material having a viscosity less than 5,000 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.

[0167] As used herein, a “solid” means a material having a viscosity of at least 5,000 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.

[0168] 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.

[0169] As used herein, a “composition” or a “coating composition” refers to a solution, mixture, or a dispersion that can produce a coating on a substrate surface.

[0170] As used herein, the term “cure,” “curing,” and similar terms, means that the reactive components that form the composition interact, react, and / or are crosslinked to form a coating, a film, a bond, or an article. In the case of a 2K composition, the composition begins tocure when the components of the composition are mixed, resulting in the reaction of the reactive functional groups of the components of the composition and / or the physical interaction of the components of the composition.

[0171] As used herein, “curing” of a composition refers to subjecting the composition to conditions that result in cure of the composition.

[0172] The term “curable,” as used in connection with a coating composition, means that the composition can be cured under ambient and / or slightly thermal conditions.

[0173] As used herein, a “coating” refers to a cured coating composition.

[0174] As used herein, a “film” refers to a cured composition that forms a solid on a substrate and that may be delaminated from the substrate following cure.

[0175] As used herein, an “article” refers to the cured composition as a formed or fabricated solid.

[0176] As used herein, a “sealant composition” refers to a coating composition that forms a sealant in its cured state.

[0177] As used herein, a “sealant” refers to a coating or a film that can provide a protective barrier against moisture, chemicals, and other environmental factors, preventing corrosion and extending the lifespan of components.

[0178] As used herein, an “adhesive composition” refers to a coating composition that forms an adhesive in its cured state.

[0179] As used herein, an “adhesive” refers to a cured coating or a 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 D1002-10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute at room temperature.

[0180] As used herein, a “structural adhesive composition” refers to a coating composition that, in a cured state, produces a structural adhesive.

[0181] As used herein, a “structural adhesive” refers to a cured coating or a film that forms a load bearing joint having a lap shear strength of at least 5 MPa measured according to ASTM D1002-10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute at room temperature.

[0182] As used herein, a “gap filler composition” refers to a composition that forms a gap filler in its cured state.

[0183] As used herein, a “gap filler” refers to a coating that fills a gap between two substrates in order to eliminate air voids, such as filling a crack, a hole, or a butt joint. As used herein, “butt joint” refers to a joint formed by two surfaces abutting at right angles.

[0184] As used herein, a “pottant composition” refers to a composition that, when cured, forms a pottant.

[0185] As used herein, a “pottant” refers to an encapsulant.

[0186] As used herein, a “pre-preg” refers to a composition pre-impregnating reinforcement fibers prior to cure.

[0187] As used herein, “ambient conditions” generally refer to room temperature (e.g., 23°C), pressure (1 atm), and humidity conditions or temperature, pressure, 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” include temperatures that are slightly above ambient conditions, such as greater than 40°C to no more than 60°C.

[0188] 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.

[0189] As used herein, the term “urethane linkage” means a bond formed between two molecules forming the linkage — NHC(O)O —.

[0190] As used herein, a dash (“ — ”) that is not between two letters or symbols is used to indicate a point of bonding for a substituent or between two atoms. For example, — CONH2 refers to an amide functional group that is bonded to another chemical moiety through the carbon atom.

[0191] As used herein, “reprocessability” means that the composition can undergo 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 aprocess such as compression molding, extrusion, or the like (i.e., the material is recycled). The reprocessing may further comprise heating.

[0192] 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.

[0193] As used herein, “self-healing” means that a material can repair 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.

[0194] As used herein, “monosubstituted” refers to a compound or functional group in which one hydrogen is substituted by a different atom or functional group.

[0195] 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 or prepolymer backbone, or monosubstituted with respect to a monomer or non-polymerizable molecules.

[0196] As used herein, “backbone” when used with respect to a polymer refers to the longest series of covalently bound atoms, which forms the continuous chain of a polymer.

[0197] 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).”

[0198] As used herein, “prepolymer” refers to a molecule comprising a reaction product of two or more molecules that can be further polymerized or crosslinked.

[0199] As used herein, “polymer” refers to a molecule having more than one repeating unit and includes oligomers and homopolymers.

[0200] 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 not purposefully added to a mixture or composition, respectively, and 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.

[0201] In view of the foregoing description, the present disclosure relates to the following Aspects 1 to 91 without being limited thereto.Aspects

[0202] 1. A composition comprising:a first component comprising a furan-containing compound comprising (i) a furan functional group, (ii) an isocyanate functional group, and (iii) a urethane linkage;a second component comprising a dienophile-containing compound comprising a dienophile; anda polar organic solvent in an amount greater than 15% by weight based on total weight of the composition,wherein the polar organic solvent is not reactive with the furan-containing compound or the dienophile-containing compound at ambient conditions.

[0203] 2 The composition of aspect 1, wherein the polar organic solvent is present in the first component or the second component.

[0204] 3. The composition of aspect 1 or aspect 2, wherein the polar organic solvent is non-reactive with the furan-containing compound and the dienophile containing compound.

[0205] 4. The composition of any of the preceding aspects, wherein the polar organic solvent has a boiling point of no more than 180°C at 1 atm.

[0206] 5. The composition of any of the preceding aspects, wherein the polar organic solvent comprises a ketone, an ester, an amide, a nitrile, a haloalkane, a haloarene, an alcohol, and / or a nitroalkane functionality.

[0207] 6. The composition of any preceding aspect, comprising the polar organic solvent in an amount of at least 15% by weight based on total weight of the composition, such as at least 20% by weight.

[0208] 7. The composition of any preceding aspect, comprising the polar organic solvent in an amount of no more than 90% by weight based on total weight of the composition, such as no more than 85% by weight.

[0209] 8. The composition of any of aspects 1 to 5 or 7, comprising the solvent in an amount of greater than 15% by weight to 90% by weight based on total weight of the composition, such as 20% by weight to 85% by weight.

[0210] 9 The composition of any preceding aspect, wherein the urethane linkage is between the furan functional group and the isocyanate functional group.

[0211] 10. The composition of any preceding aspect, wherein the furan-containing compound comprises 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 allophonate moiety, a benzoguanamine moiety, an iminooxadiazinedione moiety, or a polymeric moiety different from the urethane linkage; and R2 comprises a substituted or unsubstituted alkyl group, an ester moiety, an ether moiety, and / or a urethane moiety.

[0212] 11. The composition of aspect 10, wherein R2 comprises one carbon.

[0213] 12. The composition of aspect 10 or aspect 11, wherein Ri comprises isocyanurate, allophonate, or iminooxadiazinedione, R2 comprises CH2, and X comprises O.

[0214] 13. The composition of any of aspects 10 to 12, wherein 1 < m < 12, 1 < n < 12, and / or 2 < m+n < 13.

[0215] 14. The composition of any of aspects 10 to 13, wherein m+n > 2.

[0216] 15. The composition of any preceding aspect, wherein the furan-containing compound is substantially free of an ether linkage.

[0217] 16. The composition of any preceding aspect, wherein the furan-containing compound comprises a monomer, a prepolymer, and / or a polymer.

[0218] 17. The composition of any preceding aspect, wherein the furan-containing compound comprises one furan functional group or two furan functional groups.

[0219] 18. The composition of any preceding aspect, wherein the furan-containing compound comprises three or more furan functional groups.

[0220] 19. The composition of any preceding aspect, wherein the furan-containing compound comprises a furan equivalent weight of at least 180 g / eq, such as at least 200 g / eq.

[0221] 20. The composition of any preceding aspect, wherein the furan-containing compound comprises a furan equivalent weight of no more than 1,000 g / eq, such as 800 g / eq.

[0222] 21. The composition of any preceding aspect, wherein the furan-containing compound comprises a furan equivalent weight of 180 g / eq to 1,000 g / eq, such as 200 g / eq to 800 g / eq.

[0223] 22. The composition of any preceding aspect, wherein the furan-containing compound has an isocyanate equivalent weight of at least 200 g / eq.

[0224] 23. The composition of any preceding aspect, wherein the furan-containing compound has an isocyanate equivalent weight of no more than 1,000 g / eq, such as 800 g / eq.

[0225] 24. The composition of any preceding aspect, wherein the furan-containing compound has an isocyanate equivalent weight of 200 g / eq to 1,000 g / eq, such as 200 g / eq to 800 g / eq.

[0226] 25. The composition of any preceding aspect, wherein the furan-containing compound comprises the furan functional group and the isocyanate functional group in a molar ratio of at least 0.15:1, such as at least 0.2:1.

[0227] 26. The composition of any preceding aspect, wherein the furan-containing compound comprises the furan functional group and the isocyanate functional group in a molar ratio of at least 0.3:1.

[0228] 27. The composition of any preceding aspect, wherein the furan-containing compound comprises the furan functional group and the isocyanate functional group in a molar ratio of no more than 5:1, such as no more than 4:1.

[0229] 28. The composition of any preceding aspect, wherein the furan-containing compound comprises the furan functional group and the isocyanate functional group in a molar ratio of no more than 2:1.

[0230] 29. The composition of any preceding aspect, wherein the furan-containing compound comprises the furan functional group and the isocyanate functional group in a molar ratio of 0.15:1 to 5:1, such as 0.2:1 to 4:1.

[0231] 30. The composition of any of aspects 1 to 24, 26, or 28, wherein the furan-containing compound comprises the furan functional group and the isocyanate functional group in a molar ratio of 0.3: 1 to 2: 1.

[0232] 31. The composition of any preceding aspect, wherein the furan-containing compound comprises a reaction product of reactants comprising:(a) a furan-containing reactant comprising a furan functional group and an active hydrogen-containing functional group; and(b) a polyisocyanate-containing reactant comprising an isocyanate functional group.

[0233] 32. The composition of aspect 31, wherein the active hydrogen-containing functional group comprises a hydroxyl functional group, an amine functional group, and / or a thiol functional group.

[0234] 33. The composition of aspect 31 or aspect 32, wherein the active hydrogencontaining functional group is present in a sub-stoichiometric amount of the isocyanate functional group.

[0235] 34. The composition of any of aspects 31 to 33, wherein the active hydrogencontaining functional group of the furan-containing reactant and the isocyanate functional group of the isocyanate-containing reactant are present in a molar ratio of less than 1:1, such as no more than 0.3:1.

[0236] 35. The composition of any of aspects 31 to 34, wherein the active hydrogencontaining functional group of the furan-containing reactant and the isocyanate functional group of the isocyanate-containing reactant are present in a molar ratio of no more than 0.25: 1, such as no more than 0.15:1.

[0237] 36. The composition of any of aspects 31 to 35, wherein the furan functional group of the furan-containing reactant is monosubstituted and / or terminal.

[0238] 37. The composition of any preceding aspect, wherein the furan functional group of the furan-containing compound and the dienophile of the dienophile-containing compound are present in a molar ratio of at least 0.5:1, such as at least 0.6:1.

[0239] 38. The composition of any preceding aspect, wherein the furan functional group of the furan-containing compound and the dienophile of the dienophile-containing compound are present in a molar ratio of no more than 2:1, such as no more than 1.5:1.

[0240] 39. The composition of any preceding aspect, wherein the furan functional group of the furan-containing compound and the dienophile of the dienophile-containing compound are present in a molar ratio of 0.5:1 to 2:1, such as 0.6:1 to 1.5:1.

[0241] 40. The composition of any preceding aspect, wherein the dienophile-containing compound has a dienophile equivalent weight of 150 g / eq to 800 g / eq.

[0242] 41. The composition of any preceding aspect, wherein the furan functional group of the furan-containing compound and the dienophile of the dienophile-containing compound are reactive under ambient conditions.

[0243] 42. The composition of any preceding aspect, wherein the composition further comprises a third compound, wherein the third compound is reactive with the isocyanate functional group of the furan-containing compound.

[0244] 43. The composition of aspect 42, wherein the third compound is present in the second component and / or the third component.

[0245] 44. The composition of aspect 42 or aspect 43, wherein the third compound comprises a hydroxyl functional group.

[0246] 45. The composition of aspect 44, wherein the third compound comprises a polyol.

[0247] 46. The composition of aspect 44 or aspect 45, wherein the isocyanate functional group on the furan-containing compound and the hydroxyl functional group on the third compound are present in a molar ratio of at least 0.2: 1, such as at least 0.4: 1.

[0248] 47. The composition of any of aspects 44 to 46, wherein the isocyanate functional group on the furan-containing compound and the hydroxyl functional group on the third compound are present in a molar ratio of no more than 3:1, such as no more than 2: 1.

[0249] 48. The composition of any of aspects 44 to 47, wherein the isocyanate functional group on the furan-containing compound and the hydroxyl functional group on the third compound are present in a molar ratio of 0.2: 1 to 3:1, such as 0.4:1 to 2:1.

[0250] 49. The composition of aspect 48, wherein the second furan-containing compound is present in the second component and / or the third component.

[0251] 50. The composition of aspect 48 or aspect 49, wherein the second furan-containing compound has a furan equivalent weight of at least 68 g / eq, such as at least 80 g / eq.

[0252] 51. The composition of any of aspects 48 to 50, wherein the second furan-containing compound has a furan equivalent weight of no more than 1,500 g / eq, such as no more than 1,000 g / eq.

[0253] 52. The composition of any of aspects 48 to 51, wherein the second furan-containing compound has a furan equivalent weight of 68 g / eq to 1,500 g / eq, such as 80 g / eq to 1,000 g / eq.

[0254] 53. The composition of any preceding aspect, further comprising a filler, such as a thermally conductive filler, a thermally expandable material, a blowing agent, an additive, elastomeric particles, and / or an accelerator.

[0255] 54. The composition of aspect 53, wherein the filler is present in the first component, the second component, and / or the third component.

[0256] 55. The composition of aspect 53 or aspect 54, wherein the composition comprises the filler in an amount of at least 1% by volume based on total solids volume of the composition, such as at least 5% by volume.

[0257] 56. The composition of any of aspects 53 to 55, wherein the composition comprises the filler in an amount of at least 40% by volume based on total solids volume of the composition.

[0258] 57. The composition of any of aspects 53 to 56, wherein the composition comprises the filler in an amount of no more than 90% by volume based on total solids volume of the composition, such as no more than 85% by volume.

[0259] 58. The composition of any of aspects 53, 54, or 57, wherein the composition comprises the filler in an amount of no more than 20% by volume based on total solids volume of the composition.

[0260] 59. The composition of any of aspects 53 to 55 or 57, wherein the composition comprises the filler in an amount of 1% by volume to 90% by volume based on total solids volume of the composition such as 40% by volume to 85% by volume.

[0261] 60. The composition of any of aspects 53, 54, 57, or 58, wherein the composition comprises the filler in an amount of 5% by volume to 20% by volume based on total solids volume of the composition.

[0262] 61. The composition of any of aspects 53 to 60, wherein the composition comprises the thermally expandable material in an amount of at least 0.5% by weight based on total weight of the composition, such as at least 1% by weight.

[0263] 62. The composition of any of aspects 53 to 61, wherein the composition comprises the thermally expandable material in an amount of no more than 20% by weight based on total weight of the composition, such as no more than 10% by weight.

[0264] 63. The composition of any of aspects 53 to 62, wherein the composition comprises the thermally expandable material in an amount of 0.5% by weight to 20% by weight based on total weight of the composition, such as 1% by weight to 10% by weight.

[0265] 64. The composition of any of aspects 53 to 63, wherein the blowing agent is present in an amount of at least 0.5% by weight based on total weight of the composition, such as at least 1% by weight.

[0266] 65. The composition of any of aspects 53 to 64, wherein the blowing agent is present in an amount of no more than 20% by weight based on total weight of the composition, such as no more than 10% by weight.

[0267] 66. The composition of any of aspects 53 to 65, wherein the blowing agent is present in an amount of 0.5% by weight to 20% by weight based on total weight of the composition, such as 1% by weight to 10% by weight.

[0268] 67. The composition of any of aspects 53 to 66, wherein the composition comprises the additive in a combined amount of at least 0.01% by weight based on total weight of the composition, such as at least 0.1% by weight.

[0269] 68. The composition of any of aspects 53 to 67, wherein the composition comprises the additive in a combined amount of no more than 15% by weight based on total weight of the composition, such as no more than 10% by weight.

[0270] 69. The composition of any of aspects 53 to 68, wherein the composition comprises the additive in a combined 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.

[0271] 70. The composition of any of aspects 53 to 69, 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.

[0272] 71. The composition of any of aspects 53 to 70, comprising the elastomeric particles in an amount of no more than 35% by weight based on total weight of the composition, such as no more than 20% by weight.

[0273] 72. The composition of any of aspects 53 to 71, comprising the elastomeric particles in an amount of 0.1% by weight to 35% by weight based on total weight of the composition, such as 1% by weight to 20% by weight.

[0274] 73. The composition of any of aspects 53 to 72, 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.

[0275] 74. The composition of any of aspects 53 to 73, comprising the accelerator in an amount of no more than 5% by weight based on total weight of the composition, such as no more than 2% by weight.

[0276] 75. The composition of any of aspects 53 to 74, comprising the accelerator in an amount of 0.001% by weight to 5% by weight based on total weight of the composition, such as 0.01% by weight to 2% by weight.

[0277] 76. The composition of any of the preceding aspects, wherein the first component and the second component are liquid at ambient conditions, are mixable at ambient conditions, and / or are curable at ambient conditions.

[0278] 77. The composition of any of the preceding aspects, wherein the composition is substantially free, essentially free, or completely free of an oxanorbornene moiety before mixing the first component and the second component.

[0279] 78. A substrate comprising a surface coated with or embedded in the composition of any of the preceding aspects.

[0280] 79. The coating of aspect 78, wherein the coating has:an average pull-off strength of no more than 1.8 MPa at 90°C as measured using a hydraulic pull-off adhesion tester; and / oran average pull-off strength of at least 1.0 MPa at ambient conditions as measured using a hydraulic pull-off adhesion tester.

[0281] 80. The coating of aspect 78 or aspect 79, wherein the coating is reversibly curable.

[0282] 81. A film formed from the composition of any of aspects 1 to 77.

[0283] 82. The film of aspect 81, wherein the film is reversibly curable.

[0284] 83. A kit comprising:the composition of any of aspects 1 to 77; anda thermally conductive adhesive composition.

[0285] 84. A battery comprising:a battery cell;a battery component; anda coating of any of aspects 78 to 80 positioned between the battery cell and the battery component.

[0286] 85. A substrate comprising:an adhesive; anda reversible coating formed on the adhesive, wherein the reversible coating is formed from the composition of any of aspects 1 to 77.

[0287] 86. The substrate of aspect 85, wherein the adhesive coating is a thermally conductive adhesive.

[0288] 87. The substrate of aspect 85 or aspect 86, further comprising a dielectric coating formed on a portion of the reversible coating.

[0289] 88. A method of separating two substrates bonded by a coating formed from the composition of any of aspects 1 to 77, comprising heating the coating above a reflow onset temperature of the coating and separating the substrates.

[0290] 89. A use of the composition of any of aspects 1 to 77 to form a coating comprising:an average pull-off strength of no more than 1.8 MPa at 90°C; and / oran average pull-off strength of at least 1.0 MPa at ambient conditions,wherein pull-off strength is measured using a hydraulic pull-off adhesion tester.

[0291] 90. A use of the composition of any of aspects 1 to 77 to form a reversibly curable coating.

[0292] 91. A use of the composition of any of aspects 1 to 77 to form a reversibly curable film.

[0293] Illustrating the disclosed subject matter are the following examples that are not to be considered as limiting the disclosure to their details.ExamplesSynthesis Example ATable 1: Synthesis of Monofuran / Bisisocyanate Functional PolymerIngredients Parts by weightPart 1Desmodur N39001482.8Dibutyl tin dilaurate20.299Part 2Furfuryl Alcohol387.4AnalyticIsocyanate Equivalent Weight 318.00 g / eqFuran Equivalent Weight (theoretical) 603.00 g / eq1An aliphatic polyisocyanate resin based on hexamethylene diisocyanate trimer commercially available from Covestro2Commercially available from Evonik Industries3Commercially available from Sigma Aldrich

[0294] Part #1 was added to a 1000-milliliter, 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. Part #2 was then added to the flask 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 as determined by titration. Then, the reaction mixture was allowed to cool to 40°C and poured into an appropriately sized container with an N2 blanket.

[0295] The isocyanate equivalent weight was determined by titration of a sample of the polymer using a Metrohm 808 or 888 Titrando, using a sample of 1 g per 420 g / eq of predicted NCO equivalent weight and dissolving the sample in 30 mL of a solution comprising 20 m of dibutylamine and 980 mL of n-methyl pyrrolidone, followed by titration with 0.2 N HC1 solution in isopropanol titration agent. The theoretical furan equivalent weight was determined by dividing the theoretical molecular weight of the furfuryl alcohol by the theoretical number of furan functional groups.Synthesis Example BTable 2: Synthesis of Bisfuran / Monoisocyanate polymerIngredients Parts by weightPart 1Desmodur N3900 483.1Dibutyltin dilaurate 0.34Part 2Furfuryl Alcohol 177.7AnalyticTotal 661.1Furan Equivalent Weight (theoretical) 365.0 g / eqIsocyanate Equivalent Weight 750.0 g / eq

[0296] Part #1 was added to a 1000-milliliter, 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 mixture was heated to 60°C. At 60°C, Part #2 was then added to the flask at a rate such that the temperature of the mixture did not exceed 80°C. After all the furfuryl alcohol was added, the reaction mixture was held at 80°C until the isocyanate equivalent weight was stalled as determined by titration as set forth in Synthesis Example A.Synthesis Example CTable 3: Synthesis of Trifunctional Furan PolymerIngredients Parts by weightPart 1Desmodur N3900 402.3Dibutyl tin dilaurate 0.31Part 2Furfuryl Alcohol 220.8AnalyticFuran Equivalent Weight (theoretical) 277 g / eq

[0297] Part #1 was added to a 1000-milliliter, 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 heat to 60°C. Part #2 was then added to the flask at a rate such that the temperature of the mixture did not exceed 80°C. After Part #2 was added, the reaction mixture was held at 80°C until IR spectroscopy showed the absence of the characteristic NCO band (2269 cm'1) using a Thermo Scientific Nicolet iS5 FT-IR. The reaction mixture was then cooled to 40°C and poured into an appropriately sized container with an N2 blanket. The theoretical furan equivalent weight was calculated as set forth in Synthesis Example A.Synthesis Example DTable 4: Synthesis of Unsaturated Polyester Dienophile PrepolymerIngredients Parts by weightPart 1Dipropylene glycol1134.17Maleic Anhydride2130.75IONOL30.70Monobutyltin oxide40.13Part 22-ethylhexyl glycidyl ether5127.3AnalyticHydroxyl Equivalent Weight (measured) 453.50 g / eqDienophile Equivalent Weight (Theoretical) 302.00 g / eq1Commercially available from Sigma Aldrich2Commercially available from TCI America32,6-di-tert-Butyl-4-methylphenol commercially available from Sasol Chemicals (USA) LLC4Commercially available from ARKEMA INC5Commercially available from Negase America LLC

[0298] Part #1 was added to a 1000-milliliter, 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, measured by titration using a Metrohm 888 Titrando with 0.1 N KOH solution in methanol as the titration reagent. Then, the mixture was cooled to 120°C before Part #2 was added. The mixture was heated to 140°C andheld at that temperature until the acid value measured less than 2. The mixture was then cooled to 80°C and poured into an appropriately sized container.Preparation and Testing of Coatings

[0299] The experimental compositions for Examples 1 to 6 were prepared using the materials and quantities listed in Tables 5-9.

[0300] 4” x 4” 2024 aluminum panels (0.063” thick) were used in Examples 1 to 5 and 4” x 4” 5005 aluminum panels (0.032” thick) pretreated with a UV-curable dielectric coating composition (Envirocron® PCF 10103-US, commercially available from PPG Industries, Inc.) were used in Example 6. All testing panels were prepared by solvent-wiping with a methyl ethyl ketone (MEK) solvent-wipe and deoxidizing with ChemDeox® (commercially available from PPG Industries, Inc.) at 37.8°C for 1 minute.

[0301] Part A and Part B of each composition were formed by blending the components in the reported amounts and mixing for 2 minutes at 2200 RPM using a Dual-Asymmetric Mixer (SpeedMixer®). Next, the corresponding Parts A and B were combined and subsequently mixed using a spatula for 10-20 seconds to form the composition. The composition was then applied in duplicate to separate pretreated 4” x 4” 2024 aluminum panels via a single foam brushstroke, allowing the final film thickness to be dictated by the dilution of the respective composition. The coatings were cured at 25°C and 40% relative humidity in a Cincinnati Sub-Zero ZPH-16-3.503.5-SC / AC environmental chamber for at least 24 hours.

[0302] 20 mm aluminum dollies for PosiTest AT Adhesion Testers (commercially available from DeFelsko®) were prepared by the solvent-wipe and deoxidation process described above. The aluminum dollies were then adhered on top of the coating using a thermally conductive adhesive (“TCA”) (Coratherm® 4180, commercially available from PPG Industries, Inc.) applied at a coating thickness of 20 mils. The thermally conductive adhesive was cured at 25°C and 40% relative humidity in a Cincinnati Sub-Zero ZPH-16-3.503.5-SC / AC environmental chamber for at least one week. The comparative example was prepared by adhering dollies as described above directly to pretreated aluminum panels.

[0303] PATTI adhesion testing was performed with a PosiTest AT-A automatic adhesion tester available from DeFelsko® at a pull rate of 4.0 MPa / s. To perform pull-off testing at 60°C or 90°C, a hot plate was equilibrated to 60°C or 90°C, respectively. The panel containing the coating, adhesive, and pull-off dollies was then placed onto the surface of the hot plate andallowed to equilibrate for five minutes. If the dollies slid off without an applied lateral force, a value of zero was recorded. For those dollies that remained adhered to the surface, a Teflon liner was placed around the dolly, and a pull-off value was recorded. “N / T” means that a value was not tested.

[0304] Film builds were tested using a Fisher Technology, Inc. FISCHERSCOPE MMS Permascope measuring system. Dry film build was recorded in three locations across the 4” x 4” aluminum panel and averaged to yield the reported values.

[0305] The A Pull-Off Strength of a coating was calculated by subtracting the pull-off strength measured at ambient conditions from the pull-off strength measured at 90°C. The Percent Reduction in Pull-Off Strength was calculated by dividing the A Pull-Off Strength by the pull-off strength measured at ambient conditions and multiplying by 100. The failure mode was also recorded. FIG. 10 provides a legend of the failure modes under which the examples were categorized.Example 1Table 5: Compositions and Test Results for Compositions 1-Ato 1-D and Comparative Comp Comp Comp Comp Comparative (TCA Direct to 1-A 1-B 1-C 1-DMetal)(g)(g) (g) (g)(g)Part AMonofuran / Bisisocyanate 2.50 2.50 2.50 2.50 0Polymer (SynthesisExample A)Trifunctional Furan 2.75 2.75 2.75 2.75 0Polymer (SynthesisExample C)SolventAcetone12.45 0 0 0 0Butyl Acetate20 2.45 0 0 0Heptane30 0 2.45 0 0Deionized Water 0 0 0 2.45 0Part BUnsaturated Polyester 3.25 3.25 3.25 3.25 0Dienophile Prepolymer(Synthesis Example D)SolventAcetone11.20 0 0 0 0Butyl Acetate20 1.20 0 0 0Heptane30 0 1.20 0 0Deionized Water 0 0 0 1.20 0ResultsPull-off Strength at Ambient 4.73 5.62 Failure to Failure to 4.9 Conditions (MPa) Mix MixFailure Mode (at Ambient Cohesive Cohesive N / T N / T Cohesive failure in Conditions) failure in failure in TCATCA TCAPull-off Strength at 90°C 1.0 1.18 Failure to Failure to 2.7(MPa) Mix MixFailure Mode (at 90°C) Cohesive Cohesive N / T N / T Cohesive failure in failure in failure in TCACoating CoatingA Pull-off Strength (MPa) -3.7 -4.44 N / T N / T -2.2Percent Reduction in Pull- 78% 79% N / T N / T 45%off Strength1Commercially available from Millipore Sigma2Commercially available from Millipore Sigma3Commercially available from Millipore Sigma

[0306] The data in Table 5 demonstrate that both Composition 1-A comprising acetone (a ketone solvent) and Composition 1-B comprising butyl acetate (an ester solvent) mixed well. The coatings prepared therefrom provided 4.73 MPa and 5.62 MPa of pull-off strength at ambient conditions, respectively, while demonstrating a 78% and 79% reduction in pull-off strength at 90°C (i.e., reversibility of the bond between substrates). In contrast, Composition 1-C comprising heptane and Composition 1-D comprising deionized water could not be mixed due tolack of incorporation of the resins into the respective solvent. These data demonstrate that using an organic polar solvent in the composition provided the desired mechanical performance, while compositions comprising a nonpolar organic solvent or water are not mixable with the resin system. Furthermore, the comparative sample (TCA directly applied to metal) demonstrated similar strength to Compositions 1-A and 1-B at ambient conditions, but still possessed a pull-off strength of 2.7 MPa (a 45% reduction in pull-off strength) at 90°C. Therefore, the comparative did not exhibit reversibility.Example 2Table 6: Compositions and Test Results for Compositions 2-Ato 2-F and Comparative Comp Comp Comp Comp Comp Comp Comparat ive (TCA 2-A 2-B 2-C 2-D 2-E 2-FDirect to (g)(g) (g) (g) (g) (g) Metal) (g) Part AMonofuran / Bisisocyanate 2.50 2.50 2.50 2.50 2.50 1.25 0 Polymer (SynthesisExample A)Trifunctional Furan 2.75 2.75 2.75 2.75 2.75 1.38 0 Polymer (SynthesisExample C)SolventAcetone 0 0.70 1.50 2.45 10.00 18.75 0’art BUnsaturated Polyester 3.25 3.25 3.25 3.25 3.25 1.63 0 Dienophile Prepolymer(Synthesis Example D)SolventAcetone 0 0.25 0.63 1.20 2.75 5.50 0ResultsSolvent Loading (wt %) 0 10 20 30 60 85 0Pull-off Strength at Failure to Failure to 5 4.73 5.7 4.9 4.9 Ambient Conditions Mix Mix(MPa)Failure Mode (Ambient) N / T N / T Cohesive Cohesive Cohesive Cohesive Cohesive failure in failure in failure in failure in failure in TCA TCA TCA TCA TCAPull-off Strength at 60°C Failure to Failure to 2.92 1.10 3.6 3.2 3.2 (MPa) Mix MixFailure Mode (60°C) N / T N / T Cohesive Cohesive Cohesive Cohesive Cohesive failure in failure in failure in failure in failure in Coating Coating Coating TCA TCA Pull-off Strength at 90°C Failure to Failure to 0.22 1.0 0.81 1.8 2.7 (MPa) Mix MixFailure Mode (90°C) N / T N / T Adhesive Cohesive Adhesive Adhesive Cohesive failure failure in failure failure failure in between Coating between between TCA TCA and TCA and TCA and Coating Coating CoatingA Pull-off Strength (MPa) N / T N / T -5 -3.7 -4.94 -4.7 -2.2 Percent Reduction in N / T N / T 100% 78% 87% 96% 45% Pull-off StrengthDry Film Build (mil) N / T N / T 2.6 2.2 0.76 0.20 N / T

[0307] The results displayed in Table 6 demonstrate the variety of film builds attainable by using varying amounts of solvent. The solvent loading in Compositions 2-A through 2-F increased from 0% by weight in Composition 2-A to 85% by weight in Composition 2-F. As solvent loading is increased, film build is decreased. Parts A and B of Compositions 2-A and 2-B were too viscous and not mixable. Coatings formed from Compositions 2-C to 2-F demonstrated pull-off strengths at ambient conditions between 4.73 MPa and 5.7 MPa at film thicknesses ranging from 0.20 mil to 2.6 mil, as reported in Table 6. Additionally, reversibility of the adhesive was demonstrated by substrates treated with one of Compositions 2-C to 2-F, with reductions in pull-off strength at 90°C ranging from 78% to 100%. In contrast, thecomparative maintained a pull-off strength of 2.7 MPa at 90°C (only a 45% reduction in pull-off strength). Therefore, the comparative did not demonstrate reversibility.Example 3Table 7: Compositions and Test Results for Compositions 3 -A to 3-C and Comparative Comp Comp Comp Comparative (Direct to Metal) 3-A 3-B 3-C (g)(g)(g) (g)Part ABisfuran / Monoisocyanate 4.00 1.00 0 0Polymer (SynthesisExample A)Monofuran / Bisisocyanate 0 0 2.50 0(Synthesis Example B)Trifunctional Furan 0 3.00 2.75 0Polymer (SynthesisExample C)SolventAcetone 2.25 2.25 2.45 0Part BBMI-68911.25 2.85 0 0Unsaturated Polyester 2.75 0.68 3.25 0Dienophile Prepolymer(Synthesis Example D)SolventAcetone 1.20 1.00 1.20 0ResultsAverage Furan 313.0 390.0 504.8 0Equivalent Weight (g / eq)Pull-off Strength at 5.4 5.8 4.73 4.9Ambient Conditions(MPa)Failure Mode (Ambient) Cohesive Cohesive Cohesive Cohesive failure in TCA failure in failure in failure inTCA TCA TCAPull-off Strength at 90°C 1.12 1.50 1.0 2.7(MPa)Failure Mode (90°C) Adhesive Adhesive Cohesive Cohesive failure in TCA failure failure failure inbetween between CoatingTCA and TCA andCoating CoatingA Pull-off Strength (MPa) -4.3 -4.3 -3.7 -2.2Percent Reduction in 80% 74% 78% 45%Pull-off Strength1Abismaleimide commercially available from Designer Molecules

[0308] The results in Table 7 demonstrate that coatings prepared from one of Compositions 3 -A to 3-C demonstrated reversibility across a range of average furan equivalent weights of the furan-containing compound. The amount of the maleimide-containing compound (BMI-689) was varied across the compositions to maintain a stoichiometric ratio of furan functionality and maleimide functionality in the compositions. Coatings prepared by Compositions 3-A to 3-C demonstrated a pull-of strength of 5.4 MPa, 5.8 MPa, and 4.73 MPa at ambient conditions, respectively. The pull-off strength of the coatings formed from Compositions 3-A to 3-C demonstrated a percent reduction in pull-off strength at 90°C of 80%, 74%, 78%, respectively, and thus all demonstrated reversibility. In contrast, the comparative coating only demonstrated only a 45% reduction in pull-off strength at 90°C and thus did not demonstrate reversibility.Example 4Table 8: Compositions and Test Results for Compositions 4-Ato 4-C and Comparative Comp Comp Comp Comparative (Direct to Metal)4-B 4-C (g)4-A (g) (g)(g)Part AMonofuran / Bisisocyanate 2.50 2.50 1.00 0Polymer (SynthesisExample A)Trifunctional Furan 2.75 4.20 5.00 0Polymer (SynthesisExample C)SolventAcetone 2.45 3.50 3.00 0Part BBMI-140010 3.00 8.00 0Unsaturated Polyester 3.25 3.25 1.30 0Dienophile Prepolymer(Synthesis Example D)SolventAcetone 1.20 2.05 3.50 0ResultsAverage Dienophile 302.0 568.6 779.8 0Equivalent Weight(g / mol)Pull-off Strength at 4.73 4 5.1 4.9Ambient Conditions(MPa)Failure Mode (at Cohesive Cohesive Cohesive Cohesive failure in TCA Ambient) failure in failure in failure inTCA TCA TCAPull-off Strength at 90°C 1.0 0.49 0.17 2.7(MPa)Failure Mode (at 90°C) Cohesive Cohesive Cohesive Cohesive failure in TCA failure in failure in failure inCoating Coating CoatingA Pull-off Strength (MPa) -3.7 -3.5 -4.9 -2.2Percent Reduction in 78% 88% 96% 45%Pull-off Strength1Abismaleimide commercially available from Designer Molecules

[0309] The results displayed in Table 8 demonstrate that coatings prepared from one of Compositions 4-A to 4-C, having a range of maleimide (dienophile) equivalent weights of the dienophile-containing compound all demonstrated reversibility. The coatings prepared from one of Examples 4-A to 4-C demonstrated pull-off strength at ambient conditions close to that of the comparative while also demonstrating reversibility at 90°C, with percent reductions in pull-off strengths at 90°C of 78%, 88%, and 96%, respectively. In contrast, the direct-to-metal comparative demonstrated a reduction in pull-off strength of 45% when heated to 90°C, indicating no reversibility. These data demonstrate that the average equivalent weight of the dienophile may be tuned to achieve desirable mechanical properties while maintaining reversibility.Example 5Table 9: Compositions and Test Results for Compositions 5-Ato 5-F and ComparativeComp Comp Comp Comp Comp Comp Comp Comp Comparati 5-A 5-B 5-C 5-D 5-E 5-F 5-G 5-H ve (Direct (g) (g) (g) (g) (g) (g) (g) (g) to Metal)(g) Part AMonofuran / Bisisocyanate 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 0 Polymer (SynthesisExample A)Trifunctional Furan 10.00 7.25 4.25 2.75 1.85 1.25 0.83 1.00 0 Polymer (SynthesisExample C)SolventAcetone15.00 4.40 3.10 2.45 2.05 1.80 1.65 1.00 0Part BUnsaturated Polyester 0.0 3.25 3.25 3.25 3.25 3.25 3.25 0.0 0 Dienophile Prepolymer(Synthesis Example D)BMI-68922.40 0.0 0.0 0.0 0.0 0.0 0.0 5.80 0 PolyTHF-25030.70 0.0 0.0 0.0 0.0 0.0 0.0 0.70 0SolventAcetone11.80 1.20 1.20 1.20 1.20 1.20 1.20 3.30 0Table 9: Compositions and Test Results for Compositions 5-Ato 5-F and Comparative (continued)Comp Comp Comp Comp Comp Comp Comp Comp Comparati 5-A 5-B 5-C 5-D 5-E 5-F 5-G 5-H ve (Direct (g) (g) (g) (g) (g) (g) (g) (g) to Metal)(g) ResultsDienophile: Diene 0.25 0.50 0.75 1.00 1.25 1.50 1.75 3.0 0 Molar RatioPull-off Strength at 4.0 4.76 5.7 4.73 5.35 5.6 5.3 4.5 4.9 Ambient Conditions(MPa)Failure Mode (Ambient) Cohesive Cohesive Cohesive Cohesive Cohesive Cohesive Cohesive Cohesive Cohesive failure in failure in failure in failure in failure in failure in failure in failure in failure in Coating TCA TCA TCA TCA TCA TCA Coating TCA Pull-off Strength at 90°C 0.36 0.5 0.8 1.0 1.12 1.7 1.8 0.45 2.7 (MPa)Failure Mode (90°C) Cohesive Adhesive Adhesive Cohesive Adhesive Adhesive Adhesive Cohesive Cohesive failure in failure failure failure in failure failure failure failure in failure in Coating between between Coating between between between Coating TCA TCA and TCA and TCA and TCA and TCA andCoating Coating Coating Coating CoatingΔ Pull-off Strength (MPa) -3.6 -4.3 -4.9 -3.7 -4.2 -3.9 -3.5 -4.1 -2.2 Percent Reduction in 90% 90% 86% 78% 79% 70% 66% 77% 45%Pull-off Strength

[0310] The results displayed in Table 9 provide measured mechanical properties of compositions containing a range of stoichiometry between the diene (the furan-containing compound) and dienophile (the maleimide-containing compound) in the coating system.Coatings prepared from one of Compositions 5-A to 5-H demonstrated pull-off strengths at ambient conditions ranging from 4.0 MPa to 5.7 MPa, while demonstrating pull-off strengths at 90°C of 1.8 MPa or less, with a percent reduction in pull-off strength ranging from 66% to 90%. Therefore, the experimental Compositions 5-A to 5-H all demonstrated reversibility. In contrast, the comparative direct-to-metal demonstrated a pull-off strength of 4.9 MPa and maintained a pull-off strength of 2.7 MPa (a 45% reduction in pull-off strength), thus not demonstrating reversibility.Example 6

[0311] The samples for Example 6 were prepared as set forth above and the pull-off strength of each sample was measured as set forth above at ambient conditions, 60°C, and 90°C. The pull-off strength and failure mode were recorded in Table 10. The A Pull-off Strength and Percent Reduction in Pull-off Strength were calculated as set forth above and recorded in Table 10.Table 10: Compositions and Test Results for Composition 6-A and Comparative Composition 6-A Comparative (Direct to(g) Dielectric Coating)(g)Part AMonofuran / Bisisocyanate 2.50 —Polymer (SynthesisExample A)Trifunctional Furan 2.75 —Polymer (SynthesisExample C)SolventAcetone 2.45 —Part BUnsaturated Polyester 3.25 —Dienophile Prepolymer(Synthesis Example D)SolventAcetone 1.20 —ResultsPull-off Strength at 1.02 2.53Ambient Conditions(MPa)Failure Mode (at Cohesive failure in Coating Adhesive failure between Ambient) dielectric and substratePull-off Strength at 60°C 0.31 1.7(MPa)Failure Mode (at 60°C) Cohesive failure in Coating Cohesive failure in TCAPull-off Strength at 90°C 0 1.08(MPa)Failure Mode (at 90°C) Cohesive failure in Coating Cohesive failure in TCAΔ Pull-off Strength (MPa) -1.02 -1.45Percent Reduction in 100% 57%Pull-off Strength

[0312] The results displayed in Table 10 demonstrate compatibility of the coating system with a dielectric coating. The coating prepared from Composition 6-A demonstrated a pull -off strength of 1.02 MPa at ambient conditions and a pull-off strength of 0 MPa (a 100% reduction in pull-off strength) at 90°C, demonstrating reversibility. In contrast, the comparative, in which the dollies were adhered directly to the dielectric coating with the thermally conductive adhesive, demonstrated only a 57% reduction in pull-off strength when heated from ambient conditions to 90°C, and thus did not demonstrate reversibility.Example 7

[0313] Compositions 7-A to 7-D were prepared using the materials and quantities listed in Table 11 and the methods set forth above. 4” x 6” 2024 aluminum panels were prepared as set forth above. The respective composition was then brushed and drawn down (at 5 Mil thickness) onto separate pretreated 4” x 6” 2024 aluminum panels. The coatings were cured at 25°C and 40% relative humidity in a Cincinnati Sub-Zero ZPH-16-3.503.5-SC / AC environmental chamber for at least 24 hours. After curing, aluminum dollies for PosiTest AT Adhesion Tests (from DeFelsko®) were adhered on top of the coating using a thermally conductive adhesive (Coratherm® 4180, commercially available from PPG Industries, Inc.) applied at 10 Mil thickness. Prior to adhesive application, the dollies were prepared by abrading the bonding surface with 50-grit sandpaper, followed by the solvent wipe and deoxidation process described above. The thermally conductive adhesive cured at 25 °C and 40% relative humidity in a Cincinnati Sub-Zero ZPH-16-3.503.5-SC / AC environmental chamber for at least one week.

[0314] The comparative composition was a dielectric powder not formulated to be reversible (Envirocron® PCF 10103-US, commercially available from PPG Industries). The comparative composition was prepared according to the manufacturer’s instructions, then spray-applied to a bare 3003 alloy aluminum panel. The comparative coating was formed in a two-layer process by spray-applying a coating having a target thickness of 4 mils, gelling the coating at 191°C for 3 minutes, applying a second coating having a target thickness of 4 mils onto the initial coating, and then curing at 191°C for 10 minutes, resulting in a final coating thickness of 7.1 mils. Dollies were bonded to the comparative coating surface using the thermally conductive adhesive and methods as described above.

[0315] Pull-off testing was performed with a PosiTest AT -A automatic adhesion tester available from DeFelsko. To perform pull-off testing at 90°C, a hot plate holding an Erlenmeyer flask of deionized water was equilibrated to 90°C indicated by an internal thermocouple. The panel containing the coating, adhesive, and pull-off dollies was then placed onto the surface of the hot plate and allowed to equilibrate for five minutes. If the dollies slid off with an applied lateral force, a value of zero was recorded. For those dollies that remained adhered to the surface, a Teflon liner was placed around the dolly, and a pull-off value was recorded as described above. The results are provided in Table 11.Table 11: Compositions and Test Results for Compositions 7A-7D and Comparative Comp Comp Comp Comp 7-D ENVIROCRON PCF 10103 7-A 7-B 7-C (g) (Comparative)(g) (g) (g) (g)Part AFuran / Isocyanate 3.53 2.40 1.97 1.34 —Functional Polymer(Synthesis Example A)Multifunctional Furan 3.80 2.66 3.16 3.67 —Polymer (SynthesisExample B)SolventAcetone 0 0.87 0.97 1.07 —Butyl Acetate 1.25 0 0 0 —Part BBMI-689 0 0 0.85 1.78Unsaturated Polyester 4.59 3.13 2.54 1.78Prepolymer (SynthesisExample C)SolventAcetone 0 0.93 0.51 0.36 —Butyl Acetate 1.83 0 0 0 —ResultsPull-off Strength at 5.7 5.6 5.0 6.95 (no 2.9Ambient Conditions duplicate)(MPa)Pull-off Strength at 90 °C 0.3 0.3 0 0 0.6(MPa)A Pull-off Strength (MPa) -5.4 -5.3 -5.0 -6.95 -2.3Percent Reduction in 95% 95% 100% 100% 79%Pull-off Strength

[0316] Coatings prepared from one of Compositions 7-A to 7-D all demonstrated reversibility, with percent reductions in pull-off strength of 95% to 100% when heated from ambient conditions to 90°C. These data demonstrate that reversibility may be achieved with varying levels of isocyanate functionality in Part A and different functionalities of the dienophile in Part B. Furthermore, Composition 7-A was prepared with butyl acetate and compositions 7-B to 7-D were prepared with acetone. Coatings prepared from one of the four compositions, respectively, demonstrated the desired reversible performance, exemplifying that different polar organic solvents may be used in the compositions. The coating prepared from the comparative composition demonstrated a pull-off strength of 2.9 MPa at ambient conditions, which was lower than the pull-off strength at ambient conditions demonstrated by Compositions 7-A to 7-D.Example 8Table 12: Compositions and Test Results for Compositions 8-A to 8-E and Comparative Comp Comp Comp Comp Comp Comparative 8-A 8-B 8-C 8-D 8-E (Direct to (g) (g) (g) (g) (g) Metal)(g)Part AMonofuran / Bisisocyanate 2.00 5.00 8.00 9.00 10.00 —Polymer (SynthesisExample A)Bisfuran / Monoisocyanate 10.0 5.00 3.00 2.00Polymer (SynthesisExample B)SolventAcetone 6.00 5.00 6.00 6.00 5.00 —Part BBMI-689 6.60 4.40 4.00 3.70 2.80 —PolyTHF-250 2.10 2.20 2.80 2.90 2.90SolventAcetone 3.00 2.20 3.00 1.60 1.80 -- ResultsTheoretical Urethane: 0.961 1.519 2.100 2.383 3.153 —Diels-Alder Molar RatioTheoretical Mols of 0.018 0.019 0.024 0.026 0.025 —Urethane BondsTheoretical Mols of 0.019 0.013 0.012 0.011 0.008 —Diels-Alder BondsPull-off Strength at 5.7 5.47 5.31 5.57 5.3 4.9 Ambient Conditions(MPa)Failure Mode (at Cohesive Cohesive Cohesive Cohesive Cohesive Cohesive Ambient) failure in failure in failure in failure in failure in failure in TCA TCA TCA TCA TCA TCAPull-off Strength at 90°C 0.90 1.5 1.97 1.87 2.2 2.7(MPa)Failure Mode (at 90°C) Cohesive Mixed Cohesive Cohesive Cohesive Cohesive failure in Cohesive failure in failure in failure in failure in TCA Coating failure in TCA TCA TCACoating / TCA Δ Pull-off Strength (MPa) -4.8 -4.0 -3.34 -3.70 -3.1 -2.2Percent Reduction in 84% 73% 63% 66% 58% 55%Pull-off Strength

[0317] The theoretical urethane to Diels- Alder molar ratio was calculated and recorded in Table 12. The theoretical urethane to Diels- Alder molar ratio represents the theoretical total moles of urethane bonds divided by the theoretical total moles of Diels- Alder bonds. The data provided in Table 12 demonstrate that when the theoretical urethane to Diels-Alder molar ratio exceeded 1 (Compositions 8-B to 8-E), coatings prepared from the compositions did not demonstrate reversibility (as demonstrated by a failure mode at 90°C of cohesive failure in TCA). As shown by the data, as the theoretical molar ratio increased, the reduction in pull-off strength decreased. When the theoretical urethane to Diels-Alder molar ratio (Composition 8-A) was less than 1, the coating demonstrated reversibility, with a reduction in pull-off strength of 84% and a failure mode at 90°C of cohesive failure in coating.

[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 composition comprising:a first component comprising a furan-containing compound comprising (i) a furan functional group, (ii) an isocyanate functional group, and (iii) a urethane linkage;a second component comprising a dienophile-containing compound; anda polar organic solvent in an amount greater than 15% by weight based on total weight of the composition,wherein the polar organic solvent is not reactive with the furan-containing compound or the dienophile-containing compound at ambient conditions.

2. The composition of claim 1, wherein the polar organic solvent has a boiling point of no more than 180°C at 1 atm.

3. The composition of claim 1 or claim 2, wherein the polar organic solvent is present in an amount of no more than 90% by weight based on total weight of the composition.

4. The composition of any of the preceding claims, wherein the urethane linkage is between the furan functional group and the isocyanate functional group.

5. The composition of any of the preceding claims, wherein the compound comprises Structure I:(I)wherein X comprises O, N, or S, m > 1, n > 1, Ri comprises a substituted or unsubstituted alkyl group, an alkylene group, a (cyclo)alkyl group, an aromatic group, an iminooxadiazinedione moiety, an allophonate moiety, a benzoguanamine moiety, or a polymeric moiety different fromthe urethane linkage, and R2 comprises a substituted or unsubstituted alkyl group, an ester moiety, an ether moiety, or a urethane moiety.

6. The composition of any of the preceding claims, wherein the furan-containing compound is substantially free of an ether linkage.

7. The composition of any of the preceding claims, wherein the dienophile comprises a maleimide functional group, a maleate functional group, and / or a fumarate functional group.

8. The composition of claim 7, comprising the furan functional group of the furan-containing compound and the maleimide functional group of the dienophile-containing compound in a molar ratio of 0.5:1 to 2:1.

9. The composition of any of the preceding claims, wherein the dienophile-containing compound comprises a dienophile equivalent weight of 150 g / eq to 800 g / eq.

10. The composition of any of the preceding claims, wherein the second component comprises an additional compound that is reactive with the isocyanate functional group.

11. The composition of any of the preceding claims, further comprising a thermally expandable material, a blowing agent, a filler, an additive, elastomeric particles, and / or an accelerator.

12. The composition of any of the preceding claims, wherein the composition is substantially free of oxanorbornene.

13. A substrate comprising a surface coated with or embedded in the composition of any of the preceding claims.

14. A film formed from the composition of any of claims 1 to 12.

15. A battery comprising:a battery cell;a battery component; anda coating formed from the composition of any of claims 1 to 12 positioned between the battery cell and the battery component.

16. A method of separating two substrates bonded by a coating formed from the composition of any of claims 1 to 12 comprising heating the coating above a reflow onset temperature of the coating and separating the substrates.

17. A substrate comprising:an adhesive; anda reversible coating formed on a portion of the adhesive, wherein the reversible coating is formed from the composition of any of claims 1 to 12.

18. The substrate of claim 17, wherein the adhesive is a thermally conductive adhesive coating.

19. The substrate of claim 17 or claim 18, further comprising a dielectric coating formed on a portion of the reversible coating.

20. A kit comprising:(a) the composition of any of claims 1 to 12; and(b) a thermally conductive adhesive composition.

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