Coating compositions that cure at low temperatures

Abstract

Coating compositions that include (a) a polymer obtained from components containing (i) a compound that includes functional groups reactive with a carboxylic acid or corresponding anhydride and (ii) a compound that includes carboxylic acid or corresponding anhydride functional groups, where the polymer includes carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and (b) a crosslinking agent containing functional groups reactive with the carboxylic acid or anhydride groups in the polymer. The polymer (a) can have an acid value of at least 10, such as at least 12, at least 14, at least 15 or at least 20 and can range from 10 to 100, such as 12 to 75, 14 to 60, 15 to 100 or 15 to 50 mg KOH per gram of polymer based on the total resin solids of the polymer (a).

Description

COATING COMPOSITIONS THAT CURE AT LOW TEMPERATURES CROSS-REFERENCE TO RELATED APPLICATION

[0001] This application claims the benefit of priority of U.S. Provisional Application 63 / 601,586 filed under 35 U.S.C.119 on November 21, 2023, titled “Coating Compositions That Cure At Low Temperatures”, which is incorporated herein by reference. FIELD

[0002] This disclosure generally relates to coating compositions that cure at relatively low temperatures for application to a substrate, methods of forming coating layers and systems therefor. BACKGROUND

[0003] Coatings can be applied to a wide variety of substrates to provide color and other visual effects, corrosion resistance, abrasion resistance, chemical resistance, and the like. In addition, various types of coatings, such as coatings applied to packaging and automotive substrates, can be formed from compositions that can be baked and formed at relatively low cure temperatures. SUMMARY

[0004] The present disclosure is directed to coating compositions, that include: (a) a polymer obtained from components containing (i) a compound that includes functional groups reactive with a carboxylic acid or corresponding anhydride and (ii) a compound that includes carboxylic acid or corresponding anhydride functional groups, where the polymer includes carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and (b) a crosslinking agent containing functional groups reactive with the carboxylic acid or anhydride groups in the polymer.

[0005] The polymer (a) can have an acid value of at least 10, such as at least 12, at least 14, at least 15 or at least 20 and can be up to 100, such as up to 75, up to 60, or up to 50 mg KOH pergram of polymer and can range from 10 to 100, such as 12 to 75, 14 to 60, 15 to 100 or 15 to 50 mg KOH per gram of polymer based on the total resin solids of the polymer (a). DETAILED DESCRIPTION

[0006] For the purposes of the following detailed description, it is to be understood that the disclosure may assume various alternative variations and step sequences, except where expressly specified to the contrary. Moreover, other than in any operating examples, or where otherwise indicated, all numbers expressing, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term “about”. Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties to be obtained by the present disclosure. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. I. Definitions

[0007] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the disclosure are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard variation found in their respective testing measurements.

[0008] Also, it should be understood that any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of “1 to 10” is intended to include all sub-ranges between (and including) the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10.

[0009] In this application, the use of the singular includes the plural and plural encompasses the singular, unless specifically stated otherwise. In addition, in this application, the use of “or” means “and / or” unless specifically stated otherwise, even though “and / or” may be explicitly used in certain instances. Further, in this application, the use of “a” or “an” means “at least one” unlessspecifically stated otherwise. For example, “a” polymer, “an” acid, and the like refer to one or more of any of these items.

[0010] Unless otherwise indicated, ambient conditions of temperature and pressure are ambient temperature (20-25 °C) and standard pressure of 101.3 kPa (1 atm) at a relative humidity in the air of 35% to 75%.

[0011] As used herein, “acid value” refers to a quantified acidity of a given chemical substance based on the milligrams (mg) of potassium hydroxide (KOH) required to neutralize the acidic constituents in 1 gram of the non-volatile components according to ASTM D 4662-15 (2015). Theoretical or calculated theoretical values refer to the value expected to be obtained if the test method was performed.

[0012] As used herein, “actinic radiation” refers to electromagnetic radiation capable of initiating photochemical reactions, such as, without limitation, UVB and UVC radiation (180–315 nm) and near-UV radiant energy in the 320–380 nm (or 400 nm) range.

[0013] As used herein, the term “ASTM” refers to publications of ASTM International, West Conshohocken, PA.

[0014] As used herein, the term “addition polymer” refers to a polymer that forms by simple linking of monomers without the co-generation of other products, as a nonlimiting example, by free radical polymerization.

[0015] As used herein, the term “aqueous dispersion” refers to particles separated from each other in a water-based system where the interface between the water, as the dispersion medium, and the surface of the dispersed particles is generated resulting in water in a continuous phase and the particles as a dispersed phase.

[0016] As used herein, the terms “backbone” and “polymer backbone” refer to the main chain of monomeric repeat units making up the main chain of a polymer.

[0017] As used herein, the term “basecoat” refers to a coating layer that is applied onto a primer coat, another basecoat layer; and / or directly onto a substrate, optionally including components (such as colorants) that impact the color and / or provide other visual impact. A clearcoat may be applied over the basecoat layer.

[0018] As used herein the term “clearcoat” refers to a coating layer that is at least substantially transparent, tinted or fully transparent and often does not include a colorant. The term “substantially transparent” refers to a coating, wherein a surface beyond the coating layer is at leastpartially visible to the naked eye when viewed through the coating. The term “fully transparent” refers to a coating, wherein a surface beyond the coating layer is completely visible to the naked eye when viewed through the coating.

[0019] As used herein, the term “coating” refers to the finished product resulting from applying one or more coating compositions to a substrate and forming the coating, as a nonlimiting example by curing. A primer coat, basecoat or color coat layer and clear coat layer can include part of a coating. As used herein, the term “coating layer” is used to refer to the result of applying one or more coating compositions on a substrate in one or more applications of such one or more coating compositions. As a nonlimiting example, a single coating layer, referred to as a “color coat” or “topcoat” can be used to provide the function of both a basecoat and a clearcoat and can include the result of two or more applications of a color coat coating composition.

[0020] As used herein, the term “coil coating application” refers to a coil coating process where a metal coil is first unwound, cleaned and pre-treated, a coating composition applied on a flat continuous sheet, heat cured at, as a nonlimiting example from 140 °C to 240 °C, cooled and rewound for shipment.

[0021] As used herein, the term “colorant” refers to any substance that imparts color and / or other opacity and / or other visual effect to a coating composition and can include, without limitation dyes and pigments.

[0022] As used herein, the transitional term “comprising” (and other comparable terms, e.g., “containing” and “including”) is “open-ended” and open to the inclusion of unspecified matter. Although described in terms of “comprising”, the terms “consisting essentially of’ and “consisting of’ are also within the scope of the disclosure. As used herein, “consisting essentially of’ means the specified materials or steps listed as well as those that do not materially affect the basic characteristics disclosed; “consisting of’ means only the specified materials or steps.

[0023] As used herein, the term “core-shell particle”, and similar terms, refer to polymeric molecules that contain moieties that are chemically different in how they relate to their environment or a continuous phase and orient such that a shell portion encapsulates at least a portion of a core portion that may be immiscible in the environment or continuous phase, such as water. As a nonlimiting example, a polymer can include hydrophobic groups (groups in a polymer that aggregate in an aqueous solution in order to exclude water molecules) that constitute a coreportion of the polymer and hydrophilic groups that constitute a shell portion of the polymer in an aqueous continuous phase.

[0024] As used herein, the terms “crosslinker” and “crosslinking agent”, used interchangeably, refers to a molecule or polymer containing functional groups that are reactive with the crosslinking-functional group of the polymers and / or resins in the coating composition.

[0025] As used herein, the term “crosslinking-functional group" refers to functional groups that are positioned in the backbone of a polymer, often, in a group pendant from the backbone of the polymer, terminally positioned on the backbone of the polymer, or combinations thereof, wherein such functional groups are capable of reacting with other crosslinking-functional groups or separate crosslinking agents during curing to produce a crosslinked coating.

[0026] As used herein, the terms “curable”, “cure”, and the like, as used in connection with a coating composition, refer to at least a portion of the components that make up the coating composition are polymerizable and / or crosslinkable, via a condensation reaction, when, as a nonlimiting example, exposed to temperatures above ambient or ultraviolet radiation.

[0027] As used herein, the term “cure at low temperature” and similar terms refer to curing a coating composition at temperatures below 110 °C, such as from 70 °C to 110 °C, from 75 °C to 105 °C or from 80 °C to 100 °C.

[0028] As used herein the term “dye” refers to a colored substance, in many cases an organic compound, that can chemically bond to a substrate or another component in a coating composition.

[0029] As used herein, the term “film-forming” materials refers to film-forming constituents of a coating composition and can include polymers, resins, crosslinking agents or any combination thereof that are film-forming constituents of the coating composition. Film-forming materials can be dried or cured, as nonlimiting examples, by exposure to elevated temperatures, actinic radiation or under ambient conditions.

[0030] As used herein, the terms “hydroxyl value”, “OH value” refer to the amount of hydroxyl groups in a sample as determined EN ISO 4629-2 (2016). Theoretical or calculated theoretical values refer to the value expected to be obtained if the test method was performed.

[0031] Unless otherwise indicated, as used herein, the term "molecular weight" refers to a weight average molecular weight as determined by gel permeation chromatography (GPC) using appropriate polystyrene standards. If a number average molecular weight is specified, the weight is determined in the same GPC manner, while calculating a number average from the thus obtainedpolymer molecular weight distribution data. “Number average molecular weight” refers to the total weight of a material divided by the number of molecules in the material and can be determined using gel permeation chromatography. Unless otherwise noted, “number average molecular weight” is in units of g / mol.

[0032] As used herein, the term “monocoat” refers to a coating layer, such as a topcoat, used to finish a surface of a substrate and not followed by the application of another coating layer, such as a clearcoat.

[0033] As used herein the term “monomer” refers to a molecule that can react together with other monomer molecules, through polymerization processes, to form a larger polymer chain or three-dimensional network.

[0034] As used herein the terms “multi component”, “multi-K” and “multi-pack” refers to a coating composition that includes two or more components, such as a first component that includes a crosslinkable resin and a second component that contains crosslinking agents. The multi-K composition can include additional components that may or may not include crosslinkable resins or crosslinking agents. The components are maintained separately until just prior to use. The crosslinkable resins and crosslinking agents are capable of reacting when combined to form a thermoset composition.

[0035] As used herein, the term “olefinic group” refers to a moiety in a molecule made up of hydrogen and carbon that contains one or more pairs of carbon atoms linked by a double bond.

[0036] As used herein the terms “one component”, “1-K” and “1-pack” refer to a coating composition where all of the coating components are maintained in the same package after manufacture, during shipping and storage and are maintained in the same container after manufacture, during storage, and the like, and may remain stable (do not react) for longer than 1 month at conditions of 40-120 °F (4-49 °C) at 0-95% relative humidity, such as longer than 3 months, longer than 6 months, longer than 9 months, or longer than 12 months.

[0037] As used herein, the term “organic solvent” refers to carbon-based substances capable of dissolving or dispersing other substances.

[0038] As used herein, the term “pigment” refers to a colored material, often an inorganic compound, that is completely or nearly insoluble, no more than 0.02 g / dl in a solvent at ambient conditions.

[0039] As used herein the prefix “poly” refers to two or more. As a nonlimiting example, a polyisocyanate refers to a compound that includes two or more isocyanate groups and a polyol refers to a compound that includes two or more hydroxyl groups.

[0040] As used herein, the term “polyester” refers to polymers that contain ester functional groups in one or more repeat units of the polymer backbone.

[0041] As used herein, the term “polyether” refers to polymers that contain monomers joined together by ether linkages along the polymer backbone and that can, without limitation, be polyols.

[0042] As used herein, the term “polyisocyanate” refers to compound having two or more isocyanate groups, such as two, three or four isocyanate groups and can include blocked (or capped) polyisocyanates as well as unblocked polyisocyanates.

[0043] As used herein, the term “polymer” includes homopolymers (formed from one monomer) and copolymers that are formed from two or more different monomers or that include two or more distinct repeat units. Further, the term "polymer" includes prepolymers, and oligomers.

[0044] As used herein, “polyol” refers to a compound having two or more hydroxyl groups, such as two, three or four hydroxyl groups.

[0045] As used herein, the term “precision application” refers to applying coating compositions using high efficiency applicator devices that can enable a coating composition to be applied over at least a portion of a substrate without overspray.

[0046] As used herein, the terms “primer coat” and “primer coating layer” refer to an undercoating layer that can be applied onto a substrate in order to prepare the surface for application of a protective or decorative coating composition.

[0047] As used herein, the term “resin solids” refers to the solid, organic components that make up the binder or film-forming components of the composition, excluding inorganic components such as pigments and fillers. As used herein, a weight percentage based on “resin solids” refers to an amount of a component based on a total weight of the binder or film-forming components of a composition.

[0048] As used herein the term “self-emulsifying polymer” and similar terms refers to a polymer, that when added to water, will form an emulsion without the use of other surface-active materials, such as surfactants.

[0049] As used herein, the term “substrate” refers to an article surface to be coated and can refer to a coating layer has been previously disposed on an article, which is also considered a substrate.

[0050] As used herein, the term “thermoset” refers to a polymer or resin that has functional groups that react with functional groups in a crosslinking agent or another polymer or molecule to form a network material, irreversibly transforming the “soft” polymer to a more rigid form. Thermosetting in many cases refers to resins that “set” irreversibly upon curing or crosslinking, wherein the polymer chains of the resins are joined together by covalent bonds. Once cured or crosslinked, a thermosetting resin will not melt upon the application of heat and is insoluble in solvents.

[0051] As used herein the term “thermoplastic” refers to polymers and resins that are not joined by covalent bonds and, thereby, can undergo liquid flow upon heating and can be soluble in certain solvents.

[0052] As used herein the term “topcoat” refers to an uppermost coating that is deposited over another coating layer, such as a basecoat, to provide a protective and / or decorative layer.

[0053] As used herein, the term “total solids” or “solids” or “solids content” refers to the solids content as determined in accordance with ASTM D2369 (2015).

[0054] As used herein the terms “two component”, “2-K” and “2-pack” refers to a coating composition that includes a first component that contains a crosslinkable resins and a second component that contains crosslinking agents, where the first and the second components are maintained separately until just prior to use. The crosslinkable resins and crosslinking agents are capable of reacting when combined to form a thermoset composition.

[0055] As used herein, the term “vehicle” is used in its broadest sense and includes all types of vehicles, such as but not limited to cars, mini vans, SUVs (sports utility vehicle), trucks, semi trucks; tractors, buses, vans, golf carts, motorcycles, bicycles, railroad cars, trailers, ATVs (all terrain vehicle); pickup trucks; heavy duty movers, such as, bulldozers, mobile cranes and earth movers; aircraft; boats; ships; and other modes of transport including, but not limited to all types of aircraft, spacecraft, watercraft, and ground vehicles.

[0056] As used herein, the term “volatile” refers to materials that are readily vaporizable under ambient conditions.

[0057] As used herein, the term “water miscible” refers to a material containing functional groups that allow it to mix in all proportions with water allowing a material to form a homogeneous aqueous solution or stable dispersion under ambient conditions. A material is immiscible in water when it does not mix with water under ambient conditions, as a nonlimiting example, oil and water.

[0058] As used herein, the term “water dispersible” refers to a material does not merge with water, or is water miscible, but forms colloidal system in water.

[0059] As used herein, the phrase “wt.%” refers to weight percent.

[0060] The present disclosure is directed to coating compositions, that include: (a) a polymer obtained from components containing (i) a compound that includes functional groups reactive with a carboxylic acid or corresponding anhydride and (ii) a compound that includes carboxylic acid or corresponding anhydride functional groups, where the polymer includes carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and (b) a crosslinking agent containing functional groups reactive with the carboxylic acid or anhydride groups in the polymer.

[0061] The polymer (a) can have an acid value of at least 10, such as at least 12, at least 14, at least 15 or at least 20 and can be up to 100, such as up to 75, up to 60, or up to 50 mg KOH per gram of polymer and can range from 10 to 100, such as 12 to 75, 14 to 60, 15 to 100 or 15 to 50 mg KOH per gram of polymer based on the total resin solids of the polymer (a).

[0062] The coating compositions according to this disclosure can cure at lower temperatures, which is desirable, as lower cure temperatures coincides with lower energy consumption for heating a coated article and lower carbon dioxide and carbon monoxide generation. II. Polymer (a)

[0063] The polymer (a) according to this disclosure can be obtained from components that include (i) a compound containing functional groups reactive with a carboxylic acid or corresponding anhydride and (ii) a compound containing carboxylic acid or corresponding anhydride functional groups. A. Compound (i)

[0064] The polymer (a) of the present disclosure may be formed from a polyol reactive with a carboxylic acid or corresponding anhydride (compound (i)).

[0065] The compound (i) can be a polyol that includes a first polyether and / or a polyester, where the functional groups reactive with a carboxylic acid or corresponding anhydride can include hydroxyl groups, amine groups and / or thiol groups.B. Compound (i) as the first polyether

[0066] When compound (i) is a polyether polyol, the hydroxyl groups of the polyol may be connected by a bridging group selected from: an alkylene group; an alkenylene group; an alkynylene group; or an arylene group.

[0067] Suitable polyether polyols include, but are not limited to, polyether glycols, such as poly(ethylene glycol), poly (propylene glycol), copolymers of ethylene glycol and propylene glycol, poly(butylene glycol), poly(oxytetramethylene) glycol, polyethers of C1to C10linear, branched or cyclic, aliphatic or aromatic diols, and polytetrahydrofuran and combinations thereof. C. Compound (i) as a polyester polyol

[0068] When compound (i) is a polyester polyol, it can be linear or branched and have a weight average molecular weight of from 500 to 5,000, such as from 1000 to 4500 or from 2000 to 4000 daltons. Polyester polyols can be made from mixtures of diols, triols, and dibasic carboxylic acids or their corresponding anhydrides using methods known in the art. A stoichiometric excess of hydroxyl groups over carboxylic acid functionality leads to a finished polymer is hydroxy- terminated.

[0069] Diols can include, but are not limited to, ethylene glycol; 1,2-propane diol; 1,3-propane diol; 1,2-butandiol; 1,3-butandiol; 1,4-butandiol; but-2-ene 1,4-diol; 2,3-butane diol; 2-methyl 1,3- propane diol; 2,2′-dimethyl 1,3-propanediol (neopentyl glycol); 1,5 pentane diol; 3-methyl 1,5- pentanediol; 2,4-diethyl 1,5-pentane diol; 1,6-hexane diol; 2-ethyl 1,3-hexane diol; diethylene glycol; triethylene glycol; dipropylene glycol; tripropylene glycol; 2,2,4-trimethyl pentane 1,3- diol; 1,4 cyclohexane dimethanol; tricyclodecane dimethanol; 2,2,4,4-tetramethyl cyclobutane 1,3-diol; isosorbide; 1,4-cyclohexane diol; 1,1′-isopropylidene-bis (4-cyclohexanol); and mixtures thereof.

[0070] Suitable diols may include polyether diols such as Terathane 200 and Terathane® 650 available from Invista or the PolyTHF polyether diols available from BASF.

[0071] Triols can include, but are not limited to, trimethylol propane, 1,2,6-hexantriol, glycerol, and combinations thereof.

[0072] Non limiting examples of dibasic carboxylic acids include glutaric acid, succinic acid, malonic acid, oxalic acid, trimellitic acid, phthalic acid, isophthalic acid, hexahydrophthalic acid, adipic acid, maleic acid, their corresponding anhydrides and combinations thereof. Non-limiting examples of such anhydrides include trimellitic anhydride, phthalic anhydride, maleic anhydride,succinic anhydride, malonic anhydride, oxalic anhydride, hexahydrophthalic anhydride, adipic anhydride, and combinations thereof. D. Compound (ii) that includes a carboxylic acid bonded directly to an aromatic ring

[0073] The polymer (a) according to this disclosure can be obtained from components that include compound (i) reacted with a compound (ii) containing carboxylic acid or corresponding anhydride functional groups bonded directly to an aromatic ring.

[0074] Compound (ii) can include, without limitation, phthalic acid, phthalic anhydride, trimellitic acid, trimellitic anhydride, pyromellitic acid, pyromellitic anhydride, mellitic acid, mellitic anhydride, naphthalic acid, and / or naphthalic anhydride. E. Composition of Polymer (a)

[0075] Polymer (a) can have an acid value of at least 10, such as at least 12, at least 14, at least 15 or at least 20 and can be up to 100, such as up to 75, up to 60, or up to 50 mg KOH per gram of polymer and can range from 10 to 100, such as 12 to 75, 14 to 60, 15 to 100 or 15 to 50 mg KOH per gram of polymer based on the total resin solids of the polymer (a). The acid value of Polymer (a) is typically at least high enough to provide at least water miscibility, under ambient conditions, to polymer (a).

[0076] The components that form the polymer (a) can include greater than 10, such as greater than 12 or greater than 14 wt. % of compound (i) and can be up to 75, such as up to 70 or up to 60 wt. % of the components that form the polymer (a), and the carboxylic acid or anhydride compound (ii) can make up greater than 5, such as greater than 8 or greater than 10 wt. % of the components that form polymer (a) and can be up to 50, such as up to 45 or up to 40 wt. % of the components that form the polymer (a).

[0077] As a nonlimiting example, polymer (a) can include moieties according to the formula: [(E)x– Uy– Oz-] -P where E represents a condensation polymer moiety derived from the compound (i) and the compound (ii), as described above, where the polymer contains carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and one or more hydroxyl groups; U represents a moiety that includes urethane groups; O represents a moiety in the polymer backbone that includes at least one olefinic group and one or more hydroxyl groups; P represents a moiety that includes an addition polymer that includes from 2 to 1000 repeat units reacted with and olefinic group in O, where the number of P groups can be from 1 to the number of olefinic groups in O; xcan be an integer from 1 to 10, y can be an integer from 1 to 20, where y is not greater than the sum of the number of hydroxyl groups in E and O, and z can be an integer from 1 to 10, where z is not greater than y.

[0078] The moiety that includes urethane groups, U, can include the reaction product of an isocyanate group and a hydroxyl group. The moiety that includes urethane groups, U, can be derived from a composition containing isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, 1,3,5-triisocyanato benzene, 2,4,6-triisocyanatotoluene, 4,4′-methylene- bis(cyclohexyl isocyanate), 2,2,4- trimethyl hexamethylene diisocyanate, 2,4,4-trimethyl hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate, tetramethyl xylylene diisocyanate and / or 4,4′-diphenylmethylene diisocyanate.

[0079] The moiety that includes at least one olefinic group and one or more hydroxyl groups, O, can be derived from a C1 to C20 linear, branched or cyclic, aliphatic or aromatic molecule comprising at least one alcohol and at least one polymerizable olefinic group. Nonlimiting examples of compositions the moiety comprising at least one olefinic group and one or more hydroxyl groups, O, can be derived from and includes compositions that include hydroxy ethyl (meth)acrylate, hydroxy propyl (meth)acrylate, poly(ethylene glycol) (meth)acrylate, poly(propylene glycol) (meth)acrylate, poly(tetrahydrofuran) (meth)acrylate, glycerol allyl ether, and / or (meth)acryloxy glycerol.

[0080] The addition polymer moiety, P, can include, without limitation, a polymerization product resulting from polymerizing a composition that includes the moiety containing at least one olefinic group and one or more hydroxyl groups, O; and one or more of the following monomers: monomers according to the formula CR102=CR12-C(O)-B-CR133, where R10and R12can independently be hydrogen, methyl or ethyl; B can be a difunctional radical that can be O, NR14or S; R14can be hydrogen, methyl or ethyl; and each R13can independently be a C1to C20 linear or branched aliphatic or aromatic group or a C1 to C20 linear or branched aliphatic hydroxyl containing group;monomers according to the formula CR102=CR12-C(O)-B-CR152-B-C(O)-CR12=CR102,where R10, R12and B can be as defined above and R15can be a difunctional (i.e. linked to two B groups) C1 to C20 linear or branched aliphatic and / or aromatic group; styrene; and divinyl benzene.

[0081] Polymer (a) can have a polymeric core-shell particle structure, where at least a portion of a polymeric shell of the core-shell particle is covalently bonded to at least a portion of a polymeric core of the core-shell particles. The polymeric shell of the core-shell particle can be obtained from components that include the first polyether and the carboxylic acid or anhydride thereof and in which the polymeric shell has an acid value of at least 20, such as 22 or 25 or from 20 to 45, such as 20 to 40 or 25 to 40 mg KOH based on the total resin solids of the polymer that forms the polymeric shell.

[0082] As a nonlimiting example, the shell portion of the core-shell particle can include carboxylic acid and / or at least water dispersible and / or water miscible polyether moieties and the core portion of the core-shell particle can include moieties that are generally hydrophobic or not water miscible.

[0083] Polymer (a) can be a self-emulsifying dispersion polymer. III. Crosslinking agent (b)

[0084] The crosslinking agent (b) includes functional groups reactive with the carboxylic acid or anhydride groups in polymer (a).

[0085] The crosslinking agent (b) can include, without limitation, one or more oxazoline groups according to the structurewhere each R1and R2can independently be hydrogen, methyl or ethyl and R3can be a C1 to C20 linear or branched aliphatic radical containing from 1 to 5 oxazoline groups and / or where R3is a polymeric backbone that includes from 2 to 100 oxazoline groups pendant from the polymeric backbone.

[0086] The crosslinking agent (b) can include, without limitation, a product from polymerizing a monomer solution that includes monomers according to the following structurewhere each R4and R5can methyl or ethyl; A is an optional difunctional radical that can include O, a second polyether, NR9or S; R9can be hydrogen, methyl or ethyl; each R6can independently be a C1 to C20 linear or branched aliphatic or aromatic group or both R6groups taken together form a double bonded oxygen; n can be an integer from 0 to 3; and each R7and R8can independently be hydrogen, methyl or ethyl.

[0087] The monomer solution can also include, without limitation, monomers according to the formula CR102=CR112 and / or CR102=CR12-C(O)-B-D where each R10, R11and R12can independently be hydrogen, methyl or ethyl; B can be a difunctional radical that can be O, a third polyether, a C1to C3poly(meth)acrylate, NR14or S; D can be hydrogen, hydroxyl or CR133, where each R13can independently be hydrogen, methyl, ethyl or a C1 to C20 linear or branched aliphatic or aromatic group and R14can be hydrogen, methyl or ethyl.

[0088] Nonlimiting examples of polyoxazolines suitable as crosslinking agents according to this disclosure are described in U.S. published application No.2021 / 0277179 to Zhou et al. at pages 4 to 5, paragraphs

[0050] through

[0064] , the specified portion of which is incorporated herein by reference.

[0089] The second and / or third polyether and / or poly(meth)acrylate can have a weight average molecular weight of from 1,000 to 30,000, such as 5,000 to 25,000 or 10,000 to 30,000 daltons.IV. Composition of the coating composition

[0090] The coating composition can include polymer (a) at from 20 wt. % to 95 wt. %, such as from 30 wt. % to 95 wt. %, or from 40 wt. % to 90 wt. %, or from 50 wt. % to 90 wt. % of the total resin solids of the coating composition.

[0091] The coating composition can include crosslinking agent (b) at from 1 wt. % to 40 wt. %, such as from 2 wt. % to 40 wt. %, or from 2 wt. % to 25 wt. %, or from 3 wt. % to 40 wt. %, or from 3 wt. % to 25 wt. % or from 3 wt. % to 15 wt. % of the coating composition, based on the total resin solids of the coating composition.

[0092] The coating composition can include the combination of polymer (a) and crosslinking agent (b) at from 21 wt. % to 95 wt. %, such as from 25 wt. % to 95 wt. %, or from 40 wt. % to 90 wt. %, or from 50 wt. % to 90 wt. % of the total resin solids of the coating composition.

[0093] The coating compositions described herein can have a viscosity of from 5 to 200 cps, such as from 25 to 150 cps or from 50 to 100 cps measured using a Brookfield CAP 2000+ Viscometer (AMETEK Inc.) (low torque instrument) using spindle No. 4 at 300 rpm (1,000 sec-1) at 25 °C. A. Other Additives

[0094] The present coating composition can include conventional additives for coating compositions in the art. Such additives include, without limitation, water, stabilizers, flow additives, fillers, plasticizers, antioxidants, hindered amine light stabilizers, UV light absorbers and stabilizers, catalyst blocking agents, colorants (dyes, color pigments, metallics and / or pearls), wax, defoamers, surfactants, rheology modifiers, thixotropic agents, fillers, wetting agents leveling agents, catalysts, grind vehicles, and other customary auxiliaries.

[0095] The coating composition can be water borne or solvent borne. Solvent borne compositions may include any solvent known in the art, i.e. aliphatic and / or aromatic hydrocarbons. Examples include, without limitation, toluene, xylene, butyl acetate, ethyl acetate, acetone, methyl isobutyl ketone, methyl isoamyl ketone, methyl ethyl ketone, ether, ether alcohol, ether ester, hexylglycol, butoxyethanol, 1-methoxy-propanol-2,1-ethoxy-propanol-2,1-propoxy- propanol-2,1-butoxy-propanol-2,1-isobutoxy-propanol-2, dipropylene glycol monomethyl ether; methanol, ethanol, propanol, isopropanol, butanol, pentanol, hexanol, ethylene glycol, diethylene glycol, dimethyl dipropylene glycol, diacetone alcohol, methylether of diacetone alcohol, ethoxyethyl propionate, or a mixture of any of these. Water borne means that the liquid content of the composition includes a substantial proportion of water (greater than 50 wt.% water based on the total weight of solvents), but can also include an organic co-solvent. The co-solvents used in water borne compositions include the same ones as the organic solvents mentioned above.

[0096] The coating compositions described herein can include less than 780 g / l of volatile organic compounds (VOC) based on the total composition, such as less than 420 g / l, or less than 250 g / l determined by calculating VOC in grams per liter (excluding water and exempt solvents) using the equation: VOC = (100 – wt. % solids of coating – wt. % water in coating) * X [100 – (wt. % water in coating * X) / density of water] where X is the density of the coating composition. The curable composition of the present disclosure may be entirely free of VOC.

[0097] The coating composition can have a total solids of from 10 wt. % to 90 wt. %, such as from 15 wt. % to 75 wt. %, or from 20 wt. % to 50 wt. % measured according to ASTM D 2369- 20.

[0098] The coating composition can include one or more colorants, such as a pigment and / or a dye. When the coating composition includes additional materials such as a pigment, the pigment can include a finely divided solid powder that is insoluble, but wettable, under the conditions of use. The pigment can be organic or inorganic and can be agglomerated or non-agglomerated. Pigments can be incorporated into the coating by use of a grind vehicle, such as an acrylic grind vehicle, the use of which will be familiar to one skilled in the art.

[0099] Suitable pigments and / or pigment compositions include, but are not limited to, carbazole dioxazine crude pigment, azo, monoazo, diazo, naphthol AS, salt type (flakes), benzimidazolone, isoindolinone, isoindoline and polycyclic phthalocyanine, quinacridone, perylene, perinone, diketopyrrolo pyrrole, thioindigo, anthraquinone, indanthrone, anthrapyrimidine, flavanthrone, pyranthrone, anthanthrone, dioxazine, triarylcarbonium, quinophthalone pigments, diketo pyrrolo pyrrole red (“DPPBO red”), titanium dioxide, carbon black, or mixtures thereof.

[0100] The pigment used with the coating composition can also include a special effect pigment. Suitable special effect pigments include those that produce one or more appearance effects suchas reflectance, pearlescence, metallic sheen, texture, phosphorescence, fluorescence, photochromism, photosensitivity, thermochromism, goniochromism, and / or color-change, such as transparent coated mica and / or synthetic mica, coated silica, coated alumina, aluminum flakes, a transparent liquid crystal pigment, a liquid crystal coating, or a combination thereof.

[0101] The coating composition can be a clearcoat, substantially free of a pigment. Substantially free of a pigment may mean that the coating composition includes less than 3 wt. % of pigment, based on the total solids, such as less than 2 wt. %, less than 1 wt. %, or 0 wt. %.

[0102] The coating compositions can be one-component (1-K), two-component (2-K) or multi- component compositions. When multi- or two-component compositions are used, one component can include polymer (a) and another component can include the crosslinker (b).

[0103] The coating compositions described herein can be applied, as a nonlimiting example, by forming a coating layer on at least a portion of a substrate. The method can include applying the present coating composition over at least a portion of the substrate; and exposing the coating composition to a sufficient amount of energy for a sufficient amount of time for the coating composition to cure, such as the reaction of the polyurethane resin and the crosslinker.

[0104] The coating composition can be applied using methods known in the art, such as spray application, draw down, brush application, dip application, rotary bell application, roll coater application, coil coating application and / or precision application.

[0105] The substrate described above, can include iron, steel, aluminum, plastic, wood, composite, glass, synthetic material, paper, leather, and / or another coating layer.

[0106] The coating composition can be cured, without limitation, by exposure to ambient conditions, elevated temperature and / or actinic radiation.

[0107] Thus, the present disclosure provides for a substrate at least partially coated with a coating formed from the coating composition described herein. As a nonlimiting examples, the substrate can form at least a portion of a vehicle or a package. When the substrate is a package, the package can include a metal can, an aerosol can or tube, or a monobloc aerosol can or tube.

[0108] The present disclosure also provides a multi-layer coating system that includes (1) a first basecoat layer applied over at least a portion of a substrate; and (2) a second basecoat layer applied over at least a portion of the first coating layer, where at least one of the first basecoat layer and the second basecoat layer is formed from a first basecoat composition that includes a coating composition as described herein.

[0109] The multi-layer coating system can include a primer coating layer applied over at least a portion of the substrate, where the first primer coating layer is positioned between the first basecoat layer and the substrate, and / or a topcoat layer applied over at least a portion of the second basecoat layer. As indicated above, the polymer (a) can be and / or include a self-emulsifying dispersion polymer.

[0110] Thus, a process of coating a substrate with a multi-layer coating is provided that includes (i) forming a first basecoat layer, that includes the coating composition described herein, over at least a portion of a substrate by depositing a first basecoat composition onto at least a portion of the substrate; and (ii) forming a second basecoat layer over at least a portion of the first basecoat layer by depositing a second basecoat composition directly onto at least a portion of (i) the first basecoat layer after the first basecoat composition is dehydrated or the first basecoat composition before the first basecoat composition is dehydrated. The first basecoat composition and second basecoat composition are dehydrated. In the described process, the first basecoat composition is dehydrated before application of the second basecoat composition or both the first and second basecoat compositions are simultaneously dehydrated.

[0111] This disclosure also provides a method of forming a coating layer on at least a portion of a substrate that includes (i) applying the coating composition described herein over at least a portion of the substrate; and (ii) exposing the coating composition to a sufficient amount of energy for a sufficient amount of time for the coating composition to cure and to form a uniform coating on the substrate. The coating composition can be applied using a method that includes spray application, draw down, brush application, rotary bell application, roll coater application, coil coating application and / or precision application. The substrate can include iron, steel, and aluminum, plastic, wood, glass, synthetic material, paper, leather, and / or another coating layer.

[0112] In the described methods, the coating composition can be cured by exposure to a temperature of from 50 °C to 160 °C, such as from 55 °C to 155 °C, or from 60 °C to 150 °C, or from 60 °C to 120 °C, or from 80 °C to 110 °C, or from 50 °C to 100 °C for a period of time sufficient to fully cure the coating layer.

[0113] As indicated above, the substrate can include a previously applied coating layer. As a nonlimiting example, the present coating composition can become part of a multilayer coating composition. As nonlimiting examples, the present coating composition can be a coating layer applied over a basecoat or a coating layer applied over a primer coat.

[0114] Depending on the particular use intended, the present coating composition can be applied as a topcoat, such as a clearcoat, or it can be applied as a monocoat.

[0115] Application of the present coating composition can result in a coating layer that has a dry film thickness of from 0.5 µm to 60 µm, such as 0.5 µm to 65 µm, such as 0.5 µm to 60 µm, 0.5 µm to 55 µm, 0.5 µm to 52 µm, 1 µm to 65 µm, 1 µm to 60 µm, 1 µm to 55 µm, 5 µm to 65 µm, 5 µm to 60 µm and 5 µm to 55 µm measured according to ASTM D7091-21.

[0116] The present disclosure also provides a substrate at least partially coated with a coating formed from the coating compositions described above. In particular, the coating composition can be applied to a substrate and cured to form a coating thereover. The coating can be a continuous film formed over at least a portion the substrate.

[0117] When the substrate is a vehicle, the vehicle substrate can include a component of a vehicle. As a nonlimiting example, the vehicle can include an aerospace substrate (a component of an aerospace vehicle, such as an aircraft such as, for example, airplanes (e.g., private airplanes, and small, medium, or large commercial passenger, freight, and military airplanes), helicopters (e.g., private, commercial, and military helicopters), aerospace vehicles (e.g., rockets and other spacecraft), and the like). The vehicle can also include a ground vehicle such as, for example, animal trailers (e.g., horse trailers), all-terrain vehicles (ATVs), cars, trucks, buses, vans, heavy duty equipment, tractors, golf carts, motorcycles, bicycles, snowmobiles, trains, railroad cars, and the like. The vehicle can also include watercraft such as, for example, ships, boats, hovercrafts, and the like. The vehicle substrate may include a component of the body of the vehicle, such as an automotive hood, door, trunk, roof, and the like; such as an aircraft or spacecraft wing, fuselage, and the like; such as a watercraft hull, and the like.

[0118] The coating composition can be applied over an industrial substrate which can include, without limitation, tools, heavy duty equipment, furniture such as office furniture (e.g., office chairs, desks, filing cabinets, and the like), appliances such as refrigerators, ovens and ranges, dishwashers, microwaves, washing machines, dryers, small appliances (e.g., coffee makers, slow cookers, pressure cookers, blenders, etc.), metallic hardware, extruded metal such as extruded aluminum used in window framing, other indoor and outdoor metallic building materials, and the like.

[0119] The coating composition can be applied over storage tanks, windmills, nuclear plant components, packaging substrates, wood flooring and furniture, apparel, electronic including, butnot limited to, housings and circuit boards, glass and transparencies, sports equipment, including golf balls, stadiums, buildings, bridges, and the like.

[0120] The substrate can be metallic or non-metallic. Metallic substrates include, but are not limited to, tin, steel (including electrogalvanized steel, cold rolled steel, hot-dipped galvanized steel, among others), aluminum, aluminum alloys, zinc-aluminum alloys, steel coated with a zinc- aluminum alloy, and aluminum plated steel. Non-metallic substrates include polymeric materials, plastic and / or composite material, polyester, polyolefin, polyamide, cellulosic, polystyrene, polyacrylic, poly(ethylene naphthalate), polypropylene, polyethylene, nylon, ethylene vinyl alcohol (EVOH), polylactic acid, other “green” polymeric substrates, poly(ethyleneterephthalate) (PET), polycarbonate, polycarbonate acrylobutadiene styrene (PC / ABS), wood, veneer, wood composite, particle board, medium density fiberboard, cement, stone, glass, paper, cardboard, textiles, leather, both synthetic and natural, and the like. The substrate can include a metal, and / or a plastic and / or composite material, and / or a fibrous material. The fibrous material may include a nylon and / or a thermoplastic polyolefin material with continuous strands or chopped carbon fiber. The substrate can be one that has already been treated in some manner, such as to impart visual and / or color effect, a protective pretreatment or other coating layer, and the like.

[0121] The coating composition of the present disclosure can be particularly beneficial when applied to a metallic substrate. The coatings of the present disclosure can be particularly beneficial when applied to metallic substrates that are used to fabricate automotive vehicles, such as cars, trucks, and tractors.

[0122] As a nonlimiting example, the coating composition can be applied to a substrate having multiple components, wherein the coating composition is simultaneously applied to the multiple components and simultaneously cured to form a coating over the multiple components without deforming, distorting, or otherwise degrading any of the components. The components can be parts of a larger whole of the substrate. The components can be separately formed and subsequently arranged together to form the substrate. The components can be integrally formed to form the substrate.

[0123] Non-limiting examples of components of a substrate in the vehicle context include a vehicle body (e.g., made of metal) and a vehicle bumper (e.g., made or plastic) which are separately formed and subsequently arranged to form the substrate of the vehicle. Further examples include a plastic automotive component, such as a bumper or fascia in which the bumper or fascia includes regions orsubcomponents which include more than one type of substrate. Further examples include aerospace or industrial components comprising more than one substrate type. It will be appreciated that other such multi-component substrates are contemplated within the context of this disclosure. ASPECTS 1. A coating composition comprising: (a) a polymer obtained from components comprising (i) a compound comprising functional groups reactive with a carboxylic acid or corresponding anhydride and (ii) a compound comprising carboxylic acid or corresponding anhydride functional groups, wherein the polymer comprises carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and (b) a crosslinking agent comprising functional groups reactive with the carboxylic acid or anhydride groups in the polymer; wherein the polymer (a) has an acid value of at least 10 mg KOH per gram of polymer based on the total resin solids of the polymer (a) determined according to ASTM D 4662-15 (2015). 2. The coating composition according to aspect 1, wherein the polymer (a) has an acid value of at least 20 and can be up to 100 mg KOH per gram of polymer. 3. The coating composition according to aspect 1, wherein the polymer (a) has an acid value that can range from 10 to 100 mg KOH per gram of polymer based on the total resin solids of the polymer (a) determined according to ASTM D 4662-15 (2015). 4. The coating composition according to aspect 1, wherein the polymer (a) has an acid value that can range from 12 to 75, such as from 14 to 60, or from 15 to 100 or from 15 to 50 mg KOH per gram of polymer based on the total resin solids of the polymer (a) determined according to ASTM D 4662-15 (2015). 5. The coating composition according to any previous aspect, wherein the compound (i) comprises greater than 10 wt. % of the components that form the polymer (a) and the carboxylic acid or anhydride thereof comprises greater than 5 wt. % of the components that form the polymer (a). 6. The coating composition according to any of aspects 1 through 4, wherein the compound (i) comprises greater than 12, such as greater than 14 wt. % of the components that form thepolymer (a) and the carboxylic acid or anhydride thereof comprises greater than 8, such as greater than 10 wt. % of the components that form the polymer (a). 7. The coating composition according to any previous aspect, wherein the compound (i) comprises a first polyether and / or a polyester, wherein the functional groups reactive with a carboxylic acid or corresponding anhydride comprise hydroxyl groups. 8. The coating composition according to any preceding aspect, wherein the carboxylic acid or anhydride thereof comprises phthalic acid, phthalic anhydride, trimellitic acid, trimellitic anhydride, pyromellitic acid, pyromellitic anhydride, mellitic acid, mellitic anhydride, naphthalic acid, and / or naphthalic anhydride. 9. The coating composition according to any preceding aspect, wherein the carboxylic acid or anhydride thereof comprises trimellitic anhydride. 10. The coating composition according to any preceding aspect, wherein the compound (i) comprises a first polyether comprising polyethylene glycol, polypropylene glycol, polytetrahydrofuran and / or polyethers of C1to C10linear, branched or cyclic, aliphatic and / or aromatic diols. 11. The coating composition according to any preceding aspect, wherein the compound (i) comprises a first polyether comprising polytetrahydrofuran. 12. The coating composition according to any preceding aspect, wherein the crosslinking agent (b) comprises one or more oxazoline groups according to the structure wherein R1and R2areor ethyl and R3is a C1to C20linear or branched aliphatic radical comprising from 1 to 5 oxazoline groups and / or wherein R3is a polymeric backbone comprising from 2 to 100 oxazoline groups pendant from the polymeric backbone. 13. The coating composition according to any preceding aspect, wherein the crosslinking agent (b) comprises a product from polymerizing a monomer solution comprising monomers according to the following structurewherein R4and R5are in n, methyl or ethyl; A is an optional difunctional radical that is O, a second polyether, NR9or S; R9is hydrogen, methyl or ethyl; each R6is independently a C1 to C20 linear or branched aliphatic or aromatic group or both R6groups taken together form a double bonded oxygen; n is an integer from 0 to 3; and each R7and R8are independently hydrogen, methyl or ethyl; with one or more monomers according to the formula CR102=CR112 and / or CR102=CR12-C(O)-B-D wherein R10, R11and R12are independently hydrogen, methyl or ethyl; B is a difunctional radical that can be O, a third polyether, a C1 to C3 poly(meth)acrylate, NR14or S; D is hydrogen, hydroxyl or CR133, wherein each R13is independently hydrogen, methyl, ethyl or a C1to C20linear or branched aliphatic or aromatic group and R14is hydrogen, methyl or ethyl. 14. The coating composition according to aspect 13, wherein the second and / or third polyether and / or poly(meth)acrylate has a weight average molecular weight of from 1,000 to 30,000 Daltons, determined by gel permeation chromatography (GPC) using polystyrene standards. 15. The coating composition according to aspect 13, wherein the second and / or third polyether and / or poly(meth)acrylate has a weight average molecular weight of from 5,000 to 25,000, such as 10,000 to 30,000 Daltons determined by gel permeation chromatography (GPC) using polystyrene standards. 16. The coating composition according to any preceding aspect, wherein the polymer (a) comprises from 20 wt. % to 95 wt. % of the total resin solids of the coating composition.17. The coating composition according to any preceding aspect, wherein the polymer (a) comprises from 30 wt. % to 95 wt. %, such as from 40 wt. % to 90 wt. %, or from 50 wt. % to 90 wt. % of the total resin solids of the coating composition. 18. The coating composition according to any preceding aspect, wherein the crosslinking agent (b) comprises from 1 wt. % to 40 wt. % of the coating composition, based on the total resin solids of the coating composition. 19. The coating composition according to any preceding aspect, wherein the crosslinking agent (b) comprises from 2 wt. % to 40 wt. %, such as from 2 wt. % to 25 wt. %, or from 3 wt. % to 40 wt. %, or from 3 wt. % to 25 wt. % or from 3 wt. % to 15 wt. % of the coating composition, based on the total resin solids of the coating composition. 20. The coating composition to any preceding aspect, wherein the polymer (a) comprises polymeric core-shell particles, wherein at least a portion of a polymeric shell of the core-shell particles is covalently bonded to at least a portion of a polymeric core of the core-shell particles, and wherein the polymeric shell of the core-shell particles is obtained from components comprising the compound comprising functional groups reactive with a carboxylic acid or corresponding anhydride comprising a first polyether and the carboxylic acid or anhydride thereof and in which the polymeric shell has an acid value of at least 20 mg KOH per gram of polymer based on the total resin solids of the polymer that forms the polymeric shell determined according to ASTM D 4662-15 (2015). 21. The coating composition to any preceding aspect, wherein the polymer (a) comprises polymeric core-shell particles, wherein at least a portion of a polymeric shell of the core-shell particles is covalently bonded to at least a portion of a polymeric core of the core-shell particles, and wherein the polymeric shell of the core-shell particles is obtained from components comprising the compound comprising functional groups reactive with a carboxylic acid or corresponding anhydride comprising a first polyether and the carboxylic acid or anhydride thereof and in which the polymeric shell has an acid value of at least 22, such as at least 25 mg KOH per gram of polymer based on the total resin solids of the polymer that forms the polymeric shell determined according to ASTM D 4662-15 (2015). 22. The coating composition to any preceding aspect, wherein the polymer (a) comprises polymeric core-shell particles, wherein at least a portion of a polymeric shell of the core-shellparticles is covalently bonded to at least a portion of a polymeric core of the core-shell particles, and wherein the polymeric shell of the core-shell particles is obtained from components comprising the compound comprising functional groups reactive with a carboxylic acid or corresponding anhydride comprising a first polyether and the carboxylic acid or anhydride thereof and in which the polymeric shell has an acid value of from 20 to 45, such as from 20 to 40 or from 25 to 40 mg KOH per gram of polymer based on the total resin solids of the polymer that forms the polymeric shell determined according to ASTM D 4662-15 (2015). 23. The coating composition to any preceding aspect, wherein the polymer (a) comprises moieties according to the formula: [(E)x – Uy – Oz -] -P wherein E represents a condensation polymer moiety derived from the compound (i) and the compound (ii), wherein the polymer comprises carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and one or more hydroxyl groups, wherein U represents a moiety comprising urethane groups, wherein O represents a moiety derived from a compound comprising at least one olefinic group and one or more hydroxyl groups, wherein P represents a moiety comprising an addition polymer comprising from 2 to 1000 repeat units reacted with an olefinic group in O, wherein the number of P groups can be from 1 to the number of olefinic groups in O, wherein x is an integer from 1 to 10, wherein y is an integer from 1 to 20, wherein y is not greater than the sum of the number of hydroxyl groups in E and O, and wherein z is an integer from 1 to 10, wherein z is not greater than y. 23. The coating composition according to aspect 22, wherein the moiety comprising urethane groups, U, comprises the reaction product of an isocyanate group and a hydroxyl group. 24. The coating composition according to aspect 23, wherein the moiety comprising urethane groups, U, is derived from a composition comprising isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, 1,3,5-triisocyanato benzene, 2,4,6-triisocyanatotoluene, 4,4′- methylene-bis(cyclohexyl isocyanate), 2,2,4- trimethyl hexamethylene diisocyanate, 2,4,4- trimethyl hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate, tetramethyl xylylene diisocyanate and / or 4,4′-diphenylmethylene diisocyanate.25. The coating composition according to any of aspects 22 through 24, wherein the moiety comprising at least one olefinic group and one or more hydroxyl groups, O, is derived from a C1 to C20 linear, branched or cyclic, aliphatic or aromatic molecule comprising at least one alcohol and at least one polymerizable olefinic group. 26. The coating composition according to any of aspects 22 through 25, wherein the moiety comprising at least one olefinic group and one or more hydroxyl groups, O, is derived from a composition comprising hydroxy ethyl (meth)acrylate, hydroxy propyl (meth)acrylate, poly(ethylene glycol) (meth)acrylate, poly(propylene glycol) (meth)acrylate, poly(tetrahydrofuran) (meth)acrylate, glycerol allyl ether, and / or (meth)acryloxy glycerol. 27. The coating composition according to any of aspects 22 through 26, wherein the addition polymer moiety, P, comprises a polymerization product resulting from polymerizing a composition comprising the moiety comprising at least one olefinic group and one or more hydroxyl groups, O; and one or more of a monomer according to the formula CR102=CR12-C(O)-B-CR133, wherein R10and R12are independently hydrogen, methyl or ethyl; B is14 14that can be O, NR or S; R is hydrogen, methyl or ethyl; and each R13is independently a C1to C20linear or branched aliphatic or aromatic group or a C1to C20linear or branched aliphatic hydroxyl containing group; a monomer according to the formula CR102=CR12-C(O)-B-CR152-B-C(O)-CR12=CR102, wherein R10, R12and B are as defined above and R15is a difunctional C1 to C20 linear or branched aliphatic and / or aromatic group; styrene; and divinyl benzene. 26. The coating composition according to any preceding aspect, wherein the coating composition has a total solids of from 10 wt. % to 90 wt. % measured according to ASTM D 2369- 20. 27. The coating composition according to any preceding aspect, wherein the coating composition has a total solids of from 15 wt. % to 75 wt. %, such as from 20 wt. % to 50 wt. % measured according to ASTM D 2369-20. 28. The coating composition according to any preceding aspect, wherein the coating composition comprises one or more colorants, such as a pigment and / or a dye.29. A substrate at least partially coated with a coating formed from the coating composition according to any preceding aspect. 30. The substrate of aspect 29, wherein the substrate forms at least a portion of a vehicle or a package. 31. The substrate of aspect 29, wherein the package comprises a metal can, an aerosol can or tube, or a monobloc aerosol can or tube. 32. A multi-layer coating system comprising: (1) a first basecoat layer applied over at least a portion of a substrate; and (2) a second basecoat layer applied over at least a portion of the first coating layer, wherein at least one of the first basecoat layer and the second basecoat layer is formed from a first basecoat composition comprising a coating composition according to any of aspects 1 through 28. 33. The multi-layer coating system of aspect 32, further comprising a primer coating layer applied over at least a portion of the substrate, wherein the first primer coating layer is positioned between the first basecoat layer and the substrate, and / or a topcoat layer applied over at least a portion of the second basecoat layer. 34. The multi-layer coating system of either of aspects 32 or 33, wherein the polymer (a) comprises a self-emulsifying dispersion polymer. 35. A process of coating a substrate with a multi-layer coating comprising: forming a first basecoat layer over at least a portion of a substrate by depositing a first basecoat composition onto at least a portion of the substrate; and forming a second basecoat layer over at least a portion of the first basecoat layer by depositing a second basecoat composition directly onto at least a portion of (1) the first basecoat layer after the first basecoat composition is dehydrated or (2) the first basecoat composition before the first basecoat composition is dehydrated, wherein the first basecoat composition and second basecoat composition are dehydrated, and wherein at least one of the first basecoat layer and the second basecoat layer is formed from a first basecoat composition comprising a coating composition according to any of aspects 1 through 28.36. The process of aspect 35, wherein the first basecoat composition is dehydrated before application of the second basecoat composition or both the first and second basecoat compositions are simultaneously dehydrated. 37. A method of forming a coating layer on at least a portion of a substrate comprising: applying the coating composition according to any of aspects 1 through 28 over at least a portion of the substrate; and exposing the coating composition to a sufficient amount of energy for a sufficient amount of time for the coating composition to cure and to form a uniform coating on the substrate. 38. The method according to aspect 37, wherein the coating composition is applied using a method comprising spray application, draw down, brush application, rotary bell application, roll coater application, coil coating application and / or precision application. 39. The method according to either of aspects 37 or 38, wherein the substrate comprises iron, steel, and aluminum, plastic, wood, glass, synthetic material, paper, leather, and / or another coating layer. 40. The method according to any of aspects 37 through 39, wherein the coating composition is cured by exposure to a temperature of from 50°C to 160°C for a period of time sufficient to fully cure the coating layer. 41. The method according to any of aspects 37 through 39, wherein the coating composition is cured by exposure to a temperature of from 55 °C to 155 °C, such as from 60 °C to 150 °C, or from 60 °C to 120 °C, or from 80 °C to 110 °C, or from 50 °C to 100 °C for a period of time sufficient to fully cure the coating layer. EXAMPLES

[0124] Aspects of the present disclosure are further illustrated by reference to the following examples. It will be apparent to those skilled in the art that many modifications, both to materials, and methods, may be practiced without departing from the scope of the disclosure. Example 1

[0125] An acrylic-polyurethane dispersion A was prepared by combining the contents of Table 1, charge 1, in a four-necked, 5-liter reaction flask outfitted with a stirrer, gas inlet, thermometer, and condenser. The reaction mixture was heated to 160 °C and the acid value was measured hourly.When the acid value was less than 70 mg KOH, the temperature was reduced to 150 °C and the measurements continued until a value of 60 mg KOH was reached. The batch was cooled to 100 °C and any remaining water was removed by applying vacuum for 30 minutes. Charge 2 was added and the resin was cooled to ambient temperature. The polyester had a measured solids of 78% according to ASTM D2369 (2015), a Gardner Holdt viscosity of V (ASTM D1725-12(2019) and measured acid value of 49 mg KOH. Table 1: Polyester Synthesis Raw Material Amount (grams) n.

[0126] The contents of Table 2 were added to a 4 necked round bottom flask fitted with a stirrer, gas inlet tube, addition funnel, thermometer, and condenser. The mixture was heated under an air atmosphere to 50 °C. After the exotherm subsided, the mixture was heated to 80 °C and held until the isocyanate peak was no longer evident in the IR spectrum. The heat was removed and 123 grams of 2-butoxyethanol (Butyl Cellosolve available from Dow) was added. A dispersion was produced by the addition of 24.6 grams of dimethylethanolamine and 877 grams of deionized water. The polyurethane dispersion had a solids content of 30%, a calculated theoretical acid value of 45 mg KOH and a calculated theoretical OH value of 23 mg KOH per gram of resin. Table 2: Polyurethane Dispersion Synthesis Raw Material Amount (grams)A total of 1639 grams of the polyurethane dispersion as described above (Table 2) and 1074 grams of deionized water was added to a four necked reaction flask outfitted with a stirrer, gas inlet, thermometer, and condenser. The solution was sparged with nitrogen for 1 hour to remove dissolved oxygen. The contents of Table 3 were added followed by stirring for 10 minutes. A total of 2.21 grams of 70% t-butyl hydroperoxide (LUPEROX TBH70X available from Arkema) and 50 grams of deionized water was then added over 10 minutes during which time the temperature showed an exotherm to 63°C. The reaction was then cooled to 35°C. A total of 8.9 grams of dimethylethanol amine and 10 grams of deionized water was added to form a dispersion with a solids content of 35%, a viscosity of 710 centipoise using a Brookfield CAP 2000+ Viscometer (AMETEK Inc.) (low torque instrument) using spindle No.4 at 300 rpm (1,000 sec-1) at 25 °C, a calculated theoretical acid value of 18 mg KOH and a calculated theoretical hydroxyl value of 9 mg KOH per gram of resin. Table 3: Final Synthesis of Acrylic-Polyurethane Dispersion A Methyl Methacrylate 153.8 Styrene 1538xamp e

[0127] An acrylic-polyurethane dispersion B was prepared by combining, in a four necked, 3- liter reaction flask outfitted with a stirrer, gas inlet, thermometer, and condenser, the components listed in Table 4. The reaction mixture was heated to 160 °C and the acid value measured hourly. When the acid value was less than 70 mg KOH, the temperature was reduced to 150 °C and the measurements continued until an acid value of 59 mg KOH was reached. The batch was cooled to 100°C and any remaining water was removed by applying vacuum for 30 minutes. The polyester had a measured solids of 98%, an acid value of 59 mg KOH and a calculated theoretical OH value of 118.Table 4: Polyester Synthesis Raw Material Amount (g) Polytetrahydrofuran 65011300 oration.

[0008] e contents o ab e 5 were added to a necked round bottom flask fitted with a stirrer, gas inlet tube, addition funnel, thermometer, and condenser. The mixture was heated under an air atmosphere to 50 °C. After the exotherm subsided, the mixture was heated to 80°C and held until the isocyanate peak was no longer evident in the IR spectrum. The heat was removed and 123.5 grams of 2-butoxyethanol was added. A dispersion was produced by the addition of 24.7 grams of dimethylethanolamine and 881 grams of deionized water. The polyurethane dispersion had a solids content of 30%, calculated theoretical acid value of 45 mg KOH, and a calculated theoretical hydroxyl value of 23 mg KOH per gram of resin. Table 5: Polyurethane Synthesis Raw Material Amount (g) Polyester from Table 4 379

[0129] A total of 1647 grams of the polyurethane dispersion described above (Table 5), and 1079 grams of deionized water was added to a four-necked reaction flask outfitted with a stirrer, gas inlet, thermometer, and condenser. The solution was sparged with nitrogen for 1 hour to remove dissolved oxygen. Next the contents of Table 6 were added followed by stirring for 10 minutes. Next 2.22 grams of 70% t-butyl hydroperoxide and 50 grams of deionized water was then added over 10 minutes during which time the temperature showed an exotherm to 61 °C. The reaction was then cooled to 35 °C. The final addition of 8.9 grams of dimethylethanolamine and 10 grams of deionized water created a dispersion with a solids content of 35%, a viscosity of 620 centipoisemeasured using a Brookfield CAP 2000+ Viscometer (AMETEK Inc.) (low torque instrument) using spindle No.4 at 300 rpm (1,000 sec-1) at 25 °C, a theoretical acid value of 18 mg KOH and a theoretical hydroxyl number of 9 mg KOH per gram of resin.Table 6: Final Synthesis of Acrylic-Polyurethane Dispersion B: Methylmethacrylate 154.4 Styrene 154.4

[0130] The acid functional groups in the paints that contained the acrylic-polyurethane dispersions were crosslinked with a polyoxazoline (EPOCROS WS-500 available from Nippon Shokubai). The ratios of acid groups to oxazoline groups were balanced on an equivalence basis for each paint. A series of coatings (Examples 3 through 12 in Table 7) were prepared to compare a range of oxazoline to acid group ratios from 0 up to an excess of 1.44 oxazoline groups per acid group for polyurethane resins containing an aromatic acid (Example 1 and Examples 3-7 in Table 7, Experimental) versus (Example 2 and Examples 8-12 in Table 7, Comparative). The experiment was also designed to compare the reactivity of the aromatic acid to the aliphatic acid at both standard (140 °C) and low temperature (90 °C) baking.TABLE 7: COATING COMPOSITIONS Example 3 4 5 6 7 8 9 10 11 12 61 1 53 3 3 8 1 01Solution acrylic is a resin prepared from 35 wt.% Butyl Acrylate, 30 wt.% Styrene, 18 wt.% Butyl Methacrylate, 8.5 wt.% Hydroxyethyl Acrylate and 8.5 wt.% Acrylic Acid made at 26% weight solids using t-butylperoxyacetate catalyst in 81.4 wt.% deionized water, 16.3 wt.% diethylene glycol monobutyl ether and 0.3 wt.% odorless mineral spirits and using 2 wt.% dimethylethanol amine neutralizing agent. This material functions as a water-based flow control agent. 2EPOCROS WS-500 a water soluble polyoxazoline acrylic polymer available from Nippon Shokubai Corporation of Japan. Preparation of coatings

[0131] The coatings of Example 3-12 were drawn down on 4-inch by 12-inch ED 7100 ELECTROCOAT panels available from ACT Test Panels of Hillsdale, Michigan. The coatings were applied using a #50 wire bar to achieve a target coating thickness of 0.6 to 0.9 mils. The film thickness values were determined using a Fischer DELTASCOPE MP3C unit with a EGAB1.3 probe. The coatings were baked in a box oven set at temperatures of 90° C and 140° C for thirty minutes. An ambient flash for three minutes was allowed before baking the test panels.KÖNIG Hardness Testing:

[0132] One measure of coating hardness was determined using a BYK Pendulum Hardness Tester using the KÖNIG method. The instrument was set for 3°. The hardness values were measured five days after the baking process as detailed in ASTM D 4366-16 (2021). Fischer Micro-Hardness Testing:

[0133] Another measure of coating hardness was determined using the Fischer HM 2000 Micro- Hardness Tester. The measurement used a force of 100 mN for ten seconds. Data analysis was done using WIN-HCU software, Fischer Technology INC. Solvent Resistance Testing:

[0134] The solvent resistance was determined using a modified process based on ASTM D5402- 19 which was approved on June 1, 2019 (Assessing the Solvent Resistance of Organic Coatings Using Solvent Rubs). The modifications include the use of the two-pound ball hammer method as described in the document. Methyl Ethyl Ketone-soaked gauze cloth covered the ball, and twenty-five double rubs were performed using an Aluminum panel guide on each test panel. The damage was visually rated. The width of damage to the substrate is recorded in millimeters. Coatings with wider damage are worse than those with no or narrow damage. Water Resistance Testing:

[0135] The water resistance was tested using coated panels that were cut to 3 by 4 inches in size for a two-day deionized water soak at 63° C. The panels were rated for adhesion using the ASTM D 3359-95 method which was approved on February 15, 1995. The adhesion rating is 5 for no loss of adhesion, 4 for <5% loss, 3 for 5% to 15% loss, 2 for 16% to 35% loss, 1 for 36% to 65% loss and 0 for >65% loss. The loss percentage is within the area of the scribe. A visual reference shown in the ASTM D3359-95 method was used to rate the adhesion loss. The 3M Scotch 898 tape was used. A note was made for any softness or blushing observed on the panels immediately after removal from the hot water. In some cases, the coating was so soft that a paper towels easily removed the coating from the E-Coat substrate. Any blistering observed is rated using the ASTM D 714-87 method (Standard Test Method for Evaluating Degree of Blistering of Paints) which wasapproved on May 29, 1987. ASTM D3359 Adhesion rating: 5 for no loss of adhesion, 4 for <5% loss, 3 for 5% to 15% loss, 2 for 16% to 35% loss, 1 for 36% to 65% loss and 0 for >65% loss. Testing Data and Summary of Results:

[0136] Data from coating property testing that includes coating hardness, resistance to Methyl Ethyl Ketone solvent rubs and exposure to two-day 63° C water soak testing are shown below in Tables 8 to 11. Tables 8 and 9 compare inventive vs. comparative data at low temperature baking of 90° C. Table 8: Inventive Coatings with Aromatic Acid in Dispersion: 90° C Bake for 30 minutes Ex. Oxazoline Coating Coating Hardness Solvent Resistance Water Resistance Equivalents Film geTable 9: Comparative Coatings with Aliphatic Acid in Dispersion: 90° C Bake for 30 minutes Ex. Oxazoline Coating Coating Hardness Solvent Resistance Water Resistance Equivalents Film Thickness KÖNIG Fischer Pass / Description Adhesion Description h el rsof 140° C. Table 10: Inventive Coatings with Aromatic Acid in Dispersion: 140° C Bake for 30 minutes Ex. Oxazoline Coating Coating Hardness Solvent Resistance Water Resistance Equivalents Film nTable 11: Comparative Coatings with Aliphatic Acid in Dispersion: 140° C Bake for 30 minutes Ex. Oxazoline Coating Coating Hardness Solvent Resistance Water Resistance Equivalents Film Thickness KÖNIG Fischer Pass / Description Adhesion Description e

[0138] The data shows that the inventive coatings made using the polyurethane containing aromatic acid groups (experimental Example 1) provided a higher level of hardness, more resistance to MEK solvent rubs and improved adhesion after 63° C water soak testing compared to the comparative coatings made using the polyurethane containing aliphatic acid groups (comparative Example 2). These trends are especially evident at the low temperature bake of 90° C. The polyurethane containing aromatic acid provided better curing and coating property development at the low bake temperatures.

[0139] Whereas particular embodiments of this disclosure have been described above for purposes of illustration, it will be evident to those skilled in the art that numerous variations of the details of the present disclosure can be made without departing from what is defined in the appended claims.

Claims

We claim:

1. A coating composition comprising: (a) a polymer obtained from components comprising (i) a compound comprising functional groups reactive with a carboxylic acid or corresponding anhydride and (ii) a compound comprising carboxylic acid or corresponding anhydride functional groups, wherein the polymer comprises carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and (b) a crosslinking agent comprising functional groups reactive with the carboxylic acid or anhydride groups in the polymer; wherein the polymer (a) has an acid value of at least 10, such as at least 12, at least 14, at least 15 or at least 20 and can be up to 100, such as up to 75, up to 60, or up to 50 mg KOH per gram of polymer and can range from 10 to 100, such as 12 to 75, 14 to 60, 15 to 100 or 15 to 50 mg KOH per gram of polymer based on the total resin solids of the polymer (a) determined according to ASTM D 4662-15 (2015).

2. The coating composition according to claim 1, wherein the compound (i) comprises greater than 10, such as greater than 12 or greater than 14 wt. % of the components that form the polymer (a) and the compound comprising a carboxylic acid or anhydride thereof comprises greater than 5, such as greater than 8 or greater than 10 wt. % of the components that form the polymer (a).

3. The coating composition according to either of claims 1 or 2, wherein the compound (i) comprises a first polyether and / or a polyester, wherein the functional groups reactive with a carboxylic acid or corresponding anhydride comprise hydroxyl groups.

4. The coating composition according to any preceding claim, wherein the carboxylic acid or anhydride thereof comprises phthalic acid, phthalic anhydride, trimellitic acid, trimellitic anhydride, pyromellitic acid, pyromellitic anhydride, mellitic acid, mellitic anhydride, naphthalic acid, and / or naphthalic anhydride.

5. The coating composition according to any preceding claim, wherein the compound (i) comprises a first polyether comprising polyethylene glycol, polypropylene glycol, polytetrahydrofuran and / or polyethers of C1to C10linear, branched or cyclic, aliphatic or aromatic diols.

6. The coating composition according to any preceding claim, wherein the crosslinking agent (b) comprises one or more oxazoline groups according to the structurewherein R1and R2are independe yl or ethyl and R3is a C1to C20linear or branched aliphatic radical comprising from 1 to 5 oxazoline groups and / or wherein R3is a polymeric backbone comprising from 2 to 100 oxazoline groups pendant from the polymeric backbone.

7. The coating composition according to any preceding claim, wherein the crosslinking agent (b) comprises a product from polymerizing a monomer solution comprising monomers according to the following structurewherein R4and R5are independently hydrogen, methyl or ethyl; A is an optional difunctional radical that is O, a second polyether, NR9or S; R9is hydrogen, methyl or ethyl; each R6is independently a C1 to C20 linear or branched aliphatic or aromatic group or both R6groups taken together form a double bonded oxygen; n is an integer from 0 to 3; and each R7and R8are independently hydrogen, methyl or ethyl; with one or more monomers according to the formula CR102=CR112 and / or CR102=CR12-C(O)-B-D wherein R10, R11and R12are independently hydrogen, methyl or ethyl; B is a difunctional radical that can be O, a third polyether, a C1to C3poly(meth)acrylate, NR14or S; D is hydrogen, hydroxyl or CR133, wherein each R13is independently hydrogen, methyl, ethyl or a C1 to C20 linear or branched aliphatic or aromatic group and R14is hydrogen, methyl or ethyl; wherein optionally the second and / or third polyether and / or poly(meth)acrylate has a weight average molecular weight of from 1,000 to 30,000, such as 5,000 to 25,000 or 10,000 to 30,000 Daltons determined by gel permeation chromatography (GPC) using polystyrene standards.

8. The coating composition according to any preceding claim, wherein the polymer (a) comprises from 20 wt. % to 95 wt. %, such as from 30 wt. % to 95 wt. %, or from 40 wt. % to 90 wt. %, or from 50 wt. % to 90 wt. % of the total resin solids of the coating composition; and wherein the crosslinking agent (b) comprises from 1 wt. % to 40 wt. %, such as from 2 wt. % to 40 wt. %, or from 2 wt. % to 25 wt. %, or from 3 wt. % to 40 wt. %, or from 3 wt. % to 25 wt. % or from 3 wt. % to 15 wt. % of the coating composition, based on the total resin solids of the coating composition.

9. The coating composition to any preceding claim, wherein the polymer (a) comprises polymeric core-shell particles, wherein at least a portion of a polymeric shell of the core-shell particles is covalently bonded to at least a portion of a polymeric core of the core-shell particles, and wherein the polymeric shell of the core-shell particles is obtained from components comprising the compound comprising functional groups reactive with a carboxylic acid or corresponding anhydride comprising a first polyether and the compound comprising a carboxylic acid or anhydride thereof and in which the polymeric shell has an acid value of at least 20, such as 22 or 25 or from 20 to 45, such as 20 to 40 or 25 to 40 mg KOH per gram of polymer based on the total resin solids of the polymer that forms the polymeric shell determined according to ASTM D 4662-15 (2015).

10. The coating composition to any preceding claim, wherein the polymer (a) comprises moieties according to the formula: [(E)x – Uy – Oz -] -P wherein E represents a condensation polymer moiety derived from the compound (i) and the compound (ii), wherein the polymer comprises carboxylic acid or anhydride functional groups bonded directly to an aromatic ring, and one or more hydroxyl groups, wherein U represents a moiety comprising urethane groups, wherein O represents a moiety derived from a compound comprising at least one olefinic group and one or more hydroxyl groups, wherein P represents a moiety comprising an addition polymer comprising from 2 to 1000 repeat units reacted with an olefinic group in O, wherein the number of P groups can be from 1 to the number of olefinic groups in O, wherein x is an integer from 1 to 10, wherein y is an integer from 1 to 20, wherein y is not greater than the sum of the number of hydroxyl groups in E and O, and wherein z is an integer from 1 to 10, wherein z is not greater than y; and optionally wherein the moiety comprising urethane groups, U, comprises the reaction product of an isocyanate group and a hydroxyl group; optionally wherein the moiety comprising urethane groups, U, is derived from a composition comprising isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, 1,3,5-triisocyanato benzene, 2,4,6-triisocyanatotoluene, 4,4′-methylene-bis(cyclohexyl isocyanate), 2,2,4- trimethyl hexamethylene diisocyanate, 2,4,4-trimethyl hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate, tetramethyl xylylene diisocyanate and / or 4,4′-diphenylmethylene diisocyanate; optionally wherein the moiety comprising at least one olefinic group and one or more hydroxyl groups, O, is derived from a C1 to C20 linear, branched or cyclic, aliphatic or aromatic molecule comprising at least one alcohol and at least one polymerizable olefinic group; optionally wherein the moiety comprising at least one olefinic group and one or more hydroxyl groups, O, is derived from a composition comprising hydroxy ethyl (meth)acrylate, hydroxy propyl (meth)acrylate, poly(ethylene glycol) (meth)acrylate, poly(propylene glycol) (meth)acrylate,poly(tetrahydrofuran) (meth)acrylate, glycerol allyl ether, and / or (meth)acryloxy glycerol; optionally wherein the addition polymer moiety, P, comprises a polymerization product resulting from polymerizing a composition comprising the moiety comprising at least one olefinic group and one or more hydroxyl groups, O; and one or more of a monomer according to the formula CR102=CR12-C(O)-B-CR133,wherein R10and R12are independently hydrogen, methyl or ethyl; B is a difunctional radical that can be O, NR14or S; R14is hydrogen, methyl or ethyl; and each R13is independently a C1 to C20 linear or branched aliphatic or aromatic group or a C1 to C20 linear or branched aliphatic hydroxyl containing group; a monomer according to the formula CR102=CR12-C(O)-B-CR152-B-C(O)-CR12=CR102, wherein R10, R12and B are as defined above and R15is a difunctional C1 to C20 linear or branched aliphatic and / or aromatic group; styrene; and divinyl benzene.

11. The coating composition according to any preceding claim, wherein the coating composition has a total solids of from 10 wt. % to 90 wt. %, such as from 15 wt. % to 75 wt. %, or from 20 wt. % to 50 wt. % measured according to ASTM D 2369-20.

12. The coating composition according to any preceding claim, wherein the coating composition comprises one or more colorants, such as a pigment and / or a dye.

13. A substrate at least partially coated with a coating formed from the coating composition according to any preceding claim; optionally wherein the substrate forms at least a portion of a vehicle or a package; wherein the package optionally comprises a metal can, an aerosol can or tube, or a monobloc aerosol can or tube.

14. The coating composition according to any of claims 1 through 12, wherein the coating composition forms part of a multi-layer coating system comprising: (1) a first basecoat layer applied over at least a portion of a substrate; and (2) a second basecoat layer applied over at least a portion of the first coating layer,wherein at least one of the first basecoat layer and the second basecoat layer is formed from a first basecoat composition comprising a coating composition according to any of claims 1 through 12.

15. The coating composition according to claim 14, wherein the multi-layer coating system further comprises a primer coating layer applied over at least a portion of the substrate, wherein the first primer coating layer is positioned between the first basecoat layer and the substrate, and / or a topcoat layer applied over at least a portion of the second basecoat layer.

16. The coating composition according to either of claims 14 or 15, wherein the polymer (a) of the multi-layer coating system comprises a self-emulsifying dispersion polymer.

17. A process of coating a substrate with a multi-layer coating comprising: forming a first basecoat layer over at least a portion of a substrate by depositing a first basecoat composition onto at least a portion of the substrate; and forming a second basecoat layer over at least a portion of the first basecoat layer by depositing a second basecoat composition directly onto at least a portion of (1) the first basecoat layer after the first basecoat composition is dehydrated or (2) the first basecoat composition before the first basecoat composition is dehydrated, wherein the first basecoat composition and second basecoat composition are dehydrated, and wherein at least one of the first basecoat layer and the second basecoat layer is formed from a first basecoat composition comprising a coating composition according to any of claims 1 through 12; wherein optionally the first basecoat composition is dehydrated before application of the second basecoat composition or both the first and second basecoat compositions are simultaneously dehydrated.

18. The process of claim 17, comprising a method of forming a coating layer on at least a portion of a substrate comprising: applying the coating composition according to any of claims 1 through 12 over at least a portion of the substrate; and exposing the coating composition to a sufficient amount of energy for a sufficient amount of time for the coating composition to cure and to form a uniform coating on the substrate.

19. The process of claim 18, wherein the coating composition is applied using a method comprising spray application, draw down, brush application, rotary bell application, roll coaterapplication, coil coating application and / or precision application; and optionally wherein the substrate comprises iron, steel, and aluminum, plastic, wood, glass, synthetic material, paper, leather, and / or another coating layer.

20. The process according to any of claims 17 through 19, wherein the coating composition is cured by exposure to a temperature of from 50 °C to 160 °C, such as from 55 °C to 155 °C, or from 60 °C to 150 °C, or from 60 °C to 120 °C, or from 80 °C to 110 °C, or from 50 °C to 100 °C for a period of time sufficient to fully cure the coating layer.

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