WO2025042870A1 - Coating compositions - Google Patents

Abstract

Disclosed are compositions comprising: a first component comprising an epoxy-containing compound; a second component comprising an amino-functional amide and a flexibilizing amine; and elastomeric particles. Also disclosed are substrates comprising a surface coated with any of the compositions disclosed herein. Also disclosed are methods of forming a coating and uses of coatings.Disclosed are compositions comprising: a first component comprising an epoxy-containing compound; a second component comprising an amino-functional amide and a flexibilizing amine; and elastomeric particles. Also disclosed are substrates comprising a surface coated with any of the compositions disclosed herein. Also disclosed are methods of forming a coating and uses of coatings.

Description

COATING COMPOSITIONS

CROSS-REFERENCE TO RELATED APPLICATION

[0001] This application claims priority to U.S. Provisional Application No. 63/520,819, entitled “Coating Compositions,” filed on August 21, 2023, incorporated herein by reference in its entirety.

FIELD

[0002] The present disclosure relates to compositions and coatings formed therefrom. BACKGROUND

[0003] Coating compositions, including adhesives, are utilized in a wide variety of applications to treat a variety of substrates or to bond together two or more substrate materials.

SUMMARY

[0004] The present disclosure is directed to compositions comprising: a first component comprising an epoxy-containing compound; a second component comprising an aminofunctional amide and a flexibilizing amine; and elastomeric particles.

[0005] Also disclosed are substrates comprising a coating formed from any of the compositions disclosed herein on a portion of a surface of the substrate.

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

[0007] Also disclosed are methods of forming an article, comprising extruding any of the compositions disclosed herein.

DETAILED DESCRIPTION

[0008] For purposes of this detailed description, it is to be understood that the disclosure may assume alternative variations and step sequences, except where expressly specified to the contrary. Moreover, other than in any operating examples, or where otherwise indicated, all numbers expressing, for example, quantities of ingredients used in the specification and claims, are to be understood as being modified in all instances by the term “about”. Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties to be obtained by the present disclosure. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0009] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the disclosure are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard variation found in their respective testing measurements.

[0010] Also, any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of “1 to 10” is intended to include all sub-ranges between (and including) the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10.

[0011] As used herein, “including,” “containing,” and like terms are understood in the context of this application to be synonymous with “comprising” and are therefore open-ended and do not exclude the presence of additional undescribed or unrecited elements, materials, ingredients, or method steps. As used herein, open-ended terms include closed terms such as consisting essentially of and consisting of.

[0012] As used herein, “consisting of’ is understood in the context of this application to exclude the presence of any unspecified element, ingredient, or method step.

[0013] As used herein, “consisting essentially of’ is understood in the context of this application to include the specified elements, materials, ingredients, or method steps “and those that do not materially affect the basic and novel characteristic(s)” of what is being described.

[0014] In this application, the use of the singular includes the plural and plural encompasses singular, unless specifically stated otherwise. For example, although reference is made herein to “an” epoxy-containing compound and “a” fatty acid amidoamine, a combination (i.e., a plurality) of these components may be used.

[0015] In addition, in this application, the use of “or” means “and/or” unless specifically stated otherwise, even though “and/or” may be explicitly used in certain instances.

[0016] As used herein, the terms “on,” “onto,” “applied on,” “applied onto,” “formed on,” “deposited on,” “deposited onto,” “injected on,” “injected onto” and the like mean formed, overlaid, deposited, or provided on, but not necessarily in contact with, a substrate surface. For example, a composition “applied onto” a substrate surface does not preclude the presence of one or more other intervening coating layers or films of the same or different composition located between the composition and the substrate surface.

[0017] As used herein, a “coating composition” refers to a composition, e.g., a solution, mixture, or a dispersion, that, is capable of producing a coating on a portion of a substrate surface. “Coating” as used herein includes films, layers and the like.

[0018] As used herein, an “adhesive composition” refers to a coating composition that forms an adhesive when cured.

[0019] As used herein, an “adhesive” refers to a coating that produces a load-bearing joint, such as a load-bearing joint having a lap shear strength of at least 72.5 psi measured according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1 .3 mm per minute.

[0020] As used herein, a “structural adhesive composition” refers to a coating composition that forms a structural adhesive when cured.

[0021] As used herein, a “structural adhesive” refers to a coating that produces a loadbearingjoint, such as a load-bearing joint having a lap shear strength of at least 725 psi measured according to ASTM D1002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0022] As used herein, the term “pottanf ’ refers to an encapsulant.

[0023] As used herein, the term “gap filler” refers to a coating that fills a gap.

[0024] As used herein, the term “pre-preg” refers to a composition pre-impregnating reinforcement fibers prior to cure.

[0025] As used herein, the term “liquid shim” refers to a coating that eliminates gaps between substrate surfaces.

[0026] As further defined herein, ambient conditions generally refer to room temperature (e.g., 23°C) and humidity conditions or temperature and humidity conditions that are typically found in the area in which the composition is applied to a substrate, e.g., at 10°C to 40°C and 5% to 80% relative humidity.

[0027] As used herein, the term “two-component” or “2K” refers to a composition in which a portion of the reactive components readily associate to form an interaction or react to form a bond (physically or chemically), i.e., cure, without activation from an external energy source, such as at ambient or slightly thermal conditions, when mixed. One of skill in the art understands that the two components of the composition are stored separately from each other and mixed just prior to application of the composition. Two-component compositions may optionally be heated or baked, as described below.

[0028] As used herein, the term “cure” or “curing”, means that the components that form the composition are crosslinked (i.e., interact and/or react) to form a coating or a bond. In the case of a 2K composition, the composition begins to cure when the components of the composition are mixed resulting in the reaction of the reactive functional groups of the components of the composition.

[0029] As used herein, “monoamine” refers to an organic compound having one amino functional group.

[0030] As used herein, “diamine” refers to an organic compound having two amino functional groups.

[0031] As used herein, “polyamine” refers to an organic compound having more than two amino functional groups.

[0032] As used herein, “amino functional group” refers to a functional group comprising a nitrogen atom attached by a single bond to a hydrogen atom(s), an alkyl group(s), and/or an aryl group(s).

[0033] As used herein, “epoxide functional group” refers to a functional group comprising a cyclic ether with a three-atom ring.

[0034] As used herein, “amine hydrogen” refers to the number of active hydrogens directly bonded to the nitrogen atom of an amine- or another nitrogen-containing functional group. “Active hydrogens” refer to hydrogens that can be displaced when the amine- or nitrogen-containing functional group reacts as a nucleophile with an appropriate electrophile and can be determined, for example, by the Zerewitinoff test. Active hydrogens on all accelerators and curing agents (e.g., diamines and/or polyamines) were included in the amine hydrogens of the compositions of the present disclosure.

[0035] As used herein, the “epoxide equivalent weight” refers to the weight of material in grams containing one stoichiometric equivalent of epoxy functional groups. The epoxide equivalent weight may be determined, for example, by titration of a sample using a Metrohm 808 or 888 Titrando, using a sample 0.06 g per 100 g/eq of predicted epoxy equivalent weight and dissolving the sample in 20 mL of methylene chloride or tetrahydrofuran and then adding 40 mL glacial acetic acid and one gram of tetraethylammonium bromide before titration with 0.1 N perchloric acid in glacial acetic acid.

[0036] As used herein, “Mw” refers to the weight average molecular weight, for example the theoretical value as determined by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min'¹, and two PL Gel Mixed C columns used for separation.

[0037] As used herein, “polymer” refers to a molecule comprising chemically bonded repeating or monomeric units and may include oligomers, homopolymers, and copolymers.

[0038] As used herein, “small molecule” refers to a molecule that comprises discrete chemical structures, has a molecular weight of less than 1200 g/mol and that is not a polymer (i.e., is not composed of repeating monomer units). The molecular weight of a small molecule may be determined by mass spectrometry. Appropriate mass spectrometry methods for various types of small molecules are available in many references, such as Mass Spectrometry: A Textbook (3^rd Edition, 2018, edited by Jurgen Gross).

[0039] As used herein, the term “reactive diluent” refers to a molecule or a compound that is used to lower the viscosity of a formulation and that has at least one functional group capable of reacting with a functional group(s) on molecules or compounds in a composition.

[0040] As used herein, the term “plasticizer” refers to a molecule or a compound that does not have a functional group capable of reacting with a functional group(s) on molecules or compounds in a composition and that is added to the composition to decrease viscosity, decrease glass transition temperature (Tg), and impart flexibility.

[0041] As used herein, the term “accelerator” means a substance that increases the rate or decreases the activation energy of a chemical reaction in comparison to the same reaction in the absence of the accelerator. An accelerator may be either a “catalyst,” that is, without itself undergoing any permanent chemical change, or may be reactive, that is, capable of chemical reactions and includes any level of reaction from partial to complete reaction of a reactant.

[0042] As used herein, unless indicated otherwise, the term “substantially free” means that a particular material is not purposefully added to a mixture or composition and is present only as an impurity in a trace amount of less than 5 percent by weight based on a total weight of the mixture or composition.

[0043] As used herein, unless indicated otherwise, the term “essentially free” means that a particular material is not purposefully added to a mixture or composition and is present only as an impurity in a trace amount of less than 2 percent by weight based on a total weight of the mixture or composition.

[0044] As used herein, unless indicated otherwise, the term “completely free” means that a mixture or composition does not comprise a particular material, i.e., the mixture or composition comprises 0% by weight of such material.

[0045] Disclosed herein is a composition comprising, or consisting essentially of, or consisting of: a first component comprising, or consisting essentially of, or consisting of, an epoxy-containing compound; a second component comprising, or consisting essentially of, or consisting of, an amine-functional amide and a flexibilizing amine; and elastomeric particles.

First Component

[0046] As discussed above, the first component of the composition may comprise an epoxy-containing compound.

[0047] In some cases, the epoxy-containing compound may comprise an aromatic epoxy. As used herein, the term “aromatic epoxy” refers to an epoxy-containing compound comprising at least one aromatic group.

[0048] Useful aromatic epoxies that can be used include polyepoxides (having an epoxy functionality greater than 1), epoxy adducts, or combinations thereof. Suitable polyepoxides include polyglycidyl ethers of Bisphenol A, such as Epon® 828 and 1001 epoxy resins, and Bisphenol F polyepoxides, such as Epon® 862, which are commercially available from Hexion Specialty Chemicals, Inc. Other non-limiting aromatic epoxies include bisphenol S diglycidyl ether, epoxidized Bisphenol A novolacs, epoxidized phenolic novolacs, epoxidized cresylic novolac, triglycidyl p-aminophenol, triglycidyl p-aminophenol bismaleimide, tetraglycidyl 4,4’- diaminodiphenylmethane, tetraglycidyl zw-xylylenediamine, and tetraglycidyl 4,4’- diaminodiphenylsulphone.

[0049] The aromatic epoxy may comprise a monoepoxide. Suitable aromatic monoepoxides include glycidyl ethers of phenols, such as phenyl glycidyl ether or cresyl glycidyl ether. The epoxy-containing compound may comprise a combination of any of the aromatic polyepoxides described above and any of the aromatic monoepoxides described above.

[0050] In some cases, the epoxy-containing compound may comprise an aliphatic epoxy. As used herein, the term “aliphatic epoxy” refers to epoxy-containing compounds free-from any aromatic groups. Useful aliphatic epoxies include polyglycidyl ethers of polyhydric alcohols, polyglycidyl esters of polycarboxylic acids, polyepoxides that are derived from the epoxidation of an olefinically unsaturated alicyclic compound, or polyepoxides containing oxyalkylene groups in the epoxy molecule. The epoxy-containing compound may also comprise an epoxy- containing acrylic, such as copolymers comprising glycidyl methacrylate. Non-limiting examples of aliphatic epoxies include ethylene glycol diglycidyl ether, butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, hexanediol diglycidyl ether, isosorbide diglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolethane diglycidyl ether, pentaerythritol polyglycidyl ether, sorbitol polyglycidyl ether, and triglycidyl isocyanurate.

[0051] The aliphatic epoxy may comprise a monoepoxide. Suitable aliphatic monoepoxides that may be used include glycidol, monoglycidyl ethers of aliphatic alcohols such as n-butyl glycidyl ether, isopropyl glycidyl ether, glycidyl versatate, for example, CARDURA E available from Shell Chemical Co., glycidyl ethers of fatty alcohols, for example, Epodil 748 available from Evonik, and glycidyl esters of monocarboxylic acids such as glycidyl neodecanoate, and mixtures of any of the foregoing. Further non-limiting examples include epoxidized vegetable oils, and epoxidized polyether glycols, such as polypropylene glycol diglycidyl ether or poly(tetramethylene glycol) diglycidyl ether.

[0052] The epoxy-containing compound may comprise a combination of any of the aromatic epoxides described above and any of the aliphatic epoxides described above.

[0053] The epoxy-containing compound may comprise an epoxy-adduct. The composition may comprise one or more epoxy-adducts. As used herein, the term “epoxy- adduct” refers to a reaction product comprising the residue of an epoxy and at least one other compound that does not include an epoxide functional group. The epoxy-adduct may comprise an aromatic epoxy or an aliphatic epoxy. The epoxy-containing compound may comprise a carboxyl -terminated butadiene-acrylonitrile copolymer adducted with an epoxy-containing compound. Additionally, the epoxy-adduct may comprise the reaction product of reactants comprising an epoxy, a polyol, and an anhydride. The term “epoxy-adduct” used with respect to the epoxy-containing compound is different than the epoxide-functional adduct described below.

[0054] The epoxy used to form the epoxy-adduct may comprise any of the epoxy- containing compounds listed above that may be included in the composition.

[0055] The polyol used to form the epoxy-adduct may include diols, triols, tetraols and higher functional polyols. Combinations of such polyols may also be used. The polyols may be based on a polyether chain derived from ethylene glycol, propylene glycol, butylene glycol, hexylene glycol and the like as well as mixtures thereof. The polyol may also be based on a polyester chain derived from ring opening polymerization of caprolactone (referred to as polycaprolactone-based polyols hereinafter). Suitable polyols may also include polyether polyols, polyurethane polyols, polyurea polyols, acrylic polyols, polyester polyols, polybutadiene polyols, hydrogenated polybutadiene polyols, polycarbonate polyols, polysiloxane polyols, and combinations thereof. Polyamines corresponding to polyols may also be used, and in this case, amides instead of carboxylic esters will be formed with the anhydrides.

[0056] The polyol may comprise a polycaprolactone-based polyol. The polycaprolactone-based polyols may comprise diols, triols or tetraols terminated with primary hydroxyl groups. Commercially available polycaprolactone-based polyols include those sold under the trade name Capa™ from Perstorp Group, such as, for example, Capa 2054, Capa 2077A, Capa 2085, Capa 2205, Capa 3031, Capa 3050, Capa 3091 and Capa 4101.

[0057] The polyol may comprise a polytetrahydrofuran-based polyol. The polytetrahydrofuran-based polyols may comprise diols, triols or tetraols terminated with primary hydroxyl groups. Commercially available polytetrahydrofuran-based polyols include those sold under the trade name Terathane®, such as Terathane® PTMEG 250 and Terathane® PTMEG 650 which are blends of linear diols in which the hydroxyl groups are separated by repeating tetramethylene ether groups, available from Invista. In addition, polyols based on dimer diols sold under the trade names Pripol®, Solvermol™ and Empol®, available from Cognis Corporation, or bio-based polyols, such as the tetrafunctional polyol Agrol 4.0, available from BioBased Technologies, may also be utilized.

[0058] The anhydride that may be used to form the epoxy-adduct may comprise any suitable acid anhydride known in the art. For example, the anhydride may comprise hexahydrophthalic anhydride and its derivatives (e.g., methyl hexahydrophthalic anhydride); phthalic anhydride and its derivatives (e.g., methyl phthalic anhydride); maleic anhydride; succinic anhydride; trimelletic anhydride; pyromelletic dianhydride (PMDA); 3, 3', 4,4'- oxy diphthalic dianhydride (ODPA); 3,3',4,4'-benzophenone tetracarboxylic dianhydride (BTDA); and 4,4'-diphthalic (hexafluoroisopropylidene) anhydride (6FDA).

[0059] The epoxy-adduct may comprise a diol, a monoanhydride, and a diepoxy compound, wherein the mole ratio of diol, monoanhydride, and diepoxy compounds in the epoxy-adduct may vary from 0.5:0.8: 1.0 to 0.5: 1.0:6.0.

[0060] The epoxy-adduct may comprise a triol, a monoanhydride, and a diepoxy compound, wherein the mole ratio of triol, monoanhydride, and diepoxy compounds in the epoxy-adduct may vary from 0.5:0.8: 1.0 to 0.5: 1.0:6.0.

[0061] The epoxy-adduct may comprise a tetraol, a monoanhydride, and a diepoxy compound, wherein the mole ratio of tetraol, monoanhydride, and diepoxy compounds in the epoxy-adduct may vary from 0.5:0.8: 1.0 to 0.5: 1.0:6.0.

[0062] Other suitable epoxy-containing compounds include epoxy-adducts such as epoxy polyesters formed as the reaction product of reactants comprising an epoxy-containing compound, a polyol and an anhydride, as described in U.S. Patent No. 8,796,361, col. 3, line 42 through col. 4, line 65, the cited portion of which is incorporated herein by reference.

[0063] The first component optionally may include an epoxy-containing reactive diluent such as those typically used in coating compositions such as adhesive compositions and such reactive diluents may be included as an epoxy-containing compound.

[0064] The first component may comprise the epoxy-containing compound in an amount of at least 30 percent by weight based on total weight of the first component, such as at least 35 percent by weight, such as at least 40 percent by weight. The first component may comprise the epoxy-containing compound in an amount of no more than 100 percent by weight based on total weight of the first component, such as no more than 60 percent by weight, such as no more than 55 percent by weight, such as no more than 50 percent by weight. The first component may comprise the epoxy-containing compound in an amount of up to 100 percent by weight, such as 30 percent by weight to 100 percent by weight based on total weight of the first component, such as 30 percent by weight to 60 percent by weight, such as 35 percent by weight to 55 percent by weight, such as 40 percent by weight to 50 percent by weight. [0065] As described above, the first component may comprise an aromatic monoepoxide, an aliphatic monoepoxide and/or an aliphatic polyepoxide. The first component may comprise such epoxides, if present at all, in an amount of at least 0.1 percent by weight based on total weight of the first component, such as at least 0.2 percent by weight, such as at least 0.5 percent by weight. The first component may comprise such epoxides in an amount of no more than 30 percent by weight based on total weight of the first component, such as no more than 25 percent by weight, such as no more than 20 percent by weight. The first component may comprise such epoxides, if present at all, in an amount of up to 30 percent by weight, such as 01 percent by weight to 30 percent by weight based on total weight of the first component, such as 0.2 percent by weight to 25 percent by weight, such as 0.5 percent by weight to 20 percent by weight.

Second Component

[0066] The second component may comprise an amine-functional amide. An amine- functional amide refers to any compound comprising amide bonds and amine functional groups. A fatty acid amine-functional amide refers to an amine-functional amide comprising a fatty acid residue.

[0067] Useful amine-functional amides include monoamides and polyamides derived from fatty acids and other functional groups.

[0068] Suitable examples of amides derived from fatty acids include reaction products of any acid-functional compound and any polyamine or combination of polyamines. Suitable examples of acid-functional compounds suitable for production of amine-functional amides include a fatty acid, a dimerized fatty acid, a trimerized fatty acid, an acid-functional polymer such as a polyester or acrylic polymer, and/or an acid-functional small molecule. Suitable acids include, but are not limited to, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, cyclohexanedicarboxylic acid, azelaic acid, sebacic acid, undecanedioic acid, docecanedioic acid, brassylic acid, malic acid, tartaric acid, phthalic acid, isophthalic acid, and terephthalic acid. Additional suitable acids include acrylic copolymers comprising an acid functional monomer such as acrylic acid, methacrylic acid, maleic acid or itaconic acid.

[0069] In some cases, the amine-functional amide may comprise a reaction product of reactants comprising a fatty acid, a dimerized fatty acid, and/or a trimerized fatty acid and any polyamine or combination of polyamines. Suitable amine-functional amides derived from fatty acids include Versamid 100, Versamid 125, Versamid 140, and Versamid 150 available from Huntsman Corporation. Additional suitable amides derived from fatty acids include the amidoamine Ancamide® products available from Evonik Industries AG, Jointmide products available from Epochemie International, ChemCure® amidoamines available from Cargill Inc. and Epikure^1M amidoamine curing agents available from Westlake Corporation.

[0070] In some cases, the amine-functional amide may be a reaction product of fatty acids and amines comprising an ethyleneimine subunit, such as di ethylenetriamine, triethylenetetramine, or tetraethylenepentamine.

[0071] In some cases, the amine-functional amide may be a reaction product of fatty acids and aliphatic amines or cycloaliphatic amines.

[0072] The second component may comprise a flexibilizing amine. As used herein, the term “flexibilizing amine” refers to an etheramine having a molecular weight of greater than 140 g/mol or a fatty acid dimer or trimer amine having a molecular weight greater than 295 g/mol.

[0073] Suitable flexibilizing amines include oligomeric or polymeric diamines or polyamines with a glass transition temperature of greater than -150°C and less than 30°C, calculated, for example, using the Fox Equation.

[0074] Suitable examples of flexibilizing amines include amine-terminated polyethers, such as amine-terminated polypropylene glycol) or amine-terminated poly(ethylene glycol)- poly(propylene glycol) copolymers. Suitable examples include Jeffamine D-400, Jeffamine ED- 600, and Jeffamine ED-900 available from Huntsman Corporation.

[0075] In some preferred cases, the flexibilizing amine may comprise amine-terminated polymers or oligomers comprising poly(tetramethylene ether glycol) subunits. A suitable example is amine-terminated poly(tetramethylene ether glycol)-poly(propylene glycol) copolymer available as Jeffamine THF-100 available from Huntsman.

[0076] Additional useful aliphatic etheramines include ethylene glycol bis(2-aminoethyl) ether (available as Jeffamine EDR-148 from Huntsman), diethylene glycol bis(2-aminoethyl) ether, diethylene glycol bi s(3 -aminopropyl) ether (available as Ancamine 1922A from Evonik or Baxxodur EC 130 from BASF), bis(aminopropyl) 1,4-butanediol (available from BASF SE) or combinations thereof. In some cases, these etheramines may be modified by reaction/adducting with other molecules such as epoxy, carboxylic acid, or phenol containing resins.

[0077] The flexibilizing amine comprising the etheramine may comprise a molecular weight of greater than 140 g/mol, such as at least 170 g/mol, such as at least 210 g/mol. The flexibilizing amine comprising the etheramine may comprise a molecular weight of no more than 2,000 g/mol, such as no more than 1,700 g/mol, such as no more than 1,300 g/mol, such as no more than 1,200 g/mol. The flexibilizing amine may comprise a molecular weight of greater than 140 g/mol to 2,000 g/mol, such as 170 g/mol to 1,700 g/mol, such as 210 g/mol to 1,300 g/mol, such as 210 g/mol to 1,200 g/mol. The molecular weight of the flexibilizing amine may be measured using mass spectrometry as described hereinabove.

[0078] Additional suitable examples of the flexibilizing amine include fatty acid dimer or trimer diamines available from Croda Smart Materials. Suitable examples include Priamine 1071, Priamine 1074, and Priamine 1075.

[0079] The flexibilizing amine comprising a fatty acid dimer or trimer amine may comprise a molecular weight of greater than 295 g/mol, such as at least 400 g/mol, such as at least 500 g/mol. The flexibilizing amine may comprise a molecular weight of no more than 2,000 g/mol, such as no more than 1,700 g/mol, such as no more than 1,300 g/mol, such as no more than 1200 g/mol. The flexibilizing amine may comprise a molecular weight of greater than 295 g/mol to 2,000 g/mol, such as 400 g/mol to 1,700 g/mol, such as 500 g/mol to 1,300 g/mol, such as 500 g/mol to 1,200 g/mol. The molecular weight of the flexibilizing amine may be measured using mass spectrometry as described hereinabove.

[0080] The flexibilizing amine may comprise an amine-functional aliphatic etheramineepoxy adduct (Al). As used herein, the term “amine-functional aliphatic etheramine-epoxy adduct (Al) refers to a reaction product comprising the reside of an aliphatic etheramine (A2) and an epoxy-containing compound (E2), wherein the amine hydrogen functionality of A2 is in molar excess relative to the epoxide functionality of E2. As used herein, the term “etheramine” refers to an amine comprising an ether linkage.

[0081] The amine-functional aliphatic etheramine-epoxy adduct (Al) may be substantially free or completely free, of epoxide-functional groups. As used herein, the term “substantially free,” when used with respect to the absence of an epoxide-functional group, means that the amine-functional aliphatic etheramine-epoxy adduct (Al) comprises an epoxide equivalent weight of greater than 2000. As used herein, the term “completely free,” when used with respect to the absence of epoxide-functional groups, means that such functional groups are below the limit of detection of common analytical techniques. [0082] The second component may comprise amine-functional aliphatic etheramineepoxy adducts of two or more types. That is, the amine-functional aliphatic etheramine-epoxy adduct (Al) may comprise a first amine-functional aliphatic etheramine-epoxy adduct and may further comprise, e.g., a second, a third, and/or a fourth, etc., amine-functional aliphatic etheramine-epoxy adduct (Al) in addition to the first amine-functional aliphatic etheramine- epoxy adduct (Al). As used herein with respect to amine-functional aliphatic etheramine-epoxy adduct (Al), reference to “first,” “second,” “third,” etc. is for convenience only and does not refer to order of addition to the composition or the like.

[0083] The second, third, fourth, etc. amine-functional aliphatic etheramine-epoxy adduct (Al) may be any of the amine-functional aliphatic etheramine-epoxy adducts described above.

[0084] The second component may comprise the amine-functional aliphatic etheramine- epoxy adduct (Al) in an amount of at least 10 percent by weight based on total weight of the second component, such as at least 20 weight percent. The second component may comprise the amine-functional aliphatic etheramine-epoxy adduct (Al) in an amount of no more than 100 weight percent based on total weight of the second component, such as no more than 98 weight percent. The second component may comprise the amine-functional aliphatic etheramine-epoxy adduct (Al) in an amount of 10 weight percent to 100 weight percent based on total weight of the second component, such as at least 20 weight percent to 98 weight percent.

[0085] The amine-functional aliphatic etheramine-epoxy adduct (Al) may comprise a reaction product of reactants comprising an aliphatic etheramine (A2) and an epoxy-containing compound (E2).

[0086] The aliphatic etheramine (A2) may comprise at least two amine-functional groups. For example, the aliphatic etheramine (A2) may comprise a diamine and/or a polyamine, such as a triamine, a tetraamine, or combinations thereof.

[0087] The aliphatic etheramine (A2) may comprise an ethylene glycol subunit. The term “comprising at least one ethylene glycol subunit” indicates that the etheramine contains at least one structure R(CH2CH2O)_nR, wherein R may represent any organic substituent, including by way of non-limiting examples, carbon-, hydrogen-, nitrogen- and/or oxygen-based substituents and wherein n=l to 5.

[0088] The aliphatic etheramine (A2) may comprise a primary amine functional group adjacent to a methylene group. The term “comprising a primary amine functional group adjacent to a methylene group” indicates that the etheramine contains a structure RCH2NH2 wherein R may represent any organic substituent, including by way of non-limiting examples, carbon-, hydrogen-, and/or oxygen-based substituents.

[0089] Useful aliphatic etheramines (A2) include ethylene glycol bis(2-aminoethyl) ether (available as Jeffamine EDR-148 from Huntsman), diethylene glycol bis(2-aminoethyl) ether, diethylene glycol bis(3-aminopropyl) ether (available as Ancamine 1922A from Evonik or Baxxodur EC 130 from BASF), bis(aminopropyl) 1,4-butanediol (available from BASF SE) or combinations thereof.

[0090] The aliphatic etheramine (A2) may comprise a molecular weight of at least 104 g/mol, such as at least 140 g/mol. The aliphatic etheramine may comprise a molecular weight of no more than 300 g/mol, such as no more than 230 g/mol. The aliphatic etheramine may comprise a molecular weight of 104 g/mol to 300 g/mol, such as 140 g/mol to 230 g/mol. The molecular weight of the aliphatic etheramine (A2) may be measured using mass spectrometry as described hereinabove.

[0091] As discussed above, the reactants for forming the amine-functional aliphatic etheramine-epoxy adduct (Al) may comprise an epoxy-containing compound (E2). The epoxycontaining compound (E2) may be any of the monoepoxides and/or polyepoxides disclosed above. For example, the epoxy-containing compound (E2) may comprise bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a novolac resin, tetraglycidyl methylene dianaline, triglycidyl-p-amino phenol, tetraglycidyl m-xylenediamine or combinations thereof.

[0092] The epoxy-containing compound (E2) may comprise a small molecule. For example, the epoxy-containing compound (E2) may comprise a molecular weight of no more than 600 g/mol, such as no more than 450 g/mol. The epoxy-containing compound (E2) may comprise a molecular weight of at least 160 g/mol, such as at least 300 g/mol. The epoxy- containing compound (E2) may comprise a molecular weight of 160 g/mol to 600 g/mol, such as 300 g/mol to 450 g/mol. Molecular weight of the epoxy-containing compound (E2) may be determined by mass spectrometry as described hereinabove.

[0093] The epoxy-containing compound (E2) may comprise an epoxide equivalent weight of at least 85 g/eq, such as 110 g/eq. The epoxy-containing compound (E2) may comprise an epoxide equivalent weight of no more than 300 g/eq, such as no more than 220 g/eq. The epoxy-containing compound (E2) may comprise an epoxide equivalent weight of 85 g/eq to 300 g/eq, such as 110 g/eq to 220 g/eq.

[0094] Optionally, the epoxy-containing compound (E2) may comprise an aromatic group.

[0095] Suitable examples of epoxy-containing compounds (E2) include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a novolac resin, tetraglycidyl methylene dianaline, triglycidyl-p-amino phenol, tetraglycidyl m-xylenediamine, a hydrogenated bisphenol A diglycidyl ether (such as those commercially available as Eponex 1510), butanediol diglycidyl ether or combinations thereof.

[0096] The reactants may comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of amine-hydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of at least 3: 1, such as at least 4: 1. The reactants may comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of amine-hydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of no more than 12: 1, such as no more than 7: 1. The reactants may comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of amine-hydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of 3: 1 to 12: 1, such as 4: 1 to 7: 1.

[0097] The second component optionally may include an amine-containing reactive diluent such as those typically used in coating compositions such as adhesive compositions and such reactive diluents may be included in the calculation of amine-hydrogens present in the second component.

[0098] The second component may comprise the flexibilizing amine in an amount of at least 25 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine, such as at least 30 percent by weight, such as at least 35 percent by weight, such as no more than 95 percent by weight, such as no more than 85 percent by weight, such as no more than 80 percent by weight, such as 25 percent by weight 95 percent by weight, such as 30 percent by weight to 85 percent by weight, such as 35 percent by weight to 80 percent by weight

[0099] The second component may comprise the amine-functional amide in an amount of at least 5 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine, such as at least 10 percent by weight, such as at least 15 percent by weight, such as no more than 75 percent by weight, such as no more than 50 percent by weight, such as no more than 35 percent by weight, such as 5 percent by weight to 75 percent by weight, such as 10 percent by weight to 50 percent by weight, such as 15 percent by weight to 35 percent by weight.

[0100] The second component optionally may further comprise a cycloaliphatic amine and/or a polyamine.

[0101] The composition may comprise the cycloaliphatic amine in an amount of at least 0.5 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine, such as at least 1 percent by weight, such as no more than 10 percent by weight, such as no more than 8 percent by weight, such as 0.5 percent by weight to 10 percent by weight, such as 1 percent by weight to 8 percent by weight.

[0102] The composition may comprise the polyamine in an amount of at least 0.5 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine, such as at least 1 percent by weight, such as no more than 50 percent by weight, such as no more than 40 percent by weight, such as 0.5 percent by weight to 50 percent by weight, such as 1 percent by weight to 40 percent by weight.

Elastomeric Particles

[0103] The epoxy-containing compound of the composition may further include elastomeric particles. As used herein, “elastomeric particles” refers to particles having a glass transition temperature (Tg) of -70° C to 0° C as measured by Differential Scanning Calorimetry (DSC) or Dynamic Mechanical Analysis (DMA).

[0104] The elastomeric particles may be included in an epoxy carrier resin for introduction into the coating composition. The elastomeric particles may be phase-separated from the epoxy in the epoxy-containing compound. As used herein, the term “phase-separated” means forming a discrete domain within a matrix of the epoxy-containing compound.

[0105] The elastomeric particles may have a core/shell structure. The core of the coreshell particles may comprise a Tg of less than 0 °C, such as -20 °C or less, such as -40 °C or less, such as -60 °C or less as measured by DMA.

[0106] Suitable elastomeric particles may be comprised of a silicone material. Suitable elastomeric particles may be comprised of a (meth)acrylic shell and an elastomeric core. The core may comprise natural or synthetic rubbers, polybutadiene, styrene-butadiene, polyisoprene, styrene isoprene, chloroprene, acrylonitrile butadiene, butyl rubber, polysiloxane, polysulfide, ethylene-vinyl acetate, fluoroelastomer, polyolefin, hydronated styrene-butadiene, or combinations thereof. The type of elastomeric particles and the concentration thereof is not limited as long as the particle size falls within the specified range as illustrated below.

[0107] The average particle size of the elastomeric particles may be, for example, 0.02 microns to 5 microns (20 nm to 5,000 nm), such as 20 nm to 500 nm, such as 50 nm to 250 nm, the reported particle sizes for rubber particles provided by Kaneka Texas Corporation, as measured by standard techniques known in the industry. Suitable methods of measuring particles sizes disclosed herein include, for example, as measured by transmission electron microscopy (TEM). Suitable methods of measuring particle sizes by TEM include suspending elastomeric particles in a solvent selected such that the particles do not swell, and then dropcasting the suspension onto a TEM grid which is allowed to dry under ambient conditions. For example, epoxy resin containing core-shell elastomeric particles may be diluted in butyl acetate for drop casting and measurements may be obtained from images acquired from a Tecnai T20 TEM operating at 200kV and analyzed using ImageJ software, or an equivalent solvent, instrument and software.

[0108] In an example, suitable finely dispersed core-shell elastomeric particles having an average particle size ranging from 50 nm to 250 nm may be pre-mixed or pre-dispersed in the a resin, such as in epoxy resin such as aromatic epoxides, phenolic novolac epoxy resin, bisphenol A and/or bisphenol F diepoxide, and/or aliphatic epoxides, which include cyclo-aliphatic epoxides, at concentrations ranging from 5% to 40% rubber particles by weight based on the total weight of the rubber dispersion, such as from 20% to 35%. Suitable epoxy resins may also include a mixture of epoxy resins. When utilized, the epoxy carrier resin may be an epoxycontaining component such that the weight of the epoxy-containing component present in the composition includes the weight of the epoxy carrier resin.

[0109] Exemplary non-limiting commercial core-shell elastomeric particle products using poly(butadiene) rubber particles that may be utilized in the composition include core-shell poly(butadiene) rubber powder (commercially available as PARALOID™ EXL 2650A from Dow Chemical), a core-shell poly(butadiene) rubber dispersion (25% core-shell rubber by weight) in bisphenol F diglycidyl ether (commercially available as Kane Ace MX 136), a core- shell poly (butadiene) rubber dispersion (33% core-shell rubber by weight) in Epon® 828 (commercially available as Kane Ace MX 153), a core-shell poly(butadiene) rubber dispersion (33% core-shell rubber by weight) in Epicion® EXA-835LV (commercially available as Kane Ace MX 139), a core-shell poly(butadiene) rubber dispersion (37% core-shell rubber by weight) in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 257), and a core-shell poly(butadiene) rubber dispersion (37% core-shell rubber by weight) in Epon® 863 (commercially available as Kane Ace MX 267), and core-shell poly(butadiene) rubber dispersion (40% rubber by weight) in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 150), each available from Kaneka Texas Corporation, and acrylic rubber dispersions.

[0110] Exemplary non-limiting commercial core-shell elastomeric particle products using styrene-butadiene rubber particles that may be utilized in the composition include a coreshell styrene-butadiene rubber powder (commercially available as CLEARSTRENGTH® XT 100 from Arkema), core-shell styrene-butadiene rubber powder (commercially available as PARALOID™ EXL 2650J), a core-shell styrene-butadiene rubber dispersion (33% core-shell rubber by weight) in bisphenol A diglycidyl ether (commercially available as Fortegra™ 352 from Olin™), core-shell styrene-butadiene rubber dispersion (33% rubber by weight) in low viscosity bisphenol A diglycidyl ether (commercially available as Kane Ace MX 113), a coreshell styrene-butadiene rubber dispersion (25% core-shell rubber by weight) in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 125), a core-shell styrene-butadiene rubber dispersion (25% core-shell rubber by weight) in bisphenol F diglycidyl ether (commercially available as Kane Ace MX 135), a core-shell styrene-butadiene rubber dispersion (25% core-shell rubber by weight) in D.E.N.™-438 phenolic novolac epoxy (commercially available as Kane Ace MX 215), a core-shell styrene-butadiene rubber dispersion (25% coreshell rubber by weight) in Araldite® MY-721 multi-functional epoxy (commercially available as Kane Ace MX 416), a core-shell styrene-butadiene rubber dispersion (25% core-shell rubber by weight) in MY-0510 multi-functional epoxy (commercially available as Kane Ace MX 451), a core-shell styrene-butadiene rubber dispersion (25% core-shell rubber by weight) in Syna Epoxy 21 Cyclo-aliphatic Epoxy from Synasia (commercially available as Kane Ace MX 551), and a core-shell styrene-butadiene rubber dispersion (25% core-shell rubber by weight) in polypropylene glycol (MW 400) (commercially available as Kane Ace MX 715), each available from Kaneka Texas Corporation. Other commercially available core-shell rubber particle dispersions include Fortegra 352 (33% core-shell rubber particles by weight in bisphenol A liquid epoxy resin), available from Olin Corporation. Other commercially available core-shell rubber particle dispersions include Paraloid™ EXL 2650A (core-shell poly(butadiene) commercially available from Dow.

[0111] Exemplary non-limiting commercial core-shell elastomeric particle products using polysiloxane rubber particles that may be utilized in the composition include a core-shell polysiloxane rubber powder (commercially available as GENIOPERL® P52 from Wacker), a core-shell polysiloxane rubber dispersion (40% core-shell rubber by weight) in bisphenol A diglycidyl ether (commercially available as ALBIDUR® EP2240A from Evonick), a core-shell polysiloxane rubber dispersion (25% core-shell rubber by weight) in jER™828 (commercially available as Kane Ace MX 960), a core-shell polysiloxane rubber dispersion (25% core-shell rubber by weight) in Epon® 863 (commercially available as Kane Ace MX 965) each available from Kaneka Texas Corporation.

[0112] The compositions may be substantially free, or essentially free, or completely free, of an amine-functional rubber, a carboxy-functional rubber and/or an epoxy-functional rubber.

[0113] The composition may comprise the elastomeric particles in an amount of at least 2.5 percent by weight based on total weight of the composition, such as at least 5 percent by weight, such as at least 7.5 percent by weight, such as no more than 25 percent by weight, such as no more than 22.5 percent by weight, such as no more than 20 percent by weight, such as 2.5 percent by weight to 25 percent by weight, such as 5 percent by weight to 22.5 percent by weight, such as 7.5 percent by weight to 20 percent by weight.

Fillers

[0114] Compositions disclosed herein may comprise a fdler.

[0115] Useful fillers include carbon black, calcium carbonate, precipitated calcium carbonate, calcium hydroxide, calcium silicates, aluminum powders, hydrated alumina (aluminum hydroxide), metal oxides, fumed silica (hydrophilic, hydrophobic, coated and/or uncoated), fused silica, silica, precipitated silica, and combinations of any of the foregoing. Suitable examples of filler include AEROSIL® fumed silicas from Evonik or HDK® from Wacker Chemie AG and/or Sipernat precipitated silicas from Evonik. [0116] Useful fillers also include microspheres, polystyrene foam, microspheres of polyacrylates and polyolefins, and silica microspheres such as ECCOSPHERES® (Trelleborg Applied Technologies). Other examples include alumina/silica microspheres such as FILLITE® (Pluess-Stauffer International), aluminum silicate microspheres such as Z-LIGHT®, and calcium carbonate-coated poly vinylidene copolymer microspheres such as DU ALITE 6001AE® (Pierce & Stevens Corp.). Other suitable fillers include, for example, hollow microspheres such as Expancel® microspheres (available from Nouryon) or Dualite® low density polymer microspheres (available from Henkel) or hollow borosilicate glass, such as 3M Glass bubbles type VS, K series and S series available from 3M. Compositions provided by the present disclosure include filler particles comprising an exterior surface coated with a thin coating, such as those described in U.S. Publication No. 2010/0041839 at paragraphs [0016]-[0052], the cited portion of which is incorporated herein by reference.

[0117] Suitable fillers include, for example, those described in: U.S. Pat. No. 6,525,168, column 4, lines 14-55, incorporated herein by reference; and U.S. Pat. No. 8,816,023, column 3, line 18 to column 9, line 44, incorporated herein by reference.

[0118] The compositions may comprise a filler in an amount of at least 2.5 percent by weight based on total weight of the composition, such as at least 5 percent by weight, such as no more than 30 percent by weight, such as no more than 25 percent by weight, such as 2.5 percent by weight to 30 percent by weight, such as 5 percent by weight to 25 percent by weight.

Accelerators

[0119] The multi-component composition may comprise an accelerator. Any accelerator capable of accelerating the curing of the multi-component composition may be used in the present disclosure. Suitable accelerators include non-metal-based accelerators.

[0120] Examples of suitable non-metal -based accelerators are amine-based accelerators and acid-based accelerators. Examples of amines that may be useful comprise quaternary amines, tertiary amines, cyclic tertiary amines, secondary amines, cyclic secondary amines, and primary amines. Some examples include trimethylamine, butylamine, tributylamine, octylamine, laurylamine, dibutylamines, monoethanolamines, diethanolamines, triethanolamine, diethylenetriamine, triethylenetetriamine, oleylamines, diethanolamines, triethanolamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine, dimethylguanidine, tetramethylguanidine, pentamethylguanidine, phenylguanidine, diphenylguanidine, butylbiguanide, 1-o-tolylbiguanide, 1-phenylbiguanide, l-methyl-3- nitroguanidine, l,8-bis(tetramethylguanidino)-naphthalene, N,N,N’,N’-tetramethyl-N”-[4- morpholinyl(phenylimino)methyl]guanidine, 2,4,6-tris(dimethylaminomethyl)phenol, 2,2’ - dimorpholinodiethylether, morpholine, N-methylmorpholine, 2-ethyl-4-methylimidazole, 1,8- diacabicyclo-(5,4,0)-undecene-7 (DBU), N,N-bis(N,N-dimethyl-2-aminoethyl)methylamine, N,N-dimethylcyclohexylamine, N-methylmorpholine, N-ethylmorpholine, piperidine; piperazine; pyrrolidine, homopiperazine, l,2-dimethyl-l,4,5,6-tetrahydropyrimidine, 1, 4,5,6- tetrahydropyrimidine, l,8-diazabicyclo[5.4.0]undec-7-ene; l,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-l,5,7-triazabicyclo[4.4.0]dec-5-ene, l,5-diazabicyclo[4.3.0]non-5-ene, 6- (dibutylamino)-l,8-diazabicyclo(5,4,0)undec-7-ene, l,4-diazabicyclo[2.2.2]octane, 7- azabicyclo[2.2.1]heptane, N, N-dimethylphenylamine, 4,5-dihydro-lH-imidazole, or combinations thereof.

[0121] Examples of suitable commercial products that may be used include diethanolamine and triethanolamine T85 available from BASF; and Ancamine K-54, Curezol C17Z, DABCO 33-LV, Polycat DBU, and Vestamin IPD available from Evonik.

[0122] Suitable amine-functional curing agents for use in the compositions disclosed herein can be selected from a wide variety of known amines such as primary and secondary amines, and mixtures thereof. The amine may include monoamines, or polyamines having at least two functional groups such as di-, tri-, or higher functional amines; and mixtures thereof. The amine may be aromatic or aliphatic such as cycloaliphatic, or mixtures thereof. Nonlimiting examples of suitable amines may include aliphatic polyamines such as but not limited to ethylamine, isomeric propylamines, butylamines, pentylamines, hexylamines, cyclohexylamine, ethylene diamine, 1,2-diaminopropane, 1,4-diaminobutane, 1,3 -diaminopentane, 1,6- diaminohexane, 2-methyl- 1,5 -pentane diamine, 2,5-diamino-2,5-dimethylhexane, 2,2,4- and/or

2.4.4-trimethyl-l,6-diamino-hexane, 1,11 -diaminoundecane, 1,12-diaminododecane, 1,3- and/or

1.4-cyclohexane diamine, l-amino-3,3,5-trimethyl-5-aminomethyl-cyclohexane, 2,4- and/or 2,6- hexahydrotoluoylene diamine, 2,4'- and/or 4, 4'-diamino-di cyclohexyl methane and 3,3 '-dialkyl - 4,4'-diamino-dicyclohexyl methanes (such as 3,3 '-dimethyl -4, 4'-diamino-dicyclohexyl methane and 3,3 '-diethyl-4, 4'-diamino-dicyclohexyl methane), 2,4- and/or 2,6-diaminotoluene and 2,4'- and/or 4,4'-diaminodiphenyl methane, piperazines or adducts or derivatives thereof, or mixtures thereof. [0123] Secondary amines can include polyaspartic esters which can include derivatives of compounds such as maleic acid, fumaric acid esters, aliphatic poly amines and the like, and mixtures thereof. The secondary amine may include an aliphatic amine, such as a cycloaliphatic diamine. Such amines are available commercially from Huntsman Corporation (Houston, Tex.) under the designation of JEFFLINK such as JEFFLINK 754 from BASF as Baxxoder PC136.

[0124] The amine can include an amine-functional resin. Suitable amine-functional resins can be selected from a wide variety known in the art. The amine-functional resin may be an ester of an organic acid, for example, an aspartic ester-based amine-functional reactive resin that is compatible with isocyanate. The isocyanate may be solvent-free, and/or may have a mole ratio of amine-functionality to the ester of no more than 1 : 1 so that no excess primary amine remains upon reaction. A non-limiting example of such polyaspartic esters may include the derivative of diethyl maleate and l,5-diamino-2-methylpentane, which is available commercially from Covestro under the trade name DESMOPHEN NH1220 and the derivative of diethyl maleate and 4,4’-methylenebis (cy cl ohexan-1 -amine), commercially available as Desmophen NH1420 (Covestro). Other suitable compounds containing aspartate groups may be employed as well.

[0125] The amine may include high molecular weight primary amine, such as but not limited to polyoxyalkyleneamine. Suitable polyoxyalkyleneamines may contain two or more primary amino groups attached to a backbone derived, for example, from propylene oxide, ethylene oxide, or mixtures thereof. Non-limiting examples of such amines may include those available under the designation JEFF AMINE from Huntsman Corporation. Such amines may have a number average molecular weight ranging from 200 to 7500, such as but not limited to JEFF AMINE D-230, D-400, D-2000, T-403, T-5000, XJS-616, and ED600. Other suitable amines include aliphatic and cycloaliphatic polyamines such as the Ancamine® series available from Evonik.

[0126] The compositions may comprise the accelerator in an amount of at least 0.1 percent by weight based on total weight of the composition, such as at least 0.2 percent by weight, such as at least 0.5 percent by weight, such as no more than 10 percent by weight, such as no more than 5 percent by weight, such as no more than 2.5 percent by weight, such as 0. 1 percent by weight to 10 percent by weight, such as 0.2 percent by weight to 5 percent by weight, such as 0.5 percent by weight to 2.5 percent by weight. Additives

[0127] Compositions provided by the present disclosure may further include one or more additives, including by way of non-limiting examples, adhesion promoters, colorants, thixotropic agents, solvents, plasticizers, reactive diluents, pigments, masking agents, or a combination of any of the foregoing.

[0128] The compositions may comprise the additives in an amount of at least O.Olpercent by weight based on total weight of the composition, such as at least 0.05 percent by weight, such as no more than 15 percent by weight, such as no more than 12 percent by weight, such as no more than 10 percent by weight, such as no more than 3 percent by weight, such as 0.01 percent by weight to 15 percent by weight, such as 0.01 percent by weight to 12 percent by weight, such as 0.05 percent by weight to 10 percent by weight, such as 0.05 percent by weight to 3 percent by weight.

Compositions, Coatings and Systems

[0129] The compositions disclosed herein may be provided as multi-component compositions.

[0130] A first component may comprise, or consist essentially of, or consist of, an epoxycontaining compound. A first component optionally may comprise elastomeric particles, fillers, and/or additives. A second component may comprise, or consist essentially of, or consist of, an amino-functional amide and a flexibilizing amine. A second component optionally may comprise elastomeric particles, fillers, additives, and/or an accelerator. Additional components (i.e., third components, fourth components, etc.) may comprise, or consist essentially of, or consist of, elastomeric particles, filles, additives, and/or an accelerator.

[0131] The compositions may be substantially free, or essentially free, or completely free, of a polyurethane resin.

[0132] The composition may comprise an amine hydrogen: epoxy equivalence of at least 0.75: 1, such as at least 0.9: 1, such as no more than 1.25: 1, such as no more than 1.1 : 1, such as 0.75: 1 to 1.25: 1, such as 0.9: 1 to 1.1 :1.

[0133] The composition may comprise the first component in an amount of at least 50 percent by weight based on total weight of the composition, such as at least 60 percent by weight, such as 70 percent by weight. The composition may comprise the second component in an amount of no more than 90 percent by weight based on total weight of the composition, such as no more than 85 percent by weight, such as no more than 80 percent by weight. The composition may comprise the first component in an amount of 50 percent by weight to 90 percent by weight based on total weight of the composition, such as 60 percent by weight to 85 percent by weight, such as 70 percent by weight to 80 percent by weight.

[0134] The composition may comprise the second component in an amount of at least 10 percent by weight based on total weight of the composition, such as at least 15 percent by weight, such as at least 20 percent by weight. The composition may comprise the second component in an amount of no more than 50 percent by weight based on total weight of the composition, such as no more than 40 percent by weight, such as no more than 30 percent by weight. The composition may comprise the second component in an amount of 10 percent by weight to 50 percent by weight based on total weight of the composition, such as 15 percent by weight to 40 percent by weight, such as 20 percent by weight to 30 percent by weight.

[0135] The compositions disclosed herein may be applied alone or as part of a coating system. Compositions disclosed herein may be applied directly onto the surface of a substrate or over an underlayer by any suitable coating process. Compositions can be deposited on substrates in a number of different ways, non-limiting examples of which include brushes, rollers, films, pellets, pressure injectors, spray guns and applicator guns. The system may comprise a number of the same or different layers and may further comprise other coating compositions such as pretreatment compositions, primers, and the like. A coating is typically formed when a composition that is deposited onto the substrate is cured by methods known to those of ordinary skill in the art (e.g., under ambient conditions, optionally with further cure through the use of an external energy source such as an oven or other thermal means or through the use of actinic radiation) to form a coating. A multi-component composition may at least partially cure at ambient temperature. Compositions may be cured at a temperature of 0 to 40°C, such as 10°C to 25°C, and atmospheric humidity. A composition may be cured at a higher temperature such as at least 30°C., at least 40°C., or at least 50°C. When cured at room temperature a coating provided by the present disclosure can cure to a tack free surface, for example, within 24 hours, within 20 hours, within 16 hours, within 12 hours, within 6 hours, or within 3 hours, from the time of mixing. The skilled person understands, however, that the time of curing varies with temperature. [0136] The multi-component compositions disclosed herein may comprise a coating composition, such as an adhesive composition, a sealant composition, a gap filler composition, an embedding composition, an encapsulating composition, and/or a potting composition.

[0137] The compositions may be cured to form a coating, such as an adhesive or a structural adhesive, a sealant, a pottant, a gap filler, a composite formed from a pre-preg, a liquid shim, an embedding material, an encapsulating material, and/or a potting compound.

[0138] It was surprisingly discovered that the coatings formed from the compositions disclosed herein comprise:

(a) a pot-life of at least 120 minutes; and at least one of

(b) a lap shear strength of at least 725 psi measured at ambient conditions according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute, such as at least 1000 psi, such as at least 1500 psi, such as at least 2000 psi, such as at least 3000 psi, such as at least 4000 psi;

(c) lap shear strength of at least 725 psi measured at 160°F for at least 30 minutes according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute, such as at least 800 psi, such as at least 900 psi; and

(d) a roller peel strength of at least 15 psi measured according to ASTM D3167, such as at least 25 psi, such as at least 50 psi.

[0139] Also disclosed herein are uses of the compositions disclosed herein for making a coating, wherein the coating comprises:

(a) a pot-life of at least 120 minutes; and at least one of

(b) a lap shear strength of at least 725 psi measured at ambient conditions according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute, such as at least 1000 psi, such as at least 1500 psi, such as at least 2000 psi, such as at least 3000 psi, such as at least 4000 psi;

(c) lap shear strength of at least 725 psi measured at 160°F for at least 30 minutes according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1 .3 mm per minute, such as at least 800 psi, such as at least 900 psi; and

(d) a roller peel strength of at least 15 psi measured according to ASTM D3167, such as at least 25 psi, such as at least 50 psi.

[0140] Also disclosed herein are uses of a coating formed from the any of the compositions disclosed herein, to provide a substrate comprising a coating, wherein the coating comprises:

(a) a pot-life of at least 120 minutes; and at least one of

(b) a lap shear strength of at least 725 psi measured at ambient conditions according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute, such as at least 1000 psi, such as at least 1500 psi, such as at least 2000 psi, such as at least 3000 psi, such as at least 4000 psi;

(c) lap shear strength of at least 725 psi measured at 160°F for at least 30 minutes according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute, such as at least 800 psi, such as at least 900 psi; and

(d) a roller peel strength of at least 15 psi measured according to ASTM D3167, such as at least 25 psi, such as at least 50 psi.

3D Printing

[0141] Compositions of the present disclosure may be applied or deposited using any suitable method, including those aforementioned. Alternatively, the composition may be casted, extruded, molded, or machined to form a part or a member in at least partially dried or cured state.

[0142] The compositions disclosed herein may be used in any suitable additive manufacturing technology, such as three-dimensional (3D) printing, extrusionjetting, and binder jetting. Additive manufacturing refers to a process of producing a part or member by constructing it in layers, such as one layer at a time.

[0143] The present disclosure is also directed to the production of structural articles, such as by way of a non-limiting example, sound damping pads, using an additive manufacturing process, such as 3D printing. 3D printing refers to a computerized process, optionally including artificial intelligence modulation, by which materials are printed or deposited in successive layers to produce a 3D part or member, such as, by way of a non-limiting example, sound damping pads in a battery assembly. A 3D part or member may be produced by depositing successive portions or layers over a base of any spatial configuration and thereafter depositing additional portions or layers over the underlying deposited portion or layer and/or adjacent to the previously deposited portion or layer to produce the 3D printed part or member.

[0144] It will be appreciated that the configuration of the 3D printing process, including the selection of suitable deposition equipment, depends on a number of factors such as the deposition volume, the viscosity of the composition and the complexity of the part being fabricated. Any suitable mixing, delivery, and 3D printing equipment as known to those skilled in the art, may be used. Compositions may be printed or deposited in any size and/or shape of droplets or extrudate, and in any patterns to produce the 3D structure.

[0145] Compositions as disclosed herein may be applied or deposited by any suitable 3D printing method as known to those skilled in the art. First and second components of 2K compositions may be mixed and then deposited, or the first and second components may be deposited separately, such as simultaneously and/or sequentially.

[0146] First and second components may be premixed, i.e., mixed together, prior to application, and then deposited. The mixture may be at least partially reacted or thermoset when the material is deposited; the deposited reaction mixture may react at least in part after deposition and may also react with previously deposited portions and/or subsequently deposited portions of the article such as underlying layers or overlying layers of the article.

[0147] In a non-limiting example, the first and two components may be released from their individual storage containers and pushed, such as pumped through conduits, such as hoses, to a mixer, such as a static or dynamic mixer, wherein the composition may be mixed for a time sufficient to homogenize the composition, wherein the composition may then be released through an outlet. The outlet may be a deposition device, such as a printing head, and/or the materials may exit the mixing unit and be pushed, such as by a pump, through a conduit, such as a hose, to the printing head. The printing head may optionally be mounted on a 3D rotational robotic arm to allow delivery of 3D print compositions to any base in any spatial configuration and/or the base may be manipulated in any spatial configuration during the 3D printing process. [0148] Alternatively, first and second components may be deposited independently from different printing heads. The first component may be deposited from one printing head and the second component may be deposited from a second printing head. The first and second components may be deposited in any pattern such that the first and second components comprising any deposited layer can react together as well as react with underlying and/or overlying layers to produce the 3D printed part or member.

[0149] Methods provided by the present disclosure include printing the composition on a fabricated part. Methods provided by the present disclosure include directly printing parts.

[0150] Using the methods provided by the present disclosure parts can be fabricated. The entire part can be formed from one of the compositions disclosed herein, one or more portions of a part can be formed from one of the compositions disclosed herein, one or more different portions of a part can be formed using the compositions disclosed herein, and/or one or more surfaces of a part can be formed from a composition provided by the present disclosure. In addition, internal regions of a part can be formed from a composition provided by the present disclosure.

Substrates

[0151] Still further disclosed are substrates and articles comprising, or consisting essentially of, or consisting of, coatings formed from the compositions disclosed herein. For example, also disclosed is a coated substrate, wherein at least a portion of a surface of the substrate is at least partially coated with a coating formed from a composition disclosed herein. Also disclosed is an article comprising, or consisting essentially of, or consisting of, first and second substrates and a coating positioned therebetween and in an at least partially cured state.

[0152] The substrates that may be coated by the compositions of the present disclosure are not limited. Suitable substrates useful in the present disclosure include, but are not limited to, materials such as metals or metal alloys, ceramic materials such as boron carbide or silicon carbide, polymeric materials such as hard plastics including filled and unfilled thermoplastic materials or thermoset materials, or composite materials. Other suitable substrates useful in the present disclosure include, but are not limited to, glass or natural materials such as wood. For example, suitable substrates include rigid metal substrates such as ferrous metals, aluminum, aluminum alloys, magnesium titanium, copper, and other metal and alloy substrates. The ferrous metal substrates used in the practice of the present disclosure may include iron, steel, and alloys thereof. Non-limiting examples of useful steel materials include cold rolled steel, galvanized (zinc coated) steel, electrogalvanized steel, stainless steel, pickled steel, zinc-iron alloy such as GALV ANNEAL, and combinations thereof. Combinations or composites of ferrous and nonferrous metals can also be used. Aluminum alloys of the 1XXX, 2XXX, 3XXX, 4XXX, 5XXX, 6XXX, 7XXX, or 8XXX series as well as clad aluminum alloys and cast aluminum alloys of the A356, 1XX.X, 2XX.X, 3XX.X, 4XX.X, 5XX.X, 6XX.X, 7XX.X, or 8XX.X series also may be used as the substrate. Magnesium alloys of the AZ3 IB, AZ91C, AM60B, or EV31 A series also may be used as the substrate. The substrate used in the present disclosure may also comprise titanium and/or titanium alloys of grades 1-36 including H grade variants. Other suitable nonferrous metals include copper and magnesium, as well as alloys of these materials. The compositions disclosed herein are particularly suitable for use in various industrial or transportation applications including automotive, light and heavy commercial vehicles, marine, or aerospace. Suitable metal substrates for use in the present disclosure include those that are used in the assembly of vehicular bodies (e.g., without limitation, door, body panel, trunk deck lid, roof panel, hood, roof and/or stringers, rivets, landing gear components, and/or skins used on an aircraft), a vehicular frame, vehicular parts, motorcycles, wheels, and industrial structures and components. As used herein, “vehicle” or variations thereof includes, but is not limited to, civilian, commercial and military aircraft, and/or land vehicles such as cars, motorcycles, and/or trucks. The metal substrate also may be in the form of, for example, a sheet of metal or a fabricated part. It will also be understood that the substrate may be converted, anodized, primed, organic-coated or chromate-coated, epoxy, urethane, graphite, fiberglass composite, Kevlar®, acrylics, and polycarbonates. The substrate may comprise a composite material such as a plastic or a fiberglass composite. The substrate may be a fiberglass and/or carbon fiber composite. The first and second substrates may be made of the same material or may be made of dissimilar materials. For example, a first substrate and a second substrate may be a metal and a plastic; two dissimilar plastics; a metal or a plastic and a reinforced plastic composite; or two dissimilar plastic composites.

[0153] In view of the foregoing description the present disclosure thus relates in particular to the following Aspects 1-210 without being limited thereto. ASPECTS

[0154] Aspect 1. A composition comprising: a first component comprising an epoxy-containing compound; a second component comprising an amino-functional amide and a flexibilizing amine; and elastomeric particles.

[0155] Aspect 2. The composition of aspect 1, wherein the epoxy-containing compound comprises more than one epoxy functional group.

[0156] Aspect 3. The composition of aspect 1 or aspect 2, wherein the epoxy- containing compound comprises at least two epoxy functional groups.

[0157] Aspect 4. The composition of any of the preceding aspects, wherein the epoxy-containing compound comprises an aromatic epoxide.

[0158] Aspect 5. The composition of any of the preceding aspects, wherein the epoxy-containing compound comprises an epoxy adduct.

[0159] Aspect 6. The composition of any of the preceding aspects, wherein the epoxy-containing compound comprises bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a novolac resin, tetraglycidyl methylene dianiline, triglycidyl-p-amino phenol, tetraglycidyl m-xylylenediamine or combinations thereof.

[0160] Aspect 7. The composition of any of the preceding aspects, wherein the first component comprises an aromatic monoepoxide, an aliphatic monoepoxide and/or an aliphatic polyepoxide.

[0161] Aspect 8. The composition of aspect 7, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of at least 0.1 percent by weight based on total weight of the first component.

[0162] Aspect 9. The composition of aspect 7 or aspect 8, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of at least 0.2 percent by weight based on total weight of the first component.

[0163] Aspect 10. The composition of any of aspects 7 to 9, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of at least 0.5 percent by weight based on total weight of the first component. [0164] Aspect 11. The composition of any of aspects 7 to 10, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of no more than 15 percent by weight based on total weight of the first component.

[0165] Aspect 12. The composition of any of aspects 7 to 11, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of no more than 10 percent by weight.

[0166] Aspect 13. The composition of any of aspects 7 to 12, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of 0.1 percent by weight to 15 percent by weight based on total weight of the first component.

[0167] Aspect 14. The composition of any of aspects 7 to 13, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of 0.2 percent by weight to 10 percent by weight based on total weight of the first component.

[0168] Aspect 15. The composition of any of aspects 7 to 14, wherein the first component comprises the aromatic or aliphatic monoepoxide in an amount of 0.5 percent by weight to 8 percent by weight based on total weight of the first component

[0169] Aspect 16. The composition of any of aspects 7 to 15, wherein the aliphatic epoxide comprises 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, cyclohexanedimethanol diglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, or a fatty alcohol monoglycidyl ether.

[0170] Aspect 17. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing compound in an amount of at least 30 percent by weight based on total weight of the first component.

[0171] Aspect 18. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing compound in an amount of at least 35 percent by weight based on total weight of the first component.

[0172] Aspect 19. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing compound in amount of at least 40 percent by weight based on total weight of the first component.

[0173] Aspect 20. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of no more than 100 percent by weight based on total weight of the first component. [0174] Aspect 21. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of no more than 60 percent by weight based on total weight of the first component.

[0175] Aspect 22. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of no more than 55 percent by weight based on total weight of the first component.

[0176] Aspect 23. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of no more than 50 percent by weight based on total weight of the first component.

[0177] Aspect 24. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 30 percent by weight to 100 percent by weight based on total weight of the first component.

[0178] Aspect 25. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 30 percent by weight to 60 percent by weight based on total weight of the first component.

[0179] Aspect 26. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 35 percent by weight to 55 percent by weight based on total weight of the first component.

[0180] Aspect 27. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 40 percent by weight to 50 percent by weight based on total weight of the first component.

[0181] Aspect 28. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of at least 5 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0182] Aspect 29. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of at least 10 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0183] Aspect 30. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of at least 15 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine. [0184] Aspect 31. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of no more than 75 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0185] Aspect 32. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of no more than 50 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0186] Aspect 33. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of no more than 35 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0187] Aspect 34. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of 5 percent by weight to 75 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0188] Aspect 35. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of 10 percent by weight to 50 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0189] Aspect 36. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of 15 percent by weight to 35 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0190] Aspect 37. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of at least 25 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0191] Aspect 38. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of at least 30 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine. [0192] Aspect 39. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of at least 35 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0193] Aspect 40. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of no more than 95 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0194] Aspect 41. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of no more than 85 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0195] Aspect 42. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of no more than 80 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0196] Aspect 43. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of 25 percent by weight to 95 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0197] Aspect 44. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of 30 percent by weight to 85 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0198] Aspect 45. The composition of any of the preceding aspects, wherein the second component comprises the flexibilizing amine in an amount of 35 percent by weight to 80 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine.

[0199] Aspect 46. The composition of any of the preceding aspects, wherein the amino-functional amide comprises a reaction product of reactants comprising a dimer fatty acid and an etheramine.

[0200] Aspect 47. The composition of aspect 46, wherein the etheramine comprises an aliphatic etheramine, diethylenetriamine and/or triethylenetetramine.

[0201] Aspect 48. The composition of aspect 46 or aspect 47, wherein the reaction product comprises a difunctional amine. [0202] Aspect 49. The composition of any of aspects 46 to 48, wherein the reaction product comprises two primary amines.

[0203] Aspect 50. The composition of any of aspects 46 to 49, wherein the reaction product comprises a secondary amine.

[0204] Aspect 51. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of greater than 140 g/mol measured by mass spectrometry.

[0205] Aspect 52. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of at least 170 g/mol measured by mass spectrometry.

[0206] Aspect 53. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of at least 210 g/mol measured by mass spectrometry.

[0207] Aspect 52. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of no more than 2,000 g/mol measured by mass spectrometry.

[0208] Aspect 53. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of no more than 1,700 g/mol measured by mass spectrometry.

[0209] Aspect 54. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of no more than 1,300 g/mol measured by mass spectrometry.

[0210] Aspect 55. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of no more than 1,200 g/mol measured by mass spectrometry.

[0211] Aspect 56. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of 140 g/mol to 2,000 g/mol measured by mass spectrometry.

[0212] Aspect 57. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of 170 g/mol to 1,700 g/mol measured by mass spectrometry. [0213] Aspect 58. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of 210 g/mol to 1,300 g/mol measured by mass spectrometry.

[0214] Aspect 59. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an etheramine comprising a molecular weight of 210 g/mol to 1,200 g/mol measured by mass spectrometry.

[0215] Aspect 60. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 295 g/mol measured by mass spectrometry.

[0216] Aspect 61. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 400 g/mol measured by mass spectrometry.

[0217] Aspect 62. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 500 g/mol measured by mass spectrometry.

[0218] Aspect 63. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 2,000 g/mol measured by mass spectrometry.

[0219] Aspect 64. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 1,700 g/mol measured by mass spectrometry.

[0220] Aspect 65. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 1,300 g/mol measured by mass spectrometry.

[0221] Aspect 66. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 1,200 g/mol measured by mass spectrometry.

[0222] Aspect 67. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 295 g/mol to 2,000 g/mol measured by mass spectrometry. [0223] Aspect 68. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of 400 g/mol to 1,700 g/mol measured by mass spectrometry.

[0224] Aspect 69. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of 500 g/mol to 1,300 g/mol measured by mass spectrometry.

[0225] Aspect 70. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of 500 g/mol to 1,200 g/mol measured by mass spectrometry.

[0226] Aspect 71. The composition of any of the preceding aspects, wherein the flexibilizing amine comprises an amine-functional aliphatic etheramine-epoxy adduct (Al).

[0227] Aspect 72. The composition of aspect 71, wherein the amine-functional aliphatic etheramine-epoxy adduct (Al) comprises a reaction product of reactants comprising an aliphatic etheramine (A2) and an epoxy-containing compound (E2).

[0228] Aspect 73. The composition of aspect 72, wherein the aliphatic etheramine (A2) comprises two amine-functional groups, such as a diamine, a triamine, a tetraamine, or combinations thereof.

[0229] Aspect 74. The composition of aspect 72 or aspect 73, wherein the aliphatic etheramine (A2) comprises an ethylene glycol subunit, such as ethylene glycol bis(2-aminoethyl) ether, diethylene glycol bi s(3 -aminopropyl) ether or combinations thereof.

[0230] Aspect 75. The composition of any of aspects 72 to 74, wherein the aliphatic etheramine (A2) comprises a primary amine functional group adjacent to a methylene group.

[0231] Aspect 76. The composition of any of aspects 72 to 75, wherein the aliphatic etheramine (A2) comprises a molecular weight of at least 104 g/mol measured using mass spectrometry.

[0232] Aspect 77. The composition of any of aspects 72 to 76, wherein the aliphatic eitheramine (A2) comprises a molecular weight of at least 140 g/mol measured using mass spectrometry.

[0233] Aspect 78. The composition of any of aspects 72 to 77, wherein the aliphatic eitheramine (A2) comprises a molecular weight of no more than 300 g/mol measured using mass spectrometry. [0234] Aspect 79. The composition of any of aspects 72 to 78, wherein the aliphatic eitheramine (A2) comprises a molecular weight of no more than 230 g/mol measured using mass spectrometry.

[0235] Aspect 80. The composition of any of aspects 72 to 79, wherein the aliphatic eitheramine (A2) comprises a molecular weight of 104 g/mol to 300 g/mol measured using mass spectrometry.

[0236] Aspect 81. The composition of any of aspects 72 to 80, wherein the aliphatic eitheramine (A2) comprises a molecular weight of 104 g/mol to 300 g/mol measured using mass spectrometry.

[0237] Aspect 82. The composition of any of aspects 72 to 81, wherein the aliphatic eitheramine (A2) comprises a molecular weight of 140 g/mol to 230 g/mol measured using mass spectrometry.

[0238] Aspect 83. The composition of any of aspects 72 to 82, wherein the epoxycontaining compound (E2) comprises bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a novolac resin, tetraglycidyl methylene dianaline, triglycidyl-p-amino phenol, tetraglycidyl m- xylenediamine or combinations thereof.

[0239] Aspect 84. The composition of any of aspects 72 to 83, wherein the epoxycontaining compound (E2) comprises an aromatic group.

[0240] Aspect 85. The composition of any of aspects 72 to 84, wherein the epoxycontaining compound (E2) comprises a molecular weight of no more than 600 g/mol measured by mass spectrometry.

[0241] Aspect 86. The composition of any of aspects 72 to 85, wherein the epoxycontaining compound (E2) comprises a molecular weight of no more than 450 g/mol measured by mass spectrometry.

[0242] Aspect 87. The composition of any of aspects 72 to 86, wherein the epoxycontaining compound (E2) comprises a molecular weight of at least 160 g/mol measured by mass spectrometry.

[0243] Aspect 88. The composition of any of aspects 72 to 87, wherein the epoxycontaining compound (E2) comprises a molecular weight of at least 300 g/mol measured by mass spectrometry. [0244] Aspect 89. The composition of any of aspects 72 to 88, wherein the epoxycontaining compound (E2) comprises a molecular weight of at least 160 g/mol to 600 g/mol measured by mass spectrometry.

[0245] Aspect 90. The composition of any of aspects 72 to 89, wherein the epoxycontaining compound (E2) comprises a molecular weight of at least 300 g/mol to 450 g/mol measured by mass spectrometry.

[0246] Aspect 91. The composition of any of aspects 72 to 90, wherein the epoxycontaining compound (E2) comprises an epoxide equivalent weight of at least 85 g/eq.

[0247] Aspect 92. The composition of any of aspects 72 to 91, wherein the epoxycontaining compound (E2) comprises an epoxide equivalent weight of at least 110 g/eq.

[0248] Aspect 93. The composition of any of aspects 72 to 92, wherein the epoxycontaining compound (E2) comprises an epoxide equivalent weight of no more than 300 g/eq.

[0249] Aspect 94. The composition of any of aspects 72 to 93, wherein the epoxycontaining compound (E2) comprises an epoxide equivalent weight of no more than 220 g/eq.

[0250] Aspect 95. The composition of any of aspects 72 to 94, wherein the epoxycontaining compound (E2) comprises an epoxide equivalent weight of 85 g/eq to 300 g/eq.

[0251] Aspect 96. The composition of any of aspects 72 to 95, wherein the epoxycontaining compound (E2) comprises an epoxide equivalent weight of 110 g/eq to 220 g/eq.

[0252] Aspect 97. The composition of any of aspects 72 to 96, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of aminehydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxycontaining compound (E2) of at least 3: 1.

[0253] Aspect 98. The composition of any of aspects 72 to 97, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of aminehydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxycontaining compound (E2) of at least 4: 1.

[0254] Aspect 99. The composition of any of aspects 72 to 98, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of aminehydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxycontaining compound (E2) of no more than 12: 1. [0255] Aspect 100. The composition of any of aspects 72 to 99, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of aminehydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxycontaining compound (E2) of no more than 7:1.

[0256] Aspect 101. The composition of any of aspects 72 to 100, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of aminehydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxycontaining compound (E2) of 3 : 1 to 12: 1.

[0257] Aspect 102. The composition of any of aspects 72 to 101, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of aminehydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxycontaining compound (E2) of 4: 1 to 7: 1.

[0258] Aspect 103. The composition of any of the preceding aspects, the second component further comprising a cycloaliphatic amine and/or a polyamine.

[0259] Aspect 104. The composition of aspect 103, comprising the cycloaliphatic amine in an amount of at least 0.5 percent by weight based on total weight of the aminofunctional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0260] Aspect 105. The composition of aspect 103 or aspect 104, comprising the cycloaliphatic amine in an amount of at least 1 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0261] Aspect 106. The composition of any of aspects 103 to 105, comprising the cycloaliphatic amine in an amount of no more than 10 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0262] Aspect 107. The composition of any of aspects 103 to 106, comprising the cycloaliphatic amine in an amount of no more than 8 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine

[0263] Aspect 108. The composition of any of aspects 103 to 107, comprising the cycloaliphatic amine in an amount of 0.5 perceent by weight to 10 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the poly amine. [0264] Aspect 109. The composition of any of aspects 103 to 108, comprising the cycloaliphatic amine in an amount of 1 perceent by weight to 8 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyaminesuch as 1 percent by weight to 8 percent by weight.

[0265] Aspect 110. The composition of any of aspects 103 to 109, comprising the polyamine in an amount of at least 0.5 percent by weight based on total weight of the aminofunctional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0266] Aspect 111. The composition of any of aspects 103 to 110, comprising the polyamine in an amount of at least 1 percent by weight based on total weight of the aminofunctional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0267] Aspect 112. The composition of any of aspects 103 to 111, comprising the poly amine in an amount of no more than 50 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0268] Aspect 113. The composition of any of aspects 103 to 112, comprising the poly amine in an amount of no more than 40 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0269] Aspect 114. The composition of any of aspects 103 to 113, comprising the poly amine in an amount of 0.5 percent by weight to 50 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0270] Aspect 115. The composition of any of aspects 103 to 114, comprising the polyamine in an amount of 1 percent by weight to 40 percent by weight based on total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine and the polyamine.

[0271] Aspect 116. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a core-shell structure, an amine-functional rubber, a carboxyfunctional rubber, an epoxy-functional rubber, or combinations thereof.

[0272] Aspect 117. The composition of any of the preceding aspects, wherein the first component, the second component, and/or a third component comprise the elastomeric particles.

[0273] Aspect 118. The composition of any of the preceding aspects, wherein the elastomeric particles are phase-separated from the epoxy-containing component, the fatty acid aminoamide and/or the flexibilizing amine. [0274] Aspect 119. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of at least 20 nm as measured using dynamic light scattering or a TEM.

[0275] Aspect 120. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of at least 30 nm as measured using dynamic light scattering or a TEM.

[0276] Aspect 121. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of at least 50 nm as measured using dynamic light scattering or a TEM.

[0277] Aspect 122. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of no more than 300 nm as measured using dynamic light scattering or a TEM.

[0278] Aspect 123. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of no more than 200 nm as measured using dynamic light scattering or a TEM.

[0279] Aspect 124. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of no more than 150 nm as measured using dynamic light scattering or a TEM.

[0280] Aspect 125. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of 20 nm to 300 nm as measured using dynamic light scattering or a TEM.

[0281] Aspect 126. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of 30 nm to 200 nm as measured using dynamic light scattering or a TEM.

[0282] Aspect 127. The composition of any of the preceding aspects, wherein the elastomeric particles comprise a particle size of 50 nm to 150 nm as measured using dynamic light scattering or a TEM.

[0283] Aspect 128. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of at least 2.5 percent by weight based on total weight of the composition. [0284] Aspect 129. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of at least 5 percent by weight based on total weight of the composition.

[0285] Aspect 130. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of at least 7.5 percent by weight based on total weight of the composition.

[0286] Aspect 131. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of no more than 25 percent by weight based on total weight of the composition.

[0287] Aspect 132. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of no more than 22.5 percent by weight based on total weight of the composition.

[0288] Aspect 133. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of no more than 20 percent by weight based on total weight of the composition.

[0289] Aspect 134. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of 2.5 percent by weight to 25 percent by weight based on total weight of the composition.

[0290] Aspect 135. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of 5 percent by weight to 22.5 percent by weight based on total weight of the composition.

[0291] Aspect 136. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of 7.5 percent by weight to 20 percent by weight based on total weight of the composition.

[0292] Aspect 137. The composition of any of the preceding aspects, wherein the first component, the second component, and/or a third component comprise a reinforcing filler.

[0293] Aspect 138. The composition of aspect 137, comprising the reinforcing filler in an amount of at least 2.5 percent by weight based on total weight of the composition.

[0294] Aspect 139. The composition of aspect 137 or aspect 138, comprising the reinforcing filler in an amount of at least 5 percent by weight based on total weight of the composition. [0295] Aspect 140. The composition of any of aspects 137 to 139, comprising the reinforcing filler in an amount of no more than 30 percent by weight based on total weight of the composition.

[0296] Aspect 141. The composition of any of aspects 137 to 140, comprising the reinforcing filler in an amount of no more than 25 percent by weight based on total weight of the composition.

[0297] Aspect 142. The composition of any of aspects 137 to 141, comprising the reinforcing filler in an amount of 2.5 percent by weight to 30 percent by weight based on total weight of the composition.

[0298] Aspect 143. The composition of any of aspects 137 to 142, comprising the reinforcing filler in an amount of 5 percent by weight to 25 percent by weight based on total weight of the composition.

[0299] Aspect 144. The composition of any of the preceding aspects, wherein the first component, the second component, and/or a third component comprise an additive.

[0300] Aspect 145. The composition of aspect 144, wherein the composition comprises the additive in an amount of at least 0.01 percent by weight based on total weight of the composition.

[0301] Aspect 146. The composition of aspect 144 or 145, wherein the composition comprises the additive in an amount of at least 0.05 percent by weight based on total weight of the composition.

[0302] Aspect 147. The composition of any of aspects 144 to 146, wherein the composition comprises the additive in an amount of no more than 15 percent by weight based on total weight of the composition.

[0303] Aspect 148. The composition of any of aspects 144 to 147, wherein the composition comprises the additive in an amount of no more than 12 percent by weight based on total weight of the composition.

[0304] Aspect 149. The composition of any of aspects 144 to 148, wherein the composition comprises the additive in an amount of no more than 10 percent by weight based on total weight of the composition. [0305] Aspect 150. The composition of any of aspects 144 to 149, wherein the composition comprises the additive in an amount of no more than 3 percent by weight based on total weight of the composition.

[0306] Aspect 151. The composition of any of aspects 144 to 150, wherein the composition comprises the additive in an amount of 0.01 percent by weight to 15 percent by weight based on total weight of the composition.

[0307] Aspect 152. The composition of any of aspects 144 to 151, wherein the composition comprises the additive in an amount of 0.01 percent by weight to 12 percent by weight based on total weight of the composition.

[0308] Aspect 153. The composition of any of aspects 144 to 152, wherein the composition comprises the additive in an amount of 0.05 percent by weight to 10 percent by weight based on total weight of the composition.

[0309] Aspect 154. The composition of any of aspects 144 to 153, wherein the composition comprises the additive in an amount of 0.05 percent by weight to 3 percent by weight based on total weight of the composition.

[0310] Aspect 155. The composition of any of the preceding aspects, wherein the first component, the second component, and/or a third component comprise an accelerator.

[0311 ] Aspect 156. The composition of aspect 155, comprising the accelerator in an amount of at least 0.1 percent by weight based on total weight of the composition.

[0312] Aspect 157. The composition of aspect 155 or aspect 156, comprising the accelerator in an amount of at least 0.2 percent by weight based on total weight of the composition.

[0313] Aspect 158. The composition of any of aspects 155 to 157, comprising the accelerator in an amount of at least 0.5 percent by weight based on total weight of the composition.

[0314] Aspect 159. The composition of any of aspects 155 to 158, comprising the accelerator in an amount of no more than 10 percent by weight based on total weight of the composition.

[0315] Aspect 160. The composition of any of aspects 155 to 159, comprising the accelerator in an amount of no more than 5 percent by weight based on total weight of the composition. [0316] Aspect 161. The composition of any of aspects 155 to 160, comprising the accelerator in an amount of no more than 2.5 percent by weight based on total weight of the composition.

[0317] Aspect 162. The composition of any of aspects 155 to 161, comprising the accelerator in an amount of 0.1 percent by weight to 10 percent by weight based on total weight of the composition.

[0318] Aspect 163. The composition of any of aspects 155 to 162, comprising the accelerator in an amount of 0.2 percent by weight to 5 percent by weight based on total weight of the composition.

[0319] Aspect 164. The composition of any of aspects 155 to 163, comprising the accelerator in an amount of 0.5 percent by weight to 2.5 percent by weight based on total weight of the composition.

[0320] Aspect 165. The composition of any of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free, of a polyurethane resin.

[0321] Aspect 166. The composition of any of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free, of an amine-functional rubber.

[0322] Aspect 167. The composition of any of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free, of a carb oxy -functional rubber.

[0323] Aspect 168. The composition of any of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free, of an epoxy-functional rubber.

[0324] Aspect 169. The composition of any of the preceding aspects, formulated as an adhesive composition, such as a structural adhesive composition, a pottant composition, a gap filler composition, a pre-preg composition, a liquid shim composition, or combinations thereof.

[0325] Aspect 170. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of at least 50 percent by weight based on total weight of the composition. [0326] Aspect 171. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of at least 60 percent by weight based on total weight of the composition.

[0327] Aspect 172. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of at least 70 percent by weight based on total weight of the composition.

[0328] Aspect 173. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of no more than 90 percent by weight based on total weight of the composition.

[0329] Aspect 174. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of no more than 85 percent by weight based on total weight of the composition.

[0330] Aspect 175. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of no more than 80 percent by weight based on total weight of the composition.

[0331] Aspect 176. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of 50 percent by weight to 90 percent by weight based on total weight of the composition.

[0332] Aspect 177. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of 60 percent by weight to 85 percent by weight based on total weight of the composition.

[0333] Aspect 178. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of 70 percent by weight to 80 percent by weight based on total weight of the composition.

[0334] Aspect 179. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of at least 10 percent by weight based on total weight of the composition.

[0335] Aspect 180. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of at least 15 percent by weight based on total weight of the composition. [0336] Aspect 181. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of at least 20 percent by weight based on total weight of the composition.

[0337] Aspect 182. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of no more than 50 percent by weight based on total weight of the composition.

[0338] Aspect 183. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of no more than 40 percent by weight based on total weight of the composition.

[0339] Aspect 184. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of no more than 30 percent by weight based on total weight of the composition.

[0340] Aspect 185. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of 10 percent by weight to 50 percent by weight based on total weight of the composition.

[0341] Aspect 186. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of 15 percent by weight to 40 percent by weight based on total weight of the composition.

[0342] Aspect 187. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of 20 percent by weight to 30 percent by weight based on total weight of the composition.

[0343] Aspect 188. A method of coating a substrate comprising contacting a portion of a surface of the substrate with the composition of any of the preceding aspects.

[0344] Aspect 189. The method of aspect 188, further comprising mixing the first component and the second component of any of aspects 1 to 187.

[0345] Aspect 190. The method of aspect 188 or aspect 189, further comprising contacting a surface of a second substrate to the composition such that the composition is between the substrate and the second substrate.

[0346] Aspect 191. A method of forming an article, comprising extruding the composition of any of aspects 1 to 187. [0347] Aspect 192. The method of aspect 191, wherein the extruding comprises three- dimensional printing.

[0348] Aspect 193. The article formed by the method of aspect 191 or aspect 192.

[0349] Aspect 194. A substrate comprising a coating formed from the composition of any of aspects 1 to 187 on a portion of a surface of the substrate.

[0350] Aspect 195. The substrate of aspect 194, further comprising a pretreatment coating or film and/or an additional coating, such as a primer, a basecoat and/or a topcoat.

[0351] Aspect 196. The substrate of aspect 194 or aspect 195, wherein the substrate comprises aluminum, steel, or titanium, or alloys thereof, a carbon fiber composite, a glass fiber composite, a thermoplastic, a nylon, a ceramic, or combinations thereof.

[0352] Aspect 197. The substrate of any of aspects 194 to 196, further comprising a second substrate, wherein the coating is located between the substrate and the second substrate.

[0353] Aspect 198. The substrate of any of aspects 143 to 197, wherein the coating comprises a pot-life of at least 120 minutes and a lap shear strength of at least 725 psi measured at ambient conditions according to ASTM DI 002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0354] Aspect 199. The substrate of any of aspects 1934 to 198, wherein the coating comprises a pot-life of at least 120 minutes and a lap shear strength of at least 725 psi measured at 160°F for at least 30 minutes according to ASTM D1002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0355] Aspect 200. The substrate of any of aspects 194 to 199, wherein the coating comprises a pot-life of at least 120 minutes and a roller peel strength of at least 15 psi measured according to ASTM D3167.

[0356] Aspect 201. The substrate of any of aspects 194 to 200, coated according to the method of any of aspects 188 to 190.

[0357] Aspect 202. The substrate of any of aspects 194 to 201, wherein the coating comprises an adhesive, a structural adhesive, a pottant, a gap filler, a composite formed from a pre-preg, a liquid shim, or combinations thereof.

[0358] Aspect 203. The substrate of any of aspects 194 to 202, wherein the substrate comprises an article, a part, or combinations thereof. [0359] Aspect 204. The substrate of aspect 203, wherein the article comprises a vehicle, an appliance, a personal electronic device, a circuit board, a multi-metal substrate, or combinations thereof.

[0360] Aspect 205. The substrate of aspect 203, wherein the part comprises a vehicular part.

[0361] Aspect 206. The substrate of aspect 204 or aspect 205, wherein the vehicle comprises a land vehicle or an aircraft.

[0362] Aspect 207. Use of the coating composition according to any of aspects 1 to 187 for coating a surface of a substrate, wherein the coating comprises a pot-life of at least 120 minutes and a lap shear strength of at least 725 psi measured at ambient conditions according to ASTM D1002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0363] Aspect 208. The use according to aspect 207, wherein the coating comprises a pot-life of at least 120 minutes and a lap shear strength of at least 725 psi measured at 160°F for at least 30 minutes according to ASTM D1002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.

[0364] Aspect 209. The use according to aspect 207 or aspect 208, wherein the coating comprises a pot-life of at least 120 minutes and a roller peel strength of at least 15 psi measured according to ASTM D3167.

[0365] Aspect 210. The use of any of aspects 207 to 209, wherein the coating comprises an adhesive, a structural adhesive, a pottant, a gap filler, a composite formed from a pre-preg, a liquid shim, or combinations thereof.

[0366] The following examples are intended to illustrate the disclosure and should not be construed as limiting the disclosure in any way.

EXAMPLES

Example 1 : Amine Pack 1

[0367] The amine pack was prepared by charging 80.8g of amidoamine and 19.2g of flexiblizing amine to a container, which was then mixed in a speedmixer for 1 minute. Example 2: Epoxy Pack

[0368] The epoxy pack was prepared using standard epoxy resins, elastomers and fdlers known to those skilled in the art. 33.9g of epoxy A, 15.9g of epoxy B, 29.4g of Elastomer, and 18.4g of a first filler were charged to a mixing container, which was then mixed in a speedmixer for 1 minute. Then, 2.4g of a second filler was added to the mixture and the mixture was further mixed in the speedmixer for 1 minute.

Example 3 : Adhesive Composition 1

[0369] An adhesive composition was prepared by blending 30.7 g of Amine Pack 1 and 69.3 g of Epoxy Pack 1. The adhesive was then used to prepare lap shear and peel strength samples, where the substrate used in the sample preparation was cladded 2024-T3 that was phosphoric acid anodized and coated with a primer. The work life was measured by storing 100g mixed adhesives under 70 ± 10F for 120min before making lap shear and peel specimens. After sample preparation, the samples were allowed to cure at ambient conditions for 7 days. After curing, the lap shear strength was measured according to ASTM DI 002 and the lap shear strength was measured according to ASTM D3167. The results are shown in Table 1.

Example 4: Comparative Adhesive Composition 2

[0370] A comparative adhesive composition (without a flexiblizing amine) was prepared by blending 32.7 g of amidoamine (Amine Pack 2) and 67.3 g of Epoxy Pack 1. The adhesive was then used to prepare lap shear and peel strength samples, where the substrate used in the sample preparation was cladded 2024-T3 that was phosphoric acid anodized and coated with BR-127 primer. The work life was measured by storing 100g mixed adhesives under 70 ± 10°F for 120 min before making lap shear and peel specimens. After sample preparation, the samples were allowed to cure at ambient conditions for 7 days. After curing, the lap shear strength was measured according to ASTM DI 002 and the lap shear strength was measured according to ASTM D3167.

Example 5: Comparative Adhesive Composition 3

[0371] A comparative adhesive composition (without an amidoamine) was prepared by blending 25.9 g of flexiblizing amine (Amine Pack 3) and 74.1 g of Epoxy Pack 1. The work life was measured by storing 100 g mixed adhesives under 70 ± 10°F for 120 min before making lap shear and peel specimens.

Example 6: Comparative Example 4

[0372] A comparative adhesive composition (without an amidoamine or flexiblizing amine) was prepared by blending 11.3 g of cycloaliphatic amine (Amine Pack 4) and 88.7g of Epoxy Pack 1. The work life was measured by storing 100 g mixed adhesives under 70 ± 10°F for 120 min before making lap shear and peel specimens.

Example 7: Adhesive Composition 5

[0373] Amine Pack 5 was prepared by blending 89.951 g of amidoamine, 5.55 g flexibilizing amine, and 4.50 g catalyst into a container, which was then mixed in a speed mixer for 30 seconds. Colorant (0.05 g) and filler (12.00 g) were added to the mixture and the mixture was further mixed in the speed mixer for 1 minute.

[0374] In a separate container, Epoxy Pack 2 was prepared by charging epoxy resin (53.00 g) and core-shell rubber-containing epoxy resin (47.00g) into a container and mixed in a speed mixer for 1 minute. Then fillers (22.50 g) were added to the mixture and the mixture was further mixed in the speed mixer for 2Xlminute.

[0375] Adhesive Composition 7 was prepared by mixing Epoxy Pack 2 and Amine Pack 5 at 2: 1 volume ratio.

[0376] Lap shear and roller peel specimens were prepared with cartridge extrusion. The substrate used in the sample preparation was cladded 2024-T3 that was phosphoric acid anodized and coated with a primer. After sample preparation, the samples were allowed to cure at ambient conditions for 4 days (Adhesive 5A) and 7 days (Adhesive 5B). After curing, the lap shear strength was measured according to ASTM DI 002 and the lap shear strength was measured according to ASTM D3167.

[0377] Data are reported in Table 1. TABLE 1 - Performance of Adhesives 1 to 5

[0378] Whereas features of the present disclosure have been described above for purposes of illustration, it will be evident to those skilled in the art that numerous variations of the details of the coating composition, coating, and methods disclosed herein may be made without departing from the scope in the appended claims.

Claims

We claim:

1. A composition comprising: a first component comprising an epoxy-containing compound; a second component comprising an amino-functional amide and a flexibilizing amine; and elastomeric particles.

2. The composition of claim 1, comprising:

(a) the epoxy-containing compound in an amount of at least 30 percent by weight based on total weight of the first component;

(b) the amino-functional amide in an amount of 5 percent by weight to 75 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine;

(c) the flexibilizing amine in an amount of 25 percent by weight to 95 percent by weight based on total weight of the amino-functional amide and the flexibilizing amine; and/or

(d) the elastomeric particles in an amount of 2.5 percent by weight to 25 percent by weight based on total weight of the composition.

3. The composition of claim 1 or claim 2, wherein:

(a) the first component further comprises an aromatic monoepoxide, an aliphatic monoepoxide and/or an aliphatic polyepoxide;

(b) the second component further comprises a cycloaliphatic amine;

(c) the second component further comprises a polyamine; and/or

(d) the composition further comprises an accelerator.

4. The composition of any of the preceding claims, wherein:

(a) the amino-functional amide comprises a reaction product of reactants comprising a dimer fatty acid and an etheramine, such as an aliphatic etheramine, diethylenetriamine and/or triethylenetetramine, wherein the reaction product optionally comprises a difunctional amine, two primary amines, and/or a secondary amine; and/or (b) the flexibilizing amine comprises an etheramine comprising a molecular weight of greater than 140 g/mol to 2,000 g/mol measured by mass spectrometry and/or a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 295 g/mol to 2,000 g/mol measured by mass spectrometry.

5. The composition of any of the preceding claims, wherein the flexibilizing amine comprises an amine-functional aliphatic etheramine-epoxy adduct (Al).

6. The composition of claim 5, wherein the amine-functional aliphatic etheramine-epoxy adduct (Al) comprises a reaction product of reactants comprising an aliphatic etheramine (A2) and an epoxy-containing compound (E2).

7. The composition of claim 6, wherein:

(a) the aliphatic etheramine (A2) comprises a primary amine functional group adjacent to a methylene group;

(b) the aliphatic etheramine (A2) comprises a molecular weight of 104 g/mol to 300 g/mol measured using mass spectrometry; and/or

(c) the epoxy-containing compound (E2):

(i) comprises an aromatic group;

(ii) comprises a molecular weight of 160 g/mol to 600 g/mol; and/or

(iii) an epoxide equivalent weight of 85 g/eq to 300 g/eq.

8. The composition of claim 6 or claim 7, wherein the reactants comprise the aliphatic etheramine (A2) in an amount sufficient to provide a molar ratio of amine-hydrogens from the aliphatic etheramine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of 3:1 to 12: 1.

9. The composition of any of the preceding claims, wherein the composition is substantially free, or essentially free, or completely free, of a polyurethane resin, an amine-functional rubber, a carboxy-functional rubber and/or an epoxy-functional rubber.

10. The composition of any of the preceding claims, formulated as an adhesive composition, such as a structural adhesive composition, a pottant composition, a gap filler composition, a prepreg composition, a liquid shim composition, or combinations thereof.

11. A method of coating a substrate comprising contacting a portion of a surface of the substrate with the composition of any of claims 1 to 10.

12. The method of claim 11, further comprising mixing the first component and the second component to form the composition and/or contacting a surface of a second substrate to the composition such that the composition is between the first substrate and the second substrate.

13. A method of forming an article, comprising extruding the composition of any of claims 1 to 10.

14. A substrate comprising a coating formed from the composition of any of claims 1 to 10 on a portion of a surface of the substrate.

15. The substrate of claim 14, further comprising a pretreatment coating or film and/or an additional coating, such as a primer, a basecoat and/or a topcoat.

16. The substrate of claim 14 or claim 15, wherein the substrate comprises aluminum, steel, or titanium, or alloys thereof, a carbon fiber composite, a glass fiber composite, a thermoplastic, a nylon, a ceramic, or combinations thereof.

17. The substrate of any of claims 14 to 16, further comprising a second substrate, wherein the coating is located between the substrate and the second substrate.

18. The substrate of any of claims 14 to 17, wherein the coating comprises:

(a) a pot-life of at least 120 minutes; and at least one of (b) a lap shear strength of at least 725 psi measured at ambient conditions according to ASTM D1002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute;

(c) lap shear strength of at least 725 psi measured at 160°F for at least 30 minutes according to ASTM D1002 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute; and

(d) a roller peel strength of at least 15 psi measured according to ASTM D3167.

19. The substrate of any of claims 14 to 18, wherein the substrate comprises an article such as a vehicle, an appliance, a personal electronic device, a circuit board, a multi-metal substrate, or combinations thereof, a part such as a vehicular part, or combinations thereof.

20. The substrate of claim 19, wherein the vehicle comprises a land vehicle or an aircraft.