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

Abstract

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

Description

[0001] Government Contract

[0002] This material is based on work supported by the CCDC Ground Vehicle Systems Center under Government Contract No. 201830-140914 entitled "Reversible Adhesive Phase Two". The U.S. government holds certain rights to this invention.

[0003] Cross-referencing

[0004] This application claims the benefit of U.S. Provisional Patent Application Serial No. 63 / 557,664, filed February 26, 2024, and U.S. Provisional Patent Application Serial No. 63 / 691,207, filed September 5, 2024, both entitled “Furan-Functional and Isocyanate-Functional Compounds and Reversibly Curable Compositions”, both of which are incorporated herein by reference in their entirety. Technical Field

[0005] This disclosure relates to furan-functionalized and isocyanate-functionalized compounds and compositions that can be reversibly cured, such as coating compositions. Background Technology

[0006] Coating compositions (including sealants and adhesives) are used in a wide variety of applications to treat multiple substrates or to bond two or more substrate materials together. Summary of the Invention

[0007] This article discloses compounds comprising: furan functional groups; isocyanate functional groups; and urethane bonds, urea bonds and / or thiourethane bonds.

[0008] This document also discloses compositions comprising: a first component comprising any of the compounds disclosed herein; and a second component comprising a dienophile-containing compound.

[0009] This document also discloses a method for coating a substrate, the method comprising contacting a portion of the surface of the substrate with any of the compositions disclosed herein.

[0010] This document also discloses a method for forming articles, which includes extruding any of the compositions disclosed herein.

[0011] This document also discloses hot melt adhesives formed from any of the compositions disclosed herein.

[0012] This document also discloses a substrate comprising a coating formed on a portion of the surface of the substrate by any of the hot melt adhesives disclosed herein.

[0013] This document also discloses a battery, which includes any of the battery cells disclosed herein.

[0014] This document also discloses self-supporting membranes formed from any of the compositions disclosed herein. Attached Figure Description

[0015] Figure 1 This is a schematic diagram of a top view of a cylindrical battery cell.

[0016] Figure 2 This is a schematic diagram of an exploded isometric view of an array of prismatic battery cells.

[0017] Figure 3 This is a schematic diagram of the front view of an array of pouch cell units.

[0018] Figure 4 This is a schematic diagram of an isometric view of a cylindrical battery cell located within a battery module.

[0019] Figure 5 It is a schematic diagram of an exploded perspective view of a battery pack that includes multiple battery cells.

[0020] Figure 6 is a schematic diagram of isometric views of (A) battery cell, (B) battery module and (C) battery pack.

[0021] Figure 7 This is a schematic diagram of the battery pack's perspective view.

[0022] Figure 8 This is a schematic diagram of the cell-to-battery pack configuration.

[0023] Figure 9 It is a schematic diagram of an equidistant cross-section of the unit to the chassis battery assembly.

[0024] Figure 10 shows images of (A) composition XII, (B) composition XIII and (C) composition XIV after grinding and reprocessing.

[0025] Figure 11 shows (A) optical macroscopic images of the damaged cured coating of composition XII before heating and (B) after heating to 130°C for one hour.

[0026] Figure 12 This is a bar graph of the lap shear strength of compositions VIII to XII measured at room temperature.

[0027] Figure 13This is a bar graph showing the lap shear strength of compositions VIII, IX, XI, and XII measured at 50°C.

[0028] Figure 14 This is a bar graph showing the lap shear strength of compositions VIII to XII measured at 150°C.

[0029] Figure 15 It is a graph showing the viscosity of compositions I to VII as a function of shear rate. Detailed Implementation

[0030] For the purposes of this detailed description, it should be understood that alternative variations and sequences of steps may be taken in this disclosure, except where expressly stated otherwise.

[0031] The numerical values ​​presented in the specific examples are reported as accurately as possible. However, any numerical value inherently contains some error due to the standard deviation present in its corresponding test measurement.

[0032] Furthermore, any range of values ​​described herein is intended to include all subranges contained therein. For example, the range “1 to 10” is intended to include (and include) the stated minimum value of 1 and the stated maximum value of 10, that is, all subranges having a minimum value equal to or greater than 1 and a maximum value equal to or less than 10.

[0033] As used herein, the terms “comprising,” “containing,” and similar terms are understood in the context of this application to be synonymous with “comprising” and are therefore open-ended, not excluding the presence of additional undescribed or unstated elements, materials, components, or method steps. As used herein, “consisting of” is understood in the context of this application to exclude the presence of any unspecified elements, components, or method steps. As used herein, “generally consisting of” is understood in the context of this application to include the specified elements, materials, components, or method steps “as well as elements, materials, components, or method steps that do not materially affect the essential and novel characteristics of the described content.” As used herein, open-ended terms include closed-ended terms such as “generally consisting of” and “consisting of”.

[0034] In addition, in this application, unless otherwise expressly stated, the use of “or” means “and / or”, even if “and / or” can be explicitly used in certain situations.

[0035] As used herein, the terms “on,” “to,” “applied on,” “applied to,” “formed on,” “deposited on,” “deposited on,” etc., mean to form, cover, deposit, or be disposed on a substrate surface, but not necessarily in contact with the substrate surface. For example, a composition “applied to” a substrate surface does not exclude the presence of one or more other intermediate coatings of the same or different compositions located between the composition and the substrate surface.

[0036] As used in this article, "liquid" means liquid with a pressure of less than 100,000 Pa at 25°C. A material with a viscosity of s, such as when passing through a plate with a diameter of 25 mm, a gap of 0.5 mm, and a shear rate of 1 s. -1 The measurements were taken using a parallel plate rheometer.

[0037] As used herein, "solid" means having a plate diameter of 25 mm, a gap of 0.5 mm, and a 1 s -1 The shear rate was at least 100,000 Pa, measured by parallel plate rheology at 25 °C. Materials with viscosity s.

[0038] As used herein, "partial group" refers to a portion of the chemical structure of a molecule or compound, which may include substructures such as functional groups or bonds.

[0039] As used herein, “composition” or “coating composition” refers to a solution, mixture or dispersion capable of producing a coating on a substrate surface.

[0040] As used herein, “coating” refers to a coating composition applied to a substrate and cured.

[0041] As used herein, “self-supporting film” means a coating composition that can be extruded or a coating that can be layered with a substrate after curing. As used herein, “article” means a cured composition that is formed or manufactured as a solid.

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

[0043] As used herein, “sealant” refers to a coating or self-supporting film that provides a protective barrier against moisture, chemicals and other environmental factors, thereby preventing corrosion and extending the service life of components.

[0044] As used herein, "adhesive composition" refers to a coating composition that forms an adhesive in its cured state.

[0045] As used herein, “adhesive” refers to a cured coating or self-supporting membrane that forms a load-bearing joint and has an lap shear strength of at least 0.5 MPa and less than 5 MPa, as determined at room temperature using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute, according to ASTM D1002-10.

[0046] As used herein, “structural adhesive composition” refers to a coating composition that produces a structural adhesive in a cured state.

[0047] As used herein, “structural adhesive” refers to a cured coating or self-supporting membrane that forms a load-bearing joint and has an lap shear strength of at least 5 MPa, measured at room temperature using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute, in accordance with ASTM D1002-10.

[0048] As further defined herein, “ambient conditions” generally refers to room temperature (e.g., 25°C) and humidity conditions or temperature and humidity conditions typically found in the area where the composition is applied to the substrate, such as at 10°C to 40°C and 5% to 80% relative humidity, while “microthermal conditions” are temperatures slightly above ambient conditions, such as greater than 40°C to 60°C.

[0049] As used herein, the terms "two-component" or "2K" refer to compositions in which, when mixed, the reactive components readily associate to form interactions or react to form bonds (physically or chemically) without activation from an external energy source, such as under ambient or microthermal conditions, i.e., curing. Those skilled in the art will understand that the two components of the composition are stored separately and mixed just before application.

[0050] As used herein, the term “hot melt adhesive” refers to a composition that: (i) cures to form a solid under ambient conditions, (ii) begins to reflow to form a liquid upon exposure to a reflow initiation temperature, (iii) begins to reform to a solid upon cooling to below the reflow initiation temperature, and (iv) reforms to a solid under ambient conditions.

[0051] As used herein, the term "reflux initiation temperature" refers to the temperature at which the storage modulus of the composition decreases to below 20,000,000 Pa, as can be determined by performing dynamic mechanical analysis (DMA) at a frequency of 1.0 Hz and a heating rate of 3 °C / min. The reflux initiation temperature can be the result of dynamic covalent chemistry, softening (i.e., heating above the glass transition temperature of the composition), and / or melting (i.e., conversion from a solid to a liquid).

[0052] As used herein, the term “glass transition temperature” (“Tg”) refers to the temperature at which an amorphous material (such as glass or polymer) changes from a brittle glass state to a plastic state or from a plastic state to a brittle glass state.

[0053] As used herein, the term “hot melt adhesive application” means applying hot melt adhesive to a substrate surface under thermal conditions. As used herein, “thermal conditions” include (i) thermal extrusion, (ii) heating the composition to a temperature above the reflow initiation temperature of the composition, and / or (iii) heating a substrate containing the composition to a temperature above the reflow initiation temperature of the composition.

[0054] As used herein, the terms “cured,” “cured,” and similar terms mean that the reactive components forming the composition interact, react, and / or crosslink to form a coating, self-supporting film, or bond. In the case of 2K compositions, the composition begins to cure when the components of the composition are mixed, causing a reaction and / or physical interaction of the reactive components of the composition. As used herein, “cured” means subjecting the composition to curing conditions that cause the composition to cure. As used herein, a “curable” composition means a composition that can be cured. As used herein, a curable composition can be considered “cured” if it has an lap shear strength of at least 0.5 MPa (measured according to ASTM D1002-10) and a tensile strength of at least 0.5 MPa (measured according to ISO-37 TYPE 2 using an Instron 4443 machine in tensile mode at a pull rate of 10 mm per minute) under ambient conditions. “Complete” curing is achieved when a curable composition is subjected to curing conditions without any significant increase in lap shear strength.

[0055] As used herein, the term "furan equivalent weight" is the theoretical molecular weight of a compound containing furan functional groups divided by the theoretical number of furan functional groups.

[0056] As used herein, the term "isocyanate equivalent weight" is the theoretical molecular weight of a compound containing isocyanate functional groups divided by the theoretical number of isocyanate functional groups.

[0057] As used herein, the term "maleimide equivalent weight" is the theoretical molecular weight of a compound containing maleimide functional groups divided by the theoretical number of maleimide functional groups.

[0058] As used herein, the term "promoter" refers to a substance that increases the rate of a chemical reaction or lowers the activation energy of a chemical reaction compared to the same reaction in the absence of a promoter. A promoter can be a "catalyst" (that is, one that does not undergo any permanent chemical change itself) or it can be reactive (that is, one that undergoes a permanent chemical change).

[0059] As used herein, a "latent" accelerator refers to a molecule or compound that reacts (i.e., crosslinks) or has a catalytic effect only after activation by an external energy source, as may be the case. Latent accelerators may be in solid form at room temperature and do not exhibit accelerator effects until they are heated and melted. Latent accelerators can be encapsulated or sealed. A "encapsulated" accelerator means an accelerator that can reversibly react with a second compound that prevents any accelerator effect until the reversible reaction is reversed by applying heat and the second compound is removed, thereby releasing the accelerator to increase the rate of the chemical reaction or lower the activation energy of the chemical reaction. An "encapsulated" accelerator can be encapsulated within a thermoplastic material that melts upon heating, thereby releasing the accelerator to increase the rate of the chemical reaction or lower the activation energy of the chemical reaction.

[0060] As used herein, the term "carbamate bond" refers to the bond formed between two molecules that form the bond RNHC(O)OR.

[0061] As used herein, the term "urea bond" refers to the bond formed between two molecules that form the bond RNHC(O)NHR.

[0062] As used herein, the term "thiocarbamate bond" refers to the bond formed between molecules that form the bond RNHC(O)SR.

[0063] As used herein, “reprocessability” means that the composition can be reprocessed, in which articles containing the cured composition are mechanically or chemically processed into different articles. In some cases, “reprocessing” can refer to mechanical processes in which articles containing the cured composition are ground, shredded, crushed, or mechanically processed, and then the composition is molded into new articles via processes such as compression molding or extrusion (i.e., the material is recycled). Reprocessing may further include heating.

[0064] As used in this article, "reprocessing efficiency" refers to the ratio of the mechanical properties of a material after reprocessing to the mechanical properties of the original material, usually defined as a percentage. Reprocessing efficiency can refer to the recovery efficiency of properties (such as tensile strength, Young's modulus, fracture strain, lap shear strength, etc.) after reprocessing.

[0065] As used herein, “reformability” means that a material previously molded into a fixed physical form or shape can be molded into a different fixed physical form or shape. In some cases, reformability will involve heating the material above its reflow initiation temperature to make the new shape permanent.

[0066] As used herein, "self-healing" means that a material is able to repair itself, for example, by healing cracks, scratches, or damage in the material. A self-healing process may include heating the material to a temperature above its reflow initiation temperature.

[0067] As used in this article, "monosubstituted" refers to a compound or functional group in which one of the hydrogen atoms is replaced by a different atom or functional group.

[0068] As used herein, “terminal” when used in relation to a functional group refers to a functional group located at the end of the polymer backbone or prepolymer backbone, or a functional group that is monosubstituted relative to a monomer or nonpolymerizable molecule.

[0069] As used herein, "monomer" refers to a molecule that can be polymerized to contribute repeating units to the structure of a prepolymer or polymer, such as... Pure and Applied Chemistry , 1996, 68 As defined in , 2287 (2289), “Glossary of basic terms in polymer science (IUPAC Recommendations 1996)”.

[0070] As used herein, a “prepolymer” refers to a molecule that contains a reaction product of two or more molecules that can be further polymerized or crosslinked.

[0071] As used herein, “polymer” means a molecule having more than one repeating unit and includes oligomers and homopolymers.

[0072] As used herein, unless otherwise stated, the term "substantially free of" means that a particular material is not intentionally added to the mixture or composition, and that the particular material is present only as a trace impurity of less than 0.05% by weight, based on the total weight of the mixture or composition. As used herein, unless otherwise stated, the term "largely free of" means that a particular material is present only in an amount of less than 0.01% by weight, based on the total weight of the mixture or composition. As used herein, unless otherwise stated, the term "completely free of" means that the mixture or composition does not contain the particular material, i.e., the mixture or composition contains 0% by weight of such material.

[0073] This disclosure relates to a compound comprising, substantially comprising, or comprising the following: a furan functional group; an isocyanate functional group; and a carbamate bond, a urea bond, and / or a thiocarbamate bond. The compound may comprise the following general structure:

[0074]

[0075] (I)

[0076] Wherein X contains O, N, or S; m ≥ 1; n ≥ 1; the sum of m+n ≥ 2; R1 contains a substituted or unsubstituted alkyl group, alkylene group, (cyclo)alkyl group, aromatic group, isocyanurate moiety, biuret moiety, urethane moiety, glycourea moiety, benzoguanamine moiety, iminooxadiazinedione moiety, or polymer moiety other than urethane bond, urea bond, and / or thiourethane bond; and R2 contains a substituted or unsubstituted alkyl group, ester moiety, ether moiety, or urethane moiety. Optionally, m ≤ 12; n ≤ 12; and / or m+n ≤ 13.

[0077] The compound may comprise reaction products of reactants, which include: a furan-containing compound containing an active hydrogen functional group; and a polyisocyanate-containing compound. As used herein, "furan-containing compound" means a compound containing a furan functional group. As used herein, "polyisocyanate-containing compound" means a compound containing more than one isocyanate functional group, including diisocyanates, triisocyanates, or higher isocyanates. The active hydrogen functional group on the furan-containing compound may include a hydroxyl functional group, an amine functional group, and / or a thiol functional group. The active hydrogen functional group of the furan-containing compound can react with the isocyanate group of the polyisocyanate. The compound contains at least one unreacted isocyanate group that provides isocyanate functionality to the compound.

[0078] Substoichiometric active hydrogen functional groups on furan compounds can react with isocyanate functional groups on polyisocyanate compounds. For example, the active hydrogen functional groups of furan compounds and the isocyanate groups on polyisocyanate compounds can react in equivalence ratios of less than 1:1, such as not exceeding 1:2, such as not exceeding 1:3, such as not exceeding 1:5. As used herein, "substoichiometric" means that the amount of active hydrogen functional groups from furan compounds is less than the amount required to react with all the isocyanate groups on the isocyanate groups of the polyisocyanate compound, such that the reaction product contains isocyanate functional groups from the polyisocyanate.

[0079] Suitable furan-containing compounds that can be used to form the compounds disclosed herein include, but are not limited to, furfuryl alcohol, furfurylamine, furfuryl thiol, glycidyl furfuryl ether, bis(hydroxymethyl)furan, their derivatives and / or combinations thereof.

[0080] Suitable polyisocyanate-containing compounds that can be used to form the compounds disclosed herein can be polymers containing two or more isocyanate functional groups. For example, polyisocyanates can contain 2 to 20 carbon atoms and can be linear, cyclic, aliphatic and / or aromatic polyisocyanates, or mixtures thereof.

[0081] Suitable aliphatic polyisocyanates may include alkylene isocyanates, such as: trimethylene diisocyanate; tetramethylene diisocyanate, such as 1,4-tetramethylene diisocyanate; pentamethylene diisocyanate, such as 1,5-pentamethylene diisocyanate and 2-methyl-1,5-pentamethylene diisocyanate; hexamethylene diisocyanate (“HDI”), such as 1,6-hexamethylene diisocyanate and 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethyl Hexamethylene diisocyanate or mixtures thereof; heptamethylene diisocyanate, such as 1,7-heptamethylene diisocyanate; propylene diisocyanate, such as 1,2-propylene diisocyanate; butylene diisocyanate, such as 1,2-butylene diisocyanate, 2,3-butylene diisocyanate and 1,3-butylene diisocyanate; ethylene diisocyanate; decamethylene diisocyanate, such as 1,10-decamethylene diisocyanate; ethylene diisocyanate; and butylene diisocyanate. Aliphatic polyisocyanates may also include cycloalkyl isocyanates such as: cyclopentane diisocyanates, such as 1,3-cyclopentane diisocyanate; cyclohexane diisocyanates, such as 1,4-cyclohexane diisocyanate, 1,2-cyclohexane diisocyanate, isophorone diisocyanate (“IPDI”), IPDI trimer (commercially available as Desmodur® Z 4470 SN); methylene bis(4-cyclohexyl isocyanate) (“HMDI”); polymeric methylene diphenyl diisocyanate (“MDI”); and mixed aralkyl diisocyanates, such as tetramethylxylyl diisocyanate, such as m-tetramethylxylyl diisocyanate (commercially available as TMXDI® from Allnex SA).

[0082] Suitable aromatic polyisocyanates may include arylene isocyanates, such as: phenylene diisocyanates, such as m-phenylene diisocyanate, p-phenylene diisocyanate and chlorophenylene 2,4-diisocyanate; naphthalene diisocyanates, such as 1,5-naphthalene diisocyanate and 1,4-naphthalene diisocyanate. Aromatic polyisocyanates may also include alkylene aryl isocyanates, such as: methylene-block aromatic diisocyanates, such as 4,4'-diphenylmethane diisocyanate (“MDI”), and alkylated analogs, such as 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate and polymeric methylene diphenyl diisocyanate; toluene diisocyanate (“TDI”), such as 2,4-methylphenylene or 2,6-methylphenylene diisocyanate or mixtures thereof, bitoluene diisocyanate; and 4,4-toluidine diisocyanate; xylene diisocyanate; o-anisidine diisocyanate; xylene diisocyanate; and other alkylated phenyl diisocyanates.

[0083] Suitable polyisocyanates include dimers, trimers, oligomers or prepolymers comprising any of the isocyanates listed herein.

[0084] The compound may contain, consist generally of, or consist of monomers, prepolymers, or polymers.

[0085] The compound may contain one, two, three or more furan functional groups. The furan functional groups can be linked to the compound via carbamate bonds, urea bonds and / or thiocarbamate bonds.

[0086] The compounds disclosed herein may be substantially free of, substantially free of, or completely free of ether bonds.

[0087] The compound may contain at least 100 g / eq, such as at least 200 g / eq, of furan equivalent weight. The compound may contain no more than 3,000 g / eq, such as no more than 1,500 g / eq, of furan equivalent weight. The compound may contain between 100 g / eq and 3,000 g / eq, such as between 200 g / eq and 1,500 g / eq, of furan equivalent weight.

[0088] The compound may contain at least 100 g / eq, such as at least 200 g / eq, of isocyanate equivalent weight. The compound may contain no more than 3,000 g / eq, such as no more than 1,500 g / eq, such as no more than 850 g / eq, of isocyanate equivalent weight. The compound may contain from 100 g / eq to 3,000 g / eq, such as from 200 g / eq to 1,500 g / eq, of isocyanate equivalent weight.

[0089] The compound may contain furan functional groups and isocyanate functional groups in an equivalence ratio of at least 1:5, such as at least 1:4, such as at least 1:2. The compound may contain furan functional groups and isocyanate functional groups in an equivalence ratio of no more than 5:1, such as no more than 4:1, such as no more than 2:1. The compound may contain furan functional groups and isocyanate functional groups in an equivalence ratio of 1:5 to 5:1, such as 1:4 to 4:1, such as 1:2 to 2:1.

[0090] This disclosure further relates to a composition comprising: a first component comprising any of the compounds disclosed herein; and a second component comprising a dienophile-containing compound.

[0091] The second component may comprise, consist substantially of, or consist of dienophilic compounds. As used herein, dienophile means any unsaturated functional group capable of undergoing Diels-Alder [4+2] cycloaddition with a conjugated diene. As used herein, "conjugated diene" refers to a compound containing two double bonds separated by a single covalent bond.

[0092] Suitable dienophiles may contain maleimide functional groups, maleate functional groups and / or fumarate functional groups.

[0093] Dienephile compounds may contain maleimide functional groups. The general structures of dienophile compounds containing maleimide functional groups include:

[0094]

[0095] R3 may contain hydrogen, alkyl, (cyclo)alkyl, aryl, aromatic or polymeric structures (including polyester, polyurethane, polyether, acrylic or siloxane).

[0096] Suitable maleimide-containing compounds can be prepared by reacting maleic anhydride with a difunctional or polyfunctional amine-containing compound. The amine-containing compound can be selected such that the maleimide-containing compound or mixture of maleimide-containing compounds does not crystallize. Examples of suitable maleimide-containing compounds include the reaction product of maleic anhydride with a dimer fatty acid diamine (such as BMI-689, commercially available from Designer Molecules, Inc.). Other maleimide-containing compounds include the reaction product of amine-terminated polyethers or polysiloxanes with maleic anhydride. Other suitable maleimide-containing compounds include maleimide-terminated polyimides available from Designer Molecules, Inc., or the reaction product of maleimide-functionalized carboxylic acids with epoxy, hydroxyl, or other carboxylic acid reactive functional groups.

[0097] Dienophiles can contain maleate functional groups. The general structures of diephile-containing compounds containing maleate functional groups include:

[0098]

[0099] Each X independently contains O, N, or S; R4 contains hydrogen, alkyl, (cyclo)alkyl, aryl, aromatic, or polymeric structures (including polyesters, polyurethanes, polyethers, acrylics, or siloxanes); and R5 contains hydrogen, alkyl, (cyclo)alkyl, aryl, aromatic, or polymeric structures (including polyesters, polyurethanes, polyethers, acrylics, or siloxanes). Dienophilic compounds containing maleate functional groups may contain unsaturated polyesters comprising the reaction product of maleic acid (or its anhydride or ester) with a polyol. Suitable polyols include any of those polyols described below. Dienophilic compounds containing maleate functional groups may also contain unsaturated polyesters containing maleate functional groups synthesized by other methods, such as copolymerization of epoxides with maleic anhydrides. Unsaturated polyesters may further contain other functional groups, such as hydroxyl groups. Unsaturated polyesters may comprise liquids.

[0100] Dienophile compounds may contain fumarate functional groups. The general structures of diephile compounds containing fumarate functional groups include:

[0101]

[0102] Each X independently contains O, N, or S; R6 contains hydrogen, alkyl, (cyclo)alkyl, aryl, aromatic, or polymeric structures (including polyesters, polyurethanes, polyethers, acrylics, or siloxanes); and R7 contains hydrogen, alkyl, (cyclo)alkyl, aryl, aromatic, or polymeric structures (including polyesters, polyurethanes, polyethers, acrylics, or siloxanes). Dienophilic compounds containing fumarate functional groups may contain unsaturated polyesters comprising the reaction product of fumaric acid (or its anhydride or ester) with a polyol. Suitable polyols include any of those polyols described below. Dienophilic compounds containing fumarate functional groups may also contain unsaturated polyesters containing fumarate functional groups synthesized by other methods, such as copolymerization of epoxides with maleic anhydride. Unsaturated polyesters may further contain other functional groups, such as hydroxyl groups. Unsaturated polyesters may comprise liquids.

[0103] Diester-containing compounds may contain at least 100 g / eq, such as at least 200 g / eq, of dienophilic equivalent weight. Diester-containing compounds may contain no more than 3,000 g / eq, such as no more than 1,500 g / eq, of dienophilic equivalent weight. Diester-containing compounds may contain from 100 g / eq to 3,000 g / eq, such as from 100 g / eq to 1,500 g / eq, of dienophilic equivalent weight.

[0104] The composition may contain furan functional groups on the first compound and dienophilic functional groups on the dienophilic compound in an equivalent ratio of at least 0.5:1, such as at least 0.6:1. The composition may contain furan functional groups on the first compound and dienophilic functional groups on the dienophilic compound in a molar ratio of no more than 2:1, such as no more than 1.5:1. The composition may contain furan functional groups on the first compound and dienophilic functional groups on the dienophilic compound in a molar ratio of 0.5:1 to 2:1, such as 0.6:1 to 1.5:1.

[0105] The composition may further comprise a third compound capable of reacting with isocyanate functional groups. The third compound may be present in the second component and / or the third or more components. The third compound may contain hydroxyl functional groups, such as polyols.

[0106] Suitable polyols include diols, triols, tetraols, and higher functional polyols. Combinations of such polyols can also be used. Polyols may include, for example, ethylene glycol, propylene glycol, neopentyl glycol, butanediol, pentylene glycol, hexanediol, cyclohexanediol, phenylenediol, 4,4'-isopropylidene dicyclohexanol, glycerol, trimethylolpropane, pentaerythritol, bis(trimethylolpropane) or bis(pentaerythritol). Suitable polyols may also include polyether polyols, polyester polyols, acrylic polyols, polybutadiene polyols, hydrogenated polybutadiene polyols, polycarbonate polyols, polysiloxane polyols, and combinations thereof.

[0107] Polyols may include polycaprolactone-based polyols. Polycaprolactone-based polyols may include diols capped with primary hydroxyl groups. Commercially available polycaprolactone-based polyols include those marketed under the trade name Capa™ from the Perstorp Group, such as, for example, Capa 2054, Capa 2077A, Capa 2085, Capa 2205, Capa 3031, Capa 3050, Capa 3091, and Capa 4101.

[0108] Polyols may include polyether polyols. Polyols may be based on polyether chains derived from ethylene glycol, propylene glycol, butanediol, hexanediol, or mixtures thereof. Polyols may include tetrahydrofuran-based polyols. Polytetrahydrofuran-based polyols may include diols, triols, or tetraols terminated with primary hydroxyl groups. Commercially available polytetrahydrofuran-based polyols include those sold under the trade name Terathane® from Invista, such as Terathane® PTMEG 250, Terathane® PTMEG 650, and Terathane® PTMEG 1000, which are blends of linear diols in which hydroxyl groups are separated by repeating tetramethylene ether groups. Alternatively, dimer-based polyols available from Cognis Corporation under the trade names Pripol®, Solvermol™, and Empol®, or bio-based polyols such as the tetrafunctional polyol Agrol4.0 available from BioBased Technologies, can be used. Polyols may include amine-containing polyols, such as Quadrol PM, commercially available from BASF.

[0109] The composition may contain isocyanate functional groups on the compound and hydroxyl functional groups on the third compound in an equivalent ratio of at least 0.2:1, such as at least 0.4:1. The composition may contain isocyanate functional groups on the compound and hydroxyl functional groups on the third compound in an equivalent ratio of no more than 3:1, such as no more than 2:1. The composition may contain isocyanate functional groups on the compound and hydroxyl functional groups on the third compound in an equivalent ratio of 0.2:1 to 3:1, such as 0.4:1 to 2:1.

[0110] The composition may further comprise a fourth compound containing a furan functional group, different from the compounds disclosed herein. The fourth compound may be present in the first component and / or the third or more components. The fourth compound may comprise at least 68 g / eq, such as at least 80 g / eq, of furan equivalent weight. The fourth compound may comprise no more than 1,500 g / eq, such as no more than 1,000 g / eq, of furan equivalent weight. The fourth compound may comprise from 68 g / eq to 1,500 g / eq, such as from 80 g / eq to 1,000 g / eq, of furan equivalent weight.

[0111] As used herein with respect to compounds, references to "first," "second," "third," "fourth," etc., are for convenience only and do not indicate the order in which they are added to the composition, etc. Furthermore, this language is not intended to be restrictive and does not preclude the possibility that the composition may contain more than two compounds containing furan functional groups, such as three compounds, such as four compounds.

[0112] filler

[0113] The compositions disclosed herein may further comprise fillers. The fillers may be present in the first component, the second component, and / or the third component. The fillers 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 fillers may comprise particles of a first filler material and may further comprise particles of a second (and third, fourth, etc.) filler material different from the first filler material. As used herein with respect to the type of filler material, references to “first,” “second,” etc., are for convenience only and do not indicate the order in which they are added to the composition, etc.

[0114] The composition may contain filler in an amount of at least 1% by weight, such as not more than 50% by weight, based on the total weight of the composition. The composition may contain filler in an amount of at least 50% by weight, such as not more than 90% by weight, based on the total weight of the composition. The composition may contain filler in an amount of up to 90% by weight, such as from 1% to not more than 50% by weight, or such as from 50% to 90% by weight, based on the total weight of the composition.

[0115] When the disclosed composition is a high-load composition (i.e., containing 50% to 90% by weight of filler based on the total weight of the composition), it is found that the composition is pumpable (i.e., each component has a shear stress of no more than 10 Hz measured at 25°C using a parallel plate with a diameter of 25 mm (1 mm gap) at 1 Hz using an Anton Paar MCR 301 rotational rheometer). 6 Pa (The viscosity of s). This was an unexpected result.

[0116] The filler may comprise thermally conductive filler materials, such as thermally conductive and electrically insulating filler materials (referred to herein as “TC / EI filler materials” and described in more detail below) and / or thermally conductive and electrically conductive fillers (referred to herein as “TC / EC fillers” and described in more detail below). TC / EI and / or TC / EC fillers (collectively, “thermally conductive fillers”) may be present in the first, second, and / or third components. The thermally conductive filler may comprise organic or inorganic materials and may comprise particles of a single type of filler material, or particles of two or more types of TC / EI fillers and / or two or more types of TC / EC fillers. That is, the filler may comprise a first TC / EI filler, and in addition to the first TC / EI filler, may further comprise at least a second (i.e., second, third, fourth, etc.) TC / EI filler. Similarly, the filler may comprise a first TC / EC filler, and in addition to the first TC / EC filler, may further comprise at least a second (i.e., second, third, fourth, etc.) TC / EC filler. As used in this article in relation to the type of filler, references to “first,” “second,” etc., are for convenience only and do not refer to the order in which they are added to the composition, etc.

[0117] Thermally conductive fillers (i.e., TC / EI and / or TC / EC fillers) can have at least 5% thermal conductivity at 25°C. W / m . K (measured according to ASTM D7984-21), such as at least 18 W / m . The thermal conductivity of K, and can be no more than 3,000 at 25°C. W / m . K, such as not exceeding 1,400 W / m . Thermal conductivity of K. Thermally conductive fillers can have a conductivity of 5 K at 25°C. W / m . K up to 3,000 W / m . K (measured according to ASTM D7984-21), such as 18 W / m . K up to 1,400 W / m . Thermal conductivity of K.

[0118] The filler (TC / EI and / or NTC / EI) can be electrically insulating. Electrically insulating fillers can have a strength of at least 1 Ω. . m, such as at least 10 Ω . m, such as at least 100 Ω . The volume resistivity (m). Electrical insulation can be measured according to ASTM D257-19.

[0119] The filler can be conductive. Conductive fillers can have a conductivity of less than 1 Ω. .The volume resistivity of m (measured according to ASTM D257-19) is less than 0.1 Ω. . m.

[0120] Suitable TC / EI fillers include: boron nitride (e.g., available from Saint-Gobain as CarboTherm, from Momentive as CoolFlow and PolarTherm, and from Panadyne as hexagonal boron nitride powder), silicon nitride or aluminum nitride (e.g., available from Micron Metals Inc. as aluminum nitride powder, and from Toyal as Toyalnite); metal oxides, such as boehmite, pseudoboehmite, alumina (e.g., available from Micron Metals Inc. as aluminum nitride powder, and from Toyal as Toyalnite); and metal oxides such as gibbsite, boehmite, and alumina (e.g., available from Micron Metals Inc. as aluminum nitride powder). Abrasives are commercially available from Microgrit, Nabaltec (Nabalox), Evonik (Aeroxide), and Imerys (Alodur); 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 corundum; ceramics, such as ceramic microspheres (e.g., available from Zeeospheres Ceramics or 3M); silicon carbide; and diamond. These fillers can also be surface-modified, such as PYROKISUMA 5301K available from Kyowa Chemical Industry Co., Ltd. These thermally conductive fillers can be used alone or in combination of two or more. TC / EI fillers can also be ferromagnetic, ferrimagnetic, and / or superparamagnetic.

[0121] Suitable TC / EC fillers include: metals, such as hollow particles coated with silver, zinc, copper, gold, or other metals; carbon compounds, such as graphite (e.g., Timrex available from Imerys or ThermoCarb available from Asbury Carbons), carbon black (e.g., available from Cabot Corporation as Vulcan), carbon fibers (e.g., available from Zoltek as ground carbon fibers), graphene and graphene carbon particles (e.g., xGnP graphene nanosheets available from XG Sciences and / or graphene particles as described below); carbonyl iron; copper (e.g., spheroidal powders available from Sigma-Aldrich); zinc (e.g., Ultrapure available from Purity Zinc Metals and zinc powders XL and XLP available from US Zinc), etc. Examples of “graphene carbon particles” include carbon particles having a structure comprising one or more single-atom-thick planar sheets of sp2-bonded carbon atoms closely packed in a honeycomb 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 graphene carbon particles may be substantially flat; however, at least a portion of the planar sheet may be substantially curved, curled, wrinkled, or buckled. The particles generally do not have a spherical or isometric morphology. Suitable graphene carbon particles are described in paragraphs

[0059] through

[0065] of U.S. Publication No. 2012 / 0129980, the referenced portion of which is incorporated herein by reference. Other suitable graphene carbon particles are described in U.S. Patent No. 9,562,175, 6:6 through 9:52, the referenced portion of which is incorporated herein by reference. As used herein, the term “substantially flat” means planar; “curved” or “curled” means that the material deviates from planarity due to having a non-zero curvature; and “wrinkled” or “bent” indicates that at least a portion of the area is thicker than a sheet, such that the plane is folded in half or folded itself. TC / EC fillers can also be ferromagnetic, ferrimagnetic, and / or superparamagnetic.

[0122] The composition may contain 100% by volume of thermally conductive filler material based on the total volume of the filler. The composition may contain no more than 90% by volume, such as no more than 80% by volume. The composition may contain at least 20% by volume, such as at least 50% by volume, of thermally conductive filler material based on the total volume of the filler. The composition may contain between 20% and 90% by volume, such as between 50% and 80% by volume, of thermally conductive filler material based on the total volume of the filler.

[0123] The filler may comprise non-thermally conductive filler materials, such as non-thermally conductive, electrically insulating fillers (referred to herein as "NTC / EI" fillers). As used herein, NTC / EI fillers may be present in the first, second, and / or third components. NTC / EI fillers may comprise organic or inorganic materials and may comprise particles of a single type of filler material, or particles of two or more types of NTC / EI fillers. That is, the composition may comprise a first NTC / EI filler, and may further comprise a second (i.e., second, third, fourth, etc.) NTC / EI filler in addition to the first NTC / EI filler.

[0124] Non-thermal conductive fillers can have a strength of less than 5 W / m at 25°C. . K (according to ASTM) (D7984-21 measurement), such as not exceeding 3W / m . K, such as not exceeding 1 W / m . K, such as not exceeding 0.1 W / m . K, such as not exceeding 0.05 W / m . K, such as 0.02 W / m at 25℃ . K up to 5W / m at 25℃ . Thermal conductivity of K. Thermal conductivity can be measured as described above.

[0125] Non-thermally conductive fillers can be electrically insulating. Electrically insulating fillers can have a strength of at least 1 Ω. . The volume resistivity of m (measured according to ASTM D257-19), such as at least 10 Ω. . m, such as at least 100 Ω . m.

[0126] Suitable NTC / EI fillers include, but are not limited to: mica, wollastonite, calcium carbonate, glass microspheres, clay, silica, or combinations thereof.

[0127] As used herein, the term "mica" generally refers to a flaky silicate (layered silicate) mineral. Mica can include muscovite. Muscovite is a layered silicate mineral containing aluminum and potassium, with the chemical formula KAl2(AlSi3O3). 10(F,OH)2 or (KF)2(Al2O3)3(SiO2)6(H2O). Exemplary, non-limiting, commercially available muscovite 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 includes calcium silicate minerals (CaSiO3) that may contain small amounts of iron, aluminum, magnesium, manganese, titanium, and / or potassium. Non-limiting examples of commercially available wollastonite include NYAD 400, available from NYCO Minerals, Inc.

[0128] Calcium carbonate (CaCO3) can include precipitated calcium carbonate or heavy calcium carbonate. Calcium carbonate may or may not undergo surface treatment, such as with stearic acid (such as Socal, which is commercially available from IMERYS). ® 312) Processing. 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 heavy calcium carbonate include Duramite available from IMERYS. TM And Marblewhite®, available from Specialty Minerals.

[0129] Useful clay minerals include nonionic plate-like fillers such as talc, pyrophyllite, chlorite, vermiculite, or combinations thereof.

[0130] Glass microspheres can be hollow borosilicate glass. Non-limiting examples of commercially available glass microspheres include 3M glass bubble types VS, K series, and S series, which are available from 3M.

[0131] NTC / EI packing particles (if present) may be present in an amount of at least 10% by volume, such as at least 20% by volume, based on the total volume of the packing. NTC / EI packing particles (if present) may be present in a positive amount of up to 100% by volume, such as not exceeding 80% by volume, such as not exceeding 50% by volume, based on the total volume of the packing. NTC / EI packing particles may be present in an amount of 10% to 80% by volume, such as 20% to 50% by volume, based on the total volume of the packing.

[0132] Optionally, the filler may include a surface coating. The surface coating may comprise silanes, aminosilanes, and / or polymers having multiple functional groups that can bind to or interact with the filler.

[0133] The filler may have an average particle size of at least 0.01 μm, such as at least 2 μm, in at least one dimension as reported by the manufacturer or as described below, and may have an average particle size of no more than 500 μm, such as no more than 300 μm, in at least one dimension as reported by the manufacturer or as described below. The filler may have an average particle size of 0.01 μm to 500 μm, such as 2 μm to 300 μm, in at least one dimension as reported by the manufacturer or as described below. The particle size can be measured by methods known to those skilled in the art, such as using a scanning electron microscope (SEM), such as a Quanta 250 FEG SEM or an equivalent instrument. For example, powder can be dispersed on a carbon ribbon fragment attached to an aluminum rod and coated with Au / Pd for 20 seconds. The sample can then be analyzed in an SEM under high vacuum (accelerating voltage 10 kV and spot size 3.0) to measure 30 particles from three different regions to provide the average particle size of each sample. Those skilled in the art will recognize that variations in the basic elements that preserve microscopic imaging and average representative size are possible in this procedure.

[0134] Fillers may include particles and their agglomerates, each of which has, for example, a plate-like, spherical, or needle-like shape. As used herein, “plate-like” refers to a two-dimensional material having a substantially flat surface and a thickness in one direction of less than 25% of its maximum dimension.

[0135] Other components

[0136] The composition may optionally contain one or more additives. As used herein, “additive” means rheology modifier, tackifier, thermoplastic polymer, surfactant, flame retardant, corrosion inhibitor, UV stabilizer, colorant, dye, solvent, plasticizer, adhesion promoter, antioxidant, silane, silane-terminated polymer and / or desiccant.

[0137] The compositions provided in this disclosure may contain flame retardants or combinations of flame retardants. For example, certain thermally conductive materials (such as aluminum hydroxide and magnesium hydroxide) may also be flame retardants; such materials are considered thermally conductive for the purpose of calculating the weight percentages herein. As used herein, "flame retardant" means a material that slows or prevents the spread of fire or reduces its intensity. Flame retardants may be available in powder form, which may be mixed with compositions, foams, or gels. In examples, when the compositions disclosed herein contain flame retardants, such compositions may form a coating on a substrate surface, and such coating may act as a flame retardant. Flame retardants may include: minerals, organic compounds, organohalogen compounds, organophosphorus compounds, or combinations thereof.

[0138] The composition may contain additives in an amount of at least 0.01% by weight, such as at least 0.1% by weight, based on the total weight of the composition. The composition may contain additives in an amount of no more than 15% by weight, such as no more than 10% by weight, based on the total weight of the composition. The composition may contain additives in an amount of 0.01% to 15% by weight, such as 0.1% to 10% by weight, based on the total weight of the composition.

[0139] The compositions disclosed herein may further comprise elastomer particles. As used herein, “elastomer particles” refers to particles comprising one or more materials having a glass transition temperature (Tg) greater than -150°C and less than 30°C, the glass transition temperature being calculated, for example, using the Fox equation.

[0140] Elastomer particles can have a core / shell structure. Suitable core-shell elastomer particles can consist of an acrylic shell and an elastomer core. The core can include natural or synthetic rubber, polybutadiene, styrene-butadiene, polyisoprene, chloroprene, acrylonitrile-butadiene, butyl rubber, polysiloxane, polysulfide, ethylene-vinyl acetate, fluorinated elastomer, polyolefin, or combinations thereof. Elastomer particles can include a polybutadiene core, a styrene-butadiene core, and / or a polysiloxane core.

[0141] Exemplary non-limiting commercial core-shell elastomer particle products that can be used in the compositions of this disclosure include core-shell poly(butadiene) rubber powder (which is commercially available from Dow Chemical as PARALOID™ EXL 2650A).

[0142] Exemplary non-limiting commercial core-shell elastomer particle products that can be used in compositions include core-shell styrene-butadiene rubber powder (available from Arkema under CLEARSTRENGTH). ®XT100 or commercially available as PARALOID™ EXL 2650J), and a core-shell styrene-butadiene rubber dispersion in polypropylene glycol (MW 400) (25% by weight of core-shell rubber) (commercially available from Kaneka Texas Corporation as Kane AceMX 715).

[0143] Exemplary non-limiting commercial core-shell elastomer particle products that can be used in the compositions of this disclosure include core-shell polysiloxane rubber powder (available from Wacker as GENIOPERL) ® P52 (obtained through commercial purchase).

[0144] The composition may contain elastomer particles in an amount of at least 0.1% by weight, such as at least 1% by weight, based on the total weight of the composition. The composition may contain elastomer particles in an amount of no more than 50% by weight, such as no more than 20% by weight, based on the total weight of the composition. The composition may contain a positive amount of elastomer particles in an amount of up to 25% by weight, such as from 0.1% to 50% by weight, such as from 1% to 20% by weight, based on the total weight of the composition.

[0145] The composition may further comprise an accelerator. The accelerator may be present in the first component, the second component, and / or the third or more components. The accelerator may comprise an amine or a nitrogen-based catalyst. The accelerator may comprise a tertiary amine, N - Heterocyclic carbenes or amidine / guanidine. Suitable promoters that can be used in this disclosure include N,N -Dimethylcyclohexylamine, N , N -Dimethylethanolamine, N 2,2'-Dimorpholine, 2,2'-Dimorpholine diethyl ether, dimethylaminoethoxyethanol, triethylenediamine, bis(2-dimethylaminoethyl) ether, N , N , N '-Trimethylaminoethylethanolamine, N , N , N' , N' -Tetramethyl-1,6-hexanediamine, 1,3,5-tris(dimethylaminopropyl)-hexahydro-triazine, 1,8-diazabicyclo[5.4.0]undec-7-ene, N-(3-aminopropyl)imidazolium, 1,2-dimethylimidazolium, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene. In some cases, the accelerator may include organic acids such as diphenyl phosphate, methanesulfonic acid, or trifluoromethanesulfonic acid. The accelerator may include organometallic complexes. Suitable organometallic complexes include titanates (such as tetrabutyl titanate or tetrapropyl titanate), tin compounds (such as dibutyltin dilaurate, dibutyltin diacetate, stannous octoate, or dibutyltin oxide), or other metal compounds (such as chelates of bismuth, zirconium, titanium, aluminum, or iron, such as zirconium acetylacetonate or iron acetylacetonate). In examples, the accelerator may be latent, blocked, and / or encapsulated.

[0146] The composition may contain an accelerator in an amount of at least 0.001% by weight, such as at least 0.01% by weight, based on the total weight of the composition, and may be present in an amount of no more than 2% by weight, such as no more than 1% by weight, based on the total weight of the composition. The accelerator may be present in the composition in an amount of 0.001% by weight to 2% by weight, such as 0.01% by weight to 1% by weight, based on the total weight of the composition. The composition may contain an accelerator in an amount of up to 2% by weight, such as up to 1% by weight, based on the total weight of the composition.

[0147] Compositions, hot melt adhesives, methods and systems

[0148] The first and second components can be liquids under ambient conditions, miscible at ambient temperature, and capable of solidification at ambient temperature. The composition can be formulated as a two-component composition.

[0149] The compositions according to this disclosure can be formed into hot melt adhesives. Hot melt adhesives can be used to form self-supporting films, adhesives, structural adhesives, sealants, potting compounds, gap fillers, prepregs, embedding materials, encapsulants, etc. Solid hot melt adhesives can be heated above their reflow initiation temperature and can be used to surround substrates or assemblies to substantially exclude air, water, and / or moisture from the substrate and / or increase the strength or stiffness of the substrate or assembly. Additionally, the compositions can be made to contact surfaces or assemblies as pre-formed films, and the system can be heated above the reflow initiation temperature of the composition and then cooled to produce a bonded or embedded system.

[0150] The composition may have a reflux initiation temperature of at least 50°C, such as at least 60°C. The composition may have a reflux initiation temperature of less than 150°C, such as less than 140°C. The composition may have a reflux initiation temperature of 50°C to 150°C, such as 60°C to 140°C.

[0151] The reflow initiation temperature can be achieved, for example, by heating the coating containing the coating disclosed herein and / or heating the substrate on which the coating is formed. The coating and / or substrate can be heated by direct thermal exposure, and / or indirectly heated in a substrate containing ferromagnetic, ferrimagnetic, and / or superparamagnetic materials, or in a coating formed from a composition containing ferromagnetic, ferrimagnetic, and / or superparamagnetic materials, by causing ferromagnetic heating, ferrimagnetic heating, and / or superparamagnetic heating through the application of a magnetic field.

[0152] This document discloses a method for preparing a hot melt adhesive. The method may include, or substantially comprises, or consists of: mixing a first component and a second component under ambient conditions to form one of the hot melt adhesives disclosed herein.

[0153] The compositions and hot melt adhesives disclosed herein can be applied individually or as part of a coating system. The compositions and hot melt adhesives disclosed herein can be applied directly to the surface or underlayer of a substrate by any suitable coating process, such as by manual pressure, mechanical pressure, and / or extrusion at or above the reflow initiation temperature to allow the hot melt adhesive to flow and form a liquid. When the hot melt adhesive cools to below the reflow initiation temperature and close to ambient temperature, it forms a solid. The system may include multiple identical or different layers and may further include additional coating compositions, such as pretreatment compositions, primers, etc. The coating can be formed when the compositions disclosed herein are deposited onto a substrate and cured by methods known to those skilled in the art (e.g., under ambient conditions, and may be further cured by using an external energy source (such as an oven or other thermal means) or by using photochemical radiation). The compositions can be cured at ambient temperature or slightly warmer temperatures. When cured at room temperature, the coatings provided by this disclosure can cure to a non-sticky surface, for example, within 24 hours, 20 hours, 16 hours, 12 hours, 6 hours, or 3 hours from the time of mixing. However, technicians understand that curing time varies with temperature and humidity.

[0154] Solid hot melt adhesive can be applied to the surface of the first substrate, as described above.

[0155] Methods for forming an adhesive between two substrates for a wide range of potential applications are also disclosed, wherein the adhesion between the substrates provides mechanical properties. The method may include: contacting the surface of a first substrate, as described above, with a hot melt adhesive or composition; contacting the surface of a second substrate with the hot melt adhesive or composition such that the hot melt adhesive or composition is located between the surfaces of the first and second substrates; applying sufficient pressure to ensure close contact between the hot melt adhesive or composition and the two substrates; and cooling the hot melt adhesive or composition to below its reflow initiation temperature. For example, the hot melt adhesive or composition may be applied to one or both substrate materials bonded together to form an adhesive bond therebetween, and the substrates may be aligned, with pressure and / or spacers added to control the bond thickness. As described above, an external energy source (such as heat) may be applied to the cured hot melt adhesive or composition, which may reverse crosslinking and allow the bonded substrates to separate.

[0156] The lap shear strength of the composition can decrease from >5 MPa at ambient temperature to <0.5 MPa at temperatures above 50°C, such as above 60°C.

[0157] The composition may have a Tg of at least -120°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode). The composition may have a Tg of no more than 150°C, such as no more than 100°C, such as a maximum of 90°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode). The composition may have a Tg of -120°C to 150°C, such as -120°C to 100°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode).

[0158] Hot melt adhesives or compositions can be applied to clean or unclean (i.e., including oily or greased) substrate surfaces. Hot melt adhesives or compositions can also be applied to substrates that have been pretreated, coated with an electrodepositable coating, and / or coated with another layer (such as a primer, undercoat, or topcoat).

[0159] This disclosure also relates to a method for repairing a joint in the event of joint failure or damage, wherein the bond between two substrates has broken. The bond between the two substrates can be re-formed using the method described above for bonding the two substrates, by heating the assembly to above the reflow initiation temperature of the hot melt adhesive, and then cooling the assembly as described above.

[0160] This disclosure also relates to a method for repairing articles, coatings or films formed by one of the hot melt adhesives or compositions disclosed herein.

[0161] The composition can be injected or otherwise placed in a die-casting machine or mold and cured under ambient conditions to form a part or component, and optionally can be machined into a specific configuration.

[0162] Dielectric coating compositions and dielectric coatings, as well as dielectric systems and kits

[0163] This document also discloses a dielectric coating system. The dielectric coating system may comprise: a first composition for application to a first portion of a substrate surface, the first composition comprising a dielectric coating composition; and a second composition for application to a second portion of a substrate surface, the second composition comprising any of the compositions disclosed above, which can form a second coating in a cured state. The first portion and the second portion may be located on a single substrate, or may be located on a first substrate and a second substrate, respectively.

[0164] This document also discloses a dielectric coating kit. 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 the substrate surface, the second composition comprising any of the compositions disclosed above, which, in a cured state, can form a second coating. The first and second portions may be located on a single substrate, or may be located on a first substrate and a second substrate, respectively. Optionally, the kit may include instructions regarding the application of the first and second compositions, respectively, to the first and second portions of the substrate surfaces.

[0165] When used with respect to the dielectric coating system and kit disclosed herein, the first and second portions may be identical or different, provided that the first and second portions overlap to form a coating stack, such as a second coating on top of the dielectric coating. Such a coating stack does not preclude the possibility of coatings other than the dielectric and second coatings, wherein such additional coatings may or may not be located between the dielectric and second coatings. Optionally, the coating stack may be formed between two substrates.

[0166] A dielectric coating may be formed on a first portion of the surface of a first substrate, and a second coating may be formed on a second portion of the surface of a second substrate, and the substrate may be positioned such that the first portion and the second portion overlap to form a coating stack as described above.

[0167] As used herein, “dielectric” means that the coating composition or coating has a dielectric strength of at least 10 kV / mm, such as at least 12 kV / mm, such as at least 15 kV / mm, which is measured according to ASTM D149-09 using the SefelecDielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV, Imax limit 0.1 mA, 19-second ramp, 20-second dwell, 2-second fall).

[0168] The dielectric coating composition may include a binder comprising a film-forming 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 crosslinking agent, upon solvent evaporation, and / or upon light or thermal activation. The dielectric coating composition may contain any suitable film-forming 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: polyesters, alkyd resins, urethanes, isocyanates, polyureas, epoxy resins, acrylics, polyethers, polysulfides, polyamines, polyamides, polyvinyl chloride, polyolefins, polyvinylidene fluoride, polyolefins, polysiloxanes, amine-aldehydes, resin polyols, phosphorylated polyepoxides, phosphorylated acrylic polymers, and / or amino plastics.

[0169] The dielectric coating composition may optionally include a curing agent and / or a crosslinking agent capable of crosslinking with the film-forming resin to cure the dielectric coating composition. Any suitable curing agent and / or crosslinking agent capable of crosslinking with the film-forming resin may be used. Examples of suitable curing agents include, but are not limited to: amines; amino plastics; phenolic plastics; polyisocyanates, including end-capped polyisocyanates; polyepoxides; β-hydroxyalkylamides; polybasic acids; organometallic acid functional materials; polyamines; polyamides; polysulfides; polythiols; polyolefins, such as polyacrylates; polyols; polysilanes; and combinations thereof.

[0170] The dielectric coating composition may optionally further comprise colorants, pigments, additives, and / or fillers. Suitable fillers that can be used in the dielectric coating composition include TC / EI filler materials, TC / EC filler materials, and / or NTC / EI filler materials.

[0171] The dielectric coating composition may comprise a thermosetting coating composition, wherein the coating composition cures upon crosslinking of a film-forming resin with a curing agent and / or a crosslinking agent. Alternatively, the dielectric coating composition may comprise a thermoplastic coating composition, wherein the coating composition comprises a film-forming resin that cures upon evaporation of water and / or solvent. Alternatively, the dielectric coating composition may comprise a thermosetting or thermoplastic coating composition that cures upon exposure to photochemical radiation, such as ultraviolet light.

[0172] The dielectric coating composition may comprise a liquid coating composition or a powder coating composition. As used herein, when referring to a dielectric coating composition, "liquid" means having a Pa value of less than 100,000 at 25°C. A material with a viscosity of s, such that when passed through a plate with a diameter of 25 mm, a gap of 0.5 mm, and a shear rate of 1 s... -1 The parallel plate rheology is used for measurement.

[0173] Suitable liquid coating compositions include, but are not limited to, electrodepositable coating compositions, single-component coating compositions, and / or multi-component coating compositions.

[0174] For example, a liquid dielectric coating composition may comprise an electrodepositable coating composition. The electrodepositable coating composition may comprise one or more film-forming resins containing cationic or anionic salt groups, which can be deposited onto a metal or other conductive substrate under the influence of an applied potential (i.e., by electrodeposition).

[0175] 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 radical polymerizable resin containing alkenyl unsaturation or alkene double bonds and / or a film-forming resin that can be reacted via a cationic photopolymerization mechanism. Examples of suitable UV-curable coating compositions that may be used include, but are not limited to, the RAYCRON series of UV-curable coatings commercially available from PPG Industries, Inc.

[0176] Other suitable liquid dielectric coating compositions include, but are not limited to, solvent-based coating compositions from the SPECTRACRON series and water-based coating compositions from the AQUACRON series, all of which are commercially available from PPG Industries, Inc. Liquid dielectric coatings can also be applied as two-component compositions, wherein the film-forming resin and the reactive curing agent and / or crosslinking agent are mixed immediately prior to the application of the coating composition, and can optionally be cured under ambient conditions without any external energy source.

[0177] Alternatively, the dielectric coating composition may comprise a powder coating composition. As used herein, “powder coating composition” means any dielectric coating composition in particulate form, in the form of a co-reactive solid, which may be substantially free of, substantially free of, or completely free of water and / or solvents. Suitable film-forming resins that may be used in dielectric powder coating compositions include those discussed in paragraphs

[0006] to

[0042] ,

[0057] to

[0068] ,

[0088] to

[0105] , and

[0128] to

[0139] of PCT Publication WO 2021 / 173941A1, which are incorporated herein by reference. Non-limiting examples of suitable powder compositions that may be used in this disclosure include: polyester-based ENVIROCRON series powder coating compositions (commercially available from PPG Industries, Inc.), silicone-modified polyester compositions, epoxy-polyester blends, and / or UV-curable powder compositions.

[0178] The dielectric coating composition can be applied to a substrate by any suitable method known in the art, including but not limited to electrodeposition, roll coating, spraying (such as electrostatic spraying), flow coating, spin coating, curtain coating, brush coating, dip coating, hot melt extrusion, application of self-supporting films, and / or by using a fluidized bed. Once applied to the substrate, the dielectric coating composition can be cured by any method known in the art, such as baking, induction heating, infrared heating, and / or exposure to photochemical radiation (such as UV).

[0179] The dielectric coating can be formed from the dielectric coating composition described herein.

[0180] The dielectric coating may have a dielectric strength of at least 10 kV / mm, such as at least 12 kV / mm, or at least 15 kV / mm, which is measured according to ASTM D149-09 using the Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax limit 0.1 mA, 19-second ramp-up, 20-second dwell, 2-second fall). The dielectric coating may have a dielectric strength not exceeding 120 kV / mm, such as not exceeding 100 kV / mm, which is also measured according to ASTM D149-09 using the Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax limit 0.1 mA, 19-second ramp-up, 20-second dwell, 2-second fall). The dielectric coating can have dielectric strengths ranging from 10 kV / mm to 120 kV / mm, such as 12 kV / mm to 100 kV / mm, and such as 15 kV / mm to 100 kV / mm, which are measured according to ASTM D149-09 using the Sefelec Dielectric Strength Tester (RMG12AC-DC; voltage limit 12.0 kV DC, Imax limit 0.1 mA, 19-second ramp, 20-second dwell, 2-second fall).

[0181] The dielectric coating can be formulated as a hot-melt film or a self-supporting film. As used herein, a “self-supporting film” refers to a sheet containing a cured composition that can be formed independently of the substrate surface. The self-supporting film may optionally contain an adhesive layer, such as a pressure-sensitive adhesive layer.

[0182] Any suitable method, including the methods described above, can be used to apply or deposit the compositions disclosed herein. Articles can be formed from one of the compositions disclosed herein using the methods provided herein. Articles can be formed by extrusion, casting, molding, additive manufacturing (such as 3D printing), subtractive manufacturing, and / or machining.

[0183] Additive manufacturing

[0184] The compositions disclosed herein can be used in any suitable additive manufacturing technology, such as three-dimensional (3D) printing, extrusion, jetting, and binder jetting. Additive manufacturing refers to the process of producing parts or components by building them layer by layer (such as one layer at a time).

[0185] This disclosure also relates to the use of additive manufacturing processes, such as 3D printing, to produce structural articles, such as acoustic damping liners as a non-limiting example. 3D printing refers to a computerized process, optionally including artificial intelligence modulation, through which material is printed or deposited in successive layers to produce 3D parts or components, such as acoustic damping liners in a battery assembly as a non-limiting example. 3D parts or components can be produced by depositing successive portions or layers on a base of any spatial configuration, and then depositing additional portions or layers on and / or adjacent to the previously deposited portions or layers to produce 3D-printed parts or components.

[0186] It should be understood that the configuration of the 3D printing process (including the selection of suitable deposition equipment) depends on a variety of factors, such as deposition volume, viscosity of the composition, and complexity of the part being manufactured. Any suitable mixing, delivery, and 3D printing equipment known to those skilled in the art can be used. The composition can be printed or deposited in droplets or extrusions of any size and / or shape and in any pattern to produce 3D structures.

[0187] The compositions disclosed herein can be applied or deposited using any suitable 3D printing method known to those skilled in the art. The first and second components of the compositions disclosed herein can be mixed and then deposited, or the first and second components can be deposited independently (e.g., simultaneously or sequentially).

[0188] The first and second components can be premixed, i.e., mixed together, and then deposited. When the material is deposited, the mixture may partially react or become thermosetting; the deposited reaction mixture may react after deposition and may also react with previously deposited portions of the article and / or subsequently deposited portions (such as the underlying layer or overlay of the article).

[0189] In a non-limiting example, the first and second components may be released from their respective storage containers and propelled (e.g., pumped) through conduits (e.g., hoses) to a mixer (e.g., a static or dynamic mixer), whereby the compositions can be mixed for a time sufficient to homogenize them, and the compositions can then be released through an outlet. The outlet may be a deposition device (e.g., a printhead), and / or the material may exit the mixing unit and be propelled (e.g., by pump) through conduits (e.g., hoses) to the printhead. The printhead may optionally be mounted on a 3D rotary robotic arm to allow the 3D printing composition to be delivered to any substrate in any spatial configuration, and / or the substrate may be manipulated in any spatial configuration during the 3D printing process.

[0190] Alternatively, the first and second components can be deposited independently of different printheads. The first component can be deposited from one printhead and the second component can be deposited from a second printhead. The first and second components can be deposited in any pattern, such that the first and second components, including any deposited layers, can react together and with the underlying layers and / or overlays to produce 3D printed parts or components.

[0191] The method provided in this disclosure includes printing a composition onto a manufactured part. The method provided in this disclosure also includes directly printing the part.

[0192] Uses of the composition and hot melt adhesive

[0193] The compositions disclosed herein exhibit ambient temperature curability. The hot melt adhesives formed from the compositions disclosed herein can be used to form coatings and / or self-supporting films. Surprisingly, the coatings and / or self-supporting films can be used as structural adhesives.

[0194] The coatings and / or self-supporting films disclosed herein exhibit high lap shear strength at room temperature and 50°C (determined according to ASTM D1002-10 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute), but exhibit low lap shear strength at 150°C (determined according to ASTM D1002-10 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute). This is a surprising and unexpected result.

[0195] Furthermore, articles formed from the compositions disclosed herein surprisingly exhibit high reprocessability, reshapeability, and / or self-sealing properties. The coatings and / or self-supporting films disclosed herein also surprisingly exhibit self-healing properties.

[0196] The hot melt adhesive disclosed in this article can be used to repair joints between two substrates.

[0197] The hot melt adhesive formed from the compositions disclosed herein can be used to prepare coatings and / or self-supporting films having the following properties:

[0198] (a) A lap shear strength of at least 5 MPa, such as 5 MPa to 40 MPa, measured at 25°C using a 0.063-inch thick 2024 T3 aluminum substrate according to ASTM D1002-10, such as by means of an INSTON 5567 machine in tensile mode at a pulling rate of 1.3 mm per minute.

[0199] (b) Lap shear strength of 1 MPa to 20 MPa, such as 2 MPa to 20 MPa, such as 2 MPa to 15 MPa, measured at 50°C using 0.063-inch thick 2024 T3 aluminum substrate, as measured by an INSTON 5567 machine in tensile mode at a pulling rate of 1.3 mm per minute;

[0200] (c) Lap shear strength of up to 2 MPa measured at 150°C using a 0.063-inch thick 2024 T3 aluminum substrate according to ASTM D1002-10, such as by an INSTON 5567 machine in tensile mode at a pull rate of 1.3 mm per minute; and / or

[0201] (d) Glass transition temperatures from 35°C to 55°C, as measured by dynamic chemical analysis (DMA) at a frequency of 1.0 Hz and a heating rate of 3°C / min.

[0202] substrate

[0203] The hot melt adhesives and compositions described herein can be coated or deposited on any substrate or surface, or otherwise contacted with any substrate or surface, such as, but not limited to, metals or metal alloys, polymeric materials (such as plastics, including filled and unfilled thermoplastic or thermosetting materials), and / or composite materials. Other suitable substrates include, but are not limited to, glass or natural materials (such as wood). The substrate may include any combination of two or more different materials, such as, but not limited to, two different metals; or metals and metal alloys; or metals and metal alloys with one or more composite materials.

[0204] Suitable substrates may include, but are not limited to, flexible and rigid metallic substrates, such as ferrous metals, aluminum, aluminum alloys, magnesium, titanium, copper, and other metallic and alloy substrates. Ferrous metal substrates may include, for example, iron, steel, and their alloys. Non-limiting examples of available steel materials include: cold-rolled steel, nickel-plated cold-rolled steel, galvanized (zinc-coated) steel, electro-galvanized steel, stainless steel, pickled steel, zinc-iron alloys (such as GALVANNEAL), and combinations thereof. Aluminum alloys, such as, for example, aluminum alloys of the 1XXX, 2XXX, 3XXX, 4XXX, 5XXX, 6XXX, 7XXX, or 8XXX series, as well as clad aluminum alloys and cast aluminum alloys, such as, for example, clad aluminum alloys of the A356, 1XX.X, 2XX.X, 3XX.X, 4XX.X, 5XX.X, 6XX.X, 7XX.X, or 8XX.X series, may also be used as substrates. The substrate may also include, for example, magnesium, such as magnesium alloys of the AZ31B, AZ91C, AM60B or EV31A series, titanium and / or titanium alloys, such as titanium alloys of grades 1-36, including H-grade variants, copper and copper alloys or other non-ferrous metals, and alloys of these materials. The substrate may include composite materials, such as plastics, glass fiber and / or carbon fiber composites.

[0205] It should also be understood that the substrate may include 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: zinc phosphate pretreatment solutions, such as those described in, for example, U.S. Patent Nos. 4,793,867, 3:5 to 5:8 and 5:64 to 11:50 (incorporated herein by reference) and 5,588,989, 1:65 to 10:40 (incorporated herein by reference); or zirconium-containing pretreatment solutions, such as those described in, for example, U.S. Patent Nos. 7,749,368, 1:55 to 2:12 and 2:53 to 14:60 (incorporated herein by reference) and 8,673,091, 1:53 to 2:11, 3:26 to 15:45 and 16:51 to 18:26 (incorporated herein by reference).

[0206] The substrate can be in any form, such as, but not limited to, sheets, foils, laminated foils, gaskets, prefabricated parts, components, or articles. Hot melt adhesives formed from compositions comprising the materials disclosed herein can be used to coat substrates, such as by depositing, applying, or contacting the hot melt adhesive with the substrate surface.

[0207] In the examples, the substrate may be a multi-metal article. As used herein, the term “multi-metal article” means (1) an article having a surface containing a first metal and a surface containing a second metal different from the first metal, (2) a first article having a surface containing a first metal and a second article having a surface containing a second metal different from the first metal, or (3) both (1) and (2).

[0208] The compositions disclosed herein are not limited and are particularly suitable for a wide range of industrial or transportation applications, including automotive, commercial, rail, marine, and / or aerospace applications. Suitable substrates used in this disclosure include substrates used in assemblies of vehicle bodies (e.g., but not limited to, doors, body panels, trunk lids, top panels, hoods, top and / or longitudinal beams, rivets, landing gear assemblies, and / or skins used on aircraft), vehicle frames, vehicle components, motorcycles, wheels, and industrial structures and components. As used herein, “vehicle” or variations thereof include, but are not limited to, civil vehicles, light and heavy commercial vehicles, civil and military aircraft and / or land vehicles, such as automobiles, motorcycles, and / or trucks.

[0209] Figures 1 to 9 Non-limiting examples of battery assembly components and constructions are shown, as well as non-limiting applications or uses of the compositions disclosed herein in said battery assemblies. Although Figures 1 to 9 Specific examples of cell shapes and cell arrangements are shown, but cells can be arranged in any configuration known to those skilled in the art. Additionally, the compositions disclosed herein in a cured state can be used to form gaskets, adhesives, structural adhesives, coatings, potting compounds, etc., to provide thermal protection between battery cells, within battery modules, and / or within battery packs. These materials can be used on any surface or in any space within such battery assemblies. For example, the compositions disclosed herein can also be used in battery assemblies, including but not limited to cell-to-module (C / C) modules. Figure 3 , Figure 4 , Figure 6B ) Module to Group ( Figure 6C , Figure 7 Unit to group () Figure 8 ), and the unit to chassis battery assembly ( Figure 9 Such battery assemblies can be used in, but are not limited to, any of the applications described above.

[0210] A battery assembly can be any combination of one or more battery cells (whose interconnections provide conductivity between the battery cells) and auxiliary components, such as control electronics and components that, in non-limiting instances, ensure the operation of a particular battery due to the necessary structural, mechanical, and environmental requirements (e.g., but not limited to, battery cell interconnects such as wires, battery pack housings including trays and covers, module housings, module frames and frame plates, module supports, 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).

[0211] Battery cell 10 is typically a single-cell energy storage container that can be connected in series or parallel. The battery cell can be any suitable size or shape known to those skilled in the art, such as, but not limited to, cylindrical. Figure 1 , Figure 4 and Figure 9 ), prismatic ( Figure 2 , Figures 5 to 8 ) and / or bag-shaped ( Figure 3 The battery cell 10 is enclosed to provide the desired mechanical protection and environmental isolation for the cell. For example, cylindrical and prismatic cells can be encased in metal cans, boxes, and lids, while pouch cells can be encased in multilayer laminated foil. Battery terminals 1 connect the electrodes inside the battery cell to an external circuitry, with one terminal being the positive terminal and the other the negative terminal. Figure 4 As shown, the battery cell 10 can be connected in series or in parallel with other battery cells 10 via the interconnect wire 5 so that current can flow between the cells 10.

[0212] like Figure 3 and Figure 4 As shown, battery cells 10 can be arranged in a module 100 comprising multiple cells 10 connected in series or parallel. Module 100 may include a housing of the arranged cells 10. Auxiliary components, such as those described above, may be included. Spaces of any size may be located between any inner surfaces of the multiple cells, auxiliary components, base and / or module walls or other housings 120.

[0213] Figure 1 A top view of a cylindrical battery cell 10 having terminals 1 is shown. As shown, the cells are arranged in rows, with cooling tubes 3 or dielectric insulating paper (electronic paper) 4 between the rows. As shown, materials (such as adhesive 6 and / or potting compound 7) optionally formed from the compositions disclosed herein in a cured state can be positioned between the cells 10, the cooling tubes 3 and / or the electronic paper 4.

[0214] Figure 2An exploded isometric view of an array of prismatic cell units 10 is shown. As shown, each prismatic cell 10 may include a top 11, a bottom, and a wall 13 positioned between the top and bottom, each having a surface. As shown, a material (such as a gasket 8) formed from the composition disclosed herein in a cured state may be positioned between the surfaces of the cell walls 13 of adjacent cells 10.

[0215] Figure 3 A cross-sectional front view of an array of pouch cell units 10 in module 100 is shown. Module walls 120 partially or completely surround the units 10. As shown, materials formed from the compositions disclosed herein in a cured state (such as gaskets 8) can be positioned between the surfaces of the units 10.

[0216] Figure 4 An isometric view of cylindrical cells 10 in battery module 100 is shown. Each cell may include a top 11, a bottom 12, and a wall 13 positioned between the top and bottom, each having a surface. The top 11 and bottom 12 may be terminals with opposite charges, one being a positive terminal 1 and the other a negative terminal (not shown). Battery cells may be connected at their terminals via interconnects (such as wires 5, etc.) to allow current to flow between electrical cells. Module 100 or module wall 120 may form a space with a volume. Cell 10 may be positioned within the space to consume a portion of the volume. A material formed from the coating compositions disclosed herein (such as potting compound 7) may be positioned within the space to consume a portion of the volume, such that the material is adjacent to the surface of cell wall 13 of module 100 and / or the inner surface of one or more walls of wall 120.

[0217] Figure 5 An exploded perspective view of a battery module 100 is shown, which includes one or more arrays of battery cells 10, cooling fins 230, and a cooling plate 240. Materials formed from the compositions disclosed herein in a cured state (such as gaskets 8) may be positioned between the cells 10. Additional gaskets 8 may be positioned between the cells 10, the inner surfaces of the cooling fins 230, the cooling plate 240, and / or the wall 120. Other gaskets 8 may be positioned adjacent to the outer surface of the wall 120.

[0218] Figure 6 shows battery cell 10 ( Figure 6A ) to battery module 100 ( Figure 6B ) to battery pack 200 ( Figure 6C Isometric view of the battery assembly. Battery module 100 includes a plurality of battery cells 10, and battery pack 200 includes a plurality of battery modules 100.

[0219] Figure 7A perspective view of a cutout in the battery pack 200 is shown. The battery pack includes a plurality of battery modules 100 and cells 10 located within each module 100. The base of the battery pack 200 includes a cooling plate 240. Materials formed from the compositions disclosed herein in a cured state (such as adhesive 9) may be positioned between the cooling plate 240 and the inner surface of the wall of the battery pack 200. Materials formed from the compositions disclosed herein in a cured state (such as gasket 8) may be positioned between the cells 10 within the modules 100.

[0220] Figure 8 An isometric view of the assembly of unit 10 to battery pack 200 is shown. Unit 10 is arranged within pack 200 (rather than in a separate module).

[0221] In other cases, the battery cells may be arranged on or within the article, such as, but not limited to, Figure 9 The units shown are used to construct the battery assembly from the chassis, wherein one or more units are used to build the battery assembly without prior assembly of the units into modules and / or groups. Figure 9 An isometric sectional view of the unit to the chassis battery assembly 300 is shown. The unit 10 is arranged on a base that includes a chassis 55 and is supported by a vehicle frame 45 and located below the vehicle's interior floor 35.

[0222] Any battery assembly may further include a thermal management system comprising an air or fluid circuit, which may be liquid-based (e.g., an ethylene glycol solution) or based on a direct refrigerant.

[0223] The substrate may include a coating formed by a hot melt adhesive on a portion of the surface of the substrate by one of the compositions disclosed herein, having in the cured state: (a) an lap shear strength of at least 15 MPa measured at 25°C using a 0.063-inch thick 2024 T3 aluminum substrate according to ASTM D1002-10, as measured by an INSTON 5567 machine in tensile mode at a pull rate of 1.3 mm per minute; (b) an lap shear strength of at least 5 MPa measured at 50°C using a 0.063-inch thick 2024 T3 aluminum substrate according to ASTM D1002-10, as measured by an INSTON 5567 machine in tensile mode at a pull rate of 1.3 mm per minute; and (c) an lap shear strength of not more than 2 MPa measured at 150°C using a 0.063-inch thick 2024 T3 aluminum substrate according to ASTM D1002-10, as measured by an INSTON 5567 machine in tensile mode. The glass transition temperature from 35°C to 55°C was measured by the 5567 machine at a pulling rate of 1.3 mm per minute; and / or (d) by dynamic chemical analysis (DMA) at a frequency of 1.0 Hz and a heating rate of 3°C / min.

[0224] aspect

[0225] 1. A compound comprising:

[0226] furan functional groups;

[0227] Isocyanate functional groups; and

[0228] Carbamate bonds, urea bonds and / or thiocarbamate bonds.

[0229] 2. The compound according to aspect 1, wherein the urethane bond, the urea bond and / or the thiourethane bond are located between the furan functional group and the isocyanate functional group.

[0230] 3. The compound according to aspect 1 or aspect 2, wherein the compound comprises structure I:

[0231]

[0232] Wherein X contains O, N or S, m ≥ 1, n ≥ 1, and the sum of m+n ≥ 2; R1 contains substituted or unsubstituted alkyl groups, alkylene groups, (cyclo)alkyl groups, aromatic groups, isocyanurate moieties, biuret moieties, urethane moieties, glycourea moieties, benzoguanamine moieties, iminooxadiazinedione moieties, or polymer moieties different from the urethane bonds, the urea bonds and / or the thiourethane bonds; and R2 contains substituted or unsubstituted alkyl groups, ester moieties, ether moieties and / or urethane moieties.

[0233] 4. The compound according to aspect 3, wherein R2 contains one carbon atom.

[0234] 5. The compound according to aspect 3 or aspect 4, wherein R1 comprises isocyanurate, or urethane, or iminooxadiazine dione, R2 comprises CH2, and X comprises O.

[0235] 6. The compound according to any one of aspects 3 to 5, wherein m ≤ 12, n ≤ 12, and / or m+n ≤ 13.

[0236] 7. The compound according to any one of aspects 3 to 6, wherein m+n > 2.

[0237] 8. The compound according to any one of the foregoing aspects, wherein the compound is substantially free of ether bonds.

[0238] 9. The compound according to any one of the preceding aspects, wherein the compound comprises a monomer, a prepolymer, or a polymer.

[0239] 10. The compound according to any one of the preceding aspects, wherein the compound comprises at least 100 g / eq, such as at least 200 g / eq, of furan equivalent weight.

[0240] 11. The compound according to any one of the preceding aspects, wherein the compound comprises a furan equivalent weight of not more than 3,000 g / eq, such as not more than 1,500 g / eq.

[0241] 12. The compound according to any one of the preceding aspects, wherein the compound comprises a furan equivalent weight of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0242] 13. The compound according to any one of the preceding aspects, wherein the compound comprises at least 100 g / eq, such as at least 200 g / eq, an isocyanate equivalent weight.

[0243] 14. The compound according to any one of the preceding aspects, wherein the compound comprises an isocyanate equivalent weight of not more than 3,000 g / eq, such as not more than 1,500 g / eq.

[0244] 15. The compound according to any one of the preceding aspects, wherein the compound comprises isocyanate equivalent weights of 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq.

[0245] 16. The compound according to any one of the preceding aspects, wherein the compound comprises a reaction product of a reactant, the reactant comprising:

[0246] (a) a furan-containing compound, said furan-containing compound comprising an active hydrogen functional group; and

[0247] (b) Contains polyisocyanate compounds.

[0248] 17. The compound according to aspect 16, wherein the active hydrogen functional group includes a hydroxyl functional group, an amine functional group, and / or a thiol functional group.

[0249] 18. The compound according to aspect 16 or aspect 17, wherein the isocyanate functional group comprises an isocyanate functional group derived from the polyisocyanate.

[0250] 19. The compound according to any one of aspects 16 to 18, wherein the active hydrogen functional group is present in a substoichiometric amount relative to the isocyanate functional group.

[0251] 20. The compound according to any one of aspects 16 to 19, wherein the equivalent ratio of the active hydrogen functional group to the isocyanate functional group is less than 1:1, such as not more than 1:2, such as not more than 1:3, such as not more than 1:5.

[0252] 21. The compound according to any one of aspects 16 to 20, wherein the furan functional group is monosubstituted and / or terminal.

[0253] 22. A composition comprising:

[0254] A first component, the first component comprising a compound according to any one of the foregoing aspects; and

[0255] The second component comprises a dienophile compound.

[0256] 23. The composition according to aspect 22, wherein the furan functional group of the compound and the dienophile of the dienophile-containing compound are present in an equivalent ratio of at least 0.5:1, such as at least 0.6:1.

[0257] 24. The composition according to aspect 22 or aspect 23, wherein the furan functional group of the compound and the dienophile of the dienophile-containing compound are present in an equivalent ratio not exceeding 2:1, such as not exceeding 1.5:1.

[0258] 25. The composition according to any one of aspects 22 to 24, wherein the furan functional group of the compound and the dienophile of the dienophile-containing compound are present in an equivalent ratio of 0.5:1 to 2:1, such as 0.6:1 to 1.5:1.

[0259] 26. The composition according to any one of aspects 22 to 25, wherein the dienophilic compound comprises at least 100 g / eq, such as at least 200 g / eq, of dienophilic equivalent weight.

[0260] 27. The composition according to any one of aspects 22 to 26, wherein the dienophilic compound comprises a dienophilic equivalent weight of not more than 3,000 g / eq, such as not more than 1,500 g / eq.

[0261] 28. The composition according to any one of aspects 22 to 27, wherein the dienophilic compound comprises 100 g / eq to 3,000 g / eq, such as 200 g / eq to 1,500 g / eq, in dienophilic equivalent weight.

[0262] 29. The composition according to any one of aspects 22 to 28, wherein the furan functional group and the dienophile are capable of reacting under ambient conditions.

[0263] 30. The composition according to any one of aspects 22 to 29, wherein the dienophile comprises a maleimide functional group, a maleate functional group and / or a fumarate functional group.

[0264] 31. The composition according to any one of aspects 22 to 30, wherein the second component comprises a third compound capable of reacting with the isocyanate functional group.

[0265] 32. The composition according to aspect 31, wherein the third compound comprises a hydroxyl functional group.

[0266] 33. The composition according to aspect 32, comprising the isocyanate functional group on the compound and the hydroxyl functional group on the third compound in an equivalent ratio of at least 0.2:1, such as at least 0.4:1.

[0267] 34. The composition according to aspect 32 or aspect 33, comprising the isocyanate functional group on the compound and the hydroxyl functional group on the third compound in an equivalent ratio not exceeding 3:1, such as not exceeding 2:1.

[0268] 35. The composition according to any one of aspects 32 to 34, comprising the isocyanate functional group on the compound and the hydroxyl functional group on the third compound in an equivalent ratio of 0.2:1 to 3:1, such as 0.4:1 to 2:1.

[0269] 36. The composition according to any one of aspects 22 to 35, wherein the first component further comprises a fourth compound comprising a furan functional group.

[0270] 37. The composition according to aspect 36, wherein the fourth compound comprises at least 68 g / eq, such as at least 80 g / eq, furan equivalent weight.

[0271] 38. The composition according to aspect 36 or aspect 37, wherein the fourth compound comprises a furan equivalent weight of not more than 1,500 g / eq, such as not more than 1,000 g / eq.

[0272] 39. The composition according to any one of aspects 36 to 38, wherein the fourth compound comprises 68 g / eq to 1,500 g / eq, such as 80 g / eq to 1,000 g / eq, in furan equivalent weight.

[0273] 40. The composition according to any one of aspects 22 to 39, further comprising fillers, additives, elastomer particles and / or accelerators.

[0274] 41. The composition according to aspect 40, wherein the first component, the second component and / or the third component comprises the filler, the additive, the elastomer particles and / or the accelerator.

[0275] 42. The composition according to aspect 40 or aspect 41, wherein the composition comprises the filler in an amount such as at least 0.5% by weight or at least 1% by weight based on the total weight of the composition.

[0276] 43. The composition according to any one of aspects 40 to 42, wherein the composition comprises the filler in an amount not exceeding 90% by weight, such as not exceeding 30% by weight, based on the total weight of the composition.

[0277] 44. The composition according to any one of aspects 40 to 43, wherein the composition comprises the filler in an amount such as 1% to 30% by weight based on the total weight of the composition, from 0.5% to 90% by weight.

[0278] 45. The composition according to any one of aspects 40 to 44, wherein the composition comprises the additive in an amount such as at least 0.01% by weight based on the total weight of the composition.

[0279] 46. ​​The composition according to any one of aspects 40 to 45, wherein the composition comprises the additive in an amount not exceeding 15% by weight, such as not exceeding 10% by weight, based on the total weight of the composition.

[0280] 47. The composition according to any one of aspects 40 to 46, wherein the composition comprises the additive in an amount such as 0.01% to 15% by weight or 0.1% to 10% by weight based on the total weight of the composition.

[0281] 48. The composition according to any one of aspects 40 to 47, comprising at least 0.1% by weight, such as at least 1% by weight, of the elastomer particles based on the total weight of the composition.

[0282] 49. The composition according to any one of aspects 40 to 48, comprising an amount of the elastomer particles in a quantity not exceeding 50% by weight, such as not exceeding 20% ​​by weight, based on the total weight of the composition.

[0283] 50. The composition according to any one of aspects 40 to 49, comprising the elastomer particles in an amount such as 1% to 20% by weight based on the total weight of the composition, from 0.1% to 50% by weight.

[0284] 51. The composition according to any one of aspects 40 to 50, comprising the promoter in an amount such as at least 0.001% by weight based on the total weight of the composition.

[0285] 52. The composition according to any one of aspects 40 to 51, comprising the promoter in an amount not exceeding 2% by weight, such as not exceeding 1% by weight, based on the total weight of the composition.

[0286] 53. The composition according to any one of aspects 40 to 52, comprising the promoter in an amount such as 0.001 wt% to 2 wt% based on the total weight of the composition.

[0287] 54. The composition according to any one of aspects 40 to 53, wherein:

[0288] (a) The filler includes: thermally conductive fillers, such as boron nitride, aluminum trihydrate and / or alumina, and / or non-thermally conductive fillers, such as fumed silica, wollastonite, calcium carbonate, mica iron oxide, carbon fiber or combinations thereof.

[0289] (b) The additives include rheology modifiers, tackifiers, thermoplastic polymers, surfactants, flame retardants, corrosion inhibitors, UV stabilizers, colorants, dyes, solvents, plasticizers, adhesion promoters, antioxidants, silanes, silane-terminated polymers, dehumidifiers, thixotropic adhesives and / or sagging control agents.

[0290] (c) The elastomer particles include a core-shell structure, such as comprising an acrylic shell and an elastomer core; and / or

[0291] (d) The promoters include amine catalysts and / or organometallic complexes.

[0292] 55. The composition according to aspect 54, wherein the thermally conductive filler comprises a thermally stable filler, a thermally unstable filler, a ferromagnetic material, a ferrimagnetic material, and / or a superparamagnetic material; and wherein the non-thermally conductive filler comprises a ferromagnetic material, a ferrimagnetic material, and / or a superparamagnetic material.

[0293] 56. The composition according to any one of aspects 40 to 55, wherein the composition comprises the filler in an amount of 50% to 90% by weight based on the total weight of the composition, and has a shear stress of not more than 10 measured by an Anton Paar MCR 301 rotational rheometer at 25°C and 1 Hz using parallel plates with a diameter of 25 mm (1 mm gap). 6 Pa The viscosity of s.

[0294] 57. The composition according to any one of aspects 22 to 56, having a Tg of at least -120°C (measured using a TAInstruments Q800 DMA V21.3 in single cantilever mode).

[0295] 58. The composition according to any one of aspects 22 to 57, having a Tg of not more than 150°C, such as not more than 100°C, such as up to 90°C (measured using TA Instruments Q800 DMA V21.3 in single cantilever mode).

[0296] 59. The composition according to any one of aspects 22 to 58, having a Tg of -120°C to 150°C, such as -120°C to 100°C (measured using a TA Instruments Q800 DMA V21.3 in single cantilever mode).

[0297] 60. The composition according to any one of aspects 22 to 59, wherein the composition is formulated as a two-component composition.

[0298] 61. The composition according to any one of aspects 22 to 60, wherein the composition is formulated to cure under ambient conditions.

[0299] 62. A method for coating a substrate, the method comprising:

[0300] A portion of the surface of the substrate is brought into contact with the composition according to any one of aspects 22 to 61.

[0301] 63. The method according to aspect 58, further comprising: mixing the first component and the second component to form a composition according to any one of aspects 22 to 61; and optionally heating the composition after the contact.

[0302] 64. The method according to aspect 62 or 63, further comprising: contacting the surface of the second substrate with the composition such that the composition is located between the first substrate and the second substrate.

[0303] 65. The method according to aspect 64, wherein prior to the contact, the joint between the first substrate and the second substrate is broken, and wherein the contact forms a repair joint.

[0304] 66. A method of forming an article, comprising: extruding the composition according to any one of aspects 22 to 61.

[0305] 67. The method according to aspect 66, wherein the extrusion includes three-dimensional printing.

[0306] 68. An article of manufacture formed by the method according to aspect 66 or aspect 67.

[0307] 69. The article of any one of aspects 66 to 68, wherein the article of any one of aspects exhibits reformability, reprocessability and / or self-healing properties.

[0308] 70. A substrate comprising a coating formed on a portion of the surface of the substrate by the composition according to any one of aspects 22 to 61.

[0309] 71. The substrate according to aspect 70, which is coated according to any one of aspects 62 to 65.

[0310] 72. The substrate according to aspect 70 or aspect 71, wherein the coating comprises: a sealant, an adhesive, a gap filler, a potting compound, an encapsulating agent, such as a solid or gel, and / or a liner, such as a pre-formed liner, a pre-made liner, or an in-situ formed liner.

[0311] 73. The substrate according to any one of aspects 70 to 72, wherein the substrate includes articles, components or combinations thereof.

[0312] 74. The substrate according to aspect 73, wherein the article of manufacture includes vehicles, appliances, personal electronic devices, circuit boards, battery cells, multi-metal substrates or combinations thereof.

[0313] 75. The substrate according to aspect 73, wherein the component includes a vehicle component.

[0314] 76. The substrate according to aspect 74, wherein the vehicle includes a land vehicle or an aircraft.

[0315] 77. The substrate according to aspect 76, wherein the land vehicle includes a bicycle, such as an electric bicycle.

[0316] 78. A preformed membrane comprising the composition according to any one of aspects 22 to 61.

[0317] 79. Use of the composition according to any one of aspects 22 to 57, wherein the use includes repairing a joint between two substrates.

[0318] 80. The use of the coating as described in aspect 79, wherein the coating has an lap shear strength of at least 15 MPa, measured according to ASTM D1002-10 using a 0.063-inch thick 2024 T3 aluminum substrate at 25°C, as measured by an INSTON 5567 machine in tensile mode at a pulling rate of 1.3 mm per minute.

[0319] 81. The use of a coating for preparing a coating according to aspect 79 or aspect 80, wherein the coating has an lap shear strength of at least 5 MPa, measured according to ASTM D1002-10 using a 0.063-inch thick 2024 T3 aluminum substrate at 50°C, as measured by an INSTON 5567 machine in tensile mode at a pulling rate of 1.3 mm per minute.

[0320] 82. Use for preparing a coating according to any one of aspects 79 to 81, said coating having an lap shear strength not exceeding 2 MPa, measured according to ASTM D1002-10 using a 0.063-inch thick 2024 T3 aluminum substrate at 150°C, as measured by an INSTON 5567 machine in tensile mode at a pulling rate of 1.3 mm per minute.

[0321] 83. Use for preparing a coating according to any one of aspects 79 to 82, wherein the coating has a glass transition temperature of 35°C to 55°C as measured by dynamic chemical analysis (DMA) at a frequency of 1.0 Hz and a heating rate of 3°C / min.

[0322] 84. A battery comprising a battery cell and a composition according to any one of aspects 22 to 61 in a cured state, and optionally further comprising a battery component.

[0323] 85. The battery according to aspect 80, wherein the battery cell and the composition are housed in a module and / or battery pack, and / or wherein the battery cell and the composition are adjacent to the vehicle chassis.

[0324] 86. The battery according to aspect 85, wherein the module is housed in a group.

[0325] 87. A system comprising:

[0326] A first composition, the first composition being applied to a portion of a substrate surface, the first composition comprising a dielectric coating composition; and

[0327] A second composition, the second composition being applied to the surface of the substrate having the portion thereon of the first composition, the second composition comprising the composition according to any one of aspects 22 to 61.

[0328] 88. A kit comprising:

[0329] A first composition, the first composition being applied to a portion of a substrate surface, the first composition comprising a dielectric coating composition; and

[0330] A second composition, for application to the portion having the first composition thereon, the second composition comprising the composition according to any one of aspects 22 to 61.

[0331] 89. The kit according to aspect 88, further comprising instructions for applying the first composition and the second composition.

[0332] 90. The system or kit according to any one of aspects 87 to 89, wherein the dielectric coating composition comprises:

[0333] Adhesives comprising film-forming resins such as polyesters, alkyd resins, urethanes, isocyanates, polyureas, epoxy resins, acrylics, polyethers, polysulfides, polyamines, polyamides, polyvinyl chloride, polyolefins, polyvinylidene fluoride, polyvinyl chloride, polyolefins, polysiloxanes, amine-aldehydes, resin polyols, phosphorylated polyepoxides, phosphorylated acrylic polymers, amino plastics, or combinations thereof; and / or

[0334] Curing agents and / or crosslinking agents capable of crosslinking with the film-forming resin to cure the dielectric coating composition, such as: amines; amino plastics; phenolic plastics; polyisocyanates, including end-capped polyisocyanates; polyepoxides; β-hydroxyalkylamides; polybasic acids; organometallic acid functional materials; polyamines; polyamides; polysulfides; polythiols; polyolefins, such as polyacrylates; polyols; polysilanes; and combinations thereof.

[0335] 91. The system or kit according to any one of aspects 87 to 90, wherein the dielectric coating composition comprises a powder coating composition and / or a liquid coating composition, such as an electrodepositable coating composition, a UV-curable coating composition, and / or a solvent-based coating composition.

[0336] 92. A substrate comprising:

[0337] Dielectric coating, said dielectric coating being formed on a portion of the surface of the substrate by a dielectric coating composition; and

[0338] A second coating and / or a self-supporting film, wherein the second coating and / or the self-supporting film is formed on the portion of the surface by the composition according to any one of aspects 22 to 61.

[0339] 93. The substrate according to aspect 92, wherein the dielectric coating composition comprises:

[0340] Adhesives comprising film-forming resins such as polyesters, alkyl groups, urethanes, isocyanates, polyureas, epoxy resins, acrylics, polyethers, polysulfides, polyamines, polyamides, polyvinyl chloride, polyolefins, polyvinylidene fluoride, polyvinyl chloride, polyolefins, polysiloxanes, amine-aldehydes, resin polyols, phosphorylated polyepoxides, phosphorylated acrylic polymers, amino plastics, or combinations thereof; and / or

[0341] Curing agents and / or crosslinking agents capable of crosslinking with the film-forming resin to cure the dielectric coating composition, such as: amines; amino plastics; phenolic plastics; polyisocyanates, including end-capped isocyanates; polyepoxides; β-hydroxyalkylamides; polybasic acids; organometallic acid functional materials; polyamines; polyamides; polysulfides; polythiols; polyolefins, such as polyacrylates; polyols; polysilanes; and combinations thereof.

[0342] 94. The substrate according to aspect 92 or aspect 93, wherein the dielectric coating composition comprises a powder coating composition and / or a liquid coating composition, such as an electrodepositable coating composition, a UV-curable coating composition and / or a solvent-based coating composition.

[0343] 95. A self-supporting membrane formed from the composition according to any one of aspects 22 to 61.

[0344] The following examples illustrate the disclosed subject matter and should not be construed as limiting this disclosure to its details. Unless otherwise indicated, all parts and percentages in the examples and throughout the specification are by weight.

[0345] Example

[0346] Unless otherwise stated, all quantities in the following tables are measured in grams.

[0347]

[0348] Compositions I through V were prepared using the materials and amounts listed in Table 1. Desmodur N3300 or Desmodur N3900 was placed in an appropriately sized flask and covered with nitrogen to avoid interaction with moisture. Dibutyltin dilaurate was added as a catalyst, and the mixture was heated to 60°C. Furfuryl alcohol was then added at a rate that kept the temperature of the mixture below 80°C. After all the furfuryl alcohol had been added, the reaction was maintained at 80°C until the isocyanate equivalent weight no longer changed by titration (determined using a Metrohm 888 Titrando; by titration of a sample of the mixture (~2.00 g) dissolved in 30 mL of a solution containing 20 mL of dibutylamine and 980 mL of N-methylpyrrolidone, followed by titration with a 0.2 N HCl isopropanol titrant solution).

[0349] Composition VI (a blend of furan-functionalized and isocyanate prepolymers) was prepared as follows: Desmodur N3900 and Composition V were added to an appropriately sized flask in the amounts listed in Table 1, such that the theoretical furan equivalent and theoretical isocyanate equivalent were equal to those of Composition IV. Composition V (139 g) was covered with nitrogen and heated to 60°C. Then, Desmodur N3900 (44.9 g) was added. The solution was stirred at 60°C for 90 minutes. The isocyanate equivalent weight was then titrated using the method described above until it no longer changed.

[0350] Example 1 – 3D Printing and Reprocessing Efficiency Test

[0351] In this example, the practicality and reprocessability of extrusion-based 3D printing of the two-component formulations were tested. Materials from components A and B of compositions VII to IX provided in Table 2 were weighed into separate dual asymmetric centrifuge (DAC) cups and mixed at 1200 RPM for 3 minutes at room temperature until homogeneous via a Speedmixer program.

[0352] Components A and B of compositions VII to IX are transferred from the DAC cup to the Optimum barrel for 3D printing via environmental reactive extrusion through a Viscotec 2K extruder mounted to a gantry (such as a Lulzbot Taz 6). For compositions VII and IX, component B and component A are printed at a volume mixing ratio of 1.4:1.0.

[0353]

[0354] The reworkability of compositions VII, VIII, and IX was tested by compression molding. To rework the material, printed parts were broken into fragments and placed into a rectangular aluminum mold (40 mm x 30 mm x 15 mm). The mold containing the material was placed in a compressor preheated to 110°C for 15 minutes to achieve temperature equilibrium. The mold temperature was monitored by a Barnat 100 thermocouple. A pressure of 2 tons was then applied and maintained constant for 15 minutes. After rework, the sample was removed from the mold while still hot. Images of the ground and reworked material of compositions VII through IX are shown below. Figures 10A to 10C In this study, it was found that composition VII, containing only the compounds of this disclosure, is reprocessable under these conditions.

[0355] The mechanical properties of the reprocessed composition VII, obtained by compression molding, were determined using rectangular samples (40 mm x 7 mm x 0.8 mm, approximate dimensions) tested at a tensile rate of 50 mm / min in an Instron Model 5567. The reprocessed material was placed in a hot chamber at 71°C for 24 h prior to the tensile tests. Mechanical properties were tested after each reprocessing cycle and compared with the original material. The results are reported in Table 3. Compositions VIII and IX were not tested because they could not be reprocessed into suitable samples.

[0356] Table 3. Tensile properties of composition VII after multiple reprocessing cycles.

[0357]

[0358] This example demonstrates that the compositions disclosed herein can retain their mechanical properties and modulus after repeated reprocessing.

[0359] The self-healing properties of composition VII were tested by making small cuts or creating small cracks or defect areas in the cured coating made with composition VII using scissors. Figure 11A shows the cured coating with defects. The coating was then heated to 130°C in an oven for 1 hour. Figure 11B shows the cured coating after heating. The cut size before heat healing was measured using an optical macromicroscope. w 0, 98.76 µm) and incision size after heat healing ( w f The self-healing efficiency of the material (59.25 µm) was calculated using Equation 1. The calculated self-healing efficiency was 40%. This indicates that the composition disclosed herein is capable of self-healing.

[0360]

[0361] Example 2 – Overlap Shear Test

[0362] The deoxygenation composition (DEOX-1) was prepared using 18.2 liters of deionized water, 180.5 g of fluorosilicic acid (23% solution), 80 g of zirconium fluoride (45% solution), 11.61 g of potassium hydrogen fluoride, and 31.6 g of Chemfil buffer (commercially available from PPG Industries, Inc.).

[0363] Compositions X through XIV were prepared by blending the components listed in Table 4 and mixing at 2350 RPM for 2 minutes using a Dual-Asymmetric Mixer (SpeedMixer®). Overlap shear samples (17.5 mm x 12.8 mm x 0.52 mm) were prepared using 0.063'' 2024 T3 aluminum. Oil was removed from the panels with acetone and methyl ethyl ketone, and the panels were treated with DEOX-1. The panels were then primed by applying a 0.005'' thick primer layer to the panels using a two-component epoxy adhesive composition, Corabond® CB8111 (available from PPG), and baking at 140°C for 5 minutes. One of compositions X through XIV was applied to one side of a panel and overlapped with a second panel (overlap size 1'' x ½''). The two panels were held together using a long-tail clip, and excess composition was removed from the joint using a metal trowel. The samples were allowed to cure under ambient conditions for at least 7 days prior to testing. Then use Instron Model 5567 and 30 A kN force sensor was used to measure the lap shear strength (LSS) at room temperature (RT, 25℃), 50℃, and 150℃, and a pulling rate of 1.3 mm / min. The results were obtained at... Figures 12 to 14 Provided in [the document / source]. T values ​​were obtained using TA Instruments Q800 DMA V21.3 in single cantilever mode. g Data. Frequency set to 1. Hz, and the temperature rises at a rate of 3℃ / minute from 0℃ to 150℃.

[0364]

[0365] Compositions X through XIV all exhibit high lap shear strength at room temperature. The lap shear strength at 50°C can be adjusted by changing the ratio of isocyanate functional groups to furan functional groups, while maintaining reversibility at 150°C, as defined by an lap shear strength not exceeding 2 MPa.

[0366] Example 3. Viscosity Measurement

[0367] The viscosities of compositions I through VI were determined rheologically and are recorded in Table 5. Measurements were performed at 25°C using a 25 mm parallel plate apparatus and a gap height of 0.2 to 0.3 mm. The span was at least 0.1 to 10 s. -1 The viscosity of the composition was measured using shear rate. Viscosity as a function of shear rate was... Figure 15 As shown in the figure, and all reagents in 1 s -1 The viscosities at the shear rates are listed in Table 5.

[0368] Table 5

[0369]

[0370] Example 4. Synthesis Example

[0371] Examples A and B below provide descriptions of the synthesis of furan / isocyanate functional polymers.

[0372] Table 6

[0373]

[0374] 1 The DESMODUR N3900 is available from Covestro.

[0375] 2 Dibutyltin dilaurate is commercially available from Evonik Industries.

[0376] 3 Furfuryl alcohol is commercially available from Sigma Aldrich.

[0377] Part 1 was added to a 2000 mL four-necked round-bottom flask equipped with a motor-driven stainless steel stirring blade, a water-cooled condenser, a nitrogen-covered flask, and a heating hood with a thermometer connected via a temperature feedback control device. The reaction mixture was heated to 60 °C. Part 2 was then added at a rate that ensured the temperature of the mixture did not exceed 80 °C. After the addition of Part 2, the reaction was maintained at 80 °C until the isocyanate equivalent weight no longer changed. The isocyanate equivalent weight was determined by sample titration. A sample was prepared by dissolving 1 g of isocyanate per 420 g / eq of the predicted isocyanate equivalent weight in 30 mL of a solution containing 20 mL of dibutylamine and 980 mL of N-methyl-2-pyrrolidone. The sample was then titrated using a Metrohm 808 or 888 Titrando with a 0.2 N HCl isopropanol titrant solution. The reaction mixture was maintained at 80 °C until the isocyanate equivalent weight no longer changed. The reaction mixture was then poured off at 40 °C with a nitrogen-covered flask.

[0378] Example C below provides a description of the synthesis of alternative dienophilic prepolymers.

[0379] Table 7

[0380]

[0381] 1Dipropylene glycol is commercially available from Sigma Aldrich.

[0382] 2 Maleic anhydride is commercially available from TCI America.

[0383] 3 IONOL is 2,6-di-tert-butyl-4-methylphenol and is commercially available from Sasol Chemicals (USA) LLC.

[0384] 4 Monobutyltin oxide is available from ARKEMA Acquired by INC. through commercial purchase.

[0385] 5 2-Ethylhexyl glycidyl ether is commercially available from Negase America LLC.

[0386] Part 1 was added to a 1000 mL four-necked round-bottom flask equipped with a motor-driven stainless steel stirring blade, a water-cooled condenser, and a heating hood with a thermometer connected via a temperature feedback control device. The mixture was heated to 220 °C and held until the acid value remained constant at approximately 150 mg KOH / g by titration. The mixture was then cooled to 120 °C and Part 2 was added. The mixture was heated to 140 °C and held until the acid value was less than 2 mg KOH / g by titration. The mixture was then cooled to 80 °C and poured into a suitably sized container. The final OH equivalent weight was determined by titration to be 302 g / eq. The hydroxyl value was determined by esterification with excess acetic anhydride at elevated temperatures using imidazole as a catalyst. The excess acetic anhydride was converted to acetic acid by hydrolysis and potentiometric titration with standard potassium hydroxide.

[0387] Example 5. Overlap Shear Test

[0388] DEOX-1 was prepared as described above.

[0389] Composition XV was formed by blending the components in Table 8 at the described ratios and mixing at 2350 RPM for 4 minutes using a Dual-Asymmetric Mixer (SpeedMixer®). Overlap shear samples (25.6 mm x 12.8 mm) were prepared using 0.063'' 2024 T3 aluminum. Oil was removed from the panels with acetone and methyl ethyl ketone, and the panels were treated with DEOX-1. Overlap shear samples were prepared by applying Composition XV to one side of a primed panel and then overlapping it with a second panel (overlap size 1'' x ½''). The two panels were held together using a long-tail clip, and excess composition was removed from the joint using a metal trowel. Samples were allowed to cure under ambient conditions for at least 7 days prior to testing. Overlap shear strength (at a pull rate of 1.3 mm / min, measured using Instron) was measured at room temperature (25°C) and 150°C. Model (5567 and 30kN force sensors). After testing, the samples were reconnected and held together with long-tail clips. The samples were then heated to 120°C for 2 hours, allowed to cool overnight, and retested at 25°C. The retest measurements were recorded as the reconnected lap shear strength. The results are provided in Table 8.

[0390] Table 8

[0391]

[0392] This example demonstrates that the compositions disclosed herein form coatings exhibiting good mechanical properties and re-bonding properties.

[0393] While aspects of this disclosure have been described in detail, those skilled in the art will understand that various modifications and alternatives to those details can be developed based on the general teachings of this disclosure. Therefore, the specific arrangements disclosed are intended to be illustrative only and not to limit the scope of this disclosure, which is defined by the full scope of the appended claims and aspects and any and all equivalents thereof.

Claims

1. A compound comprising: furan functional groups; Isocyanate functional groups; and Carbamate bonds, urea bonds and / or thiocarbamate bonds.

2. The compound according to claim 1, wherein the urethane bond, the urea bond and / or the thiourethane bond are located between the furan functional group and the isocyanate functional group.

3. The compound according to claim 1 or claim 2, comprising structure I: Wherein X contains O, N or S, m ≥ 1, n ≥ 1, and the sum of m+n ≥ 2; R1 contains substituted or unsubstituted alkyl groups, alkylene groups, (cyclo)alkyl groups, aromatic groups, isocyanurate moieties, iminooxadiazinedione moieties, biuret moieties, urethane moieties, glycourea moieties, benzoguanidine moieties, or polymer moieties different from the urethane bonds or the urea bonds; and R2 contains substituted or unsubstituted alkyl groups, ester moieties, ether moieties, or urethane moieties.

4. The compound according to any one of the preceding claims, wherein the compound is substantially free of ether bonds.

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

6. A composition comprising: A first component, the first component comprising a compound according to any one of the preceding claims; and The second component comprises a dienophile compound.

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

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

1.

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

10. The composition according to any one of claims 6 to 9, wherein the second component comprises a third compound capable of reacting with the isocyanate functional group.

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

12. A method for coating a substrate, the method comprising: A portion of the surface of the substrate is brought into contact with the composition according to any one of claims 6 to 11.

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

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

15. A substrate comprising a coating formed on a portion of the surface of the substrate by the hot melt adhesive according to claim 14.

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

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

18. A battery comprising the battery cell according to claim 17.

19. A self-supporting membrane formed from the composition according to any one of claims 6 to 11.

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