Coating composition

Abstract

Disclosed is a composition comprising: a first component, the first component comprising an epoxy group-containing compound; a second component comprising an amino functional amide and a toughening amine; and elastomeric particles. Also disclosed is a substrate comprising a surface coated with any of the compositions disclosed herein. Methods of forming the coating and uses of the coating are also disclosed.

Description

[0001] Cross Reference to Related Applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 520,819 “Coating Compositions” filed August 21, 2023, the entirety of which is incorporated herein by reference. TECHNICAL FIELD

[0003] The present disclosure relates to compositions and coatings formed therefrom. BACKGROUND

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

[0005] The present disclosure relates to a composition comprising: a first component comprising an epoxy-containing compound; a second component comprising an amino-functional amide and a toughening amine; and an elastomeric particle.

[0006] Also disclosed is a substrate comprising a coating formed from any of the compositions disclosed herein on a portion of a surface of the substrate.

[0007] Also disclosed is a method of coating a substrate comprising contacting a portion of a surface of the substrate with any of the compositions disclosed herein.

[0008] Also disclosed is a method of forming an article comprising extruding any of the compositions disclosed herein. DETAILED DESCRIPTION

[0009] For the purposes of this detailed description, it is to be understood that the disclosure can assume alternative variations and step sequences, except where expressly

[0010] 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 deviation found in their respective testing measurements.

[0011] Also, any numerical ranges recited herein are intended to include all sub-ranges of the same numbers. 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 equal to or less than 10.

[0012] As used herein, "including," "containing," and like terms are understood in the context of this application to mean "comprising" and are therefore open-ended and do not exclude the presence of additional undescribed or unrecited elements, materials, components or method steps. As used herein, open terms include closed terms such as consists essentially of and consists of.

[0013] As used herein, "consisting of is understood in the context of this application to exclude the presence of any unspecified elements, ingredients, components, or method steps.

[0014] As used herein, "consisting essentially of is understood in the context of this application to include the specified elements, ingredients, components, or method steps "and those that do not materially affect the basic and novel characteristics of the composition or method described."

[0015] In this application, the use of the singular includes the plural, and vice versa, unless explicitly controlled by the context. For example, although reference is made herein to "a" epoxy-containing compound and "a" fatty acid amidoamine, combinations of these components (i.e., a plurality of these components) can be used.

[0016] Also, in this application, the use of "or" means "and / or" unless specifically stated otherwise, even though "and / or" can be explicitly used in certain instances.

[0017] 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, covered, deposited, or disposed on a surface of a substrate, but not necessarily in contact with the surface of the substrate. For example, a composition "applied onto" a surface of a substrate does not exclude the presence of one or more other intermediate coatings or films of the same or different compositions located between the composition and the surface of the substrate.

[0018] As used herein, "coating composition" means a composition, such as a solution, mixture, or dispersion, capable of producing a coating on a portion of a surface of a substrate. As used herein, "coating" includes films, layers, and the like.

[0019] As used herein, "adhesive composition" means a coating composition that forms an adhesive upon curing.

[0020] As used herein, "adhesive" means 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 D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute.

[0021] As used herein, "structural adhesive composition" means a coating composition that forms a structural adhesive upon curing.

[0022] As used herein, "structural adhesive" means a coating that produces a load bearing joint, 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 at a pull rate of 1.3 mm per minute.

[0023] As used herein, the term "potting agent" means an encapsulant.

[0024] As used herein, the term "gap filler" means a coating that fills a gap.

[0025] As used herein, the term "prepreg" means a composition that pre-impregnates a reinforcing fiber prior to curing.

[0026] As used herein, the term "liquid gasket" means a coating that eliminates a gap between surfaces of substrates.

[0027] As further defined herein, ambient conditions generally refer to room temperature (e.g., 23°C) and humidity conditions or temperatures and humidity conditions generally found in the area where the composition is applied to a substrate, for example, at 10°C to 40°C and 5% to 80% relative humidity.

[0028] 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 (either physically or chemically), i.e., cure without activation from an external energy source, such as at ambient conditions or under mild heat conditions, when mixed. It will be understood by one skilled in the art that the two components of the composition are stored separately from one another and mixed just prior to applying the composition. The two-component composition can optionally be heated or baked, as described below.

[0029] As used herein, the term "cure" or "curing" means crosslinking (i.e., interacting and / or reacting) of the components of the composition to form a coating or bond. In the case of a 2K composition, the composition begins to cure when the components of the composition are mixed such that the reactive functionalities of the components of the composition react.

[0030] As used herein, "monoamine" means an organic compound having one amino functionality.

[0031] As used herein, "diamine" means an organic compound having two amino functionalities.

[0032] As used herein, "polyamine" means an organic compound having more than two amino functionalities.

[0033] As used herein, "amino functionality" means a functional group that includes a nitrogen atom bonded to a hydrogen atom, an alkyl group, and / or an aryl group through a single bond.

[0034] As used herein, "epoxide functionality" means a functional group that includes a cyclic ether having a three-atom ring.

[0035] As used herein, "amine hydrogens" means the number of active hydrogens directly bonded to a nitrogen atom of an amine or another nitrogen-containing functional group. "Active hydrogen" means a hydrogen that can be displaced when an amine- or nitrogen-containing functional group reacts as a nucleophile with a suitable electrophile, and can be determined, for example, by the Zerewitinoff test. Active hydrogens on all accelerators and curatives (e.g., diamines and / or polyamines) are included in the amine hydrogens of the compositions of the present disclosure.

[0036] As used herein, “epoxide equivalent weight” refers to the weight (in grams) of a material containing a stoichiometric equivalent of epoxide functionality. The epoxide equivalent weight can be determined, for example, by titrating a sample using a Metrohm 808 or 888 Titrando, using 0.06 g / 100 g / equivalent to predict the epoxide resin equivalent, and dissolving the sample in 20 mL of dichloromethane or tetrahydrofuran, and then adding 40 mL of glacial acetic acid and one gram of tetraethylammonium bromide, followed by titration with 0.1 N perchloric acid in glacial acetic acid.

[0037] As used herein, “Mw” refers to weight average molecular weight, for example, a theoretical value determined by gel permeation chromatography using a Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, tetrahydrofuran (THF) is used as the eluent at a flow rate of 1 ml min -1

[0038] As used herein, “polymer” refers to a molecule comprising chemically bonded repeating units or monomeric units and can include oligomers, homopolymers, and copolymers.

[0039] As used herein, “small molecule” refers to a molecule comprising a discrete chemical structure, a molecular weight of less than 1200 g / mol, and is not a polymer (i.e., is not composed of repeating monomeric units). The molecular weight of a small molecule can be determined by mass spectrometry. Numerous references such as Mass Spectrometry: A Textbook (3rd Edition, 2018, edited by Jürgen Gross) provide appropriate mass spectrometry methods for various types of small molecules.

[0040] As used herein, the term “reactive diluent” refers to a molecule or compound used to reduce the viscosity of a formulation and has at least one functional group capable of reacting with a functional group on a molecule or compound in the composition.

[0041] As used herein, the term “plasticizer” refers to a molecule or compound that does not have a functional group capable of reacting with a functional group on a molecule or compound in the composition and is added to the composition to reduce the viscosity, lower the glass transition temperature (Tg), and impart flexibility.

[0042] As used herein, the term “promoter” means a substance that increases the rate of a chemical reaction or lowers the activation energy of a chemical reaction compared to the same reaction in the absence of the promoter. The promoter can be a “catalyst,” i.e., does not itself undergo any permanent chemical change; or can be reactive, i.e., capable of undergoing a chemical reaction and includes any level of reaction from partial to complete reaction of the reactants. ​

[0043] As used herein, unless otherwise specified, the term "substantially free of means that a particular material is not intentionally added to a mixture or composition, and that the particular material is present only in an incidental amount of less than 5% by weight based on the total weight of the mixture or composition.

[0044] As used herein, unless otherwise specified, the term "substantially free of means that a particular material is not intentionally added to a mixture or composition, and that the particular material is present only in an incidental amount of less than 2% by weight based on the total weight of the mixture or composition.

[0045] As used herein, unless otherwise specified, the term "completely free of means that a mixture or composition does not include a particular material, i.e., the mixture or composition includes 0% by weight of such material.

[0046] 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 toughening amine; and an elastomer particle.

[0047] First Component

[0048] As discussed above, the first component of the composition can comprise an epoxy-containing compound.

[0049] In some cases, the epoxy-containing compound can include an aromatic epoxy resin. As used herein, the term "aromatic epoxy resin" refers to an epoxy-containing compound comprising at least one aromatic group.

[0050] Useful aromatic epoxy resins 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 epoxy resins include bisphenol S diglycidyl ether, epoxidized bisphenol A novolac, epoxidized phenol formaldehyde novolac, epoxidized cresylic novolac, triglycidyl p-aminophenol, triglycidyl p-aminophenol bismaleimide, tetraglycidyl 4,4'-diaminodiphenylmethane, tetraglycidyl m-xylylenediamine, and tetraglycidyl 4,4'-diaminodiphenyl sulfone.

[0051] The aromatic epoxy resin can include a monoepoxide. Suitable aromatic monoepoxides include glycidyl ethers of phenols, such as phenyl glycidyl ether or cresyl glycidyl ether. The epoxy-containing compound can include a combination of any of the aforementioned aromatic polyepoxides and any of the aforementioned aromatic monoepoxides.

[0052] In some cases, the epoxy-containing compound can include an aliphatic epoxy resin. As used herein, the term "aliphatic epoxy resin" refers to an epoxy-containing compound that does not contain any aromatic groups. Useful aliphatic epoxy resins include polyglycidyl ethers of polyols, polyglycidyl esters of polycarboxylic acids, epoxidized polyepoxides derived from olefinically unsaturated alicyclic compounds, or polyepoxides containing oxyalkylene groups in the epoxy molecule. The epoxy-containing compound can also include an epoxy-containing acrylic compound, such as a copolymer comprising glycidyl methacrylate. Non-limiting examples of aliphatic epoxy resins 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 isocyanuric acid triglycidyl ester.

[0053] The aliphatic epoxy resin can include a monoepoxide. Suitable aliphatic monoepoxides that can be used include glycidol, mono glycidyl ethers of aliphatic alcohols (such as n-butyl glycidyl ether, isopropyl glycidyl ether, glycidyl versatate (e.g., CARDURA E, commercially available from Shell Chemical Co.), glycidyl ethers of fatty alcohols (e.g., Epodil 748, commercially 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 diols, such as polypropylene glycol diglycidyl ether or poly(tetramethylene glycol) diglycidyl ether.

[0054] The epoxy-containing compound can include a combination of any of the aforementioned aromatic epoxides and any of the aforementioned aliphatic epoxides.

[0055] The epoxy-containing compound can include an epoxy adduct. The composition can include one or more epoxy adducts. As used herein, the term "epoxy adduct" refers to a reaction product including a residue of an epoxy resin and at least one other compound that does not contain an epoxide functionality. The epoxy adduct can include an aromatic epoxy resin or an aliphatic epoxy resin. The epoxy-containing compound can include a carboxyl-terminated butadiene-acrylonitrile copolymer that is adducted with the epoxy-containing compound. Additionally, the epoxy adduct can include a reaction product of reactants including an epoxy resin, a polyol, and an anhydride. The term "epoxy adduct" as used with respect to the epoxy-containing compound is different from the epoxide-functional adduct described below.

[0056] The epoxy used to form the epoxy adduct can include any of the epoxy-containing compounds listed above that can be included in the composition.

[0057] The polyol used to form the epoxy adduct can include diols, triols, tetraols, and higher functional polyols. Combinations of such polyols can also be used. The polyol can be based on polyether chains resulting from the ring-opening polymerization of ethylene glycol, propylene glycol, butylene glycol, hexanediol, and the like, and mixtures thereof. The polyol can also be based on polyester chains resulting from the ring-opening polymerization of caprolactone (hereinafter referred to as polycaprolactone-based polyols). Suitable polyols can 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 the polyols can also be used, and in this case, amides will be formed with the anhydride rather than carboxylic acid esters.

[0058] The polyol can include polycaprolactone-based polyols. The polycaprolactone-based polyols can include diols, triols, or tetraols terminated with primary hydroxyl groups. Commercially available polycaprolactone-based polyols include those sold under the trade designation Capa™ from Perstorp Group, for example, Capa 2054, Capa 2077A, Capa 2085, Capa 2205, Capa 3031, Capa 3050, Capa 3091, and Capa 4101.

[0059] The polyol can include a polytetramethylene-based polyol. The polytetramethylene-based polyol can include a diol, triol, or tetraol terminated with primary hydroxyl groups. Commercially available polytetramethylene-based polyols include those sold under the trade designation Terathane® available from Invista, 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. Additionally, di-monomol-based polyols sold under the trade designations Pripol®, Solvermol™, and Empol® available from Cognis Corporation or biobased polyols such as tetrafunctional polyol Agrol 4.0 available from BioBased Technologies can also be utilized.

[0060] Anhydrides that can be used to form the epoxy adduct can include any suitable anhydride known in the art. For example, the anhydride can include hexahydrophthalic anhydride and derivatives thereof (e.g., methyl hexahydrophthalic anhydride); phthalic anhydride and derivatives thereof (e.g., methyl phthalic anhydride); maleic anhydride; succinic anhydride; trimellitic anhydride; pyromellitic dianhydride (PMDA); 3,3',4,4'-oxydiphthalic anhydride (ODPA); 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA); and 4,4'-(hexafluoroisopropylidene) diphthalic anhydride (6FDA).

[0061] The epoxy adduct can include a diol, a mono-anhydride, and a diepoxide, where the molar ratio of the diol, the mono-anhydride, and the diepoxide in the epoxy adduct can be in the range of 0.5:0.8:1.0 to 0.5:1.0:6.0.

[0062] The epoxy adduct can include a triol, a mono-anhydride, and a diepoxide, where the molar ratio of the triol, the mono-anhydride, and the diepoxide in the epoxy adduct can be in the range of 0.5:0.8:1.0 to 0.5:1.0:6.0.

[0063] The epoxy adduct can include a tetraol, a mono-anhydride, and a diepoxide, where the molar ratio of the tetraol, the mono-anhydride, and the diepoxide in the epoxy adduct can be in the range of 0.5:0.8:1.0 to 0.5:1.0:6.0.

[0064] Other suitable epoxy-containing compounds include epoxy adducts, such as epoxy polyesters formed as reaction products of reactants including an epoxy-containing compound, a polyol, and an anhydride, as described in U.S. Patent No. 8,796,361 at column 3, line 42 to column 4, line 65, the cited portions of which are incorporated herein by reference.

[0065] The first component optionally can include an epoxy-containing reactive diluent, such as those commonly used in coating compositions, such as adhesive compositions, and such reactive diluents can be included as epoxy-containing compounds.

[0066] The first component can include an epoxy-containing compound in an amount of at least 30 weight %, such as at least 35 weight %, such as at least 40 weight %, based on the total weight of the first component. The first component can include an epoxy-containing compound in an amount of no more than 100 weight %, such as no more than 60 weight %, such as no more than 55 weight %, such as no more than 50 weight %, based on the total weight of the first component. The first component can include an epoxy-containing compound in an amount of at most 100 weight %, such as 30 weight % to 100 weight %, such as 30 weight % to 60 weight %, such as 35 weight % to 55 weight %, such as 40 weight % to 50 weight %, based on the total weight of the first component.

[0067] As noted above, the first component can include aromatic monoepoxides, aliphatic monoepoxides, and / or aliphatic polyepoxides. If present, the first component can include such epoxides in an amount of at least 0.1 weight %, such as at least 0.2 weight %, such as at least 0.5 weight %, based on the total weight of the first component. The first component can include such epoxides in an amount of no more than 30 weight %, such as no more than 25 weight %, such as no more than 20 weight %, based on the total weight of the first component. The first component can include such epoxides (if present) in an amount of at most 30 weight %, such as 0.1 weight % to 30 weight %, such as 0.2 weight % to 25 weight %, such as 0.5 weight % to 20 weight %, based on the total weight of the first component.

[0068] Second Component

[0069] The second component can include an amine-functional amide. An amine-functional amide refers to any compound that includes an amide linkage and an amine functional group. A fatty acid amine-functional amide refers to an amine-functional amide that includes a fatty acid residue.

[0070] Useful amine-functional amides include monoamides and polyamides derived from fatty acids and other functional groups.

[0071] Suitable examples of amides derived from fatty acids include the reaction product of any acid-functional compound and any polyamine or combination of polyamines. Suitable examples of acid-functional compounds suitable for producing amine-functional amides include fatty acids, dimer fatty acids, trimer fatty acids, acid-functional polymers such as polyesters or acrylic polymers, and / or acid-functional small molecules. 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, dodecanedioic acid, brassylic acid, tridecanedioic acid, malic acid, tartaric acid, phthalic acid, isophthalic acid, and terephthalic acid. Additional suitable acids include acrylic copolymers that include acid-functional monomers such as acrylic acid, methacrylic acid, maleic acid, or itaconic acid.

[0072] In some cases, the amine-functional amide can include the reaction product of reactants including a fatty acid, a dimer fatty acid, and / or a trimer fatty acid with any polyamine or combination of polyamines. Suitable amine-functional amides derived from fatty acids include Versamid 100, Versamid 125, Versamid 140, and Versamid 150, which are commercially available from Huntsman Corporation. Additional suitable amides derived from fatty acids include amidoamines Ancamide® products, which are commercially available from Evonik Industries AG, Jointmide products, which are commercially available from Epochemie International, amidoamines ChemCure® available from Cargill Inc., and Epikure amidoamines available from Westlake Corporation. TM Amidoamine curing agents.

[0073] In some cases, the amine-functional amide can be the reaction product of a fatty acid and an amine including an ethyleneimine subunit, such as diethylenetriamine, triethylenetetramine, or tetraethylenepentamine.

[0074] In some cases, the amine-functional amide can be the reaction product of a fatty acid and an aliphatic or cycloaliphatic amine.

[0075] The second component can include a toughening amine. As used herein, the term “toughening amine” refers to an ether amine having a molecular weight greater than 140 g / mol or a fatty acid dimer or trimer amine having a molecular weight greater than 295 g / mol.

[0076] Suitable toughening amines include oligomeric or polymeric diamines or polyamines having a glass transition temperature greater than -150 o C and less than 30 o C, for example calculated using the Fox equation.

[0077] Suitable examples of toughening amines include amine-terminated polyethers such as amine-terminated poly(propylene glycol) or amine-terminated poly(ethylene glycol)-poly(propylene glycol) copolymers. Suitable examples include Jeffamine D-400, Jeffamine ED-600, and Jeffamine ED-900, commercially available from Huntsman Corporation.

[0078] In some preferred cases, the toughening amine can include an amine-terminated polymer or oligomer including poly(tetramethylene ether glycol) subunits. A suitable example is an amine-terminated poly(tetramethylene ether glycol)-poly(propylene glycol) copolymer, commercially available as Jeffamine THF-100 from Huntsman.

[0079] Additional useful aliphatic ether amines include ethylene glycol bis(2-aminoethylether) (commercially available as Jeffamine EDR-148 from Huntsman), diethylene glycol bis(2-aminoethylether), diethylene glycol bis(3-aminopropyl ether) (commercially available as Ancamine 1922A from King Industries, Inc. or as Baxxodur EC 130 from BASF), bis(aminopropyl) 1,4-butanediol (commercially available from BASF SE), or combinations thereof. In some cases, these ether amines can be modified by reaction / addition with other molecules such as epoxy, carboxylic acid, or phenol containing resins.

[0080] The toughening amines including ether amines can include a molecular weight of greater than 140 g / mol, such as at least 170 g / mol, such as at least 210 g / mol. The toughening amines including ether amines can include 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 toughening amines can include 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 toughening amines can be measured using mass spectrometry as described above.

[0081] Additional suitable examples of toughening amines include fatty acid dimer or trimer diamines commercially available from Croda Smart Materials. Suitable examples include Priamine 1071, Priamine 1074, and Priamine 1075.

[0082] The toughening amine comprising a fatty acid dimer or trimer amine can 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 toughening amine can 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 toughening amine can 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 toughening amine can be measured using mass spectrometry as described above.

[0083] The toughening amine can comprise an amine-functional aliphatic ether amine-epoxy adduct (A1). As used herein, the term “amine-functional aliphatic ether amine-epoxy adduct (A1)” refers to a reaction product comprising a residue of an aliphatic ether amine (A2) and an epoxy-containing compound (E2), wherein the amine hydrogen functionality of A2 is in molar excess to the epoxide functionality of E2. As used herein, the term “ether amine” refers to an amine comprising an ether linkage.

[0084] The amine-functional aliphatic ether amine-epoxy adduct (A1) can be substantially free or completely free of epoxide functionality. As used herein, the term “substantially free” when used in reference to the absence of epoxide functionality means that the amine-functional aliphatic ether amine-epoxy adduct (A1) comprises an epoxide equivalent weight of greater than 2000. As used herein, the term “completely free” when used in reference to the absence of epoxide functionality means that such functionality is below the detection limit of common analytical techniques.

[0085] The second component can comprise two or more types of amine-functional aliphatic ether amine-epoxy adducts. That is, the amine-functional aliphatic ether amine-epoxy adduct (A1) can comprise a first amine-functional aliphatic ether amine-epoxy adduct and, in addition to the first amine-functional aliphatic ether amine-epoxy adduct (A1), can further comprise, for example, a second, third, and / or fourth, etc. amine-functional aliphatic ether amine-epoxy adduct (A1). As used herein with respect to the amine-functional aliphatic ether amine-epoxy adduct (A1), reference to “first,” “second,” “third,” etc. is merely for convenience and does not refer to the order in which the same are added to a composition, etc.

[0086] The second, third, fourth, etc. amine-functional aliphatic ether amine-epoxy adduct (A1) can be any of the amine-functional aliphatic ether amine-epoxy adducts described above.

[0087] The second component can include the amine-functional aliphatic ether amine-epoxy adduct (A1) in an amount of at least 10 weight percent, such as at least 20 weight percent, based on the total weight of the second component. The second component can include the amine-functional aliphatic ether amine-epoxy adduct (A1) in an amount of not more than 100 weight percent, such as not more than 98 weight percent, based on the total weight of the second component. The second component can include the amine-functional aliphatic ether amine-epoxy adduct (A1) in an amount of 10 weight percent to 100 weight percent, such as at least 20 weight percent to 98 weight percent, based on the total weight of the second component.

[0088] The amine-functional aliphatic ether amine-epoxy adduct (A1) can include a reaction product of reactants including an aliphatic ether amine (A2) and an epoxy-containing compound (E2).

[0089] The aliphatic ether amine (A2) can include at least two amine functional groups. For example, the aliphatic ether amine (A2) can include a diamine and / or a polyamine, such as a triamine, a tetraamine, or a combination thereof.

[0090] The aliphatic ether amine (A2) can include an ethylene glycol subunit. The term “includes at least one ethylene glycol subunit” means that the ether amine contains at least one structure R(CH2CH2O) n R, where R can represent any organic substituent, including the following non-limiting examples: substituents based on carbon, hydrogen, nitrogen, and / or oxygen, and where n = 1 to 5.

[0091] The aliphatic ether amine (A2) can include a primary amine functional group adjacent to a methylene group. The term “includes a primary amine functional group adjacent to a methylene group” means that the ether amine contains the structure RCH2NH2, where R can represent any organic substituent, including the following non-limiting examples: substituents based on carbon, hydrogen, and / or oxygen.

[0092] Useful aliphatic ether amines (A2) include ethylene glycol bis(2-aminoethylether) (available as Jeffamine EDR-148 from Huntsman), diethylene glycol bis(2-aminoethylether), diethylene glycol bis(3-aminopropyl ether) (available as Ancamine 1922A from King Industries, or as Baxxodur EC 130 from BASF SE), bis(amino propyl) 1,4-butanediol (available from BASF SE), or a combination thereof.

[0093] The aliphatic ether amine (A2) can include a molecular weight of at least 104g / mol, such as at least 140 g / mol. The aliphatic ether amine can include a molecular weight of no more than 300 g / mol, such as no more than 230 g / mol. The aliphatic ether amine can include a molecular weight of 104g / mol to 300 g / mol, such as 140 g / mol to 230 g / mol. The molecular weight of the aliphatic ether amine (A2) can be measured using mass spectrometry as described above.

[0094] As discussed above, the reactants used to form the amine-functional aliphatic ether amine-epoxy adduct (A1) can include an epoxy-containing compound (E2). The epoxy- containing compound (E2) can be any of the mono- and / or poly-epoxides disclosed above. For example, the epoxy-containing compound (E2) can include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a phenol-formaldehyde resin, tetraglycidyl methylenedianiline, triglycidyl p-aminophenol, tetraglycidyl m-xylylenediamine, or a combination thereof.

[0095] The epoxy-containing compound (E2) can include a small molecule. For example, the epoxy-containing compound (E2) can include a molecular weight of no more than 600 g / mol, such as no more than 450 g / mol. The epoxy-containing compound (E2) can include a molecular weight of at least 160 g / mol, such as at least 300 g / mol. The epoxy-containing compound (E2) can include a molecular weight of 160 g / mol to 600 g / mol, such as 300 g / mol to 450 g / mol. The molecular weight of the epoxy-containing compound (E2) can be determined by mass spectrometry as described above.

[0096] The epoxy-containing compound (E2) can include an epoxide equivalent weight of at least 85 g / eq, such as 110 g / eq. The epoxy-containing compound (E2) can include an epoxide equivalent weight of no more than 300 g / eq, such as no more than 220 g / eq. The epoxy- containing compound (E2) can include an epoxide equivalent weight of 85 g / eq to 300 g / eq, such as 110 g / eq to 220 g / eq.

[0097] Optionally, the epoxy-containing compound (E2) can include an aromatic group.

[0098] Suitable examples of the epoxy-containing compound (E2) include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a phenol-formaldehyde resin, tetraglycidyl methylenedianiline, triglycidyl p-aminophenol, tetraglycidyl m-xylylenediamine, hydrogenated bisphenol A diglycidyl ether (such as those commercially available as Eponex 1510), butanediol diglycidyl ether, or a combination thereof.

[0099] The reactants can include an aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functionality from the epoxy-containing compound (E2) of at least 3: 1, such as at least 4: 1. The reactants can include an aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functionality from the epoxy-containing compound (E2) of no more than 12: 1, such as no more than 7: 1. The reactants can include an aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functionality from the epoxy-containing compound (E2) of 3: 1 to 12: 1, such as 4: 1 to 7: 1.

[0100] The second component optionally can include amine-containing reactive diluents, such as those typically used in coating compositions, such as adhesive compositions, and such reactive diluents can be included in the calculation of amine hydrogens present in the second component.

[0101] The second component can include a flexibilizing amine in an amount of at least 25 weight %, such as at least 30 weight %, such as at least 35 weight %, such as no more than 95 weight %, such as no more than 85 weight %, such as no more than 80 weight %, such as 25 weight % to 95 weight %, such as 30 weight % to 85 weight %, such as 35 weight % to 80 weight %, based on the total weight of the amino-functional amide and the flexibilizing amine.

[0102] The second component can include an amine-functional amide in an amount of at least 5 weight %, such as at least 10 weight %, such as at least 15 weight %, such as no more than 75 weight %, such as no more than 50 weight %, such as no more than 35 weight %, such as 5 weight % to 75 weight %, such as 10 weight % to 50 weight %, such as 15 weight % to 35 weight %, based on the total weight of the amino-functional amide and the flexibilizing amine.

[0103] The second component optionally also can include a cycloaliphatic amine and / or a polyamine.

[0104] The composition can include a cycloaliphatic amine in an amount of at least 0.5 weight %, such as at least 1 weight %, such as no more than 10 weight %, such as no more than 8 weight %, such as 0.5 weight % to 10 weight %, such as 1 weight % to 8 weight %, based on the total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine, and the polyamine.

[0105] The composition can include a polyamine in an amount of at least 0.5 weight %, such as at least 1 weight %, such as no more than 50 weight %, such as no more than 40 weight %, such as 0.5 weight % to 50 weight %, such as 1 weight % to 40 weight %, based on the total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine, and the polyamine.

[0106] Elastomeric Particles

[0107] The epoxy-containing compound of the composition can further include an elastomeric particle. As used herein, "elastomeric particle" refers to a particle having a glass transition temperature (Tg) of -70 °C to 0 °C as measured by differential scanning calorimetry (DSC) or dynamic mechanical analysis (DMA).

[0108] The elastomeric particle can be included in the epoxy carrier resin to introduce into the coating composition. The elastomeric particle can be phase separated from the epoxy in the epoxy-containing compound. As used herein, the term "phase separated" means the formation of discrete domains within the matrix of the epoxy-containing compound.

[0109] The elastomeric particle can have a core / shell structure. The core of the core-shell particle can include 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.

[0110] Suitable elastomeric particles can be composed of silicone material. Suitable elastomeric particles can be composed of a (meth)acrylic shell and an elastomeric core. The core can include natural or synthetic rubber, polybutadiene, styrene-butadiene, polyisoprene, styrene isoprene, chlorobutadiene, acrylonitrile butadiene, butyl rubber, polysiloxane, polysulfide, ethylene-vinyl acetate, fluoroelastomer, polyolefin, hydrogenated styrene-butadiene, or combinations thereof. The type of elastomeric particle and its concentration are not limited so long as the particle size is within the specified range as shown below.

[0111] The average particle size of the elastomeric particle can 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, as reported particle size of rubber particles provided by Kaneka Texas Corporation as measured by standard techniques known in the industry. Suitable methods of measuring particle size disclosed herein include, for example, measurement by transmission electron microscopy (TEM). Suitable methods of measuring particle size by TEM include suspending the elastomeric particle in a solvent selected such that the particle does not swell, and then casting the suspension onto a TEM grid, drying the TEM grid under ambient conditions. For example, an epoxy resin containing core-shell elastomeric particles can be diluted in butyl acetate for casting and results can be obtained from images collected from a Tecnai T20 TEM operating at 200 kV and analyzed using ImageJ software or equivalent solvent, instrument, and software.

[0112] In examples, suitable finely dispersed core-shell elastomer particles having an average particle size in the range of 50 nm to 250 nm can be pre-mixed or pre-dispersed in a resin, such as in an epoxy resin, such as an aromatic epoxy, a novolac epoxy, a bisphenol A and / or bisphenol F diepoxide, and / or an aliphatic epoxy, including cycloaliphatic epoxies, at a concentration of rubber particles ranging from 5 wt% to 40 wt%, such as 20 wt% to 35 wt%, based on the total weight of the rubber dispersion. Suitable epoxy resins can also include mixtures of epoxy resins. When utilized, the epoxy carrier resin can be the epoxy-containing component, such that the weight of the epoxy-containing resin component present in the composition includes the weight of the epoxy carrier resin.

[0113] Exemplary non-limiting commercial core-shell elastomer particle products that can be used in the compositions utilizing poly(butadiene) rubber particles include core-shell poly(butadiene) rubber powder (commercially available as PARALOID™ EXL 2650A from The Dow Chemical Company), a dispersion of core-shell poly(butadiene) rubber in bisphenol F diglycidyl ether (commercially available as Kane Ace MX 136) (25 wt% core-shell rubber), a dispersion of core-shell poly(butadiene) rubber in Epon 828 (commercially available as Kane Ace MX 153) (33 wt% core-shell rubber), a dispersion of core-shell poly(butadiene) rubber in Epiclon EXA-835LV (commercially available as Kane Ace MX 139) (33 wt% core-shell rubber), a dispersion of core-shell poly(butadiene) rubber in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 257) (37 wt% core-shell rubber), and a dispersion of core-shell poly(butadiene) rubber in Epon 863 (commercially available as Kane Ace MX 267) (37 wt% core-shell rubber), and a dispersion of core-shell poly(butadiene) rubber in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 150) (40 wt% rubber) (each of the dispersions are commercially available from Showa Denko Texas, LLC) and an acrylic rubber dispersion. ® 828 (commercially available as Kane Ace MX 153) (33 wt% core-shell rubber), a dispersion of core-shell poly(butadiene) rubber in Epiclon ® EXA-835LV (commercially available as Kane Ace MX 139) (33 wt% core-shell rubber), a dispersion of core-shell poly(butadiene) rubber in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 257) (37 wt% core-shell rubber), and a dispersion of core-shell poly(butadiene) rubber in Epon ® 863 (commercially available as Kane Ace MX 267) (37 wt% core-shell rubber), and a dispersion of core-shell poly(butadiene) rubber in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 150) (40 wt% rubber) (each of the dispersions are commercially available from Showa Denko Texas, LLC) and an acrylic rubber dispersion.

[0114] Exemplary non-limiting commercial core-shell elastomer particle products that can be used in the compositions utilizing poly(butadiene) rubber particles include core-shell poly(butadiene) rubber powder (commercially available as PARALOID™ EXL 2650A from The Dow Chemical Company), a dispersion of core-shell poly(butadiene) rubber in bisphenol F diglycidyl ether (commercially available as Kane Ace MX 136) (25 wt% core-shell rubber), a dispersion of core-shell poly(butadiene) rubber in Epon ®XT100 commercially available from Arkema), core-shell styrene-butadiene rubber powder (commercially available as PARALOID™ EXL 2650J), dispersion of core-shell styrene-butadiene rubber in bisphenol A diglycidyl ether (commercially available as Fortegra™ 352 from Olin™) (33 wt% of core-shell rubber), dispersion of core-shell styrene-butadiene rubber in low viscosity bisphenol A diglycidyl ether (commercially available as Kane Ace MX 113) (33 wt% of rubber), dispersion of core-shell styrene-butadiene rubber in bisphenol A diglycidyl ether (commercially available as Kane Ace MX 125) (25 wt% of core-shell rubber), dispersion of core-shell styrene-butadiene rubber in bisphenol F diglycidyl ether (commercially available as Kane Ace MX 135) (25 wt% of core-shell rubber), dispersion of core-shell styrene-butadiene rubber in D.E.N. TM 438 phenol novolac epoxy resin (commercially available as Kane Ace MX 215) (25 wt% of core-shell rubber), dispersion of core-shell styrene-butadiene rubber in Araldite® MY-721 multifunctional epoxy resin (commercially available as Kane Ace MX 416) (25 wt% of core-shell rubber), dispersion of core-shell styrene-butadiene rubber in MY-0510 multifunctional epoxy resin (commercially available as Kane Ace MX 451) (25 wt% of core-shell rubber), dispersion of core-shell styrene-butadiene rubber in Syna Epoxy 21 cycloaliphatic epoxy resin from Synasia (commercially available as Kane Ace MX 551) (25 wt% of core-shell rubber), and dispersion of core-shell styrene-butadiene rubber in polypropylene glycol (MW 400) (commercially available as Kane Ace MX 715) (25 wt% of core-shell rubber), each of which is commercially available from King Industries, Inc. Other commercially available core-shell rubber particle dispersions include Fortegra 352 (bisphenol A liquid epoxy resin containing 33 wt% of core-shell rubber particles) available from Olin Corporation. Other commercially available core-shell rubber particle dispersions include Paraloid EXL 2650A (core-shell poly(butadiene)). TM EXL 2650A (core-shell poly(butadiene)).

[0115] Exemplary non-limiting commercially available core-shell elastomer particle products that can be used in the composition including core-shell silicone rubber powder (commercially available as GENIOPERL ®P52 commercially available from Wacker), dispersion of core-shell silicone rubber in bisphenol A diglycidyl ether (as ALBIDUR ® dispersion of core-shell silicone rubber in jER™ 828 (as Kane Ace MX 960 commercially available) dispersion of core-shell silicone rubber in Epon ® 863 (as Kane Ace MX 965 commercially available), each available from Momentive Performance Materials Inc.

[0116] The composition can be substantially free, or essentially free, or completely free of amine functional rubber, carboxyl functional rubber, and / or epoxy functional rubber.

[0117] The composition can comprise an amount of the elastomer particles, based on the total weight of the composition, of at least 2.5 wt%, such as at least 5 wt%, such as at least 7.5 wt%, such as not more than 25 wt%, such as not more than 22.5 wt%, such as not more than 20 wt%, such as from 2.5 wt% to 25 wt%, such as from 5 wt% to 22.5 wt%, such as from 7.5 wt% to 20 wt%.

[0118] Filler

[0119] The composition disclosed herein can comprise a filler.

[0120] Useful fillers include carbon black, calcium carbonate, precipitated calcium carbonate, calcium hydroxide, calcium silicate, aluminum powder, hydrated aluminum oxide (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 fillers include AEROSIL® fumed silica from Evonik Industries AG or HDK® and / or Sipernat precipitated silica from Wacker Chemie AG.

[0121] Useful fillers also include microspheres, microspheres of polystyrene foam, polyacrylate and polyolefin, 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 polyvinylidene fluoride copolymer microspheres such as DUALITE 6001AE® (Pierce & Stevens Corp.). Other suitable fillers include, for example, hollow microspheres such as Expancel® microspheres (available from Nouryon) or Dualite® low density polymeric microspheres (available from Henkel) or hollow borosilicate glass such as 3M Micro Pore® glass bubbles Type VS, K Series, and S Series available from 3M. Compositions provided by the present disclosure include filler particles having an outer surface coated with a thin coating such as those described in paragraphs

[0016] to

[0052] of U.S. Publication No. 2010 / 0041839, the incorporated by reference portions of which are incorporated herein by reference.

[0122] Suitable fillers include, for example, those described in U.S. Patent No. 6,525,168 at column 4, line 14 to column 55, incorporated herein by reference; and U.S. Patent No. 8,816,023 at column 3, line 18 to column 9, line 44, incorporated herein by reference.

[0123] The composition can include a filler in an amount of at least 2.5 weight %, such as at least 5 weight %, such as no more than 30 weight %, such as no more than 25 weight %, such as 2.5 weight % to 30 weight %, such as 5 weight % to 25 weight %, based on the total weight of the composition.

[0124] Promoter

[0125] The multi-component composition can include an accelerator. Any accelerator capable of accelerating the cure of the multi-component composition can be used in the present disclosure. Suitable accelerators include non-metal based accelerators.

[0126] Examples of suitable non-metal based accelerators are amine based accelerators and acid based accelerators. Examples of amines that can be useful include quaternary amines, tertiary amines, cyclic tertiary amines, secondary amines, cyclic secondary amines, and primary amines. Some examples include trimethylamine, butylamine, tributylamine, octylamine, laurylamine, dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, diethanolamine, triethanolamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine, dimethylguanidine, tetramethylguanidine, pentamethylguanidine, phenylguanidine, diphenylguanidine, butylbiguanide, 1-o-tolylbiguanide, 1-phenylbiguanide, 1-methyl-3-nitroguanidine, 1,8-bis(tetramethylguanidino)-naphthalene, N,N,N',N'-tetramethyl-N''-[4-morpholinyl(phenylimino)methyl]guanidine, 2,4,6-tris(dimethylaminomethyl)phenol, 2,2'-dimorpholinyl diethyl ether, morpholine, N-methylmorpholine, 2-ethyl-4-methylimidazole, 1,8-diazabicyclo-(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, 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine, 1,4,5,6-tetrahydropyrimidine, 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 6-(dibutylamino)-1,8-diazabicyclo(5,4,0)undec-7-ene, 1,4-diazabicyclo[2.2.2]octane, 7-azabicyclo[2.2.1]heptane, N,N-dimethylaniline, 4,5-dihydro-1H-imidazole, or combinations thereof.

[0127] Examples of suitable commercial products that can be used include diethanolamine and triethanolamine T85 available from BASF SE; and Ancamine K-54, Curezol C17Z, DABCO 33-LV, Polycat DBU, and Vestamin IPD available from Evonik Industries.

[0128] Suitable amine-functional curing agents for use in the compositions disclosed herein can be selected from a variety of known amines, such as primary and secondary amines, and mixtures thereof. The amines can include monoamines or polyamines having at least two functional groups, such as di-, tri-, or higher functional amines; and mixtures thereof. The amines can be aromatic or aliphatic, such as cycloaliphatic, or mixtures thereof. Non-limiting examples of suitable amines can include aliphatic polyamines, for example, but not limited to, ethylamine, isomeric propylamines, butylamines, pentylamines, hexylamines, cyclohexylamine, ethylenediamine, 1,2-diaminopropane, 1,4-diaminobutane, 1,3-diaminopentane, 1,6-diaminohexane, 2-methyl-1,5-pentanediamine, 2,5-diamino-2,5-dimethylhexane, 2,2,4- and / or 2,4,4-trimethyl-1,6-diamino-hexane, 1,11-diaminoundecane, 1,12-diaminododecane, 1,3- and / or 1,4-cyclohexanediamine, 1-amino-3,3,5-trimethyl-5-aminomethyl-cyclohexane, 2,4- and / or 2,6-hexahydrotoluidine, 2,4'- and / or 4,4'-diamino-dicyclohexylmethane and 3,3'-dialkyl-4,4'-diamino-dicyclohexylmethane (such as 3,3'-dimethyl-4,4'-diamino-dicyclohexylmethane and 3,3'-diethyl-4,4'-diamino-dicyclohexylmethane), 2,4- and / or 2,6-diaminotoluene and 2,4'- and / or 4,4'-diaminodiphenylmethane, piperazine, or adducts or derivatives thereof, or mixtures thereof.

[0129] The secondary amines can include polyaspartic esters, which can include derivatives of compounds such as maleic acid, fumaric acid esters, aliphatic polyamines, and mixtures thereof. The secondary amines can include aliphatic amines, such as cycloaliphatic diamines. Such amines can be commercially available from Huntsman Corporation (Houston, TX) under the name JEFFLINK, such as JEFFLINK 754, or from BASF under the name Baxxoder PC136.

[0130] The amine can comprise an amine-functional resin. Suitable amine-functional resins can be selected from a variety of resins known in the art. The amine-functional resin can be an ester of an organic acid, for example, an aspartic ester-based amine-functional reactive resin compatible with isocyanates. The isocyanate can be solventless, and / or can have a molar ratio of amine functionality to ester of no more than 1 : 1, such that no excess primary amine remains upon reaction. Non-limiting examples of such polyaspartic esters can include derivatives of diethyl maleate and 1,5-diamino-2-methylpentane (commercially available from Covestro under the trade designation DESMOPHEN NH 1220), and derivatives of diethyl maleate and 4,4'-methylenebis(cyclohexane-1-amine) (commercially available as Desmophen NH 1420 (Covestro)). Other suitable compounds containing aspartic ester groups can also be employed.

[0131] The amine can comprise a high molecular weight primary amine, such as but not limited to a polyoxyalkylene amine. Suitable polyoxyalkylene amines can contain two or more primary amino groups attached to a backbone derived from propylene oxide, ethylene oxide, or mixtures thereof. Non-limiting examples of such amines can include those available from Huntsman under the name JEFFAMINE. The number average molecular weight of such amines can range from 200 to 7500, such as but not limited to JEFFAMINE 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 King Industries.

[0132] The composition can comprise a promoter in an amount of at least 0.1 wt%, such as at least 0.2 wt%, such as at least 0.5 wt%, such as no more than 10 wt%, such as no more than 5 wt%, such as no more than 2.5 wt%, such as from 0.1 wt% to 10 wt%, such as from 0.2 wt% to 5 wt%, such as from 0.5 wt% to 2.5 wt%, based on the total weight of the composition.

[0133] Additive

[0134] The composition provided by the present disclosure can further include one or more additives, including as non-limiting examples, adhesion promoters, colorants, thixotropic agents, solvents, plasticizers, reactive diluents, pigments, masking agents, or combinations of any of the foregoing.

[0135] The composition can include the additive in an amount of at least 0.01 wt%, such as at least 0.05 wt%, such as no more than 15 wt%, such as no more than 12 wt%, such as no more than 10 wt%, such as no more than 3 wt%, such as from 0.01 wt% to 15 wt%, such as from 0.01 wt% to 12 wt%, such as from 0.05 wt% to 10 wt%, such as from 0.05 wt% to 3 wt%, based on the total weight of the composition.

[0136] Compositions, Coatings, and Systems

[0137] The compositions disclosed herein can be provided as a multi-component composition.

[0138] The first component can include, consist essentially of, or consist of an epoxy-containing compound. The first component optionally can include elastomer particles, fillers, and / or additives. The second component can include, consist essentially of, or consist of an amino-functional amide and a flexibilizing amine. The second component optionally can include elastomer particles, fillers, additives, and / or accelerators. Additional components (i.e., third component, fourth component, etc.) can include, consist essentially of, or consist of elastomer particles, fillers, additives, and / or accelerators.

[0139] The composition can be substantially free, or consist essentially of, or consist entirely of, of a polyurethane resin.

[0140] The composition can include an amine hydrogen:epoxy equivalent ratio 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 from 0.75: 1 to 1.25: 1, such as from 0.9: 1 to 1.1: 1.

[0141] The composition can include the first component in an amount of at least 50 wt%, such as at least 60 wt%, such as 70 wt%, based on the total weight of the composition. The composition can include the second component in an amount of no more than 90 wt%, such as no more than 85 wt%, such as no more than 80 wt%, based on the total weight of the composition. The composition can include the first component in an amount of from 50 wt% to 90 wt%, such as from 60 wt% to 85 wt%, such as from 70 wt% to 80 wt%, based on the total weight of the composition.

[0142] The composition can include the second component in an amount of at least 10 wt%, such as at least 15 wt%, such as at least 20 wt%, based on the total weight of the composition. The composition can include the second component in an amount of no more than 50 wt%, such as no more than 40 wt%, such as no more than 30 wt%, based on the total weight of the composition. The composition can include the second component in an amount of from 10 wt% to 50 wt%, such as from 15 wt% to 40 wt%, such as from 20 wt% to 30 wt%, based on the total weight of the composition.

[0143] The compositions disclosed herein can be applied alone or as part of a coating system. The compositions disclosed herein can be applied directly onto the surface of a substrate or onto a primer layer by any suitable coating method. The compositions can be deposited on the substrate in a variety of different ways, non-limiting examples of which include brushes, rollers, films, pellets, pressurized syringes, spray guns, and applicator guns. The system can include many layers that are the same or different and can further include other coating compositions, such as pretreatment compositions, primers, and the like. The coating is generally formed when the composition deposited on the substrate is cured by methods known to those skilled in the art (e.g., at ambient conditions, optionally further cured by the use of external energy sources such as ovens or other thermal means or by the use of actinic radiation) to form a coating. The multi-component composition can be at least partially cured at ambient temperature. The composition can be cured at a temperature of 0 °C to 40 °C, such as 10 °C to 25 °C, and atmospheric humidity. The composition can be cured at higher temperatures, such as at least 30 °C, at least 40 °C, or at least 50 °C. When cured at room temperature, the coating provided by the present disclosure can be cured 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. However, the skilled artisan understands that the time to cure varies with temperature.

[0144] The multi-component compositions disclosed herein can comprise a coating composition, such as an adhesive composition, a sealant composition, a gap filler composition, an embedding composition, an encapsulant composition, and / or a potting composition.

[0145] The composition can be cured to form a coating, such as an adhesive or structural adhesive, a sealant, a potting agent, a gap filler, a composite material formed from a prepreg, a liquid gasket, an embedding material, an encapsulant material, and / or a potting compound.

[0146] Surprisingly, it has been found that the coating formed from the compositions disclosed herein comprises:

[0147] (a) a pot life of at least 120 minutes; and at least one of

[0148] (b) a lap shear strength of at least 725 psi, 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, measured according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at ambient conditions;

[0149] (c) a lap shear strength of at least 725 psi, such as at least 800 psi, such as at least 900 psi, measured according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at 160 °F for at least 30 minutes; and

[0150] (d) a roll peel strength of at least 15 psi, such as at least 25 psi, such as at least 50 psi, measured according to ASTM D3167.

[0151] Also disclosed herein is the use of any of the compositions disclosed herein to prepare a coating, wherein the coating comprises:

[0152] (a) a pot life of at least 120 minutes; and at least one of

[0153] (b) a lap shear strength of at least 725 psi, 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, measured according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at ambient conditions;

[0154] (c) a lap shear strength of at least 725 psi, such as at least 800 psi, such as at least 900 psi, measured according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at 160 °F for at least 30 minutes; and

[0155] (d) a roll peel strength of at least 15 psi, such as at least 25 psi, such as at least 50 psi, measured according to ASTM D3167.

[0156] Also disclosed herein is the use of any of the compositions disclosed herein to prepare a coating, wherein the coating comprises:

[0157] (a) a pot life of at least 120 minutes; and at least one of

[0158] (b) a lap shear strength of at least 725 psi, 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, measured according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at ambient conditions;

[0159] (c) a lap shear strength of at least 725 psi, such as at least 800 psi, such as at least 900 psi, measured according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at 160 °F for at least 30 minutes; and

[0160] (d) a roll peel strength of at least 15 psi, such as at least 25 psi, such as at least 50 psi, measured according to ASTM D3167.

[0161] 3D Printing

[0162] Any suitable method, including those mentioned above, can be used to apply or deposit the compositions of the present disclosure. Alternatively, the compositions can be cast, extruded, molded, or machined to form a part or member in an at least partially dried or cured state.

[0163] The compositions disclosed herein can be used in any suitable additive manufacturing technique, such as three-dimensional (3D) printing, extrusion, jetting, and binder jetting. Additive manufacturing refers to a method of producing a part or member by building up in layers, such as one layer at a time.

[0164] The present disclosure also relates to the use of additive manufacturing methods, such as 3D printing, to produce a structural article, such as a sound-deadening mat as a non-limiting example. 3D printing refers to a computerized method, optionally including artificial intelligence modulation, by which a material is printed or deposited in successive layers to produce a 3D part or member, such as a sound-deadening mat in a battery assembly as a non-limiting example. The 3D part or member can be produced by depositing successive portions or layers on a base of any spatial configuration and then depositing additional portions or layers on the underlying deposited portions or layers and / or adjacent to previously deposited portions or layers to produce the 3D printed part or member.

[0165] It will be appreciated that the configuration of the 3D printing method, including the selection of suitable deposition equipment, depends on a variety of factors, such as the deposition volume, the viscosity of the composition, and the complexity of the part being manufactured. Any suitable mixing, delivery, and 3D printing equipment known to those skilled in the art can be used. The composition can be printed or deposited in droplets or extrudates of any size and / or shape and in any pattern to produce the 3D structure.

[0166] The compositions as disclosed herein can be applied or deposited by any suitable 3D printing method known to those skilled in the art. The first component and the second component of the 2K composition can be mixed and then deposited, or the first component and the second component can be deposited separately, such as simultaneously and / or sequentially.

[0167] The first component and the second component can be pre-mixed (i.e., mixed together) prior to application and then deposited. The mixture can at least partially react or thermoset as the material is deposited; the deposited reaction mixture can at least partially react after deposition and can also react with previously deposited portions and / or subsequently deposited portions of the article, such as lower or overlying layers of the article.

[0168] In non-limiting examples, the first component and the second component can be released from their respective storage containers and pushed (such as pumped) through a conduit (such as a hose) to a mixer (such as a static mixer or a dynamic mixer), where the composition can be mixed for a sufficient time to homogenize the composition, where the composition can then be released through an outlet. The outlet can be a deposition device (such as a print head), and / or the material can exit the mixing unit and be pushed (such as by a pump) through a conduit (such as a hose) to a print head. The print head can optionally be mounted on a 3D rotating robotic arm to allow the 3D printing composition to be delivered to any substrate in any spatial configuration, and / or the substrate can be manipulated in any spatial configuration during the 3D printing process.

[0169] Alternatively, the first component and the second component can be deposited independently from different print heads. The first component can be deposited from one print head and the second component can be deposited from a second print head. The first component and the second component can be deposited in any pattern such that the first component and the second component making up any deposited layer can react together and with underlying and / or overlying layers to produce a 3D printed part or member.

[0170] The methods provided by the present disclosure include printing a composition on a manufactured part. The methods provided by the present disclosure include directly printing a part.

[0171] Using the methods provided by the present disclosure, a part can be manufactured. The entire part can be formed from one of the compositions disclosed herein, one or more portions of the part can be formed from one of the compositions disclosed herein, one or more different portions of the part can be formed using the compositions disclosed herein, and / or one or more surfaces of the part can be formed from a composition provided by the present disclosure. Additionally, interior regions of the part can be formed from a composition provided by the present disclosure.

[0172] Substrate

[0173] Still further disclosed are substrates and articles comprising, consisting essentially of, or consisting of a coating 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 the compositions disclosed herein. Also disclosed is an article comprising, consisting essentially of, or consisting of a first substrate and a second substrate and a coating layer positioned therebetween and in an at least partially cured state.

[0174] The substrate that can be coated by the compositions of the present disclosure is 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 (including filled and unfilled thermoplastic or thermoset materials) such as hard plastics, 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. Ferrous metal substrates used in the practice of the present disclosure can 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, acid pickled steel, zinc-iron alloys such as GALVANNEAL, and combinations thereof. Combinations or composites of ferrous and non-ferrous 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 can also be used as substrates. Magnesium alloys of the AZ31B, AZ91C, AM60B, or EV31A series can also be used as substrates. Substrates used in the present disclosure can also include titanium and / or titanium alloys of Grade 1-36, including the H-variant. Other suitable non-ferrous metals include copper and magnesium, and alloys of these materials. The compositions disclosed herein are particularly useful 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 substrates used in the assembly of vehicle bodies, for example, but not limited to, doors, body panels, trunk lids, roof panels, hoods, roof and / or stringers, rivets, landing gear components, and / or skins used on aircraft, vehicle frames, vehicle components, motorcycles, vehicle 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 automobiles, motorcycles, and / or trucks. The metal substrate can also be in the form of, for example, a metal sheet or a finished component. It will also be appreciated that the substrate can be conversion coated, anodized, primed, organic coated, or chromate coated, epoxy, urethane, graphite, fiberglass composite, Kevlar®, acrylic, and polycarbonate. The substrate can include a composite material, for example, a plastic or fiberglass composite. The substrate can be a fiberglass and / or carbon fiber composite. The first substrate and the second substrate can be made of the same material or can be made of different materials. For example, the first substrate and the second substrate can be metal and plastic; two different plastics; metal or plastic and a reinforced plastic composite; or two different plastic composites.

[0175] In view of the foregoing description, the present disclosure thus relates in particular to aspects 1 to 210 below, but is not limited thereto.

[0176] Aspects

[0177] Aspect 1. A composition comprising:

[0178] a first component comprising an epoxy-containing compound;

[0179] a second component comprising an amino-functional amide and a toughening amine; and

[0180] an elastomeric particle.

[0181] Aspect 2. The composition of aspect 1, wherein the epoxy-containing compound comprises more than one epoxy functional group.

[0182] Aspect 3. The composition of aspect 1 or aspect 2, wherein the epoxy-containing compound comprises at least two epoxy functional groups.

[0183] Aspect 4. The composition of any of the preceding aspects, wherein the epoxy-containing compound comprises an aromatic epoxy.

[0184] Aspect 5. The composition of any of the preceding aspects, wherein the epoxy-containing compound comprises an epoxy adduct.

[0185] Aspect 6. The composition of any of the preceding aspects, wherein the epoxy-containing compound comprises bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, novolac resin, tetraglycidyl methylenedianiline, triglycidyl-p-aminophenol, tetraglycidyl-m-xylylenediamine, or a combination thereof.

[0186] 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.

[0187] Aspect 8. The composition of aspect 7, wherein the first component comprises the aromatic monoepoxide or aliphatic monoepoxide in an amount of at least 0.1 wt% based on the total weight of the first component.

[0188] Aspect 9. The composition of aspect 7 or aspect 8, wherein the first component comprises the aromatic monoepoxide or aliphatic monoepoxide in an amount of at least 0.2 wt% based on the total weight of the first component.

[0189] Aspect 10. The composition of any one of aspects 7 to 9, wherein the first component comprises the aromatic mono-epoxide or aliphatic mono-epoxide in an amount of at least 0.5 weight percent, based on the total weight of the first component.

[0190] Aspect 11. The composition of any one of aspects 7 to 10, wherein the first component comprises the aromatic mono-epoxide or aliphatic mono-epoxide in an amount of no more than 15 weight percent, based on the total weight of the first component.

[0191] Aspect 12. The composition of any one of aspects 7 to 11, wherein the first component comprises the aromatic mono-epoxide or aliphatic mono-epoxide in an amount of no more than 10 weight percent.

[0192] Aspect 13. The composition of any one of aspects 7 to 12, wherein the first component comprises the aromatic mono-epoxide or aliphatic mono-epoxide in an amount of 0.1 weight percent to 15 weight percent, based on the total weight of the first component.

[0193] Aspect 14. The composition of any one of aspects 7 to 13, wherein the first component comprises the aromatic mono-epoxide or aliphatic mono-epoxide in an amount of 0.2 weight percent to 10 weight percent, based on the total weight of the first component.

[0194] Aspect 15. The composition of any one of aspects 7 to 14, wherein the first component comprises the aromatic mono-epoxide or aliphatic mono-epoxide in an amount of 0.5 weight percent to 8 weight percent, based on the total weight of the first component.

[0195] Aspect 16. The composition of any one 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.

[0196] Aspect 17. The composition of any one of the preceding aspects, wherein the first component comprises the epoxy-containing compound in an amount of at least 30 weight percent, based on the total weight of the first component.

[0197] Aspect 18. The composition of any one of the preceding aspects, wherein the first component comprises the epoxy-containing compound in an amount of at least 35 weight percent, based on the total weight of the first component.

[0198] Aspect 19. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing compound in an amount of at least 40 weight percent, based on the total weight of the first component.

[0199] 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 weight percent, based on the total weight of the first component.

[0200] 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 weight percent, based on the total weight of the first component.

[0201] 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 weight percent, based on the total weight of the first component.

[0202] 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 weight percent, based on the total weight of the first component.

[0203] Aspect 24. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 30 weight percent to 100 weight percent, based on the total weight of the first component.

[0204] Aspect 25. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 30 weight percent to 60 weight percent, based on the total weight of the first component.

[0205] Aspect 26. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 35 weight percent to 55 weight percent, based on the total weight of the first component.

[0206] Aspect 27. The composition of any of the preceding aspects, wherein the first component comprises the epoxy-containing component in an amount of 40 weight percent to 50 weight percent, based on the total weight of the first component.

[0207] 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 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0208] 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 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0209] 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 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0210] 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 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0211] 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 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0212] 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 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0213] Aspect 34. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of 5 weight percent to 75 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0214] Aspect 35. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of 10 weight percent to 50 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0215] Aspect 36. The composition of any of the preceding aspects, wherein the second component comprises the amino-functional amide in an amount of 15 weight percent to 35 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0216] Aspect 37. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of at least 25 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0217] Aspect 38. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of at least 30 weight percent based on the total weight of the amino-functional amide and the toughening amine.

[0218] Aspect 39. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of at least 35 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0219] Aspect 40. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of not more than 95 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0220] Aspect 41. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of not more than 85 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0221] Aspect 42. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of not more than 80 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0222] Aspect 43. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of 25 weight percent to 95 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0223] Aspect 44. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of 30 weight percent to 85 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0224] Aspect 45. The composition of any of the preceding aspects, wherein the second component comprises the toughening amine in an amount of 35 weight percent to 80 weight percent, based on the total weight of the amino-functional amide and the toughening amine.

[0225] Aspect 46. The composition of any of the preceding aspects, wherein the amino- functional amide comprises a reaction product of reactants comprising a dimerized fatty acid and an ether amine.

[0226] Aspect 47. The composition of Aspect 46, wherein the ether amine comprises an aliphatic ether amine, diethylenetriamine, and / or triethylenetetramine.

[0227] Aspect 48. The composition of Aspect 46 or Aspect 47, wherein the reaction product comprises a difunctional amine.

[0228] Aspect 49. The composition of any of Aspects 46 to 48, wherein the reaction product comprises two primary amines.

[0229] Aspect 50. The composition of any of Aspects 46-49, wherein the reaction product comprises a secondary amine.

[0230] Aspect 51. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of greater than 140 g / mol as measured by mass spectrometry.

[0231] Aspect 52. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of at least 170 g / mol as measured by mass spectrometry.

[0232] Aspect 53. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of at least 210 g / mol as measured by mass spectrometry.

[0233] Aspect 52. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of not more than 2,000 g / mol as measured by mass spectrometry.

[0234] Aspect 53. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of not more than 1,700 g / mol as measured by mass spectrometry.

[0235] Aspect 54. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of not more than 1,300 g / mol as measured by mass spectrometry.

[0236] Aspect 55. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of not more than 1,200 g / mol as measured by mass spectrometry.

[0237] Aspect 56. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of 140 g / mol to 2,000 g / mol as measured by mass spectrometry.

[0238] Aspect 57. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of 170 g / mol to 1,700 g / mol as measured by mass spectrometry.

[0239] Aspect 58. The composition of any of the preceding Aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of 210 g / mol to 1,300 g / mol as measured by mass spectrometry.

[0240] Aspect 59. The composition of any of the preceding aspects, wherein the toughening amine comprises an ether amine comprising a molecular weight of 210 g / mol to 1,200 g / mol as measured by mass spectrometry.

[0241] Aspect 60. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 295 g / mol as measured by mass spectrometry.

[0242] Aspect 61. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 400 g / mol as measured by mass spectrometry.

[0243] Aspect 62. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of greater than 500 g / mol as measured by mass spectrometry.

[0244] Aspect 63. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 2,000 g / mol as measured by mass spectrometry.

[0245] Aspect 64. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 1,700 g / mol as measured by mass spectrometry.

[0246] Aspect 65. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 1,300 g / mol as measured by mass spectrometry.

[0247] Aspect 66. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of no more than 1,200 g / mol as measured by mass spectrometry.

[0248] Aspect 67. The composition of any of the preceding aspects, wherein the toughening 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 as measured by mass spectrometry.

[0249] Aspect 68. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of 400 g / mol to 1,700 g / mol as measured by mass spectrometry.

[0250] Aspect 69. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of 500 g / mol to 1,300 g / mol as measured by mass spectrometry.

[0251] Aspect 70. The composition of any of the preceding aspects, wherein the toughening amine comprises a fatty acid dimer or a fatty acid trimer comprising a molecular weight of 500 g / mol to 1,200 g / mol as measured by mass spectrometry.

[0252] Aspect 71. The composition of any of the preceding aspects, wherein the toughening amine comprises an amine-functional fatty ether amine-epoxy adduct (A1).

[0253] Aspect 72. The composition of aspect 71, wherein the amine-functional fatty ether amine-epoxy adduct (A1) comprises a reaction product of reactants comprising a fatty ether amine (A2) and an epoxy-containing compound (E2).

[0254] Aspect 73. The composition of aspect 72, wherein the fatty ether amine (A2) comprises two amine functional groups, such as a diamine, a triamine, a tetraamine, or a combination thereof.

[0255] Aspect 74. The composition of aspect 72 or aspect 73, wherein the fatty ether amine (A2) comprises an ethylene glycol subunit, such as ethylene glycol bis(2-aminoethylether), diethylene glycol bis(3-aminopropyl)ether, or a combination thereof.

[0256] Aspect 75. The composition of any of aspects 72 to 74, wherein the fatty ether amine (A2) comprises a primary amine functional group adjacent to a methylene group.

[0257] Aspect 76. The composition of any of aspects 72 to 75, wherein the fatty ether amine (A2) comprises a molecular weight of at least 104 g / mol as measured using mass spectrometry.

[0258] Aspect 77. The composition of any one of aspects 72 to 76, wherein the aliphatic ether amine (A2) comprises a molecular weight of at least 140 g / mol as measured using mass spectrometry.

[0259] Aspect 78. The composition of any one of aspects 72 to 77, wherein the aliphatic ether amine (A2) comprises a molecular weight of no more than 300 g / mol as measured using mass spectrometry.

[0260] Aspect 79. The composition of any one of aspects 72 to 78, wherein the aliphatic ether amine (A2) comprises a molecular weight of no more than 230 g / mol as measured using mass spectrometry.

[0261] Aspect 80. The composition of any one of aspects 72 to 79, wherein the aliphatic ether amine (A2) comprises a molecular weight of from 104 g / mol to 300 g / mol as measured using mass spectrometry.

[0262] Aspect 81. The composition of any one of aspects 72 to 80, wherein the aliphatic ether amine (A2) comprises a molecular weight of from 104 g / mol to 300 g / mol as measured using mass spectrometry.

[0263] Aspect 82. The composition of any one of aspects 72 to 81, wherein the aliphatic ether amine (A2) comprises a molecular weight of from 140 g / mol to 230 g / mol as measured using mass spectrometry.

[0264] Aspect 83. The composition of any one of aspects 72 to 82, wherein the epoxy-containing compound (E2) comprises bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, a phenol formaldehyde resin, tetraglycidyl methylenedianiline, triglycidyl p-aminophenol, tetraglycidyl m-xylene diamine, or a combination thereof.

[0265] Aspect 84. The composition of any one of aspects 72 to 83, wherein the epoxy-containing compound (E2) comprises an aromatic group.

[0266] Aspect 85. The composition of any one of aspects 72 to 84, wherein the epoxy-containing compound (E2) comprises a molecular weight of no more than 600 g / mol as measured by mass spectrometry.

[0267] Aspect 86. The composition of any one of aspects 72 to 85, wherein the epoxy-containing compound (E2) comprises a molecular weight of no more than 450 g / mol as measured by mass spectrometry.

[0268] Aspect 87. The composition of any one of aspects 72 to 86, wherein the epoxy group containing compound (E2) comprises a molecular weight of at least 160 g / mol as measured by mass spectrometry.

[0269] Aspect 88. The composition of any one of aspects 72 to 87, wherein the epoxy group containing compound (E2) comprises a molecular weight of at least 300 g / mol as measured by mass spectrometry.

[0270] Aspect 89. The composition of any one of aspects 72 to 88, wherein the epoxy group containing compound (E2) comprises a molecular weight of at least 160 g / mol to 600 g / mol as measured by mass spectrometry.

[0271] Aspect 90. The composition of any one of aspects 72 to 89, wherein the epoxy group containing compound (E2) comprises a molecular weight of at least 300 g / mol to 450 g / mol as measured by mass spectrometry.

[0272] Aspect 91. The composition of any one of aspects 72 to 90, wherein the epoxy group containing compound (E2) comprises an epoxide equivalent of at least 85 g / eq.

[0273] Aspect 92. The composition of any one of aspects 72 to 91, wherein the epoxy group containing compound (E2) comprises an epoxide equivalent of at least 110 g / eq.

[0274] Aspect 93. The composition of any one of aspects 72 to 92, wherein the epoxy group containing compound (E2) comprises an epoxide equivalent of no more than 300 g / eq.

[0275] Aspect 94. The composition of any one of aspects 72 to 93, wherein the epoxy group containing compound (E2) comprises an epoxide equivalent of no more than 220 g / eq.

[0276] Aspect 95. The composition of any one of aspects 72 to 94, wherein the epoxy group containing compound (E2) comprises an epoxide equivalent of 85 g / eq to 300 g / eq.

[0277] Aspect 96. The composition of any one of aspects 72 to 95, wherein the epoxy group containing compound (E2) comprises an epoxide equivalent of 110 g / eq to 220 g / eq.

[0278] Aspect 97. The composition of any of Aspects 72 to 96, wherein the reactants comprise the aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of at least 3: 1.

[0279] Aspect 98. The composition of any of Aspects 72 to 97, wherein the reactants comprise the aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of at least 4: 1.

[0280] Aspect 99. The composition of any of Aspects 72 to 98, wherein the reactants comprise the aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of no more than 12: 1.

[0281] Aspect 100. The composition of any of Aspects 72 to 99, wherein the reactants comprise the aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of no more than 7: 1.

[0282] Aspect 101. The composition of any of Aspects 72 to 100, wherein the reactants comprise the aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of 3: 1 to 12: 1.

[0283] Aspect 102. The composition of any of Aspects 72 to 101, wherein the reactants comprise the aliphatic ether amine (A2) in an amount sufficient to provide a mole ratio of amine-hydrogen from the aliphatic ether amine (A2) to epoxide functional groups from the epoxy-containing compound (E2) of 4: 1 to 7: 1.

[0284] Aspect 103. The composition of any of the preceding aspects, the second component further comprising a cycloaliphatic amine and / or a polyamine.

[0285] Aspect 104. The composition of Aspect 103, comprising the cycloaliphatic amine in an amount of at least 0.5 weight percent, based on the total weight of the amino-functional amide, the flexibilizing amine, the cycloaliphatic amine, and the polyamine.

[0286] Aspect 105. The composition of either Aspect 103 or Aspect 104, comprising the cycloaliphatic amine in an amount of at least 1 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0287] Aspect 106. The composition of any one of Aspects 103 to 105, comprising the cycloaliphatic amine in an amount of no more than 10 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0288] Aspect 107. The composition of any one of Aspects 103 to 106, comprising the cycloaliphatic amine in an amount of no more than 8 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0289] Aspect 108. The composition of any one of Aspects 103 to 107, comprising the cycloaliphatic amine in an amount of from 0.5 weight percent to 10 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0290] Aspect 109. The composition of any one of Aspects 103 to 108, comprising the cycloaliphatic amine in an amount of from 1 weight percent to 8 weight percent, such as from 1 weight percent to 8 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0291] Aspect 110. The composition of any one of Aspects 103 to 109, comprising the polyamine in an amount of at least 0.5 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0292] Aspect 111. The composition of any one of Aspects 103 to 110, comprising the polyamine in an amount of at least 1 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0293] Aspect 112. The composition of any one of Aspects 103 to 111, comprising the polyamine in an amount of no more than 50 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0294] Aspect 113. The composition of any one of Aspects 103 to 112, comprising the polyamine in an amount of no more than 40 weight percent, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0295] Aspect 114. The composition of any one of aspects 103-113, comprising the polyamine in an amount of 0.5 wt% to 50 wt%, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0296] Aspect 115. The composition of any one of aspects 103-114, comprising the polyamine in an amount of 1 wt% to 40 wt%, based on the total weight of the amino-functional amide, the toughening amine, the cycloaliphatic amine, and the polyamine.

[0297] Aspect 116. The composition of any one of the preceding aspects, wherein the elastomeric particles comprise a core-shell structure, an amine-functional rubber, a carboxyl-functional rubber, an epoxy-functional rubber, or a combination thereof.

[0298] Aspect 117. The composition of any one of the preceding aspects, wherein the first component, the second component, and / or third component comprises the elastomeric particles.

[0299] Aspect 118. The composition of any one of the preceding aspects, wherein the elastomeric particles are phase separated from the epoxy-containing component, the fatty acid amino amide, and / or the toughening amine.

[0300] Aspect 119. The composition of any one of the preceding aspects, wherein the elastomeric particles comprise a particle size of at least 20 nm as measured using dynamic light scattering or TEM.

[0301] Aspect 120. The composition of any one of the preceding aspects, wherein the elastomeric particles comprise a particle size of at least 30 nm as measured using dynamic light scattering or TEM.

[0302] Aspect 121. The composition of any one of the preceding aspects, wherein the elastomeric particles comprise a particle size of at least 50 nm as measured using dynamic light scattering or TEM.

[0303] Aspect 122. The composition of any one 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 TEM.

[0304] Aspect 123. The composition of any one 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 TEM.

[0305] Aspect 124. The composition of any one 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 TEM.

[0306] Aspect 125. The composition of any one 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 TEM.

[0307] Aspect 126. The composition of any one 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 TEM.

[0308] Aspect 127. The composition of any one 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 TEM.

[0309] Aspect 128. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of at least 2.5 wt% based on the total weight of the composition.

[0310] Aspect 129. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of at least 5 wt% based on the total weight of the composition.

[0311] Aspect 130. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of at least 7.5 wt% based on the total weight of the composition.

[0312] Aspect 131. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of not more than 25 wt% based on the total weight of the composition.

[0313] Aspect 132. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of not more than 22.5 wt% based on the total weight of the composition.

[0314] Aspect 133. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of not more than 20 wt% based on the total weight of the composition.

[0315] Aspect 134. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of 2.5 wt% to 25 wt% based on the total weight of the composition.

[0316] Aspect 135. The composition of any one of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of 5 wt% to 22.5 wt% based on the total weight of the composition.

[0317] Aspect 136. The composition of any of the preceding aspects, wherein the composition comprises the elastomeric particles in an amount of 7.5 to 20 weight percent, based on the total weight of the composition.

[0318] Aspect 137. The composition of any of the preceding aspects, wherein the first component, the second component, and / or third component comprises a reinforcing filler.

[0319] Aspect 138. The composition of Aspect 137, comprising the reinforcing filler in an amount of at least 2.5 weight percent, based on the total weight of the composition.

[0320] Aspect 139. The composition of Aspect 137 or Aspect 138, comprising the reinforcing filler in an amount of at least 5 weight percent, based on the total weight of the composition.

[0321] Aspect 140. The composition of any of Aspects 137 to 139, comprising the reinforcing filler in an amount of no more than 30 weight percent, based on the total weight of the composition.

[0322] Aspect 141. The composition of any of Aspects 137 to 140, comprising the reinforcing filler in an amount of no more than 25 weight percent, based on the total weight of the composition.

[0323] Aspect 142. The composition of any of Aspects 137 to 141, comprising the reinforcing filler in an amount of 2.5 to 30 weight percent, based on the total weight of the composition.

[0324] Aspect 143. The composition of any of Aspects 137 to 142, comprising the reinforcing filler in an amount of 5 to 25 weight percent, based on the total weight of the composition.

[0325] Aspect 144. The composition of any of the preceding aspects, wherein the first component, the second component, and / or third component comprises an additive.

[0326] Aspect 145. The composition of Aspect 144, wherein the composition comprises the additive in an amount of at least 0.01 weight percent, based on the total weight of the composition.

[0327] Aspect 146. The composition of Aspect 144 or 145, wherein the composition comprises the additive in an amount of at least 0.05 weight percent, based on the total weight of the composition.

[0328] Aspect 147. The composition of any one of aspects 144-146, wherein the composition comprises the additive in an amount of no more than 15 weight percent, based on the total weight of the composition.

[0329] Aspect 148. The composition of any one of aspects 144-147, wherein the composition comprises the additive in an amount of no more than 12 weight percent, based on the total weight of the composition.

[0330] Aspect 149. The composition of any one of aspects 144-148, wherein the composition comprises the additive in an amount of no more than 10 weight percent, based on the total weight of the composition.

[0331] Aspect 150. The composition of any one of aspects 144-149, wherein the composition comprises the additive in an amount of no more than 3 weight percent, based on the total weight of the composition.

[0332] Aspect 151. The composition of any one of aspects 144-150, wherein the composition comprises the additive in an amount of 0.01 weight percent to 15 weight percent, based on the total weight of the composition.

[0333] Aspect 152. The composition of any one of aspects 144-151, wherein the composition comprises the additive in an amount of 0.01 weight percent to 12 weight percent, based on the total weight of the composition.

[0334] Aspect 153. The composition of any one of aspects 144-152, wherein the composition comprises the additive in an amount of 0.05 weight percent to 10 weight percent, based on the total weight of the composition.

[0335] Aspect 154. The composition of any one of aspects 144-153, wherein the composition comprises the additive in an amount of 0.05 weight percent to 3 weight percent, based on the total weight of the composition.

[0336] Aspect 155. The composition of any one of the preceding aspects, wherein the first component, the second component, and / or third component comprises an accelerator.

[0337] Aspect 156. The composition of aspect 155, comprising the accelerator in an amount of at least 0.1 weight percent, based on the total weight of the composition.

[0338] Aspect 157. The composition of aspect 155 or aspect 156, comprising the accelerator in an amount of at least 0.2 weight percent, based on the total weight of the composition.

[0339] Aspect 158. The composition of any one of aspects 155-157, comprising the accelerator in an amount of at least 0.5 weight percent, based on the total weight of the composition.

[0340] Aspect 159. The composition of any one of aspects 155-158, comprising the accelerator in an amount of not more than 10 weight percent, based on the total weight of the composition.

[0341] Aspect 160. The composition of any one of aspects 155-159, comprising the accelerator in an amount of not more than 5 weight percent, based on the total weight of the composition.

[0342] Aspect 161. The composition of any one of aspects 155-160, comprising the accelerator in an amount of not more than 2.5 weight percent, based on the total weight of the composition.

[0343] Aspect 162. The composition of any one of aspects 155-161, comprising the accelerator in an amount of 0.1 weight percent to 10 weight percent, based on the total weight of the composition.

[0344] Aspect 163. The composition of any one of aspects 155-162, comprising the accelerator in an amount of 0.2 weight percent to 5 weight percent, based on the total weight of the composition.

[0345] Aspect 164. The composition of any one of aspects 155-163, comprising the accelerator in an amount of 0.5 weight percent to 2.5 weight percent, based on the total weight of the composition.

[0346] Aspect 165. The composition of any one of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free of a polyurethane resin.

[0347] Aspect 166. The composition of any one of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free of an amine-functional rubber.

[0348] Aspect 167. The composition of any one of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free of a carboxyl-functional rubber.

[0349] Aspect 168. The composition of any one of the preceding aspects, wherein the composition is substantially free, or essentially free, or completely free of an epoxy-functional rubber.

[0350] Aspect 169. The composition of any of the preceding aspects, formulated into an adhesive composition, such as a structural adhesive composition, a potting compound composition, a gap filler composition, a prepreg composition, a liquid gasket composition, or a combination thereof.

[0351] Aspect 170. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of at least 50 weight %, based on the total weight of the composition.

[0352] Aspect 171. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of at least 60 weight %, based on the total weight of the composition.

[0353] Aspect 172. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of at least 70 weight %, based on the total weight of the composition.

[0354] 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 weight %, based on the total weight of the composition.

[0355] 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 weight %, based on the total weight of the composition.

[0356] 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 weight %, based on the total weight of the composition.

[0357] Aspect 176. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of 50 weight % to 90 weight %, based on the total weight of the composition.

[0358] Aspect 177. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of 60 weight % to 85 weight %, based on the total weight of the composition.

[0359] Aspect 178. The composition of any of the preceding aspects, wherein the composition comprises the first component in an amount of 70 weight % to 80 weight %, based on the total weight of the composition.

[0360] Aspect 179. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of at least 10 weight %, based on the total weight of the composition.

[0361] Aspect 180. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of at least 15 weight percent, based on the total weight of the composition.

[0362] Aspect 181. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of at least 20 weight percent, based on the total weight of the composition.

[0363] 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 weight percent, based on the total weight of the composition.

[0364] 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 weight percent, based on the total weight of the composition.

[0365] 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 weight percent, based on the total weight of the composition.

[0366] Aspect 185. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of 10 weight percent to 50 weight percent, based on the total weight of the composition.

[0367] Aspect 186. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of 15 weight percent to 40 weight percent, based on the total weight of the composition.

[0368] Aspect 187. The composition of any of the preceding aspects, wherein the composition comprises the second component in an amount of 20 weight percent to 30 weight percent, based on the total weight of the composition.

[0369] Aspect 188. A method of coating a substrate, the method comprising contacting a portion of a surface of the substrate with the composition of any of the preceding aspects.

[0370] Aspect 189. The method of aspect 188, further comprising mixing the first component and the second component of any of aspects 1 to 187.

[0371] Aspect 190. The method of aspect 188 or aspect 189, further comprising contacting a surface of a second substrate with the composition, such that the composition is positioned between the substrate and the second substrate.

[0372] Aspect 191. A method of forming an article, the method comprising extruding the composition of any one of aspects 1 to 187.

[0373] Aspect 192. The method of aspect 191, wherein the extruding comprises three-dimensional printing.

[0374] Aspect 193. An article formed by the method of aspect 191 or aspect 192.

[0375] Aspect 194. A substrate comprising a coating formed from the composition of any one of aspects 1 to 187 on a portion of a surface of the substrate.

[0376] Aspect 195. The substrate of aspect 194, further comprising a pretreatment coating or film and / or an additional coating, such as a primer, basecoat, and / or topcoat.

[0377] Aspect 196. The substrate of aspect 194 or aspect 195, wherein the substrate comprises aluminum, steel, or titanium or alloys thereof, carbon fiber composites, glass fiber composites, thermoplastics, nylon, ceramic, or combinations thereof.

[0378] Aspect 197. The substrate of any one of aspects 194 to 196, further comprising a second substrate, wherein the coating is positioned between the substrate and the second substrate.

[0379] Aspect 198. The substrate of any one 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 according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at ambient conditions.

[0380] Aspect 199. The substrate of any one 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 according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at 160 °F for at least 30 minutes.

[0381] Aspect 200. The substrate of any one of aspects 194 to 199, wherein the coating comprises a pot life of at least 120 minutes and a roll peel strength of at least 15 psi measured according to ASTM D3167.

[0382] Aspect 201. The substrate of any one of aspects 194 to 200, coated according to the method of any one of aspects 188 to 190.

[0383] Aspect 202. The substrate of any one of aspects 194-201, wherein the coating comprises an adhesive, a structural adhesive, a potting compound, a gap filler, a composite formed from a prepreg, a liquid gasket, or a combination thereof.

[0384] Aspect 203. The substrate of any one of aspects 194-202, wherein the substrate comprises an article, a component, or a combination thereof.

[0385] 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 a combination thereof.

[0386] Aspect 205. The substrate of aspect 203, wherein the component comprises a vehicle component.

[0387] Aspect 206. The substrate of aspect 204 or aspect 205, wherein the vehicle comprises a land vehicle or an aircraft.

[0388] Aspect 207. Use of the coating composition of any one of aspects 1-187 to coat 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 according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at ambient conditions.

[0389] Aspect 208. The use of 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 according to ASTM D1002 using an Instron 5567 machine in tensile mode at a pull rate of 1.3 mm per minute at 160 °F for at least 30 minutes.

[0390] Aspect 209. The use of aspect 207 or aspect 208, wherein the coating comprises a pot life of at least 120 minutes and a roll peel strength of at least 15 psi measured according to ASTM D3167.

[0391] Aspect 210. The use of any one of aspects 207-209, wherein the coating comprises an adhesive, a structural adhesive, a potting compound, a gap filler, a composite formed from a prepreg, a liquid gasket, or a combination thereof.

[0392] The following examples are intended to illustrate the present disclosure and should not be construed as limiting the disclosure in any way.

[0393] Examples

[0394] Example 1 : Amine Package 1

[0395] An amine package was prepared by charging 80.8 g of amide amine and 19.2 g of toughening amine into a container, which was then mixed in a rapid mixer for 1 minute.

[0396] Example 2: Epoxy Package

[0397] An epoxy package was prepared using standard epoxy resins, elastomers, and fillers known to those skilled in the art. 33.9 g of epoxy resin A, 15.9 g of epoxy resin B, 29.4 g of elastomer, and 18.4 g of a first filler were charged into a mixing container, which was then mixed in a rapid mixer for 1 minute. Then, 2.4 g of a second filler was added to the mixture, and the mixture was further mixed in a rapid mixer for 1 minute.

[0398] Example 3: Adhesive Composition 1

[0399] An adhesive composition was prepared by mixing 30.7 g of amine package 1 and 69.3 g of epoxy package 1. Lap shear and peel strength samples were then prepared using the adhesive, with clad 2024-T3 anodized in phosphoric acid and coated with primer used as the substrate in sample preparation. Shelf life was measured by storing 100 g of the mixed adhesive at 70 ± 10 F for 120 min prior to making lap shear and peel samples. After sample preparation, the samples were cured for 7 days under ambient conditions. After curing, lap shear strength was measured according to ASTM D1002 and lap shear strength was measured according to ASTM D3167. Results are shown in Table 1.

[0400] Example 4: Comparative Adhesive Composition 2

[0401] A comparative adhesive composition (without toughening amine) was prepared by blending 32.7 g of amide amine (amine package 2) and 67.3 g of epoxy package 1. Lap shear and peel strength samples were then prepared using the adhesive, with clad 2024-T3 anodized in phosphoric acid and coated with BR-127 primer used as the substrate in sample preparation. Shelf life was measured by storing 100 g of the mixed adhesive at 70 ± 10 F for 120 min prior to making lap shear and peel samples. After sample preparation, the samples were cured for 7 days under ambient conditions. After curing, lap shear strength was measured according to ASTM D1002 and lap shear strength was measured according to ASTM D3167. o

[0402] Example 5: Comparative Adhesive Composition 3

[0403] ​A comparative adhesive composition (no amide amine) was prepared by blending 25.9 g of toughening amine (Amine Package 3) and 74.1 g of epoxy package 1. The useful life was measured by storing 100 g of the mixed adhesive at 70 ± 10 °F for 120 min before making lap shear and peel samples. o F for 120 min.

[0404] Example 6: Comparative Example 4

[0405] A comparative adhesive composition (no amide amine or toughening amine) was prepared by blending 11.3 g of cycloaliphatic amine (Amine Package 4) and 88.7 g of epoxy package 1. The useful life was measured by storing 100 g of the mixed adhesive at 70 ± 10 °F for 120 min before making lap shear and peel samples. o F for 120 min.

[0406] Example 7: Adhesive Composition 5

[0407] Amine Package 5 was prepared by mixing 89.951 g of amide amine, 5.55 g of toughening amine, and 4.50 g of catalyst into a container, then mixing in a high 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 a high speed mixer for 1 minute.

[0408] In a separate container, Epoxy Package 2 was prepared by charging a container with epoxy resin (53.00 g) and core-shell rubber-containing epoxy resin (47.00 g) and mixing in a high speed mixer for 1 minute. Filler (22.50 g) was then added to the mixture and the mixture was further mixed in a high speed mixer for 2 x 1 minute.

[0409] Adhesive Composition 7 was prepared by mixing Epoxy Package 2 and Amine Package 5 in a 2:1 volume ratio.

[0410] Lap shear and roll peel samples were prepared by barrel extrusion. The substrates used in sample preparation were clad 2024-T3 that was anodized in phosphoric acid and coated with primer. After sample preparation, the samples were allowed to cure for 4 days (adhesive 5A) and 7 days (adhesive 5B) at ambient conditions. After curing, lap shear strength was measured according to ASTM D1002 and lap shear strength was measured according to ASTM D3167.

[0411] The data is reported in Table 1.

[0412] Table 1 - Performance of Adhesives 1-5

[0413]

[0414] While features of the present disclosure have been described above with respect to the embodiments, it will be apparent to those skilled in the art that various changes in form and details can be made without departing from the scope of the appended claims.

Claims

1. A composition comprising: The first component comprises an epoxy-containing compound; The second component, comprising an amino-functionalized amide and a toughening amine; and Elastomer particles.

2. The composition according to claim 1, comprising: (a) Based on the total weight of the first component, at least 30% by weight of the epoxy-containing compound; (b) Based on the total weight of the amino-functionalized amide and the toughening amine, an amount of the amino-functionalized amide of 5% to 75% by weight; (c) 25% to 95% by weight of the toughening amine, based on the total weight of the amino-functionalized amide and the toughening amine; and / or (d) The amount of the elastomer particles, from 2.5% to 25% by weight, based on the total weight of the composition.

3. The composition according to claim 1 or claim 2, wherein: (a) The first component further comprises aromatic monoepoxides, aliphatic monoepoxides and / or aliphatic polyepoxides; (b) The second component also contains an alicyclic amine; (c) The second component further comprises a polyamine; and / or (d) The composition further comprises an accelerator.

4. The composition according to any one of the preceding claims, wherein: (a) The amino-functionalized amide comprises a reaction product of reactants comprising a dimer fatty acid and an ether amine, such as an aliphatic ether amine, diethylenetriamine, and / or triethylenetetramine, wherein the reaction product optionally comprises a bifunctional amine, two primary amines, and / or a secondary amine; and / or (b) The toughening amine comprises: an ether amine having a molecular weight greater than 140 g / mol to 2,000 g / mol as determined by mass spectrometry; and / or a fatty acid dimer or fatty acid trimer having a molecular weight greater than 295 g / mol to 2,000 g / mol as determined by mass spectrometry.

5. The composition according to any one of the preceding claims, wherein the toughening amine comprises an amine-functional aliphatic ether amine-epoxy adduct (A1).

6. The composition according to claim 5, wherein the amine-functionalized aliphatic ether amine-epoxy adduct (A1) comprises a reaction product containing an aliphatic ether amine (A2) and an epoxy compound (E2).

7. The composition according to claim 6, wherein: (a) The aliphatic ether amine (A2) contains a primary amine functional group adjacent to a methylene group; (b) The aliphatic ether amine (A2) comprises a molecular weight of 104 g / mol to 300 g / mol as determined by mass spectrometry; and / or (c) The epoxy-containing compound (E2): (i) Contains aromatic groups; (ii) Molecules ranging from 160 g / mol to 600 g / mol; and / or (iii) The epoxide equivalent is 85 g / eq to 300 g / eq.

8. The composition according to claim 6 or claim 7, wherein the reactant comprises the aliphatic ether amine (A2), the amount of the aliphatic ether amine being sufficient to provide a molar ratio of amine-hydrogen from the aliphatic ether amine (A2) to the epoxide functional group from the epoxy-containing compound (E2) of 3:1 to 12:

1.

9. The composition according to any one of the preceding claims, wherein the composition is substantially free of, or substantially free of, or completely free of polyurethane resin, amine functional rubber, carboxyl functional rubber and / or epoxy functional rubber.

10. The composition according to any one of the preceding claims, wherein it is formulated as an adhesive composition, such as a structural adhesive composition, a potting compound composition, a gap filler composition, a prepreg composition, a liquid gasket composition, or a combination thereof.

11. A method of coating a substrate, the method comprising contacting a portion of the surface of the substrate with a composition according to any one 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 the surface of the second substrate with the composition such that the composition is located between the first substrate and the second substrate.

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

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

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

16. The substrate according to claim 14 or claim 15, wherein the substrate comprises aluminum, steel or titanium or alloys thereof, carbon fiber composites, glass fiber composites, thermoplastics, nylon, ceramics or combinations thereof.

17. The substrate according to any one 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 according to any one of claims 14 to 17, wherein the coating comprises: (a) Applicable period of at least 120 minutes; and at least one of the following (b) A lap shear strength of at least 725 psi measured under ambient conditions in tensile mode at a pull rate of 1.3 mm per minute using an Instron 5567 machine in accordance with ASTM D1002. (c) A lap shear strength of at least 725 psi measured for at least 30 minutes in tensile mode at a pull rate of 1.3 mm / min at 160℉, using an Instron 5567 machine in tensile mode according to ASTM D1002; and (d) Roller peel strength of at least 15 psi as measured by ASTM D3167.

19. The substrate according to any one of claims 14 to 18, wherein the substrate comprises: Articles, such as vehicles, appliances, personal electronic devices, circuit boards, multi-metal substrates or combinations thereof; Components such as vehicle parts; or combinations thereof.

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

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