Antifogging coatings and methods of use thereof

Abstract

Disclosed is an anti-fog coating composition for forming a cross-linked film, the anti-fog coating composition comprising a prepolymer and at least one amine-containing cross-linking agent. The prepolymer comprises one or more charged monomer residues, one or more uncharged hydrophilic monomer residues, and one or more amine reactive monomer residues. The cross-linked film has a haze value change of less than 30% when exposed to a fogging condition for a period of more than 30 seconds. Also disclosed is a kit comprising a first compartment comprising the prepolymer and a second compartment comprising the amine-containing crosslinking agent. Also disclosed herein are anti-fog films and coated articles comprising anti-fog coatings. Also disclosed is a method of preparing an anti-fog coated substrate by applying the composition to the anti-fog coated substrate.

Description

Cross Reference to Related Applications

[0001] This application claims the benefit of priority of U.S. Provisional Application No. 63 / 491,566, filed March 22, 2023, the contents of which are incorporated by reference in their entirety. TECHNICAL FIELD

[0002] The present disclosure relates generally to anti-fog coatings and methods of making the same. Embodiments of the present disclosure also relate to compositions and kits for making such coatings, as well as films and coatings comprising such compositions, which can be applied to desired substrates that benefit from an optionally transparent anti-fog coating, such as automotive windshields, camera lenses, and refrigerator windows. BACKGROUND

[0003] Anti-fog coatings are commonly used to prevent glass or other transparent substrates from becoming obscured by water condensation. Fogging environments arise when the surface temperature is below the ambient dew point, causing water vapor to condense on the surface as droplets. The size and shape of these droplets cause them to scatter light, which can reduce the optical transparency of the surface. Some existing inventions focus on applying a hydrophobic coating, such as a silicone, to the substrate. These materials can be effective for short durations, but they can fail in strong fogging environments, leading to the formation of large droplet nuclei on the surface. A more common strategy is to use a hydrophilic coating, causing the water droplets to have a low contact angle with the coated substrate, resulting in the water forming a transparent, flat sheet.

[0004] Hydrophilic coatings face a trade-off between efficacy and durability. In fogging environments, hydrophilic coatings remain transparent by favorably interacting with liquid water, which results in a low contact angle that causes liquid water to form a flat film on the coating. However, due to these coatings’ strong interaction with liquid water, they can be easily washed off, or they can swell in the presence of liquid water or water vapor, making them prone to damage. Conversely, more mechanically durable coatings incorporate stronger intermolecular connections within the coating, such as chemical crosslinks or hydrophobic interactions, but this can reduce the hydrophilicity of the coating and decrease performance.

[0005] Despite the wide variety of “permanent anti-fog coatings” on the market, they are mostly composed of crosslinked hydrophilic polymers. At least one common drawback of these permanent anti-fog coatings is that they can be toxic or otherwise contain harmful ingredients. For example, to make an anti-fog coating using crosslinked hydrophilic polymers, harmful reagents are often required, such as aziridine crosslinkers, isocyanate-functional materials, or tin catalysts. Such harmful reagents have serious toxicity and environmental concerns; therefore, they are heavily regulated and difficult to use safely in an industrial setting.

[0006] Other common drawbacks of anti-fog coatings made from cross-linked hydrophilic polymers are that they can be difficult to apply to a surface, or that they can have poor mechanical properties when applied on a substrate. For example, coating compositions that rely on cross-linking can form high viscosity over time as the cross-linker and polymer react. As a result, it can be difficult to apply the coating composition on the surface of a substrate. For another example, other anti-fog coatings can use block cross-linkers that require extended heat treatment to form the coating on the article or end product. If the applied heat treatment is insufficient, the coating can not continue to cure to a sufficient degree under ambient conditions. The necessity of extended heat treatment can be difficult for applications.

[0007] Furthermore, another drawback of most commercially available anti-fog coating compositions is that they lack a combination of desirable characteristics of the coating required for practical applications, such as long pot life and the ability to cure quickly at room temperature. Curing is an important process step that can maximize the desired properties of the coated substrate by ensuring proper adhesion, mechanical strength, chemical resistance, and beneficial surface properties of the coating. For example, curing can prevent the coating from being washed away by water or other solvents, it can increase the hardness or modulus of the coating, or surface active additives can collect at the coating surface during curing to reduce the friction of the surface. If the coating cannot cure at room temperature, careful process control is required to ensure complete curing. Coatings that cure at room temperature avoid this risk because any incomplete curing reactions can continue after the initial application process is complete.

[0008] Pot life is another important property of any coating formulation; generally a longer pot life corresponds to a longer process window for applying the coating composition in an industrial setting. Coatings with too short a pot life can damage the application equipment through irreversible curing inside valves, pipes, or other parts. Generally, the faster a coating composition cures at room temperature, the shorter the pot life, which leads to a trade-off between two important criteria for coating application. Balancing a time-efficient curing process while maintaining an acceptable pot life of the coating composition is a challenge for both coating manufacturers and users.

[0009] Another challenge associated with applying anti-fog coating compositions on substrates or making anti-fog coatings using cross-linked hydrophilic polymers is that most polymer cross-linking reactions are highly sensitive to environmental conditions (e.g., temperature, pressure, UV light, humidity, or the presence of other chemicals). Therefore, for industrial applications of such coatings, it is necessary to have a highly controlled environment.

[0010] Another drawback of many anti-fog coatings is that they rely on "sol-gel" chemistry and require complex coating techniques. The process involves the conversion of monomers into a colloidal solution (sol) that acts as a precursor to an integrated network of discrete particles or networked polymers (or gel). For example, sol-gel processes can include the hydrolysis and condensation of alkoxysilane groups catalyzed by water. While commonly used, the sol-gel process itself and the chemical composition of the reactants used in the process can make the implementation of sol-gel technology in an industrial setting challenging. The sensitivity of the precursors to water can complicate the storage of the precursors prior to use. For example, it can be necessary to use flammable solvents with high volatile organic compound (VOC) content as carriers to store the precursors prior to use, rather than water. The complex nature of the hydrolysis and condensation can require careful control of the application conditions and can often limit the pot life of the coating prior to gelation of the coating, making it no longer useful for application as a film, and can cause damage to the application machinery. Furthermore, the final properties of such anti-fog coatings prepared using sol-gel processes can be influenced by the curing regime and, as such, careful process control is required to produce a crack-free and sufficiently durable coating.

[0011] Furthermore, anti-fog coatings made from cross-linked hydrophilic polymers can exhibit "fouling" behavior, which refers to contamination from hydrophobic molecules that adhere to the surface of the coated substrate. Fouling is undesirable when coating any substrate, as unwanted buildup of material can occur on the substrate. To make the coating "fouling resistant," additional chemicals are often required. For example, silicones or fluoropolymers are often used to provide anti-fog coatings with low surface energy and low friction properties.

[0012] The disclosed anti-fog cross-linked coating compositions are intended to overcome one or more of the problems set forth above and / or other problems of the prior art. In particular, the coating compositions disclosed herein have high anti-fog properties over time. Furthermore, when the compositions are made into coatings, they are mechanically durable and are not easily scratched, damaged, or soiled during use. Finally, in some embodiments, the coatings can be applied from a compound, or a composition, or a kit including the compound or composition, that has a long pot life, making the industrial application of the coatings versatile and easy to use.

[0013] Further, the disclosed anti-fog crosslinked polymeric coating compositions do not use highly toxic crosslinkers that can require expensive safety protocols. The disclosed coatings are capable of curing at room temperature and can be applied on a variety of types of substrates regardless of the substrate chemistry. The method of applying the disclosed coating compositions on a substrate is simple and can be used to make anti-fog coatings on a variety of substrates while ensuring sufficient curing of the coating with less expensive process controls compared to commercially available anti-fog coatings. Another advantage of the disclosed coating compositions or kits is that they have a long pot life of greater than 24 hours, which makes implementation easier, less wastage of material, and limits the risk of the coating jamming and damaging the application machinery. The disclosed compositions or kits can be stored completely or partially in water as the carrier, which reduces VOC emissions and flammability issues and is therefore less toxic and more environmentally friendly. Finally, the disclosed coatings provide strong and durable anti-fog properties to the substrates on which they are applied.

[0014] The features and advantages of the compounds, compositions, kits, coatings, and methods disclosed herein are illustrated by the following examples, which are not to be construed as limiting the scope of the disclosure in any manner. SUMMARY

[0015] According to the foregoing, in one embodiment, a composition for forming a crosslinked film that imparts anti-fog properties is described. In some embodiments, the composition comprises a prepolymer and at least one amine-containing crosslinker, the prepolymer comprising (a) one or more charged monomer residues, which can be hydrophilic; (b) one or more uncharged hydrophilic monomer residues; and (c) one or more amine-reactive monomer residues. The described crosslinked film exhibits a change in haze value of less than 30% when exposed to fogging conditions for a period of more than 30 seconds.

[0016] In another embodiment, an anti-fog film is described, the anti-fog film comprising a crosslinked polymer. In some embodiments, the crosslinked polymer comprises: (a) one or more charged monomer residues, which can be hydrophilic; (b) one or more uncharged hydrophilic monomer residues; (c) one or more amine-reactive monomer residues; and (d) at least one amine-containing crosslinker residue. The described anti-fog film exhibits a change in haze value of less than 30% when exposed to fogging conditions for a period of more than 30 seconds.

[0017] In another embodiment, a coated article is described, comprising: a substrate and a coating. In some embodiments, the coating comprises: a crosslinked polymer containing (a) one or more charged monomer residues, which may be hydrophilic; (b) one or more uncharged monomer residues; (c) one or more amine-reactive monomer residues; and (d) at least one amine-containing crosslinking agent residue, wherein the coated article exhibits a haze value change of less than 30% when exposed to fogging conditions for a period exceeding 30 seconds.

[0018] In another embodiment, a method for preparing the surface of an anti-fogging substrate is described. In some embodiments, the described method includes applying a compound to the surface of the substrate, the compound comprising: a first composition and a second composition. In some embodiments, the first composition is made of a prepolymer comprising (a) one or more charged monomer residues, which may be hydrophilic; (b) one or more uncharged monomer residues; and (c) one or more amine-reactive monomer residues. In some embodiments, the second composition comprises at least one amine-containing crosslinking agent. When exposed to fogging conditions for a period exceeding 30 seconds, the treated substrate exhibits a haze value change of less than 30%.

[0019] In another embodiment, a kit for forming a hydrophilic crosslinked membrane is described. In some embodiments, the kit includes: (A) a first component and (B) a second component, wherein the hydrophilic crosslinked membrane exhibits a haze value change of less than 30% when exposed to fogging conditions for a period exceeding 30 seconds. The first component (A) comprises a first composition comprising a prepolymer. The prepolymer comprises (a) one or more charged monomer residues, which may be hydrophilic; (b) one or more uncharged monomer residues; and (c) one or more amine-reactive monomer residues. The second component (B) comprises a second composition comprising at least one amine-containing crosslinking agent.

[0020] As described in more detail below, various embodiments may include at least one additive used to improve the properties of the composition, film, coating article or method, such as additives that aid adhesion, antifreeze, crosslinking, film formation, mechanical properties or rheological properties. Detailed Implementation

[0021] Definitions: As used herein, “haze value” refers to a numerical value representing the light scattering caused by inhomogeneity or discontinuity in the material, which may result in undesirable optical properties such as reduced transparency. Haze measuring devices, such as haze meters, can be used to measure this value. The term “Δhaze” refers to the haze value, or the change in haze measured according to ASTM D1003, before and after exposure to vapor. For example, the haze value of a sample equilibrated at 25°C is measured according to ASTM D1003. The sample is then held in a beaker of boiling water for 60 seconds, and the haze value is reassessed using ASTM D1003. The difference between the first and second measurements is defined as “Δhaze.” Typically, haze values ​​are measured as a percentage of scattered incident light and have no specific unit, expressed as a percentage. According to ASTM specifications, materials with a haze value greater than 30% are defined as “diffuse” and thus serve as the boundary between optically transparent and hazy or optically opaque samples.

[0022] As used herein, a "monomer" refers to a chemical entity that can serve as the smallest repeating unit in a polymer and has one or more reactive chemical groups configured for polymerization. For example, methacrylate is a monomer that can serve as a repeating unit in a methacrylate polymer (e.g., polymethyl methacrylate) and has a reactive olefin configured for polymerization.

[0023] As used herein, the term "hydrophilic monomer" refers to a monomer that has high solubility in water. For example, at room temperature, the solubility of a hydrophilic monomer in deionized water can be greater than 100 g / L.

[0024] As used herein, the term "charged monomer" refers to a monomer that has charged atoms or molecules when dissolved in deionized water. Charged monomers contain either a positive or negative charge. Non-limiting examples of such charged monomers include acrylic acid, or any salt formed by neutralizing acrylic acid with an alkali. In contrast, "uncharged monomers" do not contain any charge when dissolved in deionized water.

[0025] As used herein, the term "amine reactive monomer" refers to a monomer that can chemically react with amine functional groups.

[0026] As used herein, the term "amine-containing monomer" refers to a monomer that has an amine functional group in its structure. Amine-containing monomers are typically characterized by their "active hydrogens," which determine the number of additional bonds that the amine can form. For example, primary amines have two active hydrogens, while secondary amines have one.

[0027] As used herein, “monomer residue,” “crosslinker residue,” or “residue” refers to a molecule that has undergone a chemical process. For example, a residue is a monomer that has been incorporated into an oligomer, prepolymer, or polymer during a polymerization reaction. Specifically, the polymerization of methacrylate monomers produces a poly(methacrylic acid) polymer composed of methacrylate residues. Additionally, any unreacted methacrylate monomers also constitute methacrylate residues. Furthermore, chemically transformed functional groups are also residues. For example, an ester formed by the reaction of acrylic acid and methanol is an acrylic acid residue.

[0028] As used herein, “prepolymer” refers to a polymer or oligomer containing monomer residues and intended to undergo subsequent chemical reactions or processing steps, such as crosslinking.

[0029] As used herein, the term "crosslinking agent" refers to a molecule that can undergo multiple reactions to form bonds between multiple polymer chains. This may result in the molecule reacting with multiple polymer chains, or it may react with the polymer chains once before undergoing a second type of reaction that leads to a crosslinked network.

[0030] As used herein, the term "crosslinking" refers to a chemical reaction that forms chemical bonds between two or more polymer chains. It is the process of chemically combining two or more molecules to form a crosslinked network. Factors affecting crosslinking include the concentration of the crosslinking agent, such as the concentration of amine-reactive monomers and amine-containing crosslinking agents, the reaction duration, temperature, pH, solvent composition, viscosity, and steric hindrance caused by the presence of functional groups in the monomers and crosslinking agents involved in the crosslinking reaction. As used herein, the term "initiator" refers to a molecule that can initiate a polymerization reaction.

[0031] As used herein, the term "polymer functionality" refers to the presence of chemical functional groups, which are motifs or families of motifs, in the monomer residues of a polymer. Functional polymers are macromolecules with unique properties or uses. The specific polymer functionality is usually determined by the chemical functional groups present in the polymer, which are different from the functional groups in the backbone chain.

[0032] As used herein, the term “additive” means any chemical substance or material added to a system comprising the disclosed composition, wherein adding the additive to the system modifies one or more properties of the composition.

[0033] As used herein, the term "mechanical additive" refers to any chemical substance or material added to a sample comprising the disclosed composition, wherein the addition of the additive to the sample is configured to modify the mechanical properties of the composition.

[0034] As used herein, the term "fog" refers to water droplets on a surface that reduce the surface's optical transparency. Conversely, a substrate coated with an anti-fog coating can absorb water vapor before it can condense on the surface, absorb water droplets after they have formed, or allow water droplets to uniformly wet the surface to form a water film that minimizes the reduction in optical transparency.

[0035] As used herein, the term "anti-fog film or coating" refers to a film or coating configured to give the substrate a higher degree of anti-fog performance when applied to the substrate in a film-free or film-free condition relative to the same substrate.

[0036] As used herein, the term "anti-fog" surface refers to a surface whose optical transparency does not decrease when exposed to fogging conditions. One method to assess this is by measuring the change in haze value of the substrate when it is exposed to fogging conditions. For opaque substrates, such as metals or colored plastics, "anti-fog" is a qualitative assessment. One method for assessing whether an opaque sample is anti-fog is to place it over steam before visual inspection. If water droplets significantly alter the appearance of the sample, it is not anti-fog. If the substrate is clearly visible, it is anti-fog or has anti-fog properties.

[0037] As used herein, the term "fogging conditions" refers to the combination of temperature and humidity that allows water to condense on a surface. Fogging is likely to occur on a substrate when the air is humid and the substrate temperature is below the dew point.

[0038] As used in this article, the term "hydrophilic coating" refers to a coating with an equilibrium water contact angle of less than 90 degrees.

[0039] As used herein, the term "pot life" refers to the amount of time a compound can be used after being combined with other reactive compositions. After this period, the compound may become too viscous to apply, or the curing process may fail to produce acceptable properties in the final product. In some industrial use cases, "pot life" is quantified as the time required for the initial viscosity of the mixed compound to quadruple at room temperature. For example, the pot life of a kit containing two components with two different compositions can be defined as the time required for the viscosity of the mixture of the two compositions to quadruple at room temperature. For instance, if a compound formed after mixing the two compositions in two compartments of a kit has an initial viscosity of 100 cP and increases to 400 cP after 50 hours at room temperature, the pot life at room temperature is 50 hours. The pot life of a compound can be modified by changing several parameters, such as by changing the type or amount of solvent.

[0040] As used herein, the term "curing" refers to a process in which a composition undergoes a transformation, in which its mechanical and chemical properties are altered. Most typically, this requires a cross-linking reaction or the formation of chemical bonds with a substrate.

[0041] Composition Chemical composition In some embodiments, the disclosed coating composition may comprise a polymer, a prepolymer, a solvent, an additive, a crosslinking agent, and a combination of their residues.

[0042] In some embodiments, the disclosed coating composition may be a two-component (2K) system.

[0043] In some embodiments, the disclosed coating composition may require some charged molecules that are sufficiently hydrophilic.

[0044] In some embodiments, a crosslinking agent or hardener may be mixed with the coating composition prior to application and then cured on the substrate during application.

[0045] In some embodiments, the disclosed coating composition may be hydrophilic. In other embodiments, the disclosed coating composition may be superhydrophilic.

[0046] In some embodiments, the disclosed composition may not contain any catalyst or crosslinking agent that is a Class 1 mutagen, or any catalyst or crosslinking agent that is listed as having Class 1 acute toxicity, reproductive toxicity, or organ-specific toxicity as defined by GHS.

[0047] In some embodiments, one or more solvents may be used in the disclosed compositions. Non-limiting examples of such solvents include water, alcohols such as methanol, ethanol, isopropanol, n-butanol, tert-butanol, sec-butanol and 1-methoxy-2-propanol, amines such as ammonium hydroxide or triethylamine, ethers or ethylene glycol-based solvents such as ethylene glycol, propylene glycol, glycerol, ketones such as acetone, ethyl acetate or methyl ethyl ketone, or other solvents suitable for polymers or prepolymers.

[0048] In some embodiments, the disclosed composition may contain one or more solvents in sufficient quantities to achieve the desired properties of the composition without causing any serious acute toxicity or environmental problems.

[0049] In some embodiments, the disclosed composition may further comprise a catalytic acid or a catalytic base to assist the crosslinking reaction between the prepolymer and the crosslinking agent.

[0050] Compound In some embodiments, the disclosed composition may be a two-component (2K) system comprising a first component and a second component. The first component may comprise a prepolymer, and the second component may comprise an amine-containing crosslinking agent. In some embodiments, the first and second components may be present in the composition in sufficient amounts to form an antifog film, the haze value of which changes by less than 30% when exposed to fogging conditions for a period exceeding 30 seconds.

[0051] In some embodiments where the disclosed coating composition is a 2K system, the prepolymer in the first component may be dissolved, suspended, or dispersed in a carrier solvent or liquid. The carrier solvent may be 20% to 100% water and 0% to 80% a water-miscible cosolvent or cosolvent mixture. Non-limiting examples of such solvent or cosolvent may include methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or any combination thereof.

[0052] In some embodiments where the disclosed coating composition is a 2K system, the second component may include an amine-containing crosslinking agent or a mixture of crosslinking agents. In some embodiments, the second component may not contain a solvent. In other embodiments, the amine-containing crosslinking agent or mixture of crosslinking agents may be soluble in water in the second component. In other embodiments, the second component may contain an amine-containing crosslinking agent or mixture of crosslinking agents dissolved in a water-miscible solvent or solvent mixture. Non-limiting examples of such solvents include methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or any combination thereof.

[0053] In some embodiments where the disclosed coating composition is a 2K system, the first component may comprise a solution of 1 wt% to 30 wt% of a prepolymer, 0.1 wt% to 70 wt% of water, 0.1 wt% to 50 wt% of an alcohol, 0.001 wt% to 2 wt% of a leveling additive, and 0.001 wt% to 2 wt% of a UV stabilizer; wherein the prepolymer may comprise 1 wt% to 30 wt% of charged monomer residues, 0.1 wt% to 30 wt% of amine-reactive monomer residues, and 10 wt% to 80 wt% of uncharged monomer residues.

[0054] In some embodiments where the disclosed coating composition is a 2K system, the second component may comprise 1 wt% to 99.9 wt% of an amine-containing crosslinking agent and 0.1 wt% to 99 wt% of water.

[0055] In some embodiments where the disclosed coating composition is a 2K system, the second component may comprise 1 wt% to 80 wt% of an amine crosslinking agent, 0.1 wt% to 90 wt% of an alcohol, and 0.1 wt% to 25 wt% of a silane coupling agent.

[0056] Prepolymer In some embodiments, the composition comprises a prepolymer. In some embodiments, the composition may comprise a prepolymer synthesized using at least two or more hydrophilic monomers, at least a portion of which comprises a charged hydrophilic monomer.

[0057] In some embodiments, the prepolymer may contain one or more monomer residues having residues of the following: epoxy functional group, unsaturated functional group, azide functional group, propargyl functional group, acid anhydride functional group, acyl chloride functional group, aldehyde functional group or isocyanate functional group.

[0058] In some embodiments, the one or more charged monomer residues may include sulfonate functional groups, carboxyl functional groups, phosphonate functional groups, nitro functional groups, imidazolium functional groups, guanidinium functional groups, or quaternary ammonium functional groups, or monomers that can be converted into these functional groups, including: 2-acrylamido-2-methylpropanesulfonic acid, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonylpropyl)ammonium hydroxide, 2-ethyldimethylammonium ethyl methacrylate, 2-(methacryloyloxy) [Ethyl]trimethylammonium, 4-styrenesulfonic acid, p-styrenecarboxylic acid, vinylsulfonic acid, 3-acrylamide-3-methylbutyric acid, acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, 1-allyl-3-methylimidazolium chloride, maleic anhydride, itaconic acid, propyl 3-sulfonate acrylate, undecyl 11-phosphonate acrylate, vinylphosphonic acid, alginate methacrylate, propyl 3-sulfonate methacrylate, 1-vinylimidazolium, derivatives of these monomers, salts of these monomers, or combinations thereof.

[0059] In some embodiments, the one or more uncharged hydrophilic monomer residues may include hydroxyl functional groups, pyrrolidone functional groups, acetate functional groups, or ether functional groups, including: 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, n-vinyl-2-pyrrolidone, vinyl alcohol, N-(2-hydroxyethyl)methacrylamide, any acrylate or methacrylate-based monomer having polyethylene glycol or polypropylene glycol functional groups, vinyl acetate, diacetone acrylamide, tetrahydrofuran acrylate or methacrylate, acrylate or methacrylate of carbohydrates, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or combinations thereof.

[0060] In some embodiments, the one or more charged monomer residues may be monomer residues having a solubility of greater than 100 g / L in deionized water.

[0061] In some embodiments, the one or more charged monomer residues may be acidic, basic, or salts that neutralize acids or bases.

[0062] In some embodiments, the one or more uncharged hydrophilic monomer residues may be residues of monomers having a solubility of greater than 100 g / L in deionized water.

[0063] In some embodiments, the one or more amine-reactive monomer residues may include monomer residues containing epoxy groups, ketone functional groups, acid anhydride functional groups, or isocyanate functional groups, including: allyl methacrylate, vinyl methacrylate, glycidyl methacrylate, 2-isocyanoethyl methacrylate, 3,4-epoxycyclohexyl methacrylate, methyl vinyl ketone, 4-ethylene-1-cyclohexene-1,2-epoxy, allyl glycidyl ether, diacetone acrylamide, n-hydroxysuccinimide monomers, maleic anhydride, residues of these monomers or functional groups, derivatives of these monomers, or combinations thereof.

[0064] Crosslinker In some embodiments, the disclosed coating composition may comprise an epoxy amine crosslinking agent system.

[0065] In some embodiments, the composition may include an amine-containing crosslinking agent. The amine-containing crosslinking agent may be Jeffamine or a hindered amine crosslinking agent. In some embodiments, the amine-containing crosslinking agent may be used to crosslink the prepolymer to prepare the disclosed antifog coating composition.

[0066] In some embodiments, the amine-containing crosslinking agent may comprise a primary or secondary amine capable of forming one or more covalent bonds with the polymer. Such an amine-containing crosslinking agent may comprise, but is not limited to, polyether amines or polymers having a polyether backbone, including polyethylene oxide, polypropylene oxide, or other ethylene oxides containing one or more nitrogen atoms per molecule, polyoxypropylene diamine, polyoxypropylene triamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, or secondary aminosilanes such as n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide, or any combination thereof.

[0067] In some embodiments, an amine-containing crosslinking agent may contribute to a longer pot life of the disclosed composition. The amine-containing crosslinking agent may be chemically inhibited from participating in the crosslinking reaction; for example, the amine-containing crosslinking agent may be designed to have steric hindrance in the vicinity of the amine functional groups, thus resulting in a slower crosslinking reaction rate for forming the disclosed crosslinked film. Alternatively, the amine-containing crosslinking agent may be a secondary amine, thus resulting in a slower crosslinking reaction rate for forming the disclosed crosslinked film. The composition can spontaneously cure on any substrate after application. The slower crosslinking rate of the disclosed composition allows for a longer pot life and lower viscosity, and is therefore easier to apply.

[0068] Additive In some embodiments, the composition may further comprise at least one additive. The additive may be a mechanical additive, coupling agent, UV absorber, UV stabilizer, surfactant or leveling additive, dye, biocide, or antifreeze additive.

[0069] In some embodiments, the mechanical additive includes one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, cellulose nanofibers, polyhedral oligomeric silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, layered silicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, any dispersant or surface modifier necessary for processing the mechanical additive, or any combination thereof.

[0070] In some embodiments, the silane coupling agent may include: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

[0071] In some embodiments, the UV absorber may include benzophenone, benzotriazole, cyanoacrylate, phenoxytriazine, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, or any combination thereof.

[0072] In some embodiments, the UV stabilizer may include hindered amine light stabilizer (“HALS”) agents or other additives designed to prevent UV degradation, including: bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester, dimethyl succinate polymer having 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidinyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]] or any combination thereof.

[0073] In some embodiments, the surfactant, wetting agent, or leveling agent may include silicone polyether surfactants, polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, polysorbate-based surfactants, sodium dodecyl sulfate, hexadecyltrimethylammonium bromide surfactants, dispersants, styrene-maleic acid copolymers, silicone-modified polyacrylates, polyethylene-polypropylene block copolymer surfactants, other commercially available leveling or wetting additives, or any combination thereof.

[0074] In some embodiments, the antifreeze additive may include glycerol, ethylene glycol, propylene glycol, polypropylene glycol, or polyethylene glycol, or molecules comprising at least one of the above.

[0075] Pot life In some embodiments, the composition may have a shelf life of more than 8 hours, such as 24 hours, such as more than 48 hours, or more than 72 hours, or more than 96 hours at room temperature.

[0076] In some embodiments where the disclosed coating composition is a 2K system, the first and second components may be present in an amount sufficient to give the composition a working life of more than 8 hours, such as 24 hours, such as more than 48 hours, or more than 72 hours, or more than 96 hours at room temperature after the two components are mixed and stored in a sealed container with a headspace less than the volume of the composition.

[0077] In some embodiments, the composition can be applied as a single layer onto a substrate.

[0078] In some embodiments, the composition may have a low viscosity of less than 1000 cP, such as less than 800 cP, less than 600 cP, less than 400 cP, less than 200 cP, or less than 100 cP. In some embodiments, the composition can be easily sprayed onto a substrate due to its low viscosity and long pot life.

[0079] Film / coating In some embodiments, the disclosed coating may be water-absorbing. In some embodiments, the disclosed coating may have a very low contact angle with water.

[0080] Durability In some embodiments, the coating composition can produce a film or coating that is stable (i.e. retains its properties) after exposure to mechanical stress, chemical stress, or environmental stress.

[0081] In some implementations, the coating may have high resistance to cleaning solvents. For example, the anti-fog coating can be wiped with a cloth wetted with a cleaning solution selected from those containing 1% to 100% isopropanol, 0.1% to 10% sodium hypochlorite solution, 0.1% to 5% ammonia, and 0.1% to 10% dish soap, and the change in the Δhaze value in the film is less than 2%.

[0082] In some implementations, the coating can be immersed in deionized water, a 5% NaCl aqueous solution, or a 0.1% dish soap aqueous solution for 24 hours while retaining satisfactory mechanical and anti-fogging properties.

[0083] In some implementations, the coating is resistant to mechanical abrasion. For example, some implementations can be rubbed 1000 times using a linear abrasive with a 1000g load and a coarse cotton cloth rubbing head, and can exhibit a haze value change of less than 5%, such as less than 2%, and in many cases less than 1%. In another implementation, an implementation can be rubbed 1000 times using a linear abrasive with a 1000g load and a sponge rubbing head, and can exhibit a haze value change of less than 5%, such as less than 2%, and in many cases less than 1%.

[0084] In other embodiments, the coating can withstand abrasion with common household chemicals or cleaning products, including chemicals such as Windex, Formula 409, Armor All, insect repellents, leather cleaners, sunscreens, and artificial sweat. In these embodiments, a cloth dampened with the chemical is rubbed onto the coating for 10 cycles with a linear abrasive under an applied load of 500g. After removing any chemical residues, the sample may exhibit a haze value change of less than 5%, such as less than 2%, and in many cases less than 1%. The sample may still exhibit anti-fogging properties after this test.

[0085] In some implementations, the coating may exhibit excellent adhesion properties. The coating may be able to be tested according to the ASTM D3359 cross-cut adhesion test and achieve a 5B rating.

[0086] In some implementations, the coating may exhibit excellent moisture resistance. The coating can be exposed to 85°C and 95% relative humidity for 7 days without showing any visual defects. The coating retains excellent anti-fogging properties, exhibiting a Δhaze of less than 5%, such as less than 2%, and in many cases less than 1%, when tested according to a vapor test. The coating retains excellent adhesion properties after 7 days of exposure to high temperature and high humidity, achieving a 5B rating after testing according to the ASTM D3359 cross-cut adhesion test.

[0087] Coated article In some embodiments, the substrate of the coated article may be glass, plastics such as acrylic, polycarbonate, polyethylene terephthalate, poly(methyl methacrylate), poly(ethylene-co-tetrafluoroethylene), sheets of any of these polymer substrates having an adhesive backing, metals such as aluminum, ceramic materials, or any combination thereof.

[0088] In some embodiments, the substrate may include a layer applied using a pretreatment step prior to the application of the antifog coating.

[0089] In some implementations, the coated substrate or article can be an automotive or building structure, building window, camera lens, medical mirror, sensor, eyeglasses, mirror, consumer electronics, personal protective equipment, other safety equipment, or refrigerator door.

[0090] In some embodiments, the coated substrate or article may exhibit a Δhaze of less than 30%, such as less than 5%, or less than 2%, and in many cases less than 1%, during exposure to fogging conditions. In some embodiments, a substrate coated with a coating composition according to the present disclosure exhibits a Δhaze in the range of 0.1% to less than 2%, such as 0.1% to 1.7%.

[0091] In some embodiments, the coating may impart hydrophilic properties to the substrate, but not necessarily to prevent fogging. For example, in some embodiments, the coating may be applied to a metal substrate to increase its affinity for water, or the coating may be selectively applied to a metal substrate to direct water to the coated area and away from the uncoated area. In other embodiments, the coating may be applied to a rubber substrate to allow water to wet the surface more easily. In other embodiments, the coating may be applied to the surface of marine facilities to repel barnacles or other contaminants.

[0092] In some embodiments, the coating may be applied to a surface to resist frost formation. In other embodiments, the coating may be applied to a substrate to increase the rate of frost melting.

[0093] In some embodiments, the coating of the coated article is in the form of a laminate. For example, in one embodiment, the laminate may include a transparent substrate, a transparent adhesive, and a coating. In another embodiment, the adhesive may be selected from acrylic adhesives, silicone adhesives, polyurethane heat-sealing adhesives, polyethylene heat-sealing adhesives, and combinations thereof.

[0094] In some embodiments, the transparent substrate may include polyethylene, polyethylene terephthalate, polycarbonate, cellulose acetate, cellulose triacetate, polyacrylate, or combinations thereof.

[0095] In some implementations, uncharged monomers, charged monomers, amine-reactive monomers, or residues thereof may be introduced during the crosslinking step.

[0096] In some embodiments, the second composition containing the crosslinking agent also contains charged groups, and the charged groups can form chemical bonds with the prepolymer during curing.

[0097] In some embodiments, a prepolymer is prepared consisting of uncharged hydrophilic monomer residues and amine reactive monomer residues.

[0098] In some embodiments, the first composition comprises a commercially available epoxy resin. In some embodiments, the epoxy resin is hydrophilic. In some embodiments, the epoxy resin comprises polyethylene glycol having epoxy functional groups, glycerol having epoxy functional groups, or sorbitol having epoxy functional groups. In other embodiments, these resins may alternatively contain vinyl or other unsaturated functional groups.

[0099] In some embodiments, the second composition comprising the crosslinking agent further comprises a charged monomer that can bind to amine-reactive monomer residues. In some embodiments, these charged monomers have thiol functional groups. In some embodiments, these charged monomers are 3-mercapto-1-propanesulfonate, cysteine, or salts or derivatives of these monomers.

[0100] Consistent with some of the embodiments described herein, the coating may have enhanced mechanical properties.

[0101] Method of application In some embodiments, the coating composition may be applied to a glass substrate with or without the addition of primers prior to the application of the coating.

[0102] In some embodiments, the surface may be pretreated and / or primed before applying the coating composition.

[0103] In some embodiments, the coating composition may be applied to a substrate as a film-forming component.

[0104] In some embodiments, the coating composition can be applied directly to the substrate to bond with the surface.

[0105] In some embodiments, the method of applying the disclosed coating composition to a substrate may include cleaning the substrate with a surfactant, water, ethanol, isopropanol or other cleaning solution prior to pretreatment.

[0106] In some embodiments, the method may include pretreating the substrate by exposing it to corona or plasma treatment, ozone, UV-C, or another surface activation treatment before applying the coating composition.

[0107] In some embodiments, methods of applying the disclosed coating composition to a substrate may include applying the compound to the substrate by spraying, needle dispensing, film coating, brushing, roller coating, dip coating, or blade coating.

[0108] In some embodiments, the method may include thermally curing the compound after it has been applied to the substrate.

[0109] Primer In some embodiments, the method may include applying a primer of the compound to the substrate prior to applying the coating composition. The primer may contain primers or adhesion promoters. In some embodiments, a silane coupling agent or primer may be applied to the substrate prior to applying the coating composition. This may assist the coating in adhering to the substrate.

[0110] In other embodiments, depending on the nature of the substrate and the nature of the coating to be obtained, a primer that provides additional functionality to the coating system may be applied to the substrate before applying the coating composition.

[0111] The primer may be a silane coupling agent that functionalizes the substrate with an amine, epoxy, thiol, amide, carboxylic acid, or isocyanate moiety. In some embodiments, the silane coupling agent may include: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidoxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidoxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanatepropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

[0112] In other embodiments, the primer may be surface-coupled using a carboxyl group, a phosphonate group, or a catechol group. In other embodiments, the primer includes dopamine or an amino acid.

[0113] In some implementations, the substrate is pretreated with a primer, which is a material layer between the substrate and the active topcoat.

[0114] The primer can be a cross-linked polymer, and when immersed in deionized water for one hour, the percentage expansion of the dry thickness of the cross-linked polymer is less than the percentage expansion of the dry thickness of the anti-fog coating.

[0115] Primer can be applied by spraying, brushing, dipping, rolling, or scraping.

[0116] The primer may contain epoxy functionalized molecular residues, amine-containing crosslinking agents, silane coupling agents, and at least one additive.

[0117] The epoxy-functionalized molecules in the primer may include epoxy-functionalized polyethylene glycol, epoxy-functionalized glycerol, epoxy-functionalized sorbitol, or combinations thereof.

[0118] The amine-containing crosslinking in the primer may include polyetheramines or polymers having a polyether backbone, which includes polyethylene oxide, polypropylene oxide or other ethylene oxides containing one to four nitrogen atoms per molecule, or secondary aminosilanes such as n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide or any combination thereof.

[0119] The silane coupling agent in the primer may include: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

[0120] At least one additive in the primer may include mechanical additives, coupling agents, UV absorbers, UV stabilizers, surfactants and leveling agents, dyes or biocides.

[0121] In some embodiments, the method may include heating the substrate at 30°C to 150°C for 1 minute to 600 minutes after applying the composition.

[0122] In some embodiments, the method may include applying a compound to a substrate at a wetting thickness of 0.1 micrometers to 10,000 micrometers.

[0123] In some embodiments, the method may include applying a compound to a substrate at a dry thickness ranging from 0.001 micrometers to 100 micrometers.

[0124] In some embodiments, the method can be used to coat any substrate from automotive or building windows, camera lenses, medical mirrors, sensors, eyeglasses, mirrors, consumer electronics, personal protective equipment, other safety equipment, refrigerator doors, or building structures with the disclosed coating composition.

[0125] Curing conditions In some embodiments, the composition can form a hydrophilic coating that feels dry to the touch after heating at 130°C for 5 minutes.

[0126] In some embodiments, the composition can form a hydrophilic coating that cures within 48 hours at 25°C and 0% to 50% relative humidity.

[0127] In some embodiments where the disclosed composition is a 2K system, the first and second components may be present in the composition in an amount sufficient to form a hydrophilic coating that cures within 48 hours at 25°C and 0% to 50% relative humidity.

[0128] In some embodiments where the disclosed composition is a 2K system, the first and second components may be present in the composition in an amount sufficient to form a hydrophilic coating that feels dry to the touch after heating at 130°C for 5 minutes.

[0129] In some embodiments, when applied to a substrate, the composition can be cured at ambient room temperature or at high temperature and high humidity. The curing of the composition can depend on several factors, including the chemical composition, the thickness of the applied coating, the concentration of the crosslinking agent (e.g., the concentration and relative ratio of amine reactive monomers and amine-containing crosslinking agents), the reaction duration, temperature, pH, solvent composition, viscosity, and steric hindrance caused by the presence of functional groups in the monomers and crosslinking agents involved in the crosslinking reaction.

[0130] In some embodiments, when applied to a surface with a crosslinking agent or hardener, the composition can cure in less than 10 minutes at temperatures above room temperature. Non-limiting temperatures include 100°C, 120°C, 130°C, or 150°C.

[0131] In some embodiments, the composition can be cured at room temperature when applied to the surface with a crosslinking agent or hardener.

[0132] In some embodiments, the composition can be cured when applied to a surface with a crosslinking agent or hardener, such that the composition feels dry to the touch in less than 2 minutes when heated.

[0133] Fog resistance property measurement In some embodiments, the disclosed antifogging coating may be hydrophilic and exhibit excellent antifogging properties and durability against chemical, mechanical, and environmental stresses. The hydrophilic coating can absorb water vapor, causing the coating to expand rather than condensing on the substrate or expanding before condensation. Furthermore, water droplets present on the surface may form a low equilibrium contact angle of less than 30° on the coated surface. This contact angle may dynamically change over time as the coating expands. This property allows water droplets to form a flat sheet on the surface and thus prevents optical distortion.

[0134] Depending on humidity, temperature, and other environmental conditions, antifogging coatings can provide antifogging properties by absorbing water and thus expanding the coating; or by forming a low contact angle between the coating and water; or by performing both actions simultaneously or sequentially. For example, when observed with the naked eye, water droplets on a substrate with an exposed antifogging coating can be considered absorbed into the coating, and therefore no liquid layer of water is left on the surface of the substrate, thus initially providing antifogging properties to the substrate. After exposure to a fogging environment such as experiencing vapor exposure, the coating may become saturated with water, and a water film may form on the coating with a low contact angle.

[0135] Sometimes, the water film may not form uniformly, and poor transient optical properties can be easily measured while the water is still wetting the surface. For example, on a coating of uneven thickness, the water film may form unevenly, which can lead to poor but short-lived optical measurements. If the water film has partially formed, the evaluation of antifogging properties should only be performed in areas where the film has fully formed, or after the surface has been fully wetted by water.

[0136] Over time, an effective antifog coating maintains high optical transparency in foggy environments. This can be assessed visually or quantitatively using methods such as measuring the haze value of the film in a foggy environment via ASTM D1003 or measuring the degree of distortion of an image viewed through the antifog film after modifications to standard EN-168.

[0137] In some implementations, the anti-fogging properties assessment can be performed by immersing the sample in deionized water for one hour, followed by standing under ambient conditions for 24 hours.

[0138] The features and advantages of the present invention will be more fully shown by the following embodiments, which are provided for illustrative purposes and should not be construed as limiting the invention in any way.

[0139] Example Sample preparation Before coating, all glass substrates are cleaned by wiping with deionized water and isopropanol, and then pretreated with corona discharge.

[0140] Before coating, all plastic substrates (e.g., polycarbonate, acrylic) are pretreated with corona discharge.

[0141] Steam test Add 100 mL of deionized water to a 250 mL Erlenmeyer flask and heat to boiling. Use a haze meter to evaluate the haze value of the coated substrate according to ASTM D1003. Then, place the sample, coated side down, over the opening of the Erlenmeyer flask for a specific time period. Remove the sample from the flask and place it over the measuring port of the haze meter. Ten seconds after removal from the flask, measure the haze value and calculate Δhaze by subtracting the initially measured haze value from the haze value before exposure to vapor. Samples showing a Δhaze value greater than 30% are diffuse and not anti-fogging. Samples with a Δhaze value less than 30% provide anti-fogging properties. For some applications, effective use in foggy environments may require a Δhaze value less than 30%. In these applications, effective use may require a Δhaze value less than 20%, less than 10%, less than 5%, less than 2%, or even less than 1%.

[0142] Modified EN-168 test Another technique for evaluating anti-fogging performance involves modifying the EN-168 standard. This technique involves preparing a humidified chamber according to the conditions specified in EN-168 and modifying it to allow for image transparency analysis. A Siemens star is mounted on one side of the chamber, facing the opening in the chamber, as a visual target. The sample is placed over the opening, with the anti-fogging coating facing the interior of the humidified chamber. Images are captured at one second for one minute or at thirty minutes per minute, and the mode transfer function (MTF) is calculated using the NIH ImageJ image processing program and compared to the MTF calculated from images captured under fog-free conditions. The integral ratio of the MTF at set time points is compared to the integral of the initial measurement to produce a quantitative comparison over time.

[0143] Polymer definition The abbreviations of the polymers and compositions used in the following examples are summarized below.

[0144] Prepolymer-1 consists of 21.4 wt% of an alkali metal salt of 2-acrylamido-2-methylpropanesulfonic acid, 70.8 wt% of methacrylic acid (hydroxyethyl ester), and 7.8 wt% of glycidyl methacrylate.

[0145] Prepolymer-2 consists of 19 wt% of an alkali metal salt of 2-acrylamido-2-methylpropanesulfonic acid, 74.9 wt% of methacrylic acid (hydroxyethyl ester), and 6.1 wt% of glycidyl methacrylate.

[0146] Prepolymer-3 consists of 20.4 wt% of an alkali metal salt of 2-acrylamide-2-methylpropanesulfonic acid, 71.7 wt% of methacrylic acid (hydroxyethyl ester), and 7.9 wt% of glycidyl methacrylate.

[0147] Example 1 Preparation of coating composition Solution S-1-1 was prepared using 11 wt% prepolymer-1, 55.8 wt% water, 33 wt% 1-methoxy-2-propanol, 0.1 wt% polyether siloxane copolymer, and 0.51 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-1-2 was prepared using 10 wt% polyoxypropylene triamine and 90 wt% water. Solution S-1-3 was then prepared using 1 wt% (3-glycidoxypropyl)trimethoxysilane in 99 wt% ethanol.

[0148] Application of coating composition to substrate Solution S-1-3 was sprayed onto a glass slide, and the moistened slide was baked in an oven at 130°C for 10 minutes. A mixture of 4 g S-1-1 and 0.14 g S-1-2 was prepared. This mixture was then sprayed onto a glass slide, and the moistened slide was baked at 130°C for 10 minutes. This forms a coating on the glass slide.

[0149] Thickness measurement The thickness of the coating on the glass slide was measured to be 4.5 micrometers.

[0150] Haze measurement The haze value of the coating (ASTM D1003) was measured to be 0.2%. The coated glass slide was then immersed in deionized water for 10 minutes and rubbed or wiped dry with a cloth. The haze value of the coated glass slide was then measured to be 0.3%, indicating that the coating had cured and possessed sufficient mechanical properties to withstand water cleaning.

[0151] The change in haze value Δhaze was measured over time according to ASTM D1003 on the coated glass slide prepared according to Example 1. The experiment was conducted according to the steam test procedure, but for more than thirty minutes.

[0152] Table 1. Time-related antifogging response of the coated substrate prepared according to Example 1

[0153] Transmittance measurement The transmittance of the glass slides was then measured using a UV-Vis spectrophotometer. Blank glass slides were used as a control. Compared to blank glass slides in the 400 nm to 700 nm range, the transmittance of the coated glass slides was higher than 99%.

[0154] Exposure to fogging conditions The coating was subjected to a steam test, and a Δ haze of 0.1% was measured. The coated glass slide was then immersed in deionized water for one hour. The coated glass slide was then dried and conditioned at room temperature for 24 hours. The coated glass slide was then attached to a chamber designed according to EN-168 and exposed to a humid atmosphere for 60 seconds. The coated glass slide did not fog up within 60 seconds.

[0155] Mechanical strength test A coated glass slide was placed on a linear abrasive and rubbed for 1000 cycles with a coarse cotton cloth under a weight of 1 kg. After abrasion, the haze value of the coated glass slide was measured to be 0.3%, and there was no visible damage.

[0156] Frost test The sample was prepared in the same manner as in Example 1, except that an adhesive tape was used to form a mask so that only half of one side of the glass slide was coated. The process was then repeated on the opposite sides of the glass slide, and the adhesive tape was removed to obtain a sample with half of both sides of the glass slide coated.

[0157] The sample was cooled to -10°C, then removed and placed on a laboratory workbench under ambient conditions of approximately 25°C and 50% relative humidity. Within seconds, frost formed on both sides of the uncoated half of the glass slide, resulting in poor optical transparency and making it difficult to see through the slide. No frost formed on the coated half of the glass slide, and the sample was clearly visible. This demonstrates that the coating performs excellently in mitigating frost formation and can be used in applications requiring good optical transparency at low temperatures.

[0158] The sample was cooled to -40°C, then removed and placed on a laboratory workbench under ambient conditions of approximately 25°C and 50% relative humidity. Frost formed immediately over the entire sample within seconds. Within 10 seconds, the frost was observed to dissipate from the coated half of the glass slide, while the uncoated slide remained covered in frost. Within 45 seconds, the frost completely disappeared from the coated half of the sample, making the sample appear optically transparent. On the uncoated half of the sample, the frost only began to melt after 45 seconds. After 2 minutes, a significant amount of frost had melted on the uncoated half of the slide, but residual water droplets made it difficult to see through that half of the slide. This demonstrates that the coating performs excellently in anti-frost applications and provides excellent transparency in extremely cold environments.

[0159] Pot life test The S-4-3 solution was sprayed onto a glass slide and baked at 130°C for 10 minutes.

[0160] The coating solution was prepared by mixing 12 g of solution S-1-1 and 0.42 g of solution S-4-2. The solution was aged for a predetermined amount of time. Then, the viscosity was measured, and the coating was sprayed onto one of the pretreated glass slides and baked at 130°C for 10 minutes. The coated slides were evaluated by visual appearance, haze measurement (ASTM D1003), and vapor test. After all three slides had been coated, the gelation of the remaining coating solution was evaluated daily by a reverse test.

[0161] Table 2. Results of the pot life test of the coating described in Example 1

[0162] Application of coating composition using rapid drying The glass slide and coating were prepared as described in Example 1. After spraying with the coating, the glass slide was baked in an oven at 80°C for 2 minutes to form the coating on the glass slide. The coated glass slide was then removed from the oven and touched with a finger. The coating on the glass slide felt dry and was not damaged by the process. Polycarbonate sheet as substrate A coating was prepared according to Example 1 and applied to the prepared polycarbonate sheet using an 80-micron rod coater. The wetted polycarbonate sheet was then baked in an oven at 130°C for 10 minutes to form the coating. The haze value of the polycarbonate sheet with the coating was measured to be 0.2%. A vapor test yielded a Δhaze of 0.2%.

[0163] Curing at room temperature A coating was prepared according to Example 1 and applied to a pretreated polycarbonate sheet using an 80-micron rod coater to form the coating. The coated polycarbonate sheet was then left to stand at room temperature for 24 hours. The haze value of the coated polycarbonate sheet was measured to be 0.6. A vapor test yielded a Δhaze of 0.2%. The coated polycarbonate sheet was then rubbed with a damp cloth, and no signs of damage were observed, indicating that the coating had fully cured.

[0164] Acrylic sheet as substrate A coating was prepared according to Example 1, and the coating solution was applied to a pretreated acrylic sheet by spraying. The wetted acrylic sheet was baked at 80°C for 10 minutes, and then left to stand at room temperature for 24 hours to form the coating. The haze value of the acrylic sheet with the coating was measured to be 0.2. A vapor test yielded a Δhaze of 0.1%.

[0165] As described in ISO 6270, coated acrylic sheet samples were placed in a humidity chamber for 3 days. Afterward, the samples were held on a beaker containing water at 50°C for 1 minute, and no fogging was observed. Blank or uncoated acrylic sheets were used as controls. Control acrylic sheets were held on a beaker containing water at 50°C, and the control acrylic sheets immediately became foggy.

[0166] As described in ISO 6270, another sample of coated acrylic sheet was placed in a humidity chamber for 10 days. Afterwards, an ASTM D3359 cross-cut adhesion test was performed, yielding a grade of 5B. No coating removal was observed during the test.

[0167] Example 2 Preparation of coating composition Solution S-2-1 was prepared using 11 wt% prepolymer 1, 55.8 wt% water, 33 wt% 1-methoxy-2-propanol, 0.1 wt% polyether siloxane copolymer, and 0.51 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-2-2 was prepared using 10 wt% polyoxypropylene triamine, 1.5 wt% bis(3-trimethoxysilylpropyl)amine, and 88.5 wt% 1-methoxy-2-propanol. As a comparative example, solution S-2-2* was prepared identical to S-2-2 but without the 1.5 wt% bis(3-trimethoxysilylpropyl)amine.

[0168] Application of coating composition to substrate A coating composition was prepared by mixing 4 g of S-2-1 with 0.14 g of S-2-2. The coating composition was then sprayed onto a clean glass slide and baked in an oven at 130°C for 10 minutes to form a coating on the glass slide. This procedure was repeated using a comparative solution S-2-2* instead of S-2-2.

[0169] Haze value measurement The haze value of the coated glass slide was measured to be 0.2%. The vapor test yielded a Δhaze of 0.1%.

[0170] Rubbing the coated glass slide with a damp cloth and observing no visible damage indicates that the coating has cured and bonded to the substrate, possessing sufficient mechanical properties for use without additional primers. The comparative example using S-2-2* detached from the glass substrate upon exposure to steam or upon rubbing with a damp cloth.

[0171] The coating was prepared according to Example 2. Anodized aluminum substrates were cleaned with water and isopropanol and treated with corona discharge. The coating composition was brushed onto the aluminum substrate and baked at 130°C for 10 minutes to form the coating. The coated aluminum was then rubbed with a damp cloth, and the coating remained adhered to the aluminum substrate.

[0172] Example 3 Preparation of coating composition Solution S-3-1 was prepared using 11 wt% prepolymer-1, 55.8 wt% water, 33 wt% 1-methoxy-2-propanol, 0.1 wt% polyether siloxane copolymer, and 0.51 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-3-2 was prepared using 10% polyoxypropylene triamine and 90% water. Solution S-3-3 was prepared using 1% 3-methylaminopropyltrimethoxysilane in 99% ethanol.

[0173] Application of coating composition to substrate Then, the S-3-3 solution was sprayed onto a glass slide and baked in an oven at 130°C for 10 minutes. Afterward, a coating composition was prepared by mixing 4g of S-3-1 with 0.14g of S-3-2, allowing it to stand for 10 minutes, then spraying it onto a glass slide and baking it at 130°C for 10 minutes to form a coating.

[0174] Haze value measurement The haze value of the coated glass slide was measured to be 0.3%. A vapor test yielded a Δhaze of 0.1%. Rubbing the coated glass slide with a damp cloth did not reveal any visible damage, indicating that the primer provides adequate bonding between the substrate and the coating.

[0175] Example 4 Preparation of coating composition Solution S-4-1 was prepared using 16 wt% prepolymer-2, 53.7 wt% water, 30 wt% 1-methoxy-2-propanol, 0.05 wt% polyether siloxane copolymer, and 0.13 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-4-2 was prepared using 20 wt% O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol and 80 wt% water.

[0176] Application of coating composition to substrate A coating composition was prepared by mixing 0.9 g of S-4-1 with 0.05 g of S-4-2, and then coated onto a pretreated polycarbonate sheet using an 80-micron blade coater and baked at 130°C for 10 minutes to form a coating.

[0177] Haze value measurement The initial haze of the sample was measured to be 0.3%. A vapor test yielded a Δ haze of 0.2%. The sample was evaluated using a modified EN-168 method.

[0178] Table 3. Time-related antifogging response of the coated substrate prepared according to Example 7, evaluated using the EN-168 modulus transfer function method.

[0179]

[0180] Example 5 Preparation of coating composition Solution S-5-1 was prepared using 17 wt% prepolymer-3, 46.8 wt% water, 30.3 wt% 1-methoxy-2-propanol, 5.2 wt% propylene glycol, 0.02 wt% polyether siloxane copolymer, and 0.12 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-8-2 was prepared using 10 wt% polyoxypropylene diamine and 90 wt% water. Solution S-5-3 was prepared using 6 wt% polyoxypropylene diamine, 93% ethanol, and 1% polyether siloxane copolymer. Solution S-5-4 was prepared using 8.5% sorbitol polyglycidyl ether, 15% (3-glycidyl etheroxypropyl)trimethoxysilane, and 77.5% ethanol.

[0181] Application of coating composition to substrate Equal volumes of S-5-3 and S-5-4 were combined, sprayed onto a glass slide, and baked at 130°C for 10 minutes. Then, 0.53 g of solution S-5-1 was combined with 0.05 g of S-5-2, sprayed onto a glass slide, and baked at 130°C for 10 minutes.

[0182] Haze value measurement The haze value of the coated glass slide was measured to be 0.2%. The vapor test yielded a Δhaze of 0.3%.

[0183] Preparation of coating composition Glass slides were immersed in a solution of 0.1% dish soap in deionized water for 24 hours. After the samples were removed from the solution, they appeared transparent with a haze value of 0.6%. A vapor test yielded a Δhaze of 0.8%.

[0184] Example 6 Application of coating composition to substrate Solution S-6-1 was prepared using 11 wt% prepolymer-1, 31 wt% water, 51 wt% 1-methoxy-2-propanol, 6 wt% propylene glycol, 0.6 wt% alumina nanoparticles, 0.02 wt% Byk 3760, and 0.05 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-6-2 was prepared using 20 wt% O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol and 80 wt% water.

[0185] Haze value measurement The coating composition was prepared by mixing 4g of S-6-1 with 0.1g of S-6-2.

[0186] The coating was applied to the pretreated polycarbonate sheet using an 80-micron rod coater. The polycarbonate sheet was then baked at 130°C for 10 minutes to form the coating. The haze value of the coated polycarbonate sheet was measured to be 0.7%.

[0187] Example 7 Soak study Solution S-7-1 was prepared using 11 wt% prepolymer-1, 31 wt% water, 52 wt% 1-methoxy-2-propanol, 6 wt% propylene glycol, 0.02 wt% Byk 3760, and 0.05 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate. Solution S-7-2 was prepared using 20 wt% O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol and 80 wt% water. Solution S-7-3 was prepared, consisting of 7.5 wt% O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, 0.3 wt% bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, 0.2 wt% a wetting additive polyether siloxane copolymer, and 92 wt% ethanol. Solution S-7-4 was prepared, consisting of 10 wt% sorbitol polyglycidyl ether, 5 wt% (3-glycidyl etheroxypropyl)trimethoxysilane, and 85 wt% ethanol.

[0188] Preparation of coating composition Then, solutions S-7-3 and S-7-4 are mixed and sprayed onto a glass slide, and baked at 130°C for 10 minutes to form a first coating on the glass slide.

[0189] Application of coating composition to substrate The thickness of the first coating on the glass slide was measured to be 0.5 micrometers. Then, the first and second solutions were mixed and sprayed onto the glass slide, which was then baked at 130°C for 10 minutes to form a second coating. The thickness of the glass slide with the second coating on top of the first coating was measured to be 5 micrometers.

[0190] Preparation of coating composition The haze value of the coated glass slide was measured to be 1.0%. The vapor test yielded a Δhaze of 0.7%.

[0191] Application of coating composition to substrate Coating thickness Haze value measurement Industrial applicability This disclosure describes an anti-fog coating composition, kit, and coating comprising a prepolymer and an amine-containing crosslinking agent. The disclosure also describes a method for preparing the coating or coating a substrate using the composition or kit. This coating can be applied to a variety of industrial or consumer applications where optical transparency is required and fogging is detrimental to the application. Non-limiting examples of such applications include coatings on automotive windows, camera lenses, sensors such as lidar, radar, microwave, and optical sensors, eyeglasses including goggles, face shields, masks, goggles, protective covers, and sunglasses, refrigerator windows, and mirrors such as bathroom mirrors.

[0192] Furthermore, architectural designs that can benefit from using the various embodiments disclosed herein include a variety of glass and plastic products in different parts of a building, such as storefront displays and windows, greenhouses, refrigerated food display and refrigerator windows, shower doors, and glass enclosures around sporting events, such as ice hockey rinks.

[0193] The embodiments disclosed herein can be used to coat cameras attached to observation instruments used in various medical applications. For example, endoscopes including gastroscopes, bronchoscopes, cystoscopes, ureteroscopes, arthroscopes, and colonoscopes can benefit from the anti-fog properties associated with the disclosed invention.

[0194] The antifog coatings disclosed herein minimize one or more application difficulties. For example, the disclosed antifog coating compositions, compounds, or kits do not contain highly toxic chemicals, can cure at room temperature, can be applied to a variety of substrates, and have a long pot life. This application method does not require expensive machinery and process control equipment; nor does it require complex, environmentally sensitive chemical reactions, making the entire application easier and cheaper.

[0195] Other embodiments of the invention will be apparent to those skilled in the art upon consideration of the description and practice of the invention disclosed herein. The description and examples are intended to be illustrative only, and the true scope of the invention is indicated by the following claims.

Claims

1. A composition for forming a cross-linked film imparting anti-fogging properties, the composition comprising: At least one prepolymer comprising (a) one or more charged monomer residues; (b) one or more uncharged monomer residues; and (c) one or more amine-reactive monomer residues; and At least one amine-containing crosslinking agent, When exposed to fogging conditions for more than 30 seconds, the haze value of the cross-linked film changed by less than 30%.

2. The composition according to claim 1, wherein the composition is a two-component system comprising: A first component, the first component comprising at least one prepolymer; and The second component comprises at least one amine-containing crosslinking agent. The first component and the second component are present in the composition in an amount sufficient to form an antifog film, wherein the haze value of the antifog film changes by less than 30% when exposed to fogging conditions for a period of time exceeding 30 seconds.

3. The composition according to claim 2, wherein the composition comprises a molar ratio of the amine reactive monomer residue in the first component to the active hydrogen of the amine in the second component between 1:10 and 10:

1.

4. The composition according to claim 1, wherein the at least one prepolymer consists of 0.01% by weight to 30% by weight of charged monomer residues.

5. The composition according to claim 1, wherein the at least one prepolymer consists of 0.01% by weight to 80% by weight of uncharged monomer residues.

6. The composition according to claim 1, wherein the at least one prepolymer consists of 0.01% by weight to 30% by weight of amine reactive monomer residues.

7. The composition according to claim 1, wherein the one or more charged monomer residues comprise sulfonate functional groups, carboxyl functional groups, phosphonate functional groups, nitro functional groups, imidazolium functional groups, guanidinium functional groups, or quaternary ammonium functional groups, or monomers or combinations thereof capable of being converted into these functional groups.

8. The composition of claim 7, wherein the one or more charged monomer residues comprising the sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrenesulfonic acid, vinylsulfonic acid, propyl 3-sulfonate acrylate, propyl 3-sulfonate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

9. The composition of claim 7, wherein the one or more charged monomer residues comprising a carboxyl functional group include residues of acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, p-styrene carboxylic acid, 3-acrylamide-3-methylbutyric acid, maleic anhydride, itaconic acid, alginate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

10. The composition of claim 7, wherein the one or more charged monomer residues comprising the phosphonate functional group include residues of undecyl 11-phosphonate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

11. The composition of claim 7, wherein the one or more charged monomer residues comprising the imidazolium functional group include residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazolium, derivatives of these monomers, salts of these monomers, or combinations thereof.

12. The composition of claim 7, wherein the one or more charged monomer residues comprising a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonylpropyl)ammonium hydroxide, 2-ethyldimethylammonium ethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, derivatives of these monomers, salts of these monomers, or combinations thereof.

13. The composition of claim 1, wherein the one or more uncharged monomer residues comprise a hydroxyl functional group, a pyrrolidone functional group, an acetate functional group, or an ether functional group, or a combination thereof.

14. The composition of claim 13, wherein the one or more uncharged monomer residues comprising a hydroxyl functional group include residues of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, N-(2-hydroxyethyl)methacrylamide, vinyl alcohol, acrylates or methacrylates of carbohydrates, derivatives of these monomers, or combinations thereof.

15. The composition of claim 13, wherein the one or more uncharged monomer residues comprising the pyrrolidone functional group include residues of n-vinyl-2-pyrrolidone or derivatives thereof.

16. The composition of claim 13, wherein the one or more uncharged monomer residues comprising an acetate functional group include residues of vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

17. The composition of claim 13, wherein the one or more uncharged monomer residues comprising an ether functional group include residues of: tetrahydrofuran acrylate or methacrylate, any acrylate- or methacrylate-based monomer having a polyethylene glycol or polypropylene glycol functional group, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or combinations thereof.

18. The composition according to claim 1, wherein the one or more amine reactive monomer residues comprise epoxy resin functional groups, ketone functional groups, acid anhydride functional groups, olefin functional groups, or isocyanate functional groups or combinations thereof.

19. The composition of claim 18, wherein the one or more amine reactive monomer residues comprising the epoxy resin functional group include residues of glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, allyl glycidyl ether, 1,2-epoxy-4-ethylene-1-cyclohexene, derivatives of these monomers, or combinations thereof.

20. The composition of claim 18, wherein the one or more amine reactive monomer residues comprising a ketone functional group include residues of methyl vinyl ketone, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

21. The composition of claim 18, wherein the one or more amine reactive monomer residues comprising an anhydride functional group include residues of: n-hydroxysuccinimide monomers, maleic anhydride, derivatives of these monomers, or combinations thereof.

22. The composition of claim 18, wherein the one or more amine reactive monomer residues comprising an olefinic functional group include residues of allyl methacrylate, vinyl methacrylate, derivatives of these monomers, or combinations thereof.

23. The composition of claim 18, wherein the one or more amine reactive monomer residues comprising the isocyanate functional group include residues of 2-isocyanoethyl methacrylate or a derivative thereof.

24. The composition of claim 1, wherein the amine-containing crosslinking agent comprises a primary amine or a secondary amine, or a secondary aminosilane, or a combination thereof.

25. The composition of claim 1, wherein the amine-containing crosslinking agent comprises a polyether amine or a polymer having a polyether backbone, the polyether backbone comprising polyethylene oxide, polypropylene oxide or other ethylene oxides containing one or more nitrogen atoms per molecule, polyoxypropylene diamine, polyoxypropylene triamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide or combinations thereof.

26. The composition of claim 2, wherein the first component further comprises a carrier solvent comprising 20% ​​to 100% by weight of water and 0% to 80% by weight of one or more water-miscible co-solvents.

27. The composition of claim 26, wherein the water-miscible cosolvent comprises methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or combinations thereof.

28. The composition according to claim 2, wherein the second component further comprises a carrier solvent.

29. The composition of claim 28, wherein the carrier solvent comprises water, an aqueous miscible solvent, the aqueous miscible solvent comprising methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or combinations thereof.

30. The composition of claim 1, further comprising one or more additives, including mechanical additives, dispersants, coupling agents, UV absorbers, UV stabilizers, surfactants or leveling additives, curing catalysts, antifreeze additives, dyes or biocides.

31. The composition according to claim 30, wherein the one or more additives are present in the composition at a concentration greater than 0.0001% by weight and less than 40% by weight.

32. The composition of claim 30, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, cellulose nanofibers, polyhedral oligomeric silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, layered silicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or any combination thereof.

33. The composition of claim 30, wherein the coupling agent comprises a molecule having a silane functional group and one or more epoxy, amine, thiol, acid anhydride or isocyanate functional groups or combinations thereof.

34. The composition of claim 30, wherein the coupling agent comprises one or more of the following: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or combinations thereof.

35. The composition of claim 30, wherein the UV absorber comprises one or more of the following: benzophenone, benzotriazole, cyanoacrylate, phenoxytriazine, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, or any combination thereof.

36. The composition of claim 30, wherein the UV stabilizer comprises one or more hindered amine light stabilizer (HALS) agents.

37. The composition of claim 30, wherein the UV stabilizer comprises 2-bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl) 4 Piperidinyl sebacate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester, dimethyl succinate polymers having 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidinyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]] or combinations thereof.

38. The composition of claim 30, wherein the surfactant or leveling agent comprises a silicone polyether surfactant, polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, polysorbate surfactant, sodium dodecyl sulfate, hexadecyltrimethylammonium bromide surfactant, dispersant, styrene-maleic acid copolymer, silicone-modified polyacrylate, polyethylene-polypropylene block copolymer surfactant, or a combination thereof.

39. The composition according to claim 30, wherein the composition further comprises a catalytic acid or a catalytic base.

40. The composition of claim 30, wherein the antifreeze additive comprises glycerol, ethylene glycol, propylene glycol, polypropylene glycol or polyethylene glycol or a molecule comprising at least one of the above.

41. The composition of claim 2, wherein the first composition and the second composition are present in an amount sufficient to have a potency of more than 8 hours.

42. The composition according to claim 2, wherein the first component and the second component are present in an amount sufficient to form a hydrophilic film that cures within 48 hours at 25°C and 0% to 50% relative humidity.

43. The composition according to claim 2, wherein the first component and the second component are present in an amount sufficient to form a dry-to-the-touch hydrophilic film after heating at 130°C for 5 minutes.

44. An anti-fog film comprising a crosslinked polymer, said crosslinked polymer comprising: (a) One or more charged monomer residues; (b) One or more uncharged monomer residues; (c) one or more amine reactive monomer residues; and (d) at least one amine-containing crosslinking agent residue, When exposed to fogging conditions for more than 30 seconds, the antifog film showed a haze value change of less than 30%.

45. The antifog film according to claim 44, wherein the composition comprises a molar ratio of the amine reactive monomer residue to the active hydrogen residue of the amine between 1:10 and 10:

1.

46. ​​The antifog film according to claim 44, wherein the polymer consists of 0.01% by weight to 30% by weight of charged monomer residues.

47. The antifog film according to claim 44, wherein the polymer consists of 0.01% by weight to 80% by weight of uncharged monomer residues.

48. The antifog film according to claim 44, wherein the polymer consists of 0.01% by weight to 30% by weight of amine reactive monomer residues.

49. The antifog film according to claim 44, wherein the one or more charged monomer residues include sulfonate functional groups, carboxyl functional groups, phosphonate functional groups, nitro functional groups, imidazolium functional groups, guanidinium functional groups or quaternary ammonium functional groups, or monomers capable of being converted into these functional groups.

50. The antifog film of claim 49, wherein the one or more charged monomer residues comprising the sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrenesulfonic acid, vinylsulfonic acid, propyl 3-sulfonate acrylate, propyl 3-sulfonate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

51. The antifog film according to claim 49, wherein the one or more charged monomer residues comprising a carboxyl functional group include residues of acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, p-styrene carboxylic acid, 3-acrylamide-3-methylbutyric acid, maleic anhydride, itaconic acid, alginate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

52. The antifog film of claim 49, wherein the one or more charged monomer residues comprising the phosphonate functional group include residues of undecyl 11-phosphonate acrylate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

53. The antifog film of claim 49, wherein the one or more charged monomer residues comprising the imidazolium functional group include residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazolium, derivatives of these monomers, salts of these monomers, or combinations thereof.

54. The antifog film according to claim 49, wherein the one or more charged monomer residues comprising a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonylpropyl)ammonium hydroxide, 2-ethyldimethylammonium ethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, derivatives of these monomers, salts of these monomers, or combinations thereof.

55. The antifog film according to claim 44, wherein the one or more uncharged monomer residues include hydroxyl functional groups, pyrrolidone functional groups, acetate functional groups, or ether functional groups, or combinations thereof.

56. The antifog film of claim 55, wherein the one or more uncharged monomer residues comprising a hydroxyl functional group include residues of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, N-(2-hydroxyethyl)methacrylamide, vinyl alcohol, acrylates or methacrylates of carbohydrates, derivatives of these monomers, or combinations thereof.

57. The antifog film of claim 55, wherein the one or more uncharged monomer residues comprising the pyrrolidone functional group include residues of n-vinyl-2-pyrrolidone or derivatives thereof.

58. The antifog film of claim 55, wherein the one or more uncharged monomer residues comprising the acetate functional group include residues of vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

59. The antifog film of claim 55, wherein the one or more uncharged monomer residues comprising an ether functional group include residues of: tetrahydrofuran acrylate or methacrylate, any acrylate- or methacrylate-based monomer having a polyethylene glycol or polypropylene glycol functional group, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or combinations thereof.

60. The antifog film according to claim 44, wherein the one or more amine reactive monomer residues include epoxy resin functional groups, ketone functional groups, acid anhydride functional groups, olefin functional groups or isocyanate functional groups or combinations thereof.

61. The antifog film according to claim 60, wherein the one or more amine reactive monomer residues of the epoxy resin functional group include residues of glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, allyl glycidyl ether, 1,2-epoxy-4-ethylene-1-cyclohexene, derivatives of these monomers, or combinations thereof.

62. The antifog film of claim 60, wherein the one or more amine reactive monomer residues comprising ketone functional groups include residues of methyl vinyl ketone, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

63. The antifog film according to claim 60, wherein the one or more amine reactive monomer residues comprising an anhydride functional group include residues of the following: an n-hydroxysuccinimide monomer, maleic anhydride, derivatives of these monomers, or combinations thereof.

64. The antifog film of claim 60, wherein the one or more amine reactive monomer residues comprising the olefin functional group include residues of allyl methacrylate, vinyl methacrylate, derivatives of these monomers, or combinations thereof.

65. The antifog film according to claim 60, wherein the one or more amine reactive monomer residues comprising the isocyanate functional group include residues of 2-isocyanoethyl methacrylate or a derivative thereof.

66. The antifog film according to claim 44, wherein the at least one amine-containing crosslinking agent residue comprises a primary or secondary amine, or a secondary aminosilane, or a combination thereof.

67. The antifog film of claim 44, wherein the at least one amine-containing crosslinking agent residue comprises residues of: polyetheramines or polymers having a polyether backbone comprising polyethylene oxide, polypropylene oxide or other ethylene oxides containing one or more nitrogen atoms per molecule, polyoxypropylene diamine, polyoxypropylene triamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide or any combination thereof.

68. The antifog film according to claim 44, wherein the composition further comprises one or more additives, including mechanical additives, dispersants, coupling agents, UV absorbers, UV stabilizers, surfactants or leveling additives, curing catalysts, antifreeze additives, dyes or biocides.

69. The antifog film according to claim 68, wherein the concentration of the one or more additives in the composition is greater than 0.0001% by weight and less than 40% by weight.

70. The antifog film according to claim 68, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, cellulose nanofibers, polyhedral oligomeric silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, layered silicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or combinations thereof.

71. The antifog film according to claim 68, wherein the coupling agent comprises: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or combinations thereof.

72. The antifog film of claim 68, wherein the UV absorber comprises one or more of the following: benzophenone, benzotriazole, cyanoacrylate, phenoxytriazine, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, or any combination thereof.

73. The antifog film according to claim 68, wherein the UV stabilizer comprises one or more hindered amine light stabilizer (HALS) agents.

74. The antifog film according to claim 68, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl) 4 Piperidinyl sebacate, 1,10-bis(1,2,2,6,6) Pentamethyl 4 Piperidinyl esters, dimethyl succinate polymers having 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidinyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]] or combinations thereof.

75. The antifog film according to claim 68, wherein the surfactant or leveling agent comprises silicone polyether surfactant, polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, polysorbate surfactant, sodium dodecyl sulfate, hexadecyltrimethylammonium bromide surfactant, dispersant, styrene-maleic acid copolymer, silicone-modified polyacrylate, polyethylene-polypropylene block copolymer surfactant, or any combination thereof.

76. The anti-fog film according to claim 68, wherein the curing catalyst comprises a catalytic acid or a catalytic base.

77. The antifog film according to claim 44, wherein the antifog film has a thickness ranging from 0.25 micrometers to 100 micrometers.

78. A coated article comprising: A substrate and a coating, the coating comprising a composition of the following: Crosslinked polymer, the crosslinked polymer comprising: (a) One or more charged monomer residues; (b) One or more uncharged monomer residues; (c) one or more amine reactive monomer residues; and (d) at least one amine-containing crosslinking agent residue, When exposed to fogging conditions for more than 30 seconds, the coated product exhibited a haze value change of less than 30%.

79. The coated article according to claim 78, wherein the composition comprises a molar ratio of the amine reactive monomer residue to the active hydrogen residue of the amine between 1:10 and 10:

1.

80. The coated article of claim 78, wherein the polymer consists of 0.01% by weight to 30% by weight of charged monomer residues.

81. The coated article of claim 78, wherein the polymer consists of 0.01% by weight to 80% by weight of uncharged monomer residues.

82. The coated article according to claim 78, wherein the polymer consists of 0.01% by weight to 30% by weight of amine reactive monomer residues.

83. The coated article according to claim 78, wherein the one or more charged monomer residues comprise sulfonate functional groups, carboxyl functional groups, phosphonate functional groups, nitro functional groups, imidazolium functional groups, guanidinium functional groups, or quaternary ammonium functional groups, or monomers or combinations thereof capable of being converted into these functional groups.

84. The coated article of claim 83, wherein the one or more charged monomer residues comprising the sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrenesulfonic acid, vinylsulfonic acid, propyl 3-sulfonate acrylate, propyl 3-sulfonate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

85. The coated article of claim 83, wherein the one or more charged monomer residues comprising a carboxyl functional group include residues of acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, p-styrene carboxylic acid, 3-acrylamide-3-methylbutyric acid, maleic anhydride, itaconic acid, alginate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

86. The coated article of claim 83, wherein the one or more charged monomer residues comprising the phosphonate functional group include residues of undecyl 11-phosphonate acrylate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

87. The coated article of claim 83, wherein the one or more charged monomer residues comprising the imidazolium functional group include residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazolium, derivatives of these monomers, salts of these monomers, or combinations thereof.

88. The coated article of claim 83, wherein the one or more charged monomer residues comprising a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonylpropyl)ammonium hydroxide, 2-ethyldimethylammonium ethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, derivatives of these monomers, salts of these monomers, or combinations thereof.

89. The coated article according to claim 78, wherein the one or more uncharged monomer residues comprise hydroxyl functional groups, pyrrolidone functional groups, acetate functional groups, or ether functional groups, or combinations thereof.

90. The coated article of claim 89, wherein the one or more uncharged monomer residues comprising the hydroxyl functional group include residues of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, N-(2-hydroxyethyl)methacrylamide, vinyl alcohol, acrylates or methacrylates of carbohydrates, derivatives of these monomers, or combinations thereof.

91. The coated article of claim 89, wherein the one or more uncharged monomer residues comprising the pyrrolidone functional group include residues of n-vinyl-2-pyrrolidone or derivatives thereof.

92. The coated article of claim 89, wherein the one or more uncharged monomer residues comprising the acetate functional group include residues of vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

93. The coated article of claim 89, wherein the one or more uncharged monomer residues comprising the ether functional group include residues of: tetrahydrofuran acrylate or methacrylate, any acrylate- or methacrylate-based monomer having a polyethylene glycol or polypropylene glycol functional group, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or combinations thereof.

94. The coated article according to claim 78, wherein the one or more amine reactive monomer residues comprise epoxy resin functional groups, ketone functional groups, acid anhydride functional groups, olefin functional groups, or isocyanate functional groups or combinations thereof.

95. The coated article of claim 94, wherein the one or more amine reactive monomer residues of the epoxy resin functional group comprise residues of glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, allyl glycidyl ether, 1,2-epoxy-4-ethylene-1-cyclohexene, derivatives of these monomers, or combinations thereof.

96. The coated article of claim 94, wherein the one or more amine reactive monomer residues comprising the ketone functional group include residues of methyl vinyl ketone, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

97. The coated article of claim 94, wherein the one or more amine reactive monomer residues comprising an anhydride functional group include residues of: an n-hydroxysuccinimide monomer, maleic anhydride, derivatives of such monomers, or combinations thereof.

98. The coated article of claim 94, wherein the one or more amine reactive monomer residues comprising the olefin functional group include residues of allyl methacrylate, ethylene methacrylate, derivatives of these monomers, or combinations thereof.

99. The coated article according to claim 94, wherein the one or more amine reactive monomer residues comprising the isocyanate functional group include residues of 2-isocyanoethyl methacrylate or a derivative thereof.

100. The coated article of claim 78, wherein the at least one amine-containing crosslinking agent residue comprises a primary or secondary amine, or a secondary aminosilane, or a combination thereof.

101. The coated article of claim 78, wherein the at least one amine-containing crosslinking agent residue comprises residues of: polyetheramines or polymers having a polyether backbone, the polyether backbone comprising polyethylene oxide, polypropylene oxide or other ethylene oxides containing one or more nitrogen atoms per molecule, polyoxypropylene diamine, polyoxypropylene triamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide or combinations thereof.

102. The coated article according to claim 78, further comprising one or more additives, including mechanical additives, dispersants, coupling agents, UV absorbers, UV stabilizers, surfactants or leveling additives, curing catalysts, antifreeze additives, dyes or biocides.

103. The coated article according to claim 102, wherein the concentration of the one or more additives in the composition is greater than 0.0001% by weight and less than 40% by weight.

104. The coated article according to claim 102, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, cellulose nanofibers, polyhedral oligomeric silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, layered silicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or any combination thereof.

105. The coated article according to claim 102, wherein the coupling agent comprises: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

106. The coated article of claim 102, wherein the UV absorber comprises one or more of the following: benzophenone, benzotriazole, cyanoacrylate, phenoxytriazine, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, or any combination thereof.

107. The coated article according to claim 102, wherein the UV stabilizer comprises one or more hindered amine light stabilizer (HALS) agents.

108. The coated article according to claim 102, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, sebaic acid, 1-methyl-10-(1,2,2,6,6-pentamethyl) 4 Piperidinyl sebacate, 1,10-bis(1,2,2,6,6) Pentamethyl 4 Piperidinyl esters, dimethyl succinate polymers having 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidinyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]] or any combination thereof.

109. The coated article according to claim 102, wherein the surfactant or leveling agent comprises silicone polyether surfactant, polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, polysorbate surfactant, sodium dodecyl sulfate, hexadecyltrimethylammonium bromide surfactant, dispersant, styrene-maleic acid copolymer, silicone-modified polyacrylate, polyethylene-polypropylene block copolymer surfactant, or any combination thereof.

110. The coated article according to claim 102, wherein the composition further comprises a catalytic acid or a catalytic base.

111. The coated article of claim 78, wherein the coated article further comprises a primer or an adhesion promoter.

112. The coated article of claim 111, wherein the primer or adhesion promoter comprises a silane coupling agent, the silane coupling agent functionalizing the substrate with amine, epoxy, thiol, amide, carboxylic acid or isocyanate functional groups.

113. The coated article of claim 111, wherein the primer or adhesion promoter comprises: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

114. The coated article of claim 78, wherein the substrate comprises a material selected from the group consisting of glass, plastic, metal, ceramic, or a combination thereof.

115. The coated article of claim 78, wherein the coated article further comprises an adhesive layer.

116. The coated article of claim 78, wherein the coated article comprises an automotive structure or building structure, a building window, a camera lens, a medical mirror, a sensor, eyeglasses, a mirror, a consumer electronic device, personal protective equipment, other safety equipment, or a refrigerator door.

117. A method for preventing fogging on the surface of a substrate, the method comprising: A compound comprising: A first composition comprising at least one prepolymer comprising (a) one or more charged monomer residues, (b) one or more uncharged monomer residues; and (c) one or more amine-reactive monomer residues; and The second composition comprises at least one amine-containing crosslinking agent. When exposed to fogging conditions for more than 30 seconds, the treated substrate showed a haze value change of less than 30%.

118. The method of claim 117, wherein the compound comprises an amine reactive monomer residue in the first composition and an active hydrogen of the amine in the second composition in a molar ratio between 1:10 and 10:

1.

119. The method of claim 117, wherein the one or more charged monomer residues comprise sulfonate functional groups, carboxyl functional groups, phosphonate functional groups, nitro functional groups, imidazolium functional groups, guanidinium functional groups, or quaternary ammonium functional groups, or monomers or combinations thereof capable of being converted into these functional groups.

120. The method of claim 119, wherein the one or more charged monomer residues of the sulfonate functional group comprise residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrenesulfonic acid, vinylsulfonic acid, propyl 3-sulfonate acrylate, propyl 3-sulfonate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

121. The method of claim 119, wherein the one or more charged monomer residues of the carboxyl functional group comprise residues of acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, p-styrene carboxylic acid, 3-acrylamide-3-methylbutyric acid, maleic anhydride, itaconic acid, alginate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

122. The method of claim 119, wherein the one or more charged monomer residues of the phosphonate functional group comprise residues of undecyl 11-phosphonate acrylate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

123. The method of claim 119, wherein the one or more charged monomer residues of the imidazolium functional group comprise residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazolium, derivatives of these monomers, salts of these monomers, or combinations thereof.

124. The method of claim 119, wherein the one or more charged monomer residues of the quaternary ammonium functional group comprise residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonylpropyl)ammonium hydroxide, 2-ethyldimethylammonium ethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, derivatives of these monomers, salts of these monomers, or combinations thereof.

125. The method of claim 117, wherein the one or more uncharged monomer residues comprise a hydroxyl functional group, a pyrrolidone functional group, an acetate functional group, or an ether functional group, or a combination thereof.

126. The method of claim 125, wherein the one or more uncharged monomer residues of the hydroxyl functional group comprise residues of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, N-(2-hydroxyethyl)methacrylamide, vinyl alcohol, acrylates or methacrylates of carbohydrates, derivatives of these monomers, or combinations thereof.

127. The method of claim 125, wherein the one or more uncharged monomer residues of the pyrrolidone functional group comprise residues of n-vinyl-2-pyrrolidone or derivatives of the monomer.

128. The method of claim 125, wherein the one or more uncharged monomer residues of the acetate functional group comprise residues of vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

129. The method of claim 125, wherein the one or more uncharged monomer residues of the ether functional group comprise residues of: tetrahydrofuran acrylate or methacrylate, any acrylate- or methacrylate-based monomer having a polyethylene glycol or polypropylene glycol functional group, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or combinations thereof.

130. The method of claim 117, wherein the one or more amine reactive monomer residues comprise epoxy resin functional groups, ketone functional groups, acid anhydride functional groups, olefin functional groups, or isocyanate functional groups or combinations thereof.

131. The method of claim 130, wherein the one or more amine reactive monomer residues of the epoxy resin functional group comprise residues of: glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, allyl glycidyl ether, 1,2-epoxy-4-ethylene-1-cyclohexene, derivatives of these monomers, or combinations thereof.

132. The method of claim 130, wherein the one or more amine reactive monomer residues of the ketone functional group comprise residues of methyl vinyl ketone, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

133. The method of claim 130, wherein the one or more amine reactive monomer residues of the anhydride functional group comprise residues of: n-hydroxysuccinimide monomers, maleic anhydride, derivatives of these monomers, or combinations thereof.

134. The method of claim 130, wherein the one or more amine reactive monomer residues of the olefin functional group comprise residues of allyl methacrylate, vinyl methacrylate, derivatives of these monomers, or combinations thereof.

135. The method of claim 130, wherein the one or more amine reactive monomer residues of the isocyanate functional group comprise residues of 2-isocyanoethyl methacrylate or a derivative thereof.

136. The method of claim 117, wherein the amine-containing crosslinking agent comprises a primary amine or a secondary amine, or a secondary aminosilane, or a combination thereof.

137. The method of claim 136, wherein the amine-containing crosslinking agent comprises a polyether amine or a polymer having a polyether backbone, the polyether backbone comprising polyethylene oxide, polypropylene oxide or other ethylene oxides containing one or more nitrogen atoms per molecule, polyoxypropylene diamine, polyoxypropylene triamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide or combinations thereof.

138. The method of claim 117, wherein the first composition comprises a carrier solvent comprising 20% ​​to 100% water and 0% to 80% of one or more water-miscible co-solvents.

139. The method of claim 138, wherein the water-miscible co-solvent comprises methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or any combination thereof.

140. The method of claim 117, wherein the second component further comprises a carrier solvent.

141. The method of claim 140, wherein the carrier solvent comprises water, an aqueous miscible solvent comprising methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or any combination thereof.

142. The method of claim 117, wherein the composition further comprises one or more additives, including mechanical additives, dispersants, coupling agents, UV absorbers, UV stabilizers, surfactants or leveling additives, curing catalysts, antifreeze additives, dyes or biocides.

143. The method of claim 142, wherein the concentration of the one or more additives in the compound is greater than 0.0001% by weight and less than 40% by weight.

144. The method of claim 142, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, cellulose nanofibers, polyhedral oligomeric silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, layered silicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or any combination thereof.

145. The method of claim 142, wherein the coupling agent comprises one or more of the following: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidoxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidoxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

146. The method of claim 142, wherein the UV absorber comprises one or more of the following: benzophenone, benzotriazole, cyanoacrylate, phenoxytriazine, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, or any combination thereof.

147. The method of claim 142, wherein the UV stabilizer comprises one or more hindered amine light stabilizer (HALS) agents.

148. The method of claim 147, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl) 4 Piperidinyl sebacate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester, dimethyl succinate polymers having 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidinyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]] or combinations thereof.

149. The method of claim 142, wherein the surfactant or leveling agent comprises a silicone polyether surfactant, polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, polysorbate-based surfactant, sodium dodecyl sulfate, hexadecyltrimethylammonium bromide surfactant, dispersant, styrene-maleic acid copolymer, silicone-modified polyacrylate, polyethylene-polypropylene block copolymer surfactant, other commercially available leveling or wetting additives, or combinations thereof.

150. The method of claim 142, wherein the curing catalyst comprises a catalytic acid or catalytic base for assisting the crosslinking reaction for forming the crosslinked film.

151. The method of claim 142, wherein the antifreeze additive comprises glycerol, ethylene glycol, propylene glycol, polypropylene glycol or polyethylene glycol or a molecule comprising at least one of the above.

152. The method of claim 117, wherein the first composition and the second composition are present in an amount sufficient to form a hydrophilic film that cures within 48 hours at 25°C and 0% to 50% relative humidity.

153. The method of claim 117, wherein the first composition and the second composition are present in an amount sufficient to form a dry-to-the-touch hydrophilic film after heating at 130°C for 5 minutes.

154. The method of claim 117, wherein the first composition and the second composition are present in an amount sufficient to have a usability period of more than 8 hours.

155. The method of claim 117, wherein prior to pretreatment, the substrate is sequentially cleaned with a surfactant, water, acetone, isopropanol or another alcohol, a glass cleaning solution or a combination of these solutions, or several of these solutions.

156. The method of claim 117, wherein the substrate is pretreated with a surface activation treatment, primers, adhesion promoters, or a combination thereof prior to applying the antifog coating.

157. The method of claim 156, wherein the surface activation treatment comprises corona treatment, plasma treatment, UV irradiation, ozone exposure, flame activation, exposure to acid or alkali or a combination thereof.

158. The method of claim 156, wherein the primer or adhesion promoter comprises a silane coupling agent, the silane coupling agent being functionalized with an amine, epoxy, thiol, amide, carboxylic acid, or isocyanate functional group.

159. The method of claim 156, wherein the primer or adhesion promoter comprises: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or combinations thereof.

160. The method of claim 117, wherein the substrate comprises glass, plastic, polycarbonate, polyethylene terephthalate, poly(methyl methacrylate), poly(ethylene-co-tetrafluoroethylene), metal, aluminum, ceramic material, or any combination thereof.

161. The method of claim 117, wherein the substrate further comprises an adhesive layer.

162. The method of claim 117, wherein the coating is applied to the substrate by spraying, needle dispensing, film coating, brushing, roller coating, dip coating, blade coating, flow coating, or a combination thereof.

163. A kit for forming a hydrophilic cross-linked membrane, the kit comprising: (A) A first component comprising a first composition comprising at least one prepolymer comprising (a) one or more charged monomer residues, (b) one or more uncharged monomer residues; and (c) one or more amine-reactive monomer residues; and (B) A second component comprising a second composition comprising at least one amine-containing crosslinking agent. When exposed to fogging conditions for more than 30 seconds, the hydrophilic cross-linked membrane exhibited a haze value change of less than 30%.

164. The kit according to claim 163, wherein the first composition and the second composition comprise an amine reactive monomer residue in the first component and an active hydrogen of the amine in the second component in a molar ratio between 1:10 and 10:

1.

165. The kit according to claim 163, wherein the prepolymer consists of 0.01% by weight to 30% by weight of charged monomer residues.

166. The kit according to claim 163, wherein the prepolymer consists of 0.01% by weight to 80% by weight of uncharged monomer residues.

167. The kit according to claim 163, wherein the prepolymer consists of 0.01% by weight to 30% by weight of amine reactive monomer residues.

168. The kit according to claim 163, wherein the one or more charged monomer residues comprise sulfonate functional groups, carboxyl functional groups, phosphonate functional groups, nitro functional groups, imidazolium functional groups, guanidinium functional groups, or quaternary ammonium functional groups, or monomers or combinations thereof capable of being converted into these functional groups.

169. The kit of claim 168, wherein the one or more charged monomer residues comprising the sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrenesulfonic acid, vinylsulfonic acid, propyl 3-sulfonate acrylate, propyl 3-sulfonate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

170. The kit of claim 168, wherein the one or more charged monomer residues comprising a carboxyl functional group include residues of acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, p-styrene carboxylic acid, 3-acrylamide-3-methylbutyric acid, maleic anhydride, itaconic acid, alginate methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

171. The kit of claim 168, wherein the one or more charged monomer residues comprising the phosphonate functional group include residues of undecyl 11-phosphonate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

172. The kit of claim 168, wherein the one or more charged monomer residues comprising the imidazolium functional group include residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazolium, derivatives of these monomers, salts of these monomers, or combinations thereof.

173. The kit of claim 168, wherein the one or more charged monomer residues comprising a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonylpropyl)ammonium hydroxide, 2-ethyldimethylammonium ethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, derivatives of these monomers, salts of these monomers, or combinations thereof.

174. The kit according to claim 163, wherein the one or more uncharged monomer residues comprise hydroxyl functional groups, pyrrolidone functional groups, acetate functional groups, or ether functional groups, or combinations thereof.

175. The kit of claim 174, wherein the one or more uncharged monomer residues comprising a hydroxyl functional group include residues of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, N-(2-hydroxyethyl)methacrylamide, vinyl alcohol, acrylates or methacrylates of carbohydrates, derivatives of these monomers, or combinations thereof.

176. The kit of claim 174, wherein the one or more uncharged monomer residues comprising the pyrrolidone functional group include residues of n-vinyl-2-pyrrolidone or derivatives thereof.

177. The kit of claim 174, wherein the one or more uncharged monomer residues comprising an acetate functional group include residues of vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

178. The kit of claim 174, wherein the one or more uncharged monomer residues comprising an ether functional group include residues of: tetrahydrofuran acrylate or methacrylate, any acrylate- or methacrylate-based monomer having a polyethylene glycol or polypropylene glycol functional group, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or combinations thereof.

179. The kit according to claim 163, wherein the one or more amine reactive monomer residues comprise epoxy resin functional groups, ketone functional groups, acid anhydride functional groups, olefin functional groups, or isocyanate functional groups or combinations thereof.

180. The kit of claim 179, wherein the one or more amine reactive monomer residues comprising the epoxy resin functional group include residues of glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, allyl glycidyl ether, 1,2-epoxy-4-ethylene-1-cyclohexene, derivatives of these monomers, or combinations thereof.

181. The kit of claim 179, wherein the one or more amine reactive monomer residues comprising a ketone functional group include residues of methyl vinyl ketone, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

182. The kit of claim 179, wherein the one or more amine reactive monomer residues comprising an anhydride functional group include residues of the following: an n-hydroxysuccinimide monomer, maleic anhydride, derivatives of these monomers, or combinations thereof.

183. The kit of claim 179, wherein the one or more amine reactive monomer residues comprising an olefinic functional group include residues of allyl methacrylate, vinyl methacrylate, derivatives of these monomers, or combinations thereof.

184. The kit of claim 179, wherein the one or more amine reactive monomer residues comprising the isocyanate functional group include residues of 2-isocyanoethyl methacrylate or a derivative thereof.

185. The kit according to claim 163, wherein the amine-containing crosslinking agent comprises a primary amine or a secondary amine, or a secondary aminosilane, or a combination thereof.

186. The kit of claim 163, wherein the amine-containing crosslinking agent comprises a polyether amine or a polymer having a polyether backbone comprising polyethylene oxide, polypropylene oxide or other ethylene oxides containing one to four nitrogen atoms per molecule, polyoxypropylene diamine, polyoxypropylene triamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidazoles, dicyandiamide or any combination thereof.

187. The kit of claim 163, wherein the first component comprises a carrier solvent comprising 20% ​​to 100% water and 0% to 80% of one or more water-miscible cosolvents.

188. The kit of claim 187, wherein the water miscible cosolvent comprises methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or any combination thereof.

189. The kit according to claim 163, wherein the second component further comprises a carrier solvent.

190. The kit of claim 189, wherein the carrier solvent comprises water, an aqueous miscible solvent comprising methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or any combination thereof.

191. The kit according to claim 163, wherein the composition further comprises one or more additives, including mechanical additives, dispersants, coupling agents, UV absorbers, UV stabilizers, surfactants or leveling additives, curing catalysts, antifreeze additives, dyes or biocides.

192. The kit according to claim 191, wherein the concentration of the one or more additives in the composition is greater than 0.0001% by weight and less than 40% by weight.

193. The kit according to claim 191, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, cellulose nanofibers, polyhedral oligomeric silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, layered silicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or any combination thereof.

194. The composition according to claim 191, wherein the coupling agent comprises one or more of the following: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

195. The kit according to claim 191, wherein the UV absorber comprises one or more of the following: benzophenone, benzotriazole, cyanoacrylate, phenoxytriazine, zinc nanoparticles, cerium oxide nanoparticles, titanium dioxide nanoparticles, or any combination thereof.

196. The kit according to claim 191, wherein the UV stabilizer comprises one or more hindered amine light stabilizer (HALS) agents.

197. The kit according to claim 191, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl) 4 Piperidinyl sebacate, 1,10-bis(1,2,2,6,6) Pentamethyl 4 Piperidinyl esters, dimethyl succinate polymers having 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidinyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidinyl)imino]] or combinations thereof.

198. The kit according to claim 191, wherein the surfactant or leveling agent comprises silicone polyether surfactant, polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, polysorbate surfactant, sodium dodecyl sulfate, hexadecyltrimethylammonium bromide surfactant, dispersant, styrene-maleic acid copolymer, silicone-modified polyacrylate, polyethylene-polypropylene block copolymer surfactant, or any combination thereof.

199. The kit according to claim 191, wherein the curing catalyst comprises a catalytic acid or catalytic base for assisting the crosslinking reaction for forming the crosslinked film.

200. The kit according to claim 191, wherein the antifreeze additive comprises glycerol, ethylene glycol, propylene glycol, polypropylene glycol or polyethylene glycol or a molecule comprising at least one of the above.

201. The kit according to claim 163, wherein the first composition and the second composition are present in an amount sufficient to form a hydrophilic film that cures within 48 hours at 25°C and 0% to 50% relative humidity.

202. The kit according to claim 163, wherein the first composition and the second composition are present in an amount sufficient to form a dry-to-the-touch hydrophilic film after heating at 130°C for 5 minutes.

203. The kit according to claim 163, wherein the first composition and the second composition are present in an amount sufficient to have a shelf life of more than 8 hours.

204. The kit of claim 163, wherein the kit includes an optional third component comprising primers.

205. The kit of claim 204, wherein the primer comprises a silane coupling agent that functionalizes the substrate with an amine, epoxy, thiol, amide, carboxylic acid, or isocyanate functional group.

206. The kit of claim 204, wherein the primer comprises: (3-aminopropyl)triethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, (3-glycidyl etheroxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidyl etheroxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanate propyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilyl)amine, (3-triethoxysilyl)propylsuccinic anhydride, or any combination thereof.

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