Epoxy-polysiloxane coating composition with tin-free catalyst

Abstract

A composition formulated for forming an epoxy-polysiloxane coating, the composition comprising a first part, a second part, and a catalyst system. The first part includes an epoxy resin and a polysiloxane. The second part comprises an aminosilane. The catalyst system comprises (a) a first catalyst component comprising (i) a zirconium-based compound, (ii) a zinc-based compound, (iii) a bismuth-based compound, and / or (iv) a titanium-based compound, and (b) a second catalyst component comprising (i) a metal catalyst different from the first catalyst component, (ii) an acid catalyst, (iii) an amine compound, and / or (iv) an amine-neutralized catalyst.

Description

EPOXY-POLYSILOXANE COATING COMPOSITION WITH TIN-FREE CATALYSTCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to and the benefit of United States Provisional Patent Application No. 63 / 730,552, filed on December 11, 2024, the entirety of which is incorporated herein by reference.BACKGROUND

[0002] Epoxy-polysiloxane coating compositions combine the properties of epoxy resins and polysiloxanes. Such coating compositions can exhibit effective durability, chemical resistance, and weather resistance, and find use in industrial applications, marine applications, infrastructure, commercial and residential buildings, and automotive and aerospace applications.

[0003] Promoting timely curing and effective crosslinking between the epoxy components and the polysiloxane components typically involves use of a catalyst, typically an organotin catalyst. Such tin compounds, however, can be toxic to humans and the environment.SUMMARY

[0004] Disclosed herein is a composition formulated for forming an epoxy-polysiloxane coating, the composition comprising a first part, a second part, and a catalyst system. The first part includes an epoxy resin and a silicone resin. The second part comprises an aminosilane. The catalyst system comprises (a) a first catalyst component comprising (i) a zirconium-based compound, such as an alkyl zirconate and / or a zirconium beta-diketone, (ii) a zinc -based compound, such as a zinc carboxylate, (iii) a bismuth-based compound, such as a bismuth carboxylate, and / or (iv) a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone, and (b) a second catalyst component comprising (i) a metal catalyst different from the first catalyst component, (ii) an acid catalyst, (iii) an amine compound, such as a tertiary amine and / or alkanolamine, and / or (iv) an amine neutralized catalyst, such as an amine neutralized sulfonic acid catalyst. The composition can essentially omit or completely omit tincompounds such as tin-based catalysts. The catalyst system can be included in the first part and / or second part.

[0005] This summary is provided to introduce a selection of concepts in a simplified form that are further described below in the detailed description. This summary is not intended to identify key features or essential features of the claimed subject matter, nor is it intended to be used as an indication of the scope of the claimed subject matter.BRIEF DESCRIPTION OF THE DRAWINGS

[0006] Various features and advantages of this disclosure will become apparent and more readily appreciated from the following description, taken in conjunction with the accompanying drawings and the appended claims, all of which form a part of this specification.

[0007] Figure 1 is an example reaction scheme illustrating crosslinking of an epoxy resin and a polysiloxane using an aminosilane.

[0008] Figures 2A-2E show results of drying time testing (room temperature conditions) for various Example coating compositions.DETAILED DESCRIPTIONIntroduction

[0009] Epoxy-polysiloxane coating compositions combine the properties of epoxy resins and polysiloxanes. Such coating compositions can exhibit effective durability, chemical resistance, and weather resistance, and find use in industrial applications (e.g., on equipment, machinery, and structures), marine applications (e.g., ships, offshore platforms, and other marine structures), infrastructure (e.g., bridges, overpasses, and other structures), commercial and residential buildings (e.g., floors, indoor and outdoor walls), and automotive and aerospace applications (e.g., on protectable parts including exterior components).

[0010] Promoting timely curing and effective crosslinking between the epoxy components and the silicone resin components typically involves use of a catalyst. One conventional approach has favored the use of a tin-based catalyst, such as dibutylbis(pentane-2,4-dionato- O,O’)tin. While such tin-based compounds have been effective as catalysts in epoxy polysiloxane coating systems, their use has several drawbacks. Tin compounds, particularly organotin compounds such as those typically used as catalysts in epoxy polysiloxane coatingsystems, are toxic to humans and the environment. Adverse health effects associated with tin exposure include skin irritation and respiratory problems in the short term, and neurological effects, endocrine disruption, immunotoxicity, and renal / hepatic injury with longer term exposure. In the environment, organotin compounds can accumulate in the food chain and are known to be particularly harmful to marine life.

[0011] Disclosed herein is a composition formulated for forming an epoxy-polysiloxane coating, the composition comprising a first part, a second part, and a catalyst system included in the first part and / or second part. The first part includes an epoxy resin and a silicone resin. The second part comprises an aminosilane. The catalyst system comprises (a) a first catalyst component comprising (i) a zirconium-based compound, such as an alkyl zirconate and / or a zirconium beta-diketone, (ii) a zinc -based compound, such as a zinc carboxylate, (iii) a bismuth-based compound, such as a bismuth carboxylate, and / or (iv) a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone, and (b) a second catalyst component comprising (i) a metal catalyst different from the first catalyst component, (ii) an acid catalyst, and / or (iii) an amine neutralized catalyst, such as an amine neutralized sulfonic acid catalyst.

[0012] Amine compounds known in the art as useful catalysts in polysiloxane and / or epoxy systems include, for example, tertiary amines such as DABCO and / or trialkylamines, aliphatic polyamines such as triethylenetetramine and / or diethylenetriamine, heterocyclic amines such as imidazole and / or diazabicyclo compounds (e.g., diazabicycloundecene (DBU)), alkanolamines such as di- or tri-methanolamine and di- or tri -ethanolamine, guanidine compounds, and combinations thereof.

[0013] The composition can essentially omit or completely omit tin compounds such as tin-based catalysts. The disclosed coating composition, upon mixing of the first part and second part and allowing the mixture to cure, forms a coating that exhibits effective drying times comparable to those of conventional epoxy-polysiloxane coating compositions that rely on a tin-based catalyst.

[0014] The metal catalyst different from the first catalyst component can be based on a metal that is different from any metals included in the first catalyst component. For example, the metal catalyst different from the first catalyst component can include (i) a zirconium-based compound, such as an alkyl zirconate and / or a zirconium beta-diketone, (ii) a zinc -based compound, such as a zinc carboxylate, (iii) a bismuth-based compound, such as a bismuthcarboxylate, and / or (iv) a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone, so long as the metal(s) from which it is based is / are different from the metal(s) of the first catalyst component.

[0015] Figure 1 is an example reaction scheme illustrating crosslinking of an epoxy resin and a silicone resin using an aminosilane. In this example, the epoxy resin comprises a diglycidyl ether of hydrogenated bisphenol A, the silicone resin comprises an aminopropyl triethoxy silane, and the silicone resin comprises methoxy terminal groups. Other epoxy resin compounds, aminosilane compounds, and / or silicone resins may additionally or alternatively be utilized, as described in more detail below. The catalyst system can accelerate the hydrolysis of alkoxysilane groups in the silicone resin, enabling the subsequent condensation reactions, and / or can promote the epoxy-amine reaction by promoting opening of the oxirane ring of the epoxy resin to allow nucleophilic attack by the amine.

[0016] The coating composition may be formulated as a two-part composition where the epoxy resin and silicone resin are included in the first part (also synonymously referred to herein as the base part or resin part) and the aminosilane is included in the second part (also synonymously referred to herein as the hardener part). The catalyst system can be included in the first part and / or the second part, though it is typically included in the second part. The term “part'’ may be used synonymously with “container” when used in the context of separate first and second containers for holding the respective first and second parts of the composition.

[0017] The term “alkyl” is inclusive of all constitutional isomers thereof, including branched alkyl groups and unbranched / linear alkyl groups. For example, where an alkyl is propyl, the propyl may be n-propyl or iso-propyl, or where an alkyl is butyl, the butyl may be n-butyl, sec -butyl, iso-butyl, or tert-butyl. An alkyl group can have 1 to 18 carbons, such as 1 to 16 carbons, such as 1 to 14 carbons, such as 1 to 12 carbons, such as 1 to 10 carbons, such as 1 to 8 carbons, such as 1 to 6 carbons, such as 1 to 4 carbons, such as 1 or 2 carbons. An alkyl can be unsubstituted or can be substituted such as wherein any H of the alkyl is replaced by a monovalent radical such as a hydroxyl, an alkoxy (e.g., a Cl to C2 alkoxy), or a halogen.

[0018] The term “cycloalkyl” refers to any alkyl comprising a cyclic moiety such as a cyclopentane or a cyclohexane. A cycloalkyl group can have 3 to 10 carbons, such as 3 to 8 carbons, such as 5 to 6 carbons. The term cycloalkyl is also inclusive of polycyclic alkyl groups such as an adamantly or a dicyclopentanyl group.

[0019] The term “aryl", as used herein, is inclusive of substituted aryl groups wherein any H of the aryl can be replaced by a monovalent radical such as a hydroxyl, an alkyl (e.g., a Cl to C2 alkyl), or a halogen, and is inclusive of all positional isomers (e.g., ortho, meta, and para isomers) of such substituted aryl groups. An aryl group can include a phenyl group or tolyl group, for example. Aryl groups can be attached to the polysiloxanc backbone by a linker chain, such as a C1-C3 linker chain.

[0020] The term “alkoxy” refers to an alkyl group bonded to an oxygen. An alkoxy group has the formula -OR, where R is an alkyl.

[0021] The term “acyloxy” refers to an acyl group (e.g., an acetyl group) bonded to an oxygen atom according to the formula -O-C(=O)-R, where R is any monovalent radical such as H, alkyl, alkoxy, or halogen.

[0022] A “siloxy” group has the formula -O-SiH?. The siloxy can be substituted by replacing one or more H groups with a monovalent radical such as an alkyl or a halogen. For example, a “trialkylsiloxy” group has the formula -O-Si-Rs, where each R is an alkyl.

[0023] When a labelled group has multiple instances and each instance of the group is described as “independently” selected from a list of alternatives, it means that each individual instance can be selected from the recited list of alternatives without requiring, but allowing for, the same selection for each instance. For example, for a compound with mulliple Z groups, the phrase “each Z is independently an alkyl or an aryl” means that all the Z groups can be alkyl, all the Z groups can be aryl, or the Z groups can include any combination of alkyl and aryl groups such as where one or more are alkyl with the remainder being aryl, or where one or more are aryl with the remainder being alkyl.

[0024] Further, unless specified otherwise, a statement describing multiple groups as having the same genus type (e.g., “each R is an alkyl”) will be understood to allow for, but not require, different combinations of species within that genus (e.g., one or more R groups can be methyl, and one or more R groups can be ethyl).Epoxy Resin & Silicone Resin

[0025] The epoxy resin can include resins that contain more than one epoxide group (e.g., two epoxide groups) per molecule, including aromatic and / or non-aromatic (e.g., hydrogenated) compounds with two epoxide groups per molecule. The epoxy resin can include aromatic and / or cycloaliphatic epoxide resins, such as diglycidyl ethers of a bisphenol or ahydrogenated bisphenol (i.e., a dicyclohexane), such as diglycidyl ethers of bisphenol A and / or diglycidyl ethers of hydrogenated bisphenol A (the latter of which is illustrated in the example reaction scheme of Figure 1).

[0026] The epoxy -polysiloxane composition can include 10 wt. % to 60 wt. % epoxy resin, based on total weight of the composition (i.e., based on both the first and second parts combined when formulated as a two-part composition), such as 15 wt. % to 50 wt. %, or 20 wt. % to 40 wt. %, or 25 wt. % to 30 wt. %, or within a range using any two of the foregoing values as endpoints. If the composition comprises less than 10 wt. % epoxide resin, chemical resistance of the coating may be compromised. If the composition comprises greater than 60 wt. % epoxy resin, weatherability of the coating may be compromised. Including the epoxy resin within the foregoing values has been found to promote effective performance in both chemical resistance and weatherability.

[0027] The epoxy resin can include components / features of the epoxy resin described in U.S. Patent Number 5,804,616, which is incorporated herein by reference (see, e.g., column 3, line 11 to column 3, line 64).

[0028] The silicone resin can include hydrolysable functional groups (e.g., at least two per oligomer molecule). The hydrolysable groups can include an alkoxy (e.g., methoxy, ethoxy, and / or propoxy), acyloxy (e.g., acetoxy), siloxy (e.g., trialkylsiloxy such as trimethylsiloxy), halogen (e.g., chloro), oxime comprising an O bonded to an Si of the polysiloxane chain, and / or a hydroxyl. Other groups can include branched or linear / unbranched alkyl (e.g., C1-C8 alkyl), cycloalkyl (e.g., C3-C10 cycloalkyl), and / or aryl (e.g., phenyl). The silicone resin can comprise, for example, methyl, methoxy, and / or phenyl groups.

[0029] Hydrolysable functional groups of the silicone resin having less than six carbon atoms can facilitate more rapid hydrolysis of the silicone resin, which reaction is affected by the volatility of the alcohol product of the hydrolysis. Groups with less than six carbon atoms result in alcohol analogs with generally relatively higher volatility.

[0030] The oligomers of the silicone resin included in the composition can have a molecular weight (Mw) in the range of 400 to 10,000 g / mol as determined using gel permeation chromatography (GPC) such as according to ASTM D5296 - 19. A composition that includes a silicone resin with molecular weight less than 400 can result in a coating that is more brittle than desired. A composition that includes a silicone resin with molecular weight greater than 10,000 can result in a coating that is more viscous than desired. A silicone resin with amolecular weight within the foregoing range has been found to promote effective balance in performance and viscosity.

[0031] The epoxy-polysiloxane composition can include 15 wt. % to 60 wt. % silicone resin, based on total weight of the composition, (i.e., based on both the first and second parts combined when formulated as a two-part composition), such as 20 wt. % to 50 wt. %, or 25 wt. % to 40 wt. %, or 30 wt. %, or within a range using any two of the foregoing values as endpoints.

[0032] The silicone resin can include features of the silicone resin (referred to as a polysiloxane) described in U.S. Patent Number 5,804,616, which is incorporated herein by reference (see, e.g., column 3, line 65 to column 4, line 45).

[0033] A base formulation suitable for use as the first part of the disclosed composition is the resin / base portion of the two-part composition sold under the trade name PSX® 700 (available from PPG Industries Ohio, Inc.).Aminosilane

[0034] The silane crosslinker can include an amine functional group reactive with the epoxy resin and one to three groups reactive with the silicone resin. The groups reactive with the silicone resin can include, for example, alkoxy, oxime, acyloxy, and / or hydroxycarboxylate groups.

[0035] The aminosilane can be an amino functional alkoxy silane, such as a compound of the formula:wherein X is a divalent alkyl, alkoxyalkyl, or alkylaminoalkyl of 7 carbons or less, and wherein each R is independently an alkyl, hydroxyalkyl, alkoxyalkyl, or hydroxyalkoxyalkyl of 6 carbons or less, such as wherein each R is independently methyl or ethyl. For example, the aminosilane can comprise an aminoalkyl trialkoxy silane, such as an aminopropyl trialkoxy silane, such as an aminopropyl trimethoxy silane and / or aminopropyl triethoxy silane.

[0036] The coating composition may include at least 0.7 molar equivalents of amine functional group of the aminosilane per equivalent of epoxy groups in the epoxy resin. The coating composition may include 5 wt. % to 40 wt. % aminosilane, based on total weight of the composition (i.e., based on both the first and second parts combined when formulated as a two-part composition), such as 7.5 wt. % to 35 wt. %, or 10 wt. % to 30 wt. %, or 12.5 wt. % to 25 wt. %, or 15 wt. % to 20 wt. %, or within a range using any two of the foregoing values as endpoints.

[0037] The aminosilane can include features of the aminosilane described in U.S. Patent Number 5,804,616, which is incorporated herein by reference (see, e.g., column 4, line 46 to column 5, line 45).Catalyst System

[0038] The catalyst system can include (a) a first catalyst component comprising (i) a zirconium-based compound, such as an alkyl zirconate and / or a zirconium beta-diketone, (ii) a zinc -based compound, such as a zinc carboxylate, (iii) a bismuth-based compound, such as a bismuth carboxylate, and / or (iv) a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone, and (b) a second catalyst component comprising (i) a metal catalyst different from the first catalyst component, (ii) an acid catalyst, (iii) an amine compound, such as a tertiary amine and / or alkanolamine, and / or (iv) an amine neutralized catalyst, such as an amine neutralized sulfonic acid catalyst.

[0039] The metal catalyst different from the first catalyst component can include (i) a zirconium-based compound, such as an alkyl zirconate and / or a zirconium beta-diketone, (ii) a zinc -based compound, such as a zinc carboxylate, (iii) a bismuth-based compound, such as a bismuth carboxylate, and / or (iv) a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone, so long as the metal(s) from which it is based is / are different from the metal(s) of the first catalyst component.

[0040] The composition can essentially omit or completely omit tin compounds such as tin-based catalysts.

[0041] The zirconates and / or titanates of the coating composition can be according to the formula:where M is zirconium or titanium, and each R is independently a C1-C8 alkyl. The alkyl may be branched or unbranched / linear. For example, where R is propyl, the propyl may be linear or isopropyl, or where R is butyl, the butyl may be n-butyl or tert -butyl, or where R is a C8 alkyl, the C8 alkyl may be a branched ethylhexyl group, such as a 2-ethylhexyl group.

[0042] As in the ail, the term alkyl zirconate is used synonymously herein with the terms zirconium alkoxide and alkoxy zirconium. Similarly, the term alkyl titanate is used synonymously herein with the terms titanium alkoxide and alkoxy titanium. Accordingly, a tetra alkyl zirconate is equivalent to a zirconium (IV) alkoxide and to a tetra alkoxy zirconium, and a tetra alkyl titanate is equivalent to a titanium (IV) alkoxide and a tetra alkoxy titanium.

[0043] When an alkyl zirconate is included, the alkyl zirconate can comprise a tetra C1-C8 alkyl zirconate, such as a tetra propyl zirconate and / or tetra butyl zirconate, such as a tetra n- propyl zirconate, tetra n-butyl zirconate, and / or tetra tert-butyl zirconate.

[0044] When an alkyl titanate is included, the alkyl titanate can comprise a tetra C1-C8 alkyl titanate, such as a tetra propyl titanate and / or tetra butyl titanate, such as a tetra n-propyl titanate, tetra n-butyl titanate and / or tetra tert-butyl titanate.

[0045] When a zirconium beta-diketone and / or titanium beta-diketone are included, the beta-diketone of the zirconium beta-diketone and / or of the titanium beta-diketone can include a conjugate base of an acetylacetone (i.e., pentane-2, 4-dione), hexane-2, 4-dione, heptane-2,4- dione, heptane-3, 5-dione, octane-2, 4-dione, nonane-2, 4-dione, and / or 5-methyl-hexane-2,4- dione.

[0046] When a zinc carboxylate and / or bismuth carboxylate are included, the carboxylate of the zinc carboxylate and / or bismuth carboxylate can comprise (i) a C1-C17 alkyl carboxylate (where the alkyl can be branched or unbranched / linear), such as an acetate, octoate (e.g., a linear octoate and / or an ethylhexanoate, such as a 2-ethylhexanoate), neodecanoate, stearate, and / or linoleate; and / or (ii) an aromatic carboxylate, such as a benzoate and / or naphthenate.

[0047] The catalyst system can essentially omit or completely omit zirconium and / or titanium catalysts that are in the form of octoates, neodecanates, or naphthanates. Moreover, while some examples include zinc and / or bismuth catalysts that are in the form of octoates,neodecanates, or naphthanates, other examples can essentially omit or completely omit zinc and / or bismuth catalysts that are in the form of octoates, neodecanates, or naphthanates.

[0048] The amine compound can include, for example, tertiary amines such as DABCO and / or trialkylamines, aliphatic polyamines such as triethylenetetramine and / or diethylenetriamine, heterocyclic amines such as imidazole and / or diazabicyclo compounds, alkanolamines such as di- or tri-methanolamine and di- or tri -ethanolamine, guanidine compounds, and combinations thereof. For example, the diazobicyclo compound can include l,8-Diazabicyclo[5.4.0]undec-7-ene (more commonly referred to as “DBU”) and / or 1,5- Diazabicyclo[4.3.0]non-5-ene (more commonly referred to as “DBN”). The guanidine compound can include a tetra alkylguanidine, such as a tetra methylguanidine.

[0049] Suitable zinc-based compounds are sold under the trade names K-KAT XK 614, K- KAT XK 648, K-KAT XK 661, and K-KAT 670 (available from King Industries, Norwalk, Conn.). Although the formulations of these products are not provided by the manufacturer, they are understood to include a zinc complex, such as a zinc carboxylate, blended with amine compounds such as those disclosed herein.

[0050] When an acid catalyst is included, the acid catalyst can comprise an acid catalyst known in the art, such as p-toluenesulfonic acid (PTSA), methanesulfonic acid (MSA), phosphoric acid, sulfuric acid, and / or boron trifluoride complexes.

[0051] When an amine-neutralized sulfonic acid catalyst is included, the amine-neutralized sulfonic acid catalyst can comprise an amine-neutralized aromatic sulfonic acid, such as an amine-neutralized loluenesulfonic acid (TSA), such as an amine-neutralized p-toluenesulfonic acid (pTSA). Additional or alternative aromatic sulfonic acids include benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-chlorobenzenesulfonic acid, p- nitrobenzenesulfonic acid, p-sulfobenzoic acid, and 2,4,6-trinitrobenzenesulfonic acid. An “amine-neutralized” catalyst refers to a catalyst with which an amine has been used to neutralize the catalyst. This process can involve the reaction of the amine with the acidic component of the catalyst to form a salt.

[0052] The coating composition may include 0.5 wt. % to 5 wt. % catalyst system, based on total weight of the composition (i.e., based on both the first and second parts combined when formulated as a two-part composition), such as 0.65 wt. % to 2.5 wt. %, or 0.75 wt. % to 1 wt. %, or within a range using any two of the foregoing values as endpoints.

[0053] When the catalyst system comprises an alkyl zirconate and a zinc -based compound, the zinc-based compound can be included in an amount, by weight, that is greater than an amount, by weight, of the alkyl zirconate, such as wherein the zinc-based compound is included in an amount that is 1.5 to 5, or 2 to 4, or 2.5 to 3 times greater, by weight, than the alkyl zirconate.

[0054] The use of both a first catalyst component and second catalyst component in the catalyst system can beneficially improve drying times relative to an otherwise similar composition that includes only the first catalyst component. As demonstrated in the Examples, when the first part and the second part are mixed to form a coating, the resulting coating can exhibit shorter dry times in at least one of set-to-touch, tack-free, hard-dry, or through-dry condition, according to ASTM D5895-20 Test Method A: Straight Line Drying Time at room temperature, as compared to an otherwise similar coating that includes only the first catalyst system.

[0055] For example, relative to an otherwise similar composition including only a zirconium-based compound, improved drying times can be achieved when the first catalyst component comprises a zirconium-based compound and the second catalyst component includes a zinc-based compound, a bismuth-based compound, a titanium-based compound, an acid catalyst, and / or an amine-neutralized catalyst, such as where the second catalyst component comprises a zinc-based compound and / or an amine-neutralized catalyst.

[0056] In another example, relative to an otherwise similar composition including only a bismuth-based compound, improved drying times can be achieved when the first catalyst component comprises a bismuth-based compound and the second catalyst component comprises a zirconium-based compound and / or an acid catalyst, such as where the second catalyst component comprises an acid catalyst.Other Coating Composition Components

[0057] The coating composition can include other components including, for example, pigments, water, rheological modifiers, plasticizers, antifoam agents, thixotropic agents, bituminous and asphaltic extenders, anti-settling agents, diluents, UV light stabilizers, air release agents, dispersing aids, biocides, and / or other coating composition components as known in the art.Additional Terms & Definitions

[0058] While certain aspects of the present disclosure have been described in detail, with reference to specific components and / or features, the descriptions are illustrative and are not to be construed as limiting the scope of the claimed coating composition or related methods.

[0059] Furthermore, it should be understood that for any given component of a described example, any of the possible alternatives listed for that component may generally be used individually or in combination with one another, unless implicitly or explicitly stated otherwise. The various features of a given example can be combined with and / or incorporated into other examples disclosed herein. Thus, disclosure of certain features relative to a specific example should not be construed as limiting application or inclusion of said features to the specific example. Rather, it will be appreciated that other examples can also include such features.

[0060] Any headings and subheadings used herein are for organizational purposes only and are not meant to be used to limit the scope of the description or the claims.

[0061] Any standard testing method discussed herein (e.g., ASTM) will be understood to refer to the most recent version of the testing method available at the time of filing of this disclosure, unless specified otherwise.

[0062] It will also be noted that, as used in this specification and the appended claims, the singular forms “a,” “an” and “the” do not exclude plural referents unless the context clearly dictates otherwise. Thus, for example, an embodiment referencing a singular referent may also include two or more such referents.

[0063] The coating composition disclosed herein should be understood as comprising / including disclosed components, and may therefore include additional components not specifically described. Optionally, the examples disclosed herein are essentially free or completely free of components that are not specifically described. That is, non-disclosed components may optionally be completely omitted or essentially omitted from the disclosed examples. For example, resins, crosslinking agents, and catalyst compounds not specifically disclosed herein may optionally be completely omitted or essentially omitted from the disclosed coating composition.

[0064] A composition that “essentially omits” or is “essentially free of’ a component may include trace amounts and / or non-functional amounts of the component. For example, an “essentially omitted” component may be included in an amount no more than 1%, no morethan 0.1%, no more than 0.05%, no more than 0.01%, or no more than 0.005%, by total weight of the composition.

[0065] A composition that “completely omits’’ or is “completely free of’ a component does not include a detectable amount of the component (i.e., does not include an amount above any inherent background signal associated with the testing instrument) when analyzed using standard coating composition analysis techniques such as, for example, chromatographic techniques (e.g., thin-layer chromatography (TLC), gas chromatography (GC), liquid chromatography (LC)), or spectroscopy techniques (e.g., Fourier transform infrared (FTIR) spectroscopy).Example Aspects

[0066] The following is a non-exhaustive list of example aspects of the disclosed composition:1. A composition formulated for forming an epoxy -polysiloxane coating, the composition comprising: a first part comprising(a) an epoxy resin, and(b) a silicone resin; a second part comprising an aminosilane; and a catalyst system included in the first part and / or second part, wherein the catalyst system comprises(a) a first catalyst component comprising(i) a zirconium-based compound,(ii) a zinc-based compound,(iii) a bismuth-based compound, and / or(iv) a titanium-based compound, and(b) a second catalyst component comprising(i) a metal catalyst different from the first catalyst component,(ii) an acid catalyst,(iii) an amine compound, such as a tertiary amine and / or alkanolamine, and / or(iv) an amine-neutralized catalyst.2. The composition of aspect 1, wherein- the first catalyst component comprises the zirconium-based compound and the second component comprises the metal catalyst different from the first catalyst component, or- the first catalyst component comprises the zirconium-based compound and the second component comprises the acid catalyst, or- the first catalyst component comprises the zirconium-based compound and the second component comprises the amine-neutralized catalyst, or- the first catalyst component comprises the zirconium-based compound and the second component comprises the amine compound, or- the first catalyst component comprises the zinc-based compound and the second component comprises the metal catalyst different from the first catalyst component, or- the first catalyst component comprises the zinc-based compound and the second component comprises the acid catalyst, or- the first catalyst component comprises the zinc-based compound and the second component comprises the aminc-ncutralizcd catalyst, or- the first catalyst component comprises the zinc-based compound and the second component comprises the amine compound, or- the first catalyst component comprises the bismuth-based compound and the second component comprises the metal catalyst different from the first catalyst component, or- the first catalyst component comprises the bismuth-based compound and the second component comprises the acid catalyst, or- the first catalyst component comprises the bismuth-based compound and the second component comprises the amine-neutralized catalyst, or- the first catalyst component comprises the bismuth-based compound and the second component comprises the amine compound, or- the first catalyst component comprises the titanium-based compound and the second component comprises the metal catalyst different from the first catalyst component, or- the first catalyst component comprises the titanium-based compound and the second component comprises the acid catalyst, or- the first catalyst component comprises the titanium-based compound and the second component comprises the amine-neutralized catalyst, or- the first catalyst component comprises the titanium-based compound and the second component comprises the amine compound.3. The composition of any preceding aspect, wherein the zirconium-based compound comprises an alkyl zirconate.4. The composition of any preceding aspect, wherein the zirconium-based compound comprises a zirconium beta-diketone.5. The composition of any preceding aspect, wherein the zinc-based compound comprises a zinc carboxylate.6. The composition of any preceding aspect, wherein the zinc-based compound is mixed with an amine compound.7. The composition of any preceding aspect, wherein the bismuth-based compound comprise a bismuth carboxylate.8. The composition of any preceding aspect, wherein the titanium-based compound comprises an alkyl titanate.9. The composition of any preceding aspect, wherein the titanium-based compound comprises a titanium beta-diketone.10. The composition of any preceding aspect, wherein amine-neutralized catalyst comprises an amine-neutralized sulfonic acid catalyst.1 1. The composition of any preceding aspect, wherein the amine compound comprises a tertiary amine.12. The composition of any preceding aspect, wherein the amine compound comprises an alkanolamine.13. The composition of any preceding aspect, wherein the metal catalyst different from the first catalyst component comprises a compound as defined in any of aspects 3 to 9.14. The composition of any preceding aspect, wherein the composition essentially omits or completely omits tin compounds.15. The composition of any preceding aspect, wherein the alkyl zirconate comprises a tetra C1-C8 alkyl zirconate, such as a tetra propyl zirconate and / or tetra butyl zirconate, such as a tetra n-propyl zirconate, tetra n-butyl zirconate, and / or tetra tert-butyl zirconate.16. The composition of any preceding aspect, wherein the alkyl titanate comprises a tetra C1-C8 alkyl titanate, such as a tetra propyl titanate and / or tetra butyl titanate, such as a tetra n- propyl titanate, tetra n-butyl titanate, and / or tetra tert-butyl titanate.17. The composition of any preceding aspect, wherein the beta-diketone of the zirconium beta-diketone and / or the titanium beta-diketone comprises a conjugate base of an acetylacetone, hexane-2, 4-dione, heptane-2, 4-dione, heptane-3, 5-dione, octane-2, 4-dione, nonane-2, 4-dione, and / or 5-methyl-hexane-2, 4-dione.18. The composition of any preceding aspect, wherein the carboxylate of the zinc carboxylate and / or bismuth carboxylate comprises: a Cl -Cl 7 alkyl carboxylate, such as an acetate, octoate, neodecanoate, stearate, and / or linoleate; and / or an aromatic carboxylate, such as a benzoate and / or naphthenate.19. The composition of any preceding aspect, wherein the amine-neutralized sulfonic acid catalyst comprises an amine-neutralized aromatic sulfonic acid, such as an amine-neutralized toluenesulfonic acid (TSA), such as an amine-neutralized p-toluenesulfonic acid (pTSA).20. The composition of any preceding aspect, wherein the catalyst system comprises an alkyl zirconate and a zinc -based compound, wherein the zinc -based compound is included in an amount, by weight, that is greater than an amount, by weight, of the alkyl zirconate, such as wherein the zinc -based compound is included in an amount that is 1.5 to 5, or 2 to 4, or 2.5 to 3 times greater, by weight, than the alkyl zirconate.21. The composition of any preceding aspect, wherein the catalyst system is included in the second part of the composition.22. The composition of any preceding aspect, wherein: the epoxy resin is included at 10 wt. % to 60 wt. %, based on total weight of the composition; the silicone resin is included at 15 wt. % to 60 wt. %, based on total weight of the composition; the aminosilane is included at 5 wt. % to 40 wt. %, based on total weight of the composition; and / orthe catalyst system is included at 0.5 wt. % to 5 wt. %, based on total weight of the composition.23. The composition aspect 22, wherein the epoxy resin is included a 15 wt. % to 50 wt. %, based on total weight of the composition.24. The composition aspect 22, wherein the epoxy resin is included at 20 wt. % to 40 wt. %, or 25 wt. % to 30 wt. %, based on total weight of the composition.25. The composition aspect 22, wherein the epoxy resin is included at 25 wt. % to 30 wt. %, based on total weight of the composition.26. The composition of any of aspects 22 to 25, wherein the silicone resin is included at 20 wt. % to 50 wt. %, based on total weight of the composition.27. The composition of any of aspects 22 to 25, wherein the silicone resin is included at 25 wt. % to 40 wt. %, based on total weight of the composition.28. The composition of any of aspects 22 to 25, wherein the silicone resin is included at 30 wt. %, based on total weight of the composition.29. The composition of any of aspects 22 to 28, wherein the aminosilane is included at 7.5 wt. % to 35 wt. %, based on total weight of the composition.30. The composition of any of aspects 22 to 28, wherein the aminosilane is included at 10 wt. % to 30 wt. %, based on total weight of the composition.31. The composition of any of aspects 22 to 28, wherein the aminosilane is included at 12.5 wt. % to 25 wt., based on total weight of the composition.32. The composition of any of aspects 22 to 28, wherein the aminosilane is included at 15 wt. % to 20 wt. %, based on total weight of the composition.33. The composition of any of aspects 22 to 32, wherein the catalyst system is included at 0.65 wt. % to 2.5 wt. %, based on total weight of the composition.34. The composition of any of aspects 22 to 32, wherein the catalyst system is included at 0.75 wt. % to 1 wt. %, based on total weight of the composition.35. The composition of any preceding aspect, wherein the aminosilane comprises an amine functional group reactive with the epoxy resin and one to three groups reactive with the silicone resin, such as wherein the aminosilane is an amino functional alkoxy silane of the formula:wherein X is a (divalent) alkyl, alkoxyalkyl, or alkylaminoalkyl and has 7 carbons or less, and wherein each R is independently an alkyl, hydroxyalkyl, alkoxyalkyl, or hydroxyalkoxyalkyl and each R has 6 carbons or less, such as wherein each R is independently methyl or ethyl.36. The composition of aspect 35, wherein the aminosilane comprises an aminoalkyl trialkoxy silane, such as an aminopropyl trialkoxy silane, such as an aminopropyl trimethoxy silane and / or aminopropyl triethoxy silane.37. The composition of any preceding aspect, wherein the epoxy resin comprises an aromatic or cycloaliphatic epoxide resin, such as a diglycidyl ether of bisphenol or hydrogenated bisphenol, such as a diglycidyl ether of bisphenol A or hydrogenated diglycidyl ether of bisphenol A.38. The composition of any preceding aspect, wherein functional groups of the poly siloxane comprise C1-C5 alkyl, C1-C5 alkoxy, and / or aryl, such as wherein the polysiloxane comprises methyl, methoxy, and / or phenyl functional groups.39. The composition of any one of aspects 1-38, wherein the first catalyst component comprises a zirconium-based compound, such as an alkyl zirconate and / or a zirconium betadiketone, and wherein the second catalyst component comprises: a zinc -based compound, such as a zinc carboxylate; a bismuth-based compound, such as a bismuth carboxylate; a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone; an acid catalyst; and / or an amine-neutralized catalyst, such as an amine-neutralized sulfonic acid catalyst, such as wherein the second catalyst component comprises a zinc-based compound and / or an amine-neutralized catalyst.40. The composition of any one of aspects 1-38, wherein the first catalyst component comprises a bismuth-based compound, such as a bismuth carboxylate, and wherein the second catalyst component comprises: a zirconium-based compound, such as an alkyl zirconate and / or a zirconium betadiketone; and / or an acid catalyst, such as wherein the second catalyst component comprises an acid catalyst.41. The composition of any one of aspects 1-38, wherein the first catalyst component comprises a titanium-based compound, such as an alkyl titanate and / or a titanium betadiketone, and wherein the second catalyst component comprises: a zirconium-based compound, such as an alkyl zirconate and / or a zirconium betadiketone; a zinc -based compound, such as a zinc carboxylate; and / or an acid catalyst, such as wherein the second catalyst component comprises a zirconium-based compound and / or an acid catalyst.42. The composition of any one of aspects 39-41 , wherein when the first part and the second part are mixed to form a coating, the resulting coating exhibits shorter dry time in at least one of set-to-touch, tack-free, hard-dry, or through-dry condition, as tested under ASTM D5895- 20 Test Method A: Straight Line Drying Time at room temperature, as compared to an otherwise similar coating that includes only the first catalyst system.43. A coating composition formed by mixing the first part and the second part of the composition of any preceding aspect.EXAMPLES

[0067] A series of two-part coating compositions were prepared using the components listed in Table 1.Table 1: Components used in Example Compositions

[0068] The epoxy and polysiloxane mixture forming “Part A” was the base pack portion of the two-part composition sold under the trade name PSX® 700 (available from PPG Industries Ohio, Inc.), which lists the ingredients as shown in Table 2. Variations within the listed ranges are not expected to affect the test results so long as amounts are held substantially consistent across compared examples, as was the case with the presently disclosed examples. The Part A component also included minor amounts of other standard coating composition components that were not determined as relevant to the test results. The 3- aminopropyltrialkoxysilane used in these examples consisted of 3-aminopropyltriethoxysilane and 3-aminopropyltrimethoxysilane at a weight ratio of 2 to 2.5.Table 2: Components of Base / Resin Mixture used as “Part A"

[0069] The Polycat DBU product is DBU and is available from EVONIK Co., Essen, Germany. The other products are available from King Industries, Norwalk, Connecticut. The bismuth carboxylate complex sold under the trade name K-KAT XK-651 is not characterized by the manufacturer, but functions in testing similar to bismuth carboxylates in which the carboxylates are in the form of octoates, neodecanoates, and / or naphthenates, and is therefore treated as such for purposes of these examples. The zinc complexes sold under the trade names K-KAT XK-614, K-KAT XK-648, K-KAT XK-661, and K-KAT 670 are not characterized by the manufacturer, but such products function in testing similar to zinc complexes in which zinc is complexed with common carboxylates such as octoates, neodecanoates, and / or naphthenates in a blend with common amine catalysts such as a tertiary amine, bicyclic tertiary amine, and / or alkanolamine, and are therefore treated as such for purposes of these examples. The acid catalyst sold under the trade name Nacure XC311 is not characterized by the manufacturer, but functions in testing similar to an acid catalyst such as p-toluenesulfonic acid (PTSA), methanesulfonic acid (MSA), phosphoric acid, sulfuric acid, and / or boron trifluoride complexes, and is therefore treated as such for purposes of these examples. The amine- neutralized catalyst sold under the trade name Nacure 2107 is an amine-neutralized p- toluenesulfonic acid (pTSA).

[0070] Examples 1 -21 were formulated as shown in Tables 3A-3E. Example 1 included a tin-based catalyst and was the comparative example. All component values represent wt. % based on total weight of the composition.Table 3 A: Example FormulationsTable 3B: Example Formulations ContinuedTable 3C: Example Formulations ContinuedTable 3D: Example Formulations ContinuedTable 3E: Example Formulations Continued

[0071] The Examples were subjected to standardized drying tests according to ASTM D5895-20, Test Method A: Straight Line Drying Time. Testing was conducted at room temperature (75° F / 23.9° C) and 40% to 44% relative humidity. Four stages of the drying process were defined as follows:

[0072] (1) Set-to-touch condition: is reached when the film has solidified sufficiently that it no longer flows nor sticks to a finger that lightly touches it. In ASTM D5895-20, the set-to- touch time is reached when a pear-shaped depression appears in the film when the film stops flowing over the path of the recorder’ s stylus and leaves a track in the film revealing the glass substrate.

[0073] (2) T ack-free condition: is reached when the film surface has cured so that film docs not adhere to very light objects placed on it. In ASTM D5895-20, the tack-free time is reached when the continuous track in the film ceases, and the stylus starts to tear the film or leave a ragged / sharp-edged groove as it first begins to climb over the film.

[0074] (3) Dry-hard time condition: is reached when the film is not displaced nor is any noticeable mark left by pinching the panels between the thumb on the film and forefinger with a relatively strong force. In ASTM D5895-20, the dry-hard time is reached where the stylus has risen out of the film and rides on the surface, leaving only a mark without disrupting the body of the film.

[0075] (4) Dry-through time condition: is reached when the film has solidified so completely that a large, twisting force can be applied without distorting the film. In ASTM D5895-20, the dry-through time is reached when the stylus no longer leaves any visible mark on the film.

[0076] Results of the drying time testing for the room temperature condition are shown in Tables 4A-4F and Figures 2A-2F. All values are shown in hours.

[0077] The room temperature drying time results for the Examples that used single catalysts are shown in Table 4A and Figure 2 A.Table 4A: Drying Times for Examples Using Single Catalysts

[0078] The room temperature drying time results for the Examples that used a titanium- based catalyst (TNBT) mixed with other catalysts are shown in Table 4B and Figure 2B.Table 4B: Drying Times for Examples Using Titanium-Based Catalyst (TNBT)

[0079] As shown, while TNBT alone as catalyst (Example 10) performed best for drying times, coatings comprising the TNBT catalyst exhibited poorer mechanical and chemical properties in separate testing (weathering testing based on ASTM D4587 cycle 2 with color change evaluated according to ASTM D2244; abrasion resistance according to ASTM D-4060; chemical resistance according to ASTM D-1308). TNBT with TNBZ (Example 6) exhibited results substantially similar to the tin-based control. TNBT with acid catalyst (Example 16) also exhibited suitable drying times.

[0080] The room temperature drying time results for the Examples that used a zirconium- based catalyst (TNBZ) are shown in Table 4C and Figure 2C.Table 4C: Drying Times for Examples Using Zirconium-Based Catalyst (TNBZ)

[0081] These results demonstrate that a zirconium-based catalyst such as TNBZ has effective synergy with zinc -based catalysts. In all cases (Examples 2-5), the zinc -based compounds improved at least the hard- and through-drying times relative to TNBZ as a single catalyst (Example 8). As already mentioned, the combination of TNBT and TNBZ (Example 6) was also effective.

[0082] The room temperature drying time results for the Examples that used another zirconium-based catalyst (TNPZ) are shown in Table 4D and Figure 2D.Table 4D: Drying Times for Examples Using Zirconium-Based Catalyst (TNPZ)

[0083] As with TNBZ, combining TNPZ with a zinc-based compound (Example 7) resulted in improved drying times relative to TNPZ alone (Example 11). Combining TNPZ with a bismuth catalyst (Example 14), or with an acid catalyst (Example 17), or with both (Example 19) did not improve the through-dry time, but improved the other drying time stagesrelative to TNPZ alone. Combining TNPZ with a base catalyst (Example 18) significantly improved all drying time stages relative to TNPZ alone.

[0084] The room temperature drying time results for the Examples that used a bismuth- based catalyst are shown in Table 4E and Figure 2E.Table 4E: Drying Times for Examples Using Bismuth-Based Catalyst (Bi)

[0085] Combining the bismuth catalyst with TNPZ (Example 14) or with TNPZ and acid catalyst (Example 19) improved all drying time stages relative to bismuth catalyst alone (Example 12) except through-dry. Combining the bismuth catalyst with acid catalyst (Example 15) improved all drying time stages relative to bismuth alone and even performed better than the tin-based control except for hard-dry time. While these differences can partly be explained by the slightly higher overall amount of catalyst in Examples 13-15 and 19 compared to Example 12, the magnitude of the differences suggests they are least partially also due to the inclusion of multiple catalysts.

[0086] The room temperature drying time results for Examples that included an amine compound catalyst are shown in Table 4F and Figure 2F.Table 4F: Drying Times for Examples Using Amine Catalyst

[0087] As shown, while the DBU catalyst alone (Example 20) exhibited relatively long drying times, the combination of a zinc -based compound with DBU (Example 21) improved drying times relative to the DBU catalyst alone.

Claims

CLAIMS1. A composition formulated for forming an epoxy -polysiloxane coating, the composition comprising: a first part comprising(a) an epoxy resin, and(b) a silicone resin; a second part comprising an aminosilane; and a catalyst system comprising(a) a first catalyst component comprising(i) a zirconium-based compound, such as an alkyl zirconate and / or a zirconium beta-diketone,(ii) a zinc-based compound, such as a zinc carboxylate,(iii) a bismuth-based compound, such as a bismuth carboxylate, and / or(iv) a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone, and(b) a second catalyst component comprising(i) a metal catalyst different from the first catalyst component,(ii) an acid catalyst,(iii) an amine compound, such as a tertiary amine and / or alkanolamine, and / or(iv) an amine-neutralized catalyst, such as an amine-neutralized sulfonic acid catalyst.

2. The composition of claim 1, wherein the composition essentially omits or completely omits tin compounds.

3. The composition of any preceding claim, wherein the alkyl zirconate comprises a tetra C1-C8 alkyl zirconate, such as a tetra propyl zirconate and / or tetra butyl zirconate, such as a tetra n-propyl zirconate, tetra n-butyl zirconate, and / or tetra tert-butyl zirconate.

4. The composition of any preceding claim, wherein the alkyl titanate comprises a tetra C1-C8 alkyl titanate, such as a tetra propyl titanate and / or tetra butyl titanate, such as a tetra n- propyl titanate, tetra n-butyl titanate, and / or tetra tert-butyl titanate.

5. The composition of any preceding claim, wherein the beta-diketone of the zirconium beta-diketone and / or the titanium beta-diketone comprises a conjugate base of an acetylacetone, hexane-2, 4-dione, heptane-2, 4-dione, heptane-3, 5-dione, octane-2, 4-dione, nonane-2, 4-dione, and / or 5-methyl-hexane-2, 4-dione.

6. The composition of any preceding claim, wherein the carboxylate of the zinc carboxylate and / or bismuth carboxylate comprises: a Cl -Cl 7 alkyl carboxylate, such as an acetate, octoatc, ncodccanoatc, stearate, and / or linoleate; and / or an aromatic carboxylate, such as a benzoate and / or naphthenate.

7. The composition of any preceding claim, wherein the amine-neutralized sulfonic acid catalyst comprises an amine-neutralized aromatic sulfonic acid, such as an amine-neutralized toluenesulfonic acid (TSA), such as an amine-neutralized p-toluenesulfonic acid (pTSA).

8. The composition of any preceding claim, wherein the catalyst system comprises an alkyl zirconate and a zinc -based compound, wherein the zinc -based compound is included in an amount, by weight, that is greater than an amount, by weight, of the alkyl zirconate, such as wherein the zinc-based compound is included in an amount that is 1.5 to 5, or 2 to 4, or 2.5 to 3 times greater, by weight, than the alkyl zirconate.

9. The composition of any preceding claim, wherein the catalyst system is included in the second part of the composition.

10. The composition of any preceding claim, wherein: the epoxy resin is included at 10 wt. % to 60 wt. %, such as 15 wt. % to 50 wt. %, or 20 wt. % to 40 wt. %, or 25 wt. % to 30 wt. %, based on total weight of the composition; the polysiloxane is included at 15 wt. % to 60 wt. %, such as 20 wt. % to 50 wt. %, or 25 wt. % to 40 wt. %, or 30 wt. %, based on total weight of the composition; the aminosilane is included at 5 wt. % to 40 wt. %, such as 7.5 wt. % to 35 wt. %, or 10 wt. % to 30 wt. %, or 12.5 wt. % to 25 wt. %, or 15 wt. % to 20 wt. %, based on total weight of the composition; and / or the catalyst system is included at 0.5 wt. % to 5 wt. %, such as 0.65 wt. % to 2.5 wt. %, or 0.75 wt. % to 1 wt. %, based on total weight of the composition.

11. The composition of any preceding claim, wherein the aminosilane is an amino functional alkoxy silane of the formula:wherein X is a divalent alkyl, alkoxyalkyl, or alkylaminoalkyl and has 7 carbons or less, and wherein each R is independently an alkyl, hydroxyalkyl, alkoxyalkyl, or hydroxyalkoxyalkyl and each R has 6 carbons or less, such as wherein each R is independently methyl or ethyl.

12. The composition of claim 11, wherein the aminosilane comprises an aminoalkyl trialkoxy silane, such as an aminopropyl tri alkoxy silane, such as an aminopropyl trimethoxy silane and / or aminopropyl tricthoxy silane.

13. The composition of any preceding claim, wherein the epoxy resin comprises an aromatic or cycloaliphatic epoxide resin, such as a diglycidyl ether of bisphenol or hydrogenated bisphenol, such as a diglycidyl ether of bisphenol A or diglycidyl ether of hydrogenated bisphenol A diglycidyl ether.

14. The composition of any preceding claim, wherein functional groups of the polysiloxane comprise C1-C5 alkyl, C1-C5 alkoxy, and / or aryl, such as wherein the polysiloxane comprises methyl, methoxy, and / or phenyl functional groups.

15. The composition of any preceding claim, wherein the amine compound comprises a diazabicyclo compound.

16. The composition of any one of claims 1-15, wherein the first catalyst component comprises a zirconium-based compound, such as an alkyl zirconate and / or a zirconium betadiketone, and wherein the second catalyst component comprises: a zinc -based compound, such as a zinc carboxylate; a bismuth-based compound, such as a bismuth carboxylate; a titanium-based compound, such as an alkyl titanate and / or a titanium beta-diketone; an acid catalyst; an amine compound, such as a tertiary amine and / or alkanolamine; and / or an amine-neutralized catalyst, such as an amine-neutralized sulfonic acid catalyst, such as wherein the second catalyst component comprises a zinc -based compound and / or an amine-neutralized catalyst.

17. The composition of any one of claims 1-15, wherein the first catalyst component comprises a bismuth-based compound, such as a bismuth carboxylate, and wherein the second catalyst component comprises: a zirconium-based compound, such as an alkyl zirconate and / or a zirconium betadiketone; and / oran acid catalyst, such as wherein the second catalyst component comprises an acid catalyst.

18. The composition of any one of claims 1-15, wherein the first catalyst component comprises a titanium-based compound, such as an alkyl titanate and / or a titanium betadiketone, and wherein the second catalyst component comprises: a zirconium-based compound, such as an alkyl zirconate and / or a zirconium betadiketone: a zinc -based compound, such as a zinc carboxylate and / or zinc-amine complex; and / or an acid catalyst, such as wherein the second catalyst component comprises a zirconium-based compound and / or an acid catalyst.1 . The composition of any one of claims 16-18, wherein when the first part and the second part are mixed to form a coating, the resulting coating exhibits shorter dry time in at least one of set-to-touch, tack-free, hard-dry, or through-dry condition, as tested under ASTM D5895- 20 Test Method A: Straight Line Drying Time at room temperature, as compared to an otherwise similar coating that includes only the first catalyst component.

20. A coating composition formed by mixing the first part and the second part of the composition of any preceding claim.

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