Anti-fog coating and method of using the coating

Abstract

An anti-fog coating composition is disclosed that forms a crosslinked film comprising a prepolymer and at least one amine-containing crosslinking agent. The prepolymer comprises one or more charged monomer residues, one or more hydrophilic uncharged monomer residues, and one or more amine-reactive monomer residues. The crosslinked film exhibits a change in haze value of less than 30% when exposed to fogging conditions for a period longer than 30 seconds. A kit comprising a first compartment containing the prepolymer and a second compartment containing the amine-containing crosslinking agent is also disclosed. Coated articles comprising the anti-fog film and the anti-fog coating are also described herein. A method for producing a substrate by applying the composition to the anti-fog coated substrate is also disclosed.

Description

Technical Field

[0001] Cross - Reference to Related Applications

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

[0002]

[0002] The present disclosure generally relates to anti - fog coatings and methods of making the same. Embodiments of the present disclosure relate to compositions and kits used to make such coatings, as well as films and coatings containing such compositions that can be applied to desirable substrates that benefit from an optically transparent anti - fog coating, such as automotive windshields, camera lenses, and refrigerator windows.

Background Art

[0003]

[0003] Anti - fog coatings are generally used to prevent glass or other transparent substrates from fogging due to moisture condensation. A foggy environment occurs when the surface temperature is below the ambient dew point, causing water vapor to condense on the surface and form droplets. The size and shape of these water droplets can scatter light, potentially reducing the optical clarity of the surface. Some prior inventions have focused on the application of hydrophobic coatings, such as silicone, to substrates. These materials can act for a short duration but may not be able to handle intense fogging environments, and a larger number of droplet nuclei may form on the surface. A more common strategy is the use of hydrophilic coatings that give water droplets a small contact angle with the coated substrate, causing the water to form a transparent flat sheet.

[0004]

[0004] Hydrophilic coatings face a trade-off between effectiveness and durability. In cloudy environments, hydrophilic coatings remain clear as they interact favorably with liquid water, resulting in a small contact angle and the formation of a flat film across the coating by the liquid water. However, these coatings are susceptible to damage because they interact strongly with liquid water, making them easily washed off or expanding in the presence of liquid water or water vapor. Conversely, more mechanically durable coatings incorporate stronger intermolecular bonds within the coating, such as chemical crosslinking or hydrophobic interactions, which can reduce the hydrophilicity of the coating and degrade its performance. [Overview of the project] [Problems that the invention aims to solve]

[0005]

[0005] There are a variety of "permanent anti-fogging coatings" available on the market, but most of them consist of crosslinked hydrophilic polymers. At least one common drawback of these permanent anti-fogging coatings is that they may contain toxic or otherwise harmful raw materials. For example, making anti-fogging coatings using crosslinked hydrophilic polymers often requires harmful reagents, such as aziridine crosslinkers, isocyanate functional materials, or tin catalysts. Such harmful reagents are highly toxic, pose environmental concerns, are therefore strictly regulated, and are difficult to use safely in industrial environments.

[0006]

[0006] Other common drawbacks of anti-fogging coatings made from crosslinked hydrophilic polymers are that they may be difficult to apply to surfaces or may have poor mechanical properties when applied to substrates. For example, crosslinking-dependent coating compositions may develop high viscosity over time as the crosslinking agent and polymer react. As a result, it may be difficult to apply the coating composition to the surface of a substrate. In another example, other anti-fogging coatings may use blocked crosslinking agents that require prolonged heat treatment to form a coating on an article or final product. If insufficient heat treatment is applied, the coating may not continue to cure to a sufficient level under ambient conditions. The need for prolonged heat treatment may make application difficult.

[0007]

[0007] Furthermore, another drawback of most commercially available anti-fogging coating compositions is the lack of a combination of desirable coating characteristics for practical use, such as a long pot life and rapid curing ability at room temperature. Curing is a critical process step that can maximize the desirable 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 off with water or other solvents, thereby increasing the hardness or modulus of the coating, or surface-active additives can aggregate on the surface of the coating during curing to reduce friction on the surface. If it is not possible for the coating to cure at room temperature, careful process control is essential to ensure complete curing. This risk is avoided with coatings that cure at room temperature, as any incomplete curing reaction may continue after the initial application process is complete.

[0008]

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

[0009]

[0009] Another challenge associated with applying anti-fogging coating compositions to a substrate, or with creating anti-fogging coatings using crosslinked hydrophilic polymers, is that most polymer crosslinking reactions are highly sensitive to environmental conditions (e.g., temperature, pressure, UV light, humidity, or the presence of other chemicals). Therefore, a highly controlled environment is essential for the industrial application of such coatings.

[0010]

[0010] Another drawback of many anti-fogging coatings is that they rely on "sol-gel" chemistry and require complex coating techniques. This process involves the conversion of monomers into a colloidal solution (sol) that acts as a precursor to an integrated network (i.e., gel) of individual particles or network polymers. For example, the sol-gel process may involve water-catalyzed hydrolysis and alkoxy-silane group condensation. While the sol-gel process itself and the chemistry of the reactants for the process are widely used, performing sol-gel techniques is more difficult in industrial environments. The water sensitivity of precursors can complicate the storage of precursors before use. For example, instead of using water, it may be essential to store precursors using flammable solvents with a high content of volatile organic compounds (VOCs) as a support. The complex nature of hydrolysis and condensation may require careful control of application conditions and can often impose limitations on the usable life ("pot life") of the coating before it gels, thus rendering it no longer useful for application as a film and potentially causing damage to the application machinery. Furthermore, the final properties of such anti-fogging coatings prepared using a sol-gel process can be affected by the curing protocol, and therefore careful process control is essential to produce a crack-free and sufficiently durable coating.

[0011]

[0011] Furthermore, anti-fogging coatings made from crosslinked hydrophilic polymers may exhibit a behavior called "fouling," which refers to contamination caused by hydrophobic molecules adhering to the surface of the coated substrate. Fouling is undesirable when coating any substrate because it can lead to the accumulation of undesirable materials on the substrate. Additional chemicals are often required to make the coating "fouling resistant." For example, silicones or fluoropolymers are commonly used to obtain anti-fogging coatings with low surface energy and low friction. [Means for solving the problem]

[0012]

[0012] The anti-fogging crosslinked coating compositions disclosed herein are intended to overcome one or more of the problems of the prior art and / or other problems specified above. In particular, the coating compositions disclosed herein have high fogging resistance over long periods of time. Furthermore, when the compositions become coatings, they are mechanically durable and do not easily scratch, damage, or foul during use. Finally, in some embodiments, the coatings may be applied from compounds or compositions with long pot life, or from kits containing compounds or compositions, thereby diversifying the industrial applications of the coatings and making them easier to use.

[0013]

[0013] Furthermore, the disclosed anti-fogging crosslinked polymer coating composition does not use highly toxic crosslinking agents that may require expensive safety protocols. The disclosed coating can be cured at room temperature and can be applied to a variety of substrates regardless of the substrate's chemistry. The method of applying the disclosed coating composition to a substrate is simple and can be used to create anti-fogging coatings on a variety of substrates while ensuring sufficient curing of the coating with less expensive process control compared to anti-fogging coatings available on the market. Another advantage of the disclosed coating composition or kit is that it has a long pot life of more than 24 hours, which makes execution easier, reduces material waste, and limits the risk of the coating becoming immobile and damaging the application machine. The disclosed composition or kit can be stored completely or partially in water as a carrier, which mitigates concerns about VOC emissions and flammability, and is therefore less toxic and more environmentally friendly. Finally, the disclosed coating provides strong and long-lasting anti-fogging to the applied substrate.

[0014]

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

[0015]

[0015] In view of the foregoing, one embodiment describes a composition for forming a crosslinked film that imparts antifogging properties. In some embodiments, the composition comprises a prepolymer comprising (a) one or more hydrophilically charged monomer residues, (b) one or more hydrophilic uncharged monomer residues, and (c) one or more amine-reactive monomer residues, and at least one amine-containing crosslinking agent (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 longer than 30 seconds.

[0016]

[0016] In another embodiment, an anti-fog film comprising a crosslinked polymer is described. In some embodiments, the crosslinked polymer comprises (a) one or more hydrophilically charged monomer residues, (b) one or more hydrophilic uncharged monomer residues, (c) one or more amine-reactive monomer residues, and (d) at least one amine-bearing 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 longer than 30 seconds.

[0017]

[0017] In another embodiment, a coated article comprising a substrate and a coating is described. In some embodiments, the coating comprises a crosslinked polymer comprising (a) one or more hydrophilically 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, wherein the coated article exhibits a change in haze value of less than 30% when exposed to cloudy conditions for a fixed period of time longer than 30 seconds.

[0018]

[0018] In yet another embodiment, a method for making the surface of a substrate less prone to fogging is described. In some embodiments, the described method includes the step of applying a compound comprising a first composition and a second composition to the surface of a substrate. In some embodiments, the first composition is made from a prepolymer comprising (a) one or more hydrophilically charged monomer residues, (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. Upon treatment, the substrate exhibits a change in haze value of less than 30% when exposed to fogging conditions for a period longer than 30 seconds.

[0019]

[0019] In yet another embodiment, a kit for forming a hydrophilic crosslinked film is described. In some embodiments, the kit comprises (A) a first component and (B) a second component, and the hydrophilic crosslinked film exhibits a change in haze value of less than 30% when exposed to cloudy conditions for a period longer than 30 seconds. The first component (A) comprises a first composition comprising a prepolymer, the prepolymer comprising (a) one or more hydrophilically charged monomer residues, (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]

[0020] As described in more detail below, various embodiments may include at least one additive that enhances the resulting properties of the composition, film, coated article or method, such as additives that enhance adhesion, freeze-proofness, crosslinking, film-forming properties, mechanical properties or rheological properties. [Modes for carrying out the invention]

[0021] Definition:

[0021] As used herein, “haze value” refers to a number that represents the scattering of light due to inhomogenity or discontinuity in a material, which may cause undesirable optical properties, such as a decrease in clarity. Haze measuring devices, such as haze meters, may be used to measure this number. The term “Δhaze” refers to the change in haze value or haze measurement taken according to ASTM D1003 before and after vapor exposure. For example, the haze value of a sample equilibrium at 25°C was measured according to ASTM D1003. The sample was then held in a beaker of boiling water for 60 seconds, and the haze value of the sample was re-evaluated using ASTM D1003. The first measurement obtained by subtracting the second measurement is defined as “Δhaze”. Typically, the haze value is measured as a percentage of scattered incident light and is expressed as a percentage without specific units. According to the ASTM standard, materials with a haze value greater than 30% are defined as "diffusive" and can therefore act as a boundary between optically clear samples (versus) and cloudy or optically unclear samples.

[0022]

[0022] As used herein, “monomer” refers to a chemical entity that can serve as the smallest repeating unit in a polymer and may have 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 alkene configured for polymerization.

[0023]

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

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

[0025] As used herein, the term "amine-reactive monomer" refers to a monomer that is capable of undergoing a chemical reaction using an amine functional group.

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

[0026]

[0027] As used herein, the terms "monomer residue", "crosslinker residue" or "residue" refer to a molecule that has completed a chemical process. For example, a residue refers to a monomer incorporated into an oligomer, prepolymer or polymer during a polymerization reaction. Specifically, the polymerization of a methacrylate monomer produces a poly(methacrylic) polymer composed of methacrylate residues. Additionally, any unreacted methacrylate monomer also constitutes a methacrylate residue. Further, a functional group that is chemically converted is also a residue. For example, an ester formed from the reaction of acrylic acid and methanol is an acrylic acid residue.

[0027]

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

[0028]

[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 involve a second type of reaction that can produce a molecule that reacts with multiple polymer chains, or a reaction that reacts with polymer chains once and then produces a crosslinked network structure.

[0029]

[0030] As used herein, the term “crosslinking” refers to a chemical reaction in which a chemical bond is formed between two or more polymer chains. This is the process of chemical linking of two or more molecules to form a crosslinked network structure. Factors influencing crosslinking include the concentration of the crosslinking agent, e.g., 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 start a polymerization reaction.

[0030]

[0031] As used herein, the term “polymer functional group” refers to the presence of a chemical functional group, which is an atomic motif or family of motifs, in the monomer residues of a polymer. Functional polymers are polymers that have specific properties or uses. Specific polymer functional groups are often determined by the presence of chemical functional groups present in the polymer that differ from those in the main chain.

[0031]

[0032] As used herein, the term “additive” refers to any chemical substance or material added to a system containing the disclosed composition, the addition of an additive to the system alters one or more properties of the composition.

[0032]

[0033] As used herein, the term “mechanical additive” refers to any chemical substance or material added to a sample containing the disclosed composition, the addition of an additive to the sample is configured to alter the mechanical properties of the composition.

[0033]

[0034] As used herein, the term "fogging" refers to water droplets on a surface that reduce the optical clarity of the surface. In contrast, a substrate coated with an anti-fogging coating can absorb water vapor before it condenses on the surface, absorb water droplets after they have formed, or evenly wet the surface with droplets to form a water film that minimizes the reduction in optical clarity.

[0034]

[0035] As used herein, the term “anti-fogging film or coating” refers to a film or coating that, when applied to a substrate, is configured to give the substrate greater anti-fogging properties compared to the same substrate under bare or unfilmed conditions.

[0035]

[0036] As used herein, the term “fogging-resistant” surface refers to a surface whose optical clarity does not deteriorate when exposed to cloudy conditions. One way to evaluate this is by the change in the haze value when the substrate is exposed to cloudy conditions. For opaque substrates, such as metals or colored plastics, “fogging resistance” is evaluated qualitatively. One way to evaluate whether an opaque sample is fogging-resistant is to hold the sample over steam before visual inspection. If water droplets significantly alter the appearance of the sample, the sample is not fogging-resistant. If the substrate remains clearly visible, the sample is fogging-resistant or has anti-fogging properties.

[0036]

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

[0037]

[0038] As used herein, the term "hydrophilic coating" refers to a coating having 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 mixed compound can be used after the compounds of multiple reactive compositions have been combined. After this time, the compound may become too sticky to apply, or the curing process may not yield acceptable properties in the final product. In some industrial applications, “pot life” is quantified as the amount of time it takes for the initial viscosity of the mixed compound to quadruple at room temperature. For example, the pot life of a kit containing two components of two different compositions may be defined as the time required for the viscosity of the mixture of the two compositions to quadruple at room temperature. For example, if a compound formed after mixing the two compositions from two compartments of a kit has an initial viscosity of 100 cP and its viscosity rises to 400 cP after 50 hours at room temperature, the pot life is 50 hours at room temperature. The pot life of a compound can be altered by changing several parameters, for example, by varying the type or content of the solvent.

[0038]

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

[0039] composition chemistry

[0041] In some embodiments, the disclosed coating composition may include a polymer, a prepolymer, a solvent, additives, a crosslinking agent, and a combination of their residues.

[0040]

[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 that some of the charged molecules be sufficiently hydrophilic.

[0041]

[0044] In some embodiments, the crosslinking agent or curing agent can be mixed with the coating composition before application, which then cures on the substrate upon application.

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

[0042]

[0046] In some embodiments, the disclosed compositions may not contain any catalysts or crosslinking agents that are Category 1 mutagenic substances as defined by the GHS, or that are listed as having Category 1 acute toxicity, reproductive toxicity, or specific organ toxicity.

[0043]

[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, t-butanol, sec-butanol, and 1-methoxy-2-propanol, amines such as ammonium hydroxide or triethylamine, ether or glycol solvents such as ethylene glycol, propylene glycol, glycerol, ketones such as acetone, ethyl acetate or methyl ethyl ketone, or others suitable for polymers or prepolymers.

[0044]

[0048] In some embodiments, the disclosed compositions may contain one or more solvents in amounts sufficient to achieve the desired properties of the composition without causing severe acute toxicity or environmental concerns.

[0045]

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

[0046] compound

[0050] 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 are found in the composition in amounts sufficient to form an anti-fogging film that exhibits a change in haze value of less than 30% when exposed to fogging conditions for a period longer than 30 seconds.

[0047]

[0051] In some embodiments in which the disclosed coating composition is 2K-based, 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% water, or a mixture of miscible auxiliary solvents or auxiliary solvents. Non-limiting examples of such solvents or auxiliary solvents 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.

[0048]

[0052] In some embodiments where the disclosed coating composition is 2K-based, the second component may comprise an amine-containing crosslinking agent or a mixture of crosslinking agents. In some embodiments, the second component may be solvent-free. In other embodiments, the amine-containing crosslinking agent or mixture of crosslinking agents may be soluble in water in the second component. In some other embodiments, the second component may comprise an amine-containing crosslinking agent or mixture of crosslinking agents dissolved in a water-miscible solvent or mixture of solvents. 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.

[0049]

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

[0050]

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

[0055] In some embodiments in which the disclosed coating composition is 2K-based, the second component may comprise 1-80 wt% amine crosslinking agent, 0.1-90 wt% alcohol, and 0.1-25 wt% silane coupling agent.

[0051] Prepolymer

[0056] In some embodiments, the composition includes a prepolymer. In some embodiments, the composition may include a prepolymer synthesized using at least two hydrophilic monomers, at least a portion of which includes a charged hydrophilic monomer.

[0052]

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

[0053]

[0058] In some embodiments, one or more charged monomer residues are sulfonates, carboxyls, phosphonates, nitro, imidazolium, guanidinium, or quaternary ammonium functional groups, or 2-acrylamido-2-methylpropanesulfonic acid, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide, 2-ethyldimethylammonioethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, 4-styrene sulfonate, p-styrene carboxylic acid, vinyl sulfonic acid, 3-acrylamido-3-methylbutanoic acid, acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, 1-allyl-3-methylimidazolium chloride, maleic anhydride, itaconic acid, 3-sulfopropyl acrylate, 11-phosphonowndecyl acrylate, vinylphosphonic acid, alginate methacrylate. This may include monomers that can be converted to functional groups such as methacrylate, 3-sulfopropyl methacrylate, and 1-vinylimidazole, derivatives of these monomers, salts of these monomers, or combinations thereof.

[0054]

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

[0055]

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

[0061] In some embodiments, one or more charged monomer residues may be monomer residues that are acidic, basic, or a neutralized acid or base salt.

[0056]

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

[0063] In some embodiments, the one or more amine-reactive monomer residues may include an epoxy group, a ketone functional group, an anhydride functional group, or monomer residues having allyl methacrylate, vinyl methacrylate, glycidyl methacrylate, 2-isocyanatoethyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, methyl vinyl ketone, 4-vinyl-1-cyclohexene 1,2-epoxide, allyl glycidyl ether, diacetone acrylamide, an n-hydroxysuccinimide-containing monomer, an isocyanate functional group containing maleic anhydride, residues or functional groups of these monomers, derivatives of these monomers, or combinations thereof.

[0057] Crosslinking agent

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

[0058]

[0065] In some embodiments, the composition may contain 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 a prepolymer to produce the disclosed anti-fogging coating composition.

[0059]

[0066] In some embodiments, the amine-containing crosslinking agent may include a primary or secondary amine capable of forming one or more covalent bonds with the polymer. Such amine-containing crosslinking agents may include, but are not limited to, polyetheramines, or polymers having a polyether backbone containing polyethylene oxide, polypropylene oxide, or other ethylene oxides containing one or more nitrogen atoms per molecule, polyoxypropylenediamine, polyoxypropylenetriamine, 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, imidisoles, dicyandiamides, or any combination thereof.

[0060]

[0067] In some embodiments, amine-containing crosslinking agents can contribute to a longer pot life of the disclosed composition. The amine-containing crosslinking agent can be chemically inhibited in its involvement in the crosslinking reaction, for example, by being designed to have steric hindrance near the amine functional group, and thus the rate of the crosslinking reaction that produces the disclosed crosslinked film can be slowed. Alternatively, the amine-containing crosslinking agent may be a secondary amine, and thus the rate of the crosslinking reaction that produces the disclosed crosslinked film can be slowed. The composition may spontaneously cure on any substrate upon application. A slower crosslinking rate of the disclosed composition can be useful for a longer pot life and lower viscosity of the composition, and consequently for easier application.

[0061] additives

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

[0062]

[0069] In some embodiments, the mechanical additive includes one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, cellulose nanofibers, polyhedral oligomer silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, phyllosilicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, any dispersant or surface modifier essential for processing the mechanical additive, or any combination thereof.

[0063]

[0070] 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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

[0064]

[0071] In some embodiments, the UV absorber may include benzophenone, benzotriazole, cyanoacrylate, hydroxyphenyltriazine, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, or any combination thereof.

[0065]

[0072] In some embodiments, the UV stabilizer is a hindered amine light stabilizer ("HALS") activator, or bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) decandioate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester decandioate, or 4-hydroxy-2,2,6,6-tetramethyl-1 - May contain dimethyl succinate polymer containing piperidineethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]] and other additives designed to prevent UV degradation, or any combination thereof.

[0066]

[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 surfactants, sodium dodecyl sulfate, cetyltrimethylammonium 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.

[0067]

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

[0068] Pot Life

[0075] In some embodiments, the composition may have a pot life of more than 8 hours, for example, 24 hours, for example, more than 48 hours, or more than 72 hours, or more than 96 hours at room temperature.

[0069]

[0076] In some embodiments in which the disclosed coating composition is 2K-based, the first and second components may be found in amounts sufficient to give the composition a pot life of more than 8 hours, e.g., 24 hours, e.g., more than 48 hours, or more than 72 hours, or more than 96 hours, at room temperature, after the two components have been mixed and stored in a sealed container with a headspace smaller than the volume of the composition.

[0070]

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

[0078] In some embodiments, the composition may have a low viscosity of less than 1000 cP, for example less than 800 cP, for example less than 600 cP, for example less than 400 cP, for example less than 200 cP, for example 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.

[0071] Film / Coating

[0079] In some embodiments, the disclosed coating may be hygroscopic. In some embodiments, the disclosed coating may have a small contact angle with respect to water.

[0072] durability

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

[0073]

[0081] In some embodiments, the coating may have high resistance to cleaning solvents. For example, the anti-fogging coating can be rubbed with a cloth dampened 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% dishwashing detergent, and a change in the Δ-haze value of less than 2% can be observed in the film.

[0074]

[0082] In some embodiments, the coating can be immersed for 24 hours in deionized water, an aqueous solution of 5% NaCl, or an aqueous solution of 0.1% dishwashing detergent, while maintaining satisfactory mechanical properties and antifogging capabilities.

[0075]

[0083] In some embodiments, the coating can withstand mechanical friction. For example, some embodiments can be rubbed using a linear abrader with a 1000g load and 1000 cycles of a cheese cloth abrasion head, exhibiting a change in haze value of less than 5%, e.g., less than 2%, and in many cases less than 1%. In another example, embodiments can be rubbed using a linear abrader with a 1000g load and 1000 cycles of a sponge abrasion head, exhibiting a change in haze value of less than 5%, e.g., less than 2%, and in many cases less than 1%.

[0076]

[0084] In other embodiments, the coating can withstand rubbing 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, the cloth may be dampened with the chemical and rubbed on the coating with a linear friction tester at an applied load of 500 g for 10 cycles. After washing off any chemical residues, the sample may show a change in haze value of less than 5%, e.g., less than 2%, and in many cases less than 1%. The sample may still exhibit anti-fogging properties after this test.

[0077]

[0085] In some embodiments, the coating may have excellent adhesion. The coating may be tested according to the ASTM D3359 cross-hatch adhesion test and receive a score of 5B.

[0078]

[0086] In some embodiments, the coating can have excellent moisture resistance. The coating can be exposed to 85°C and 95% relative humidity for 7 days and show no visual defects whatsoever. When tested according to a vapor test, the coating can maintain excellent anti-fogging properties, showing a Δ-haze of less than 5%, for example less than 2%, and in many cases less than 1%. The coating can maintain excellent adhesion after being exposed to high temperature and high humidity for 7 days and received a score of 5B after being tested according to the ASTM D3359 cross-hatch adhesion test.

[0079] Coated articles

[0087] In some embodiments, the substrate of the coated article may be glass, plastic, such as acrylic, polycarbonate, polyethylene terephthalate, poly(methyl methacrylate), poly(ethene-co-tetrafluoroethene), a sheet having an adhesive backing of any of these polymer substrates, metal, such as aluminum, ceramic material, or any combination thereof.

[0080]

[0088] In some embodiments, the substrate may include a layer applied using a pretreatment step before applying the anti-fogging coating.

[0089] In some embodiments, the coated substrate or article may be an automotive or building structure, a building window, a camera lens, a medical scope lens, a sensor, eyewear, a mirror, a consumer electronic device, personal protective equipment, other safety equipment, or a refrigerator door.

[0081]

[0090] In some embodiments, the coated substrate or article may exhibit a Δ-haze of less than 30%, e.g., less than 5%, or less than 2%, and in many cases less than 1%, during exposure to cloudy conditions. In some embodiments, the substrate coated with the coating composition according to this disclosure exhibits a Δ-haze ranging from 0.1% to less than 2%, e.g., from 0.1% to 1.7%.

[0082]

[0091] In some embodiments, the coating can impart hydrophilicity to the substrate, but not necessarily to make the substrate antifogging. For example, in some embodiments, the coating may be applied to a metal substrate to increase its affinity for water, or it may be selectively applied to a metal substrate to direct water towards the coated area and away from the uncoated area. In other embodiments, the coating may be applied to a rubber substrate so that water can wet the surface more easily. In yet another embodiment, the coating may be applied to a ship surface to repel barnacles or other foulants.

[0083]

[0092] In some embodiments, the coating may be applied to a surface to make it resistant to frost formation. In other embodiments, the coating may be applied to a substrate to increase the rate at which frost melts.

[0084]

[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 clear adhesive, and a coating. In one embodiment, the adhesive may be selected from acrylic adhesives, silicone adhesives, urethane heat-seal adhesives, polyethylene heat-seal adhesives, and combinations thereof.

[0085]

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

[0086]

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

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

[0087]

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

[0098] In some embodiments, the first composition comprises a commercial 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 instead have vinyl or other unsaturated functional groups.

[0088]

[0099] In some embodiments, the second composition containing the crosslinking agent also includes a charged monomer that can be bound to an amine-reactive monomer residue. In some embodiments, these charged monomers have a thiol functional group. In some embodiments, these charged monomers are 3-mercapto-1-propanesulfonate, cysteine, or salts or derivatives of these monomers.

[0089]

[0100] In accordance with some embodiments described herein, the coating may have stronger mechanical properties.

[0090] How to apply

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

[0091]

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

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

[0092]

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

[0105] In some embodiments, a method for applying the disclosed coating composition to a substrate may include a step of washing the substrate with a surfactant, water, ethanol, isopropyl alcohol, or other cleaning solution before pretreatment.

[0093]

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

[0094]

[0107] In some embodiments, a method for applying the disclosed coating composition to a substrate may include the step of applying the compound to the substrate by spray coating, needle dispensing, film coating, brush coating, roller, dipping coating, or blade coating.

[0095]

[0108] In some embodiments, the method may include the step of applying the compound to a substrate and then thermally curing it.

[0096] Primer

[0109] In some embodiments, the method may include the step of applying a compound undercoat to the substrate before applying the coating composition. The undercoat may include a primer or adhesion promoter. In some embodiments, a silane coupling agent or primer may be applied to the substrate before applying the coating composition. This may help the coating adhere to the substrate.

[0097]

[0110] In other embodiments, an undercoat that imparts additional functional groups to the coating system may be applied to the substrate before applying the coating composition, depending on the properties of the substrate and the properties of the coating to be achieved.

[0098]

[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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

[0099]

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

[0100]

[0113] In some embodiments, the substrate is pre-treated with an undercoat, which is a layer of material between the substrate and the active top coating.

[0114] The undercoating may be a cross-linked polymer that, when immersed in deionized water for one hour, expands in dry thickness by a lower percentage than the percentage by which the anti-fog coating expands in dry thickness.

[0101]

[0115] Undercoating can be applied by spraying, brushing, dipping, roller coating, or blade coating.

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

[0102]

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

[0103]

[0118] The amine-containing crosslinks in the undercoating may include polyetheramines, or polymers having a polyether backbone containing polyethylene oxide, polypropylene oxide, or other ethylene oxides containing 1 to 4 nitrogen atoms per molecule, or secondary aminosilanes, such as n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidisole, dicyandiamide, or any combination thereof.

[0104]

[0119] Silane coupling agents in undercoating 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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

[0105]

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

[0106]

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

[0122] In some embodiments, the method may include the step of applying the compound to a substrate with a wet thickness of 0.1 to 10,000 microns.

[0107]

[0123] In some embodiments, the method may include the step of applying the compound to a substrate with a dry thickness in the range of 0.001 to 100 microns.

[0124] In some embodiments, the method may be used to coat any substrate from an automobile or building window, camera lens, medical scope lens, sensor, eyewear, mirror, consumer electronic device, personal protective equipment, other safety equipment, refrigerator door, or building structure with the disclosed coating composition.

[0108] Curing conditions

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

[0109]

[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, when the disclosed composition is 2K-based, the first and second components may be found in the composition in amounts sufficient to form a hydrophilic coating that cures within 48 hours at 25°C and 0% to 50% relative humidity.

[0110]

[0128] In some embodiments, when the disclosed composition is 2K-based, the first and second components may be found in the composition in amounts sufficient to form a hydrophilic coating that is touch-dry after heating at 130°C for 5 minutes.

[0111]

[0129] In some embodiments, the composition may cure under ambient room temperature conditions or high temperature and high humidity conditions when applied to a substrate. The curing of the composition may depend on several factors, including the chemical composition, the thickness of the applied coating, the concentration of the crosslinking agent, e.g., the concentrations and relative ratios 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.

[0112]

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

[0113]

[0131] In some embodiments, the composition may cure at room temperature when applied to a surface with a crosslinking agent or curing agent.

[0132] In some embodiments, the composition, when applied to a surface with a crosslinking agent or curing agent, may be heated and cured to be touch-dry in less than two minutes.

[0114] Anti-fogging measurement

[0133] In some embodiments, the disclosed anti-fog coating may be hydrophilic and may have excellent anti-fogging properties as well as durability against chemical, mechanical, and environmental stresses. The hydrophilic coating may be able to absorb water vapor, or cause the coating to expand, instead of or before the condensation of water droplets on the substrate. Furthermore, water droplets present on the surface may condense on the coated surface. o A small equilibrium contact angle of less than 1 / 2 can be formed. As the coating expands, the contact angle can change dynamically over time. This property causes the water droplet to form a flat sheet on the surface, thereby preventing optical distortion.

[0115]

[0134] Depending on humidity, temperature, and other environmental conditions, anti-fogging coatings may impart anti-fogging properties through the absorption of water by the coating, and consequently the expansion of the coating, or through the formation of a small contact angle with water by the coating, or through both actions simultaneously or sequentially. For example, when observed with the naked eye, water droplets on a substrate coated with the disclosed anti-fogging coating appear to be absorbed by the coating, and therefore no liquid layer of water remains on the surface of the substrate, thereby initially imparting anti-fogging properties to the coated substrate. After exposure to a foggy environment, such as vapor exposure, the coating may become saturated with water, and a film of water may form on the coating at a small contact angle.

[0116]

[0135] Sometimes this water film may be non-uniform even as it takes shape, and because the water is in the process of wetting the surface, poor and transient optical properties can easily be measured. For example, in a coating of uneven thickness, the water film may be non-uniform even as it takes shape, which can lead to poor and transient optical measurements. If the water film is only partially formed, the anti-fogging properties should only be evaluated on an area where the film is fully formed, or after the water has completely wetted the surface.

[0117]

[0136] An effective anti-fog coating maintains high optical clarity over extended periods in cloudy conditions. This can be quantitatively evaluated using visual observation, measurement of the film's haze value in cloudy conditions according to ASTM D1003, or measurement of image distortion seen through the anti-fog film according to a modified version of standard EN-168.

[0118]

[0137] In some embodiments, the anti-fogging evaluation may be performed after immersing the sample in deionized water for 1 hour and then allowing it to stand under ambient conditions for 24 hours.

[0138] The features and advantages of the present invention are more fully demonstrated by the following examples, which are provided for illustrative purposes only and should not be construed as limiting the invention. [Examples]

[0119] Sample preparation

[0139] Prior to coating, all glass substrates were cleaned by wiping with deionized water and isopropanol, and then pre-treated with corona discharge.

[0120]

[0140] Before coating, all plastic substrates (e.g., polycarbonate, acrylic) were pre-treated with corona discharge.

[0121] Steam test

[0141] A 250 mL Erlenmeyer flask was filled with 100 mL of deionized water and brought to a boil. The haze value of the coated substrate was evaluated using a haze meter according to ASTM D1003. The sample was then placed with the coated side down over the opening of the Erlenmeyer flask for the specified time. The sample was then removed from the flask and placed over the measuring port of the haze meter. Ten seconds after removal from the flask, the haze value was measured, and Δ-haze was calculated by subtracting the measured haze value from the haze initially measured before vapor exposure. Samples showing a Δ-haze value greater than 30% were diffusive and not anti-fogging. Samples showing a Δ-haze value less than 30% showed anti-fogging properties. In some applications, a Δ-haze value less than 30% may be required for effective use in a cloudy environment. In these applications, Δ-haze values ​​less than 20%, less than 10%, less than 5%, less than 2%, or even less than 1% may be required for effective use. Modified EN-168 Test

[0142] Another technique for evaluating anti-fogging performance is via a modification of the EN-168 standard. This technique involves preparing a humidified chamber modified to allow mapping analysis according to the conditions specified in EN-168. A Siemens star was mounted on one side of the chamber, opposite the opening in the chamber, as a visual target. The sample was placed over the opening so that the anti-fogging coating faced the inside of the humidified chamber. Images were taken at 1 second per minute or 30 minutes per minute, and the modular transfer function method was calculated using the NIH ImageJ image processing program and compared to the calculated modular transfer function of images taken under non-fogging conditions. The ratio of the integrals of the modular transfer function at a set time point was compared with that of the initial measurement to generate a quantitative comparison over time.

[0122] definition of polymer

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

[0123]

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

[0124]

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

[0125]

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

[0126] Example 1 Preparation of coating composition

[0147] Solution S-1-1 was prepared with 11 wt% prepolymer-1, 55.8 wt% water, 33 wt% 1-methoxy-2-propanol, 0.1 wt% polyethersiloxane copolymer, and 0.51 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate. Solution S-1-2 was prepared with 10 wt% polyoxypropylenetriamine and 90 wt% water. Solution S-1-3 was then prepared with 1 wt% (3-glycidyloxypropyl)trimethoxysilane in 99 wt% ethanol.

[0127] Application of coating compositions to substrates

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

[0128] Thickness measurement

[0149] The coating thickness on the glass slide was measured to be 4.5 microns.

[0129] haze measurement

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

[0130]

[0151] The change in haze value, Δ-haze of coated glass slides prepared according to Example 1, was measured as a function of time according to ASTM D1003. The experiment was conducted according to the procedure of a steam test, except that it lasted for 30 minutes.

[0131] [Table 1]

[0132] Measurement of transmittance

[0152] The transmittance of the glass slides was then measured using a UV-Vis spectrophotometer. A blank glass slide was used as a control. The transmittance of the coated glass slides exceeded 99% compared to the blank glass slides in the 400 nm to 700 nm range.

[0133] Exposure to cloudy conditions

[0153] A vapor test was performed on the coating, and a Δ-haze of 0.1% was measured. The glass slide with the coating was then immersed in deionized water for 1 hour. The glass slide with the coating was then dried and allowed to set at room temperature for 24 hours. The glass slide with the coating was then attached to a chamber designed according to EN-168 standards and exposed to a humid atmosphere for 60 seconds. The glass slide with the coating did not fog up within 60 seconds.

[0134] Mechanical strength test

[0154] A coated glass slide was placed in a linear friction tester and rubbed with a cheese cloth for 1000 cycles under a weight of 1 kg. After rubbing, the haze value of the coated glass slide was measured at 0.3%, and no damage was observed.

[0135] Frost test

[0155] The sample was prepared in the same manner as in Example 1, except that a mask was created using tape so that only half of one side of the glass slide was coated. This process was then repeated on the opposite side of the glass slide, the tape was removed, and a sample was obtained with both sides of the glass slide partially coated.

[0136]

[0156] The sample was cooled to -10°C, then removed and placed on a workbench under ambient conditions of approximately 25°C and 50% relative humidity. Frost formed on both sides of the uncoated half of the glass slide within seconds, resulting in poor optical clarity and making it difficult to see through the slide. Frost did not form on the coated half of the glass slide, and the sample was clearly visible through it. This indicates that the coating is very effective in mitigating frost formation and may be useful in applications requiring good optical clarity at low temperatures.

[0137]

[0157] The sample was cooled to -40°C, then removed and placed on a workbench under ambient conditions of approximately 25°C and 50% relative humidity. Frost immediately formed 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 glass slide remained covered in frost. Within 45 seconds, the frost had completely disappeared from the coated half of the sample, and the sample appeared optically clear. On the uncoated half of the sample, the frost only began to melt after 45 seconds. After 2 minutes, a considerable amount of frost had melted on the uncoated half of the slide, but remaining water droplets made it difficult to see through that half of the slide. This indicates that the coating is very effective for frost protection and can provide excellent clarity in extremely low-temperature environments.

[0138] Pot life test

[0158] The S-4-3 solution was sprayed onto a glass slide and baked at 130°C for 10 minutes.

[0139]

[0159] 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. The viscosity was then measured, and the coating was sprayed onto one of the pre-treated glass slides and baked at 130°C for 10 minutes. The coated slide was evaluated by visual appearance, haze measurement (ASTM D1003), and vapor test. After coating three slides, the remaining coating solution was evaluated daily for gelation by inversion test.

[0140] [Table 2]

[0141] Application of fast-drying coating compositions

[0160] Glass slides and coatings were prepared as described in Example 1. After spraying the coating, the glass slides were baked in an oven at 80°C for 2 minutes to form the coating on the glass slides. The coated glass slides were then removed from the oven and touched with a finger. The coating on the glass slides was touch-dry and was not damaged by handling.

[0142] Polycarbonate sheet as a base material

[0161] A coating was prepared according to Example 1 and applied to a prepared polycarbonate sheet using an 80-micron bar coater. The moistened polycarbonate sheet was then baked in an oven at 130°C for 10 minutes to form the coating. The haze value of the coated polycarbonate sheet was measured to be 0.2%. A Δ-haze of 0.2% was obtained by steam testing.

[0143] Curing at room temperature

[0162] A coating was prepared according to Example 1 and applied to a pre-treated polycarbonate sheet using an 80-micron bar 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 Δ-haze of 0.2% was obtained by a steam test. The coated polycarbonate sheet was then rubbed with a damp cloth, which showed no evidence of damage, indicating that the coating was fully cured.

[0144] Acrylic sheet as a base material

[0163] A coating was prepared according to Example 1, and the coating solution was applied to a pre-treated acrylic sheet by spraying. The moistened acrylic sheet was baked at 80°C for 10 minutes, and then allowed 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 Δ-haze of 0.1% was obtained by a steam test.

[0145]

[0164] Coated acrylic sheet samples were placed in a humidity chamber for 3 days as described in ISO 6270. The samples were then held in a beaker of 50°C water for 1 minute, and no clouding was observed. Blank or uncoated acrylic sheets were used as controls. The control acrylic sheets were held in a beaker of 50°C water, and the control acrylic sheets immediately became blurred.

[0146]

[0165] Another sample of the coated acrylic sheet was placed in a humidity chamber for 10 days as described in ISO 6270. Subsequently, an ASTM D3359 cross-hatch adhesive tape test was performed, yielding a score of 5B. No coating removal was observed during the test.

[0147] Example 2 Preparation of coating composition

[0166] Solution S-2-1 was prepared with 11 wt% prepolymer 1, 55.8 wt% water, 33 wt% 1-methoxy-2-propanol, 0.1 wt% polyethersiloxane copolymer, and 0.51 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate. Solution S-2-2 was prepared consisting of 10 wt% polyoxypropylenetriamine, 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, which was identical to S-2-2 except that it lacked 1.5 wt% bis(3-trimethoxysilylpropyl)amine.

[0148] Application of coating compositions to substrates

[0167] The 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 cleaned 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 the comparative solution S-2-2* instead of S-2.

[0149] Measurement of haze value

[0168] The haze value of the coated glass slide was measured at 0.2%. A Δ-haze of 0.1% was obtained by steam testing.

[0150]

[0169] When a glass slide with the coating was rubbed with a damp cloth, no damage was visible to the naked eye, indicating that the coating had hardened and bonded to the substrate with sufficient mechanical properties for use without additional primer. A comparative example using S-2-2* delaminated from the glass substrate when exposed to vapor or rubbed with a damp cloth.

[0151]

[0170] The coating was prepared according to Example 2. An anodized aluminum substrate was 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 aluminum with the coating was then rubbed with a damp cloth, and the coating remained adhered to the aluminum substrate.

[0152] Example 3 Preparation of coating composition

[0171] Solution S-3-1 was prepared with 11 wt% prepolymer-1, 55.8 wt% water, 33 wt% 1-methoxy-2-propanol, 0.1 wt% polyethersiloxane copolymer, and 0.51 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate. Solution S-3-2 was prepared with 10% polyoxypropylenetriamine and 90% water. Solution S-3-3 was prepared with 1% 3-mercaptopropyltrimethoxysilane in 99% ethanol.

[0153] Application of coating compositions to substrates

[0172] Next, the S-3-3 solution was sprayed onto a glass slide and baked in an oven at 130°C for 10 minutes. Subsequently, the coating composition was prepared by mixing 4 g of S-3-1 with 0.14 g of S-3-2, allowed to stand for 10 minutes, sprayed onto a glass slide, and baked at 130°C for 10 minutes to form the coating.

[0154] Measurement of haze value

[0173] The haze value of the coated glass slide was measured at 0.3%. A Δ-haze of 0.1% was obtained by vapor testing. When the coated glass slide was rubbed with a damp cloth, no damage was observed to the naked eye, indicating that this primer provides sufficient bonding between the substrate and the coating.

[0155] Example 4 Preparation of coating composition

[0174] Solution S-4-1 was prepared using 16 wt% prepolymer-2, 53.7 wt% water, 30 wt% 1-methoxy-2-propanol, 0.05 wt% polyethersiloxane copolymer, and 0.13 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate. Solution S-4-2 was prepared consisting of 20 wt% O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol and 80 wt% water.

[0156] Application of coating compositions to substrates

[0175] The coating composition was prepared by mixing 0.9 g of S-4-1 with 0.05 g of S-4-2. This mixture was then coated onto a pre-treated polycarbonate sheet using an 80-micron blade coater and baked at 130°C for 10 minutes to form the coating.

[0157] Measurement of haze value

[0176] The initial haze of the sample was measured at 0.3%. A Δ-haze of 0.2% was obtained by steam testing. The sample was evaluated using the modified EN-168 method.

[0158] [Table 3]

[0159] Example 5 Preparation of coating composition

[0177] Solution S-5-1 was prepared with 17 wt% prepolymer-3, 46.8 wt% water, 30.3 wt% 1-methoxy-2-propanol, 5.2 wt% propylene glycol, 0.02 wt% polyethersiloxane copolymer, and 0.12 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate. Solution S-8-2 was prepared with 10 wt% polyoxypropylenediamine and 90 wt% water. Solution S-5-3 was prepared with 6 wt% polyoxypropylenediamine, 93% ethanol, and 1% polyethersiloxane copolymer. Solution S-5-4 was prepared with 8.5% sorbitol polyglycidyl ether, 15% (3-glycidyloxypropyl)trimethoxysilane, and 77.5% ethanol.

[0160] Application of coating compositions to substrates

[0178] Equal amounts of S-5-3 and S-5-4 were combined, sprayed onto a glass slide, and baked at 130°C for 10 minutes. Next, 0.53 g of solution S-5-1 was combined with 0.05 g of S-5-2, sprayed onto a slide, and baked at 130°C for 10 minutes.

[0161] Measurement of haze value

[0179] The haze value of the coated glass slide was measured at 0.2%. A Δ-haze of 0.3% was obtained by steam testing.

[0162] Research on immersion

[0180] A glass slide was immersed in a 0.1% dishwashing detergent solution in deionized water for 24 hours. After removal from the solution, the sample appeared clear and had a haze value of 0.6%. A Δ-haze of 0.8% was obtained by steam testing.

[0163] Example 6 Preparation of coating composition

[0181] Solution S-6-1 was prepared with 11 wt% prepolymer-1, 31 wt% water, 51 wt% 1-methoxy-2-propanol, 6 wt% propylene glycol, 0.6 wt% aluminum nanoparticles, 0.02 wt% Byk 3760, and 0.05 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate. Solution S-6-2 was prepared with 20 wt% O,O'-bis(2-aminopropyl) polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol and 80 wt% water.

[0164] Application of coating compositions to substrates

[0182] The coating composition was prepared by mixing 4 g of S-6-1 and 0.1 g of S-6-2.

[0165]

[0183] The coating was applied to a pre-treated polycarbonate sheet using an 80-micron bar coater. The polycarbonate sheet was then baked at 130°C for 10 minutes to form the coating on the sheet. The haze value of the coated polycarbonate sheet was measured to be 0.7%.

[0166] Example 7 Preparation of coating composition

[0184] Solution S-7-1 was prepared with 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-piperidyl) sebacate. Solution S-7-2 was prepared consisting of 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-piperidyl) sebacate, 0.2 wt% wetting additive polyethersiloxane copolymer, and 92 wt% ethanol. Solution S-7-4 was prepared, consisting of 10 wt% sorbitol polyglycidyl ether, 5 wt% (3-glycidyloxypropyl)trimethoxysilane, and 85 wt% ethanol.

[0167] Application of coating compositions to substrates

[0185] Next, solutions S-7-3 and S-7-4 were mixed, sprayed onto a glass slide, and baked at 130°C for 10 minutes to form the first coating on the glass slide.

[0168] Coating thickness

[0186] The thickness of the first coating on the glass slide was measured to be 0.5 microns. Next, the first and second solutions were mixed, sprayed onto the glass slide, and baked at 130°C for 10 minutes to form the second coating. The thickness of the glass slide with the second coating on the upper surface of the first coating was measured to be 5 microns.

[0169] Measurement of haze value

[0187] The haze value of the coated glass slide was measured at 1.0%. A Δ-haze of 0.7% was obtained by steam testing.

[0170] Industrial applicability

[0188] This disclosure describes anti-fogging coating compositions, kits, and coatings comprising a prepolymer and an amine-containing crosslinking agent. This disclosure also describes methods for producing coatings or coated substrates using the compositions or kits. Such coatings may be applicable to a wide range of industrial or consumer applications where optical clarity is required and fogging is detrimental to their application. Non-limiting examples of such applications include coatings on automotive windows, camera lenses, sensors, e.g., lidar, radar, microwave, optical sensors, eyewear including eyeglasses, visors, masks, goggles, shields, and sunglasses, freezer windows, and mirrors, e.g., bathroom mirrors.

[0171]

[0189] Furthermore, architectural designs that can benefit from the use of the various embodiments disclosed herein include various glass and plastic products in various parts of a building, such as storefront displays and windows, windows for greenhouses, refrigerated food displays and freezers, shower room doors, and glass enclosures around sporting events, such as ice hockey rinks.

[0172]

[0190] Embodiments disclosed herein may be used to coat cameras attached to scopes used in a variety of medical applications. For example, endoscopes including gastroscopes, bronchoscopes, cystoscopes, ureteroscopes, arthroscopes, and colonoscopes can all benefit from the anti-fogging properties associated with the disclosed inventions.

[0173]

[0191] The anti-fogging coatings disclosed herein can minimize one or more application difficulties. For example, the disclosed anti-fogging coating compositions, compounds, or kits do not contain highly toxic chemicals, can be cured at room temperature, can be applied to a variety of substrate types, and have a long pot life. The application method does not require expensive machinery and process control equipment, nor does it require complex and highly environmentally sensitive chemical reactions, thereby making the overall application easier and less expensive.

[0174]

[0192] Other embodiments of the present invention will become apparent to those skilled in the art from consideration of the specification and practice of the present invention disclosed herein. The specification and examples are intended to be for illustrative purposes only, and the true scope of the present invention is indicated by the following claims.

Claims

1. A composition for forming a crosslinked film that provides anti-fogging properties, (a) one or more charged monomer residues, (b) one or more uncharged monomer residues, and (c) one or more amine-reactive monomer residues, comprising at least one prepolymer, and Crosslinking agent containing at least one amine Includes, When the aforementioned crosslinked film is exposed to cloudy conditions for a period longer than 30 seconds, it exhibits a change in haze value of less than 30%. composition.

2. The composition is A first component comprising at least one prepolymer, and A second component comprising at least one amine-containing crosslinking agent. It is a two-component system that includes, The first and second components are found in the composition in amounts sufficient to form an anti-fog film that exhibits a change in haze value of less than 30% when exposed to foggy conditions for a period longer than 30 seconds. The composition according to claim 1.

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

1.

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

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

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

7. The composition according to claim 1, wherein the one or more charged monomer residues include a sulfonate, carboxyl, phosphonate, nitro, imidazolium, guanidinium, or quaternary ammonium functional group, or a monomer that can be converted to such functional groups, or a combination thereof.

8. The composition according to claim 7, wherein the one or more charged monomer residues containing a sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrene sulfonate, vinyl sulfonic acid, 3-sulfopropyl acrylate, 3-sulfopropyl methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

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

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

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

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

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

15. The composition according to claim 13, wherein the one or more uncharged monomer residues composed of a pyrrolidone functional group include a residue of n-vinyl-2-pyrrolidone or a derivative thereof.

16. The composition according to claim 13, wherein the one or more uncharged monomer residues composed of acetate functional groups include vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

17. The composition according to claim 13, wherein the one or more uncharged monomer residues composed of an ether functional group include residues of tetrahydrofurfuryl acrylate or methacrylate, any acrylate or methacrylate 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 consist of an epoxy, ketone, anhydride, alkene, or isocyanate functional group, or a combination thereof.

19. The composition according to claim 18, wherein the one or more amine-reactive monomer residues composed of epoxy functional groups include residues of glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, allyl glycidyl ether, 4-vinyl-1-cyclohexene 1,2-epoxide, derivatives of these monomers, or combinations thereof.

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

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

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

23. The composition according to claim 18, wherein the one or more amine-reactive monomer residues composed of isocyanate functional groups include a residue of 2-isocyanatoethyl methacrylate or a derivative thereof.

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

25. The composition according to claim 1, wherein the amine-containing crosslinking agent comprises a polyetheramine, or a polymer having a polyether skeleton containing polyethylene oxide, polypropylene oxide, or other ethylene oxide containing one or more nitrogen atoms per molecule, polyoxypropylenediamine, polyoxypropylenetriamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidisole, dicyandiamide, or a combination thereof.

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

27. The composition according to claim 26, wherein the water-miscible auxiliary solvent comprises methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or a combination thereof.

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

29. The composition according to claim 28, wherein the carrier solvent comprises a water-miscible solvent including water, methanol, ethanol, isopropanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, butanol, ethylene glycol, propylene glycol, glycerol, or a combination thereof.

30. The composition according to 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 one or more of the additives are found in the composition at a concentration greater than 0.0001% by weight and less than 40% by weight.

32. The composition according to claim 30, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, cellulose nanofibers, polyhedral oligomer silsesquioxane (POSS) material, silsesquioxane material, silicone material, fumed silica, polyamide particles, phyllosilicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or any combination thereof.

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

34. The composition according to claim 30, 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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or a combination thereof.

35. The composition according to claim 30, wherein the UV absorber comprises one or more of benzophenone, benzotriazole, cyanoacrylate, hydroxyphenyltriazine, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, or any combination thereof.

36. The composition according to claim 30, wherein the UV stabilizer comprises one or more hindered amine-based light stabilizers (HALS) activators.

37. The composition according to claim 30, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) decandioate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester decandioate, dimethyl succinate polymer containing 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]] or a combination thereof.

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

39. The composition according to claim 30, further comprising a catalytic acid or a base.

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

41. The composition according to claim 2, wherein the first composition and the second composition are found in amounts sufficient to have a pot life of more than 8 hours.

42. The composition according to claim 2, wherein the first component and the second component are found in amounts 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 found in amounts sufficient to form a hydrophilic film that is touch-dry after heating at 130°C for 5 minutes.

44. An anti-fog film containing a crosslinked polymer, wherein the crosslinked polymer is (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, Includes, When exposed to cloudy conditions for a period longer than 30 seconds, it exhibits a change in haze value of less than 30%. Anti-fog film.

45. The anti-fogging film according to claim 44, wherein the composition comprises the amine-reactive monomer residues to the active hydrogen residues of the amine in a molar ratio of 1:10 to 10:

1.

46. The anti-fog film according to claim 44, wherein the polymer is composed of 0.01% to 30% by weight of charged monomer residues.

47. The anti-fogging film according to claim 44, wherein the polymer is composed of 0.01% to 80% by weight of uncharged monomer residues.

48. The anti-fogging film according to claim 44, wherein the polymer is composed of 0.01% to 30% by weight of amine-reactive monomer residues.

49. The anti-fogging film according to claim 44, wherein the one or more charged monomer residues include a sulfonate, carboxyl, phosphonate, nitro, imidazolium, guanidinium, or quaternary ammonium functional group, or a monomer that can be converted to such functional groups.

50. The anti-fogging film according to claim 49, wherein the one or more charged monomer residues containing a sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrene sulfonate, vinyl sulfonic acid, 3-sulfopropyl acrylate, 3-sulfopropyl methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

52. The anti-fogging film according to claim 49, wherein the one or more charged monomer residues containing a phosphonate functional group include residues of 11-phosphonowndecylacrylate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

53. The anti-fogging film according to claim 49, wherein the one or more charged monomer residues containing an imidazolium functional group include residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazole, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

55. The anti-fogging film according to claim 44, wherein the one or more uncharged monomer residues include a hydroxyl, pyrrolidone, acetate, or ether functional group, or a combination thereof.

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

57. The anti-fogging film according to claim 55, wherein the one or more uncharged monomer residues composed of pyrrolidone functional groups include residues of n-vinyl-2-pyrrolidone or derivatives of this monomer.

58. The anti-fogging film according to claim 55, wherein the one or more uncharged monomer residues composed of acetate functional groups include vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

59. The anti-fogging film according to claim 55, wherein the one or more uncharged monomer residues composed of an ether functional group include residues of tetrahydrofurfuryl acrylate or methacrylate, any acrylate or methacrylate 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 anti-fogging film according to claim 44, wherein the one or more amine-reactive monomer residues consist of an epoxy, ketone, anhydride, alkene, or isocyanate functional group, or a combination thereof.

61. The anti-fogging film according to claim 60, wherein the one or more amine-reactive monomer residues composed of epoxy functional groups include residues of glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, allyl glycidyl ether, 4-vinyl-1-cyclohexene 1,2-epoxide, derivatives of these monomers, or combinations thereof.

62. The anti-fogging film according to claim 60, wherein the one or more amine-reactive monomer residues composed of a ketone functional group include methyl vinyl ketone, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

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

64. The anti-fogging film according to claim 60, wherein the one or more amine-reactive monomer residues composed of an alkene functional group include allyl methacrylate, vinyl methacrylate, derivatives of these monomers, or combinations thereof.

65. The anti-fogging film according to claim 60, wherein the one or more amine-reactive monomer residues composed of isocyanate functional groups include residues of 2-isocyanatoethyl methacrylate or a derivative thereof.

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

67. The anti-fogging film according to claim 44, wherein the at least one amine-containing crosslinking agent residue comprises a polymer having a polyether skeleton containing a polyetheramine, polyethylene oxide, polypropylene oxide, or other ethylene oxide containing one or more nitrogen atoms per molecule, polyoxypropylenediamine, polyoxypropylenetriamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidisole, dicyandiamide, or any combination thereof.

68. The anti-fogging film according to claim 44, 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.

69. The anti-fog 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 anti-fogging film according to claim 68, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, cellulose nanofibers, polyhedral oligomer silsesquioxane (POSS) material, silsesquioxane material, silicone material, fumed silica, polyamide particles, phyllosilicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or combinations thereof.

71. The anti-fogging film according to claim 68, wherein the coupling agent comprises (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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or a combination thereof.

72. The anti-fog film according to claim 68, wherein the UV absorber comprises one or more of benzophenone, benzotriazole, cyanoacrylate, hydroxyphenyltriazine, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, or any combination thereof.

73. The anti-fogging film according to claim 68, wherein the UV stabilizer comprises one or more hindered amine-based light stabilizers (HALS).

74. The anti-fog film according to claim 68, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) decandioate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester decandioate, dimethyl succinate containing 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]] or a combination thereof.

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

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

77. The anti-fog film according to claim 44, having a thickness in the range of 0.25 microns to 100 microns.

78. Coated articles, The substrate and the coating are (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, A composition comprising a crosslinked polymer containing When the coated article is exposed to cloudy conditions for a period longer than 30 seconds, it exhibits a change in haze value of less than 30%. Coated articles.

79. The coated article according to claim 78, wherein the composition comprises amine-reactive monomer residues to active hydrogen residues of an amine in a molar ratio of 1:10 to 10:

1.

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

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

82. The coated article according to claim 78, wherein the polymer is composed of 0.01% 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 a sulfonate, carboxyl, phosphonate, nitro, imidazolium, guanidinium, or quaternary ammonium functional group, or a monomer that can be converted to such functional groups, or a combination thereof.

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

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

86. The coated article according to claim 83, wherein the one or more charged monomer residues containing a phosphonate functional group include residues of 11-phosphonowndecylacrylate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

88. The coated article according to claim 83, wherein the one or more charged monomer residues containing a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide, 2-ethyldimethylammonioethyl 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 a hydroxyl, pyrrolidone, acetate, or ether functional group, or a combination thereof.

90. The coated article according to claim 89, 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, carbohydrate acrylates or methacrylates, derivatives of these monomers, or combinations thereof.

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

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

93. The coated article according to claim 89, wherein the one or more uncharged monomer residues comprising an ether functional group include residues of tetrahydrofurfuryl acrylate or methacrylate, any acrylate or methacrylate 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 consist of an epoxy, ketone, anhydride, alkene, or isocyanate functional group, or a combination thereof.

95. The coated article according to claim 94, wherein the one or more amine-reactive monomer residues comprising epoxy functional groups include residues of glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, allyl glycidyl ether, 4-vinyl-1-cyclohexene 1,2-epoxide, derivatives of these monomers, or combinations thereof.

96. The coated article according to claim 94, 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.

97. The coated article according to claim 94, wherein the one or more amine-reactive monomer residues composed of anhydride functional groups include n-hydroxysuccinimide-containing monomers, maleic anhydride, derivatives of these monomers, or combinations thereof.

98. The coated article according to claim 94, wherein the one or more amine-reactive monomer residues comprising an alkene functional group include residues of allyl methacrylate, vinyl 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 composed of isocyanate functional groups include residues of 2-isocyanatoethyl methacrylate or a derivative thereof.

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

101. The coated article according to claim 78, wherein the at least one amine-containing crosslinking agent residue comprises a polyetheramine, or a polymer having a polyether skeleton containing polyethylene oxide, polypropylene oxide, or other ethylene oxide containing one or more nitrogen atoms per molecule, polyoxypropylenediamine, polyoxypropylenetriamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidisole, dicyandiamide, or a residue of a combination 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, ceria nanoparticles, titania nanoparticles, cellulose nanofibers, polyhedral oligomer silsesquioxane (POSS) material, silsesquioxane material, silicone material, fumed silica, polyamide particles, phyllosilicate 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-glycidoxypropyl)trimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, (3-glycidoxypropyl)triethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

106. The coated article according to claim 102, wherein the UV absorber comprises one or more of benzophenone, benzotriazole, cyanoacrylate, hydroxyphenyltriazine, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, or any combination thereof.

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

108. The coated article according to claim 102, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) decandioate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester decandioate, dimethyl succinate polymer containing 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]] or any combination thereof.

109. The coated article according to claim 102, 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, cetyltrimethylammonium 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 base.

111. The coated article according to claim 78, further comprising a primer or adhesion promoter.

112. The coated article according to claim 111, wherein the primer or adhesion promoter comprises a silane coupling agent that functionalizes the substrate with an amine, epoxy, thiol, amide, carboxylic acid, or isocyanate functional group.

113. The coated article according to claim 111, wherein the primer or adhesion promoter comprises (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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

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

115. The coated article according to claim 78, further comprising an adhesive layer.

116. The coated article according to claim 78, including an automobile structure or building structure, a building window, a camera lens, a medical scope lens, a sensor, eyewear, a mirror, a consumer electronic device, personal protective equipment, other safety equipment, or a refrigerator door.

117. A method for making the surface of a substrate less prone to clouding, On the surface of the substrate, A first composition comprising at least one prepolymer, wherein the at least one prepolymer comprises (a) one or more charged monomer residues, (b) one or more uncharged monomer residues, and (c) one or more amine-reactive monomer residues, and A second composition comprising at least one amine-containing crosslinking agent. The step includes applying a compound, When the treated substrate is exposed to cloudy conditions for a period longer than 30 seconds, it exhibits a change in haze value of less than 30%. method.

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

1.

119. The method according to claim 117, wherein the one or more charged monomer residues include a sulfonate, carboxyl, phosphonate, nitro, imidazolium, guanidinium, or quaternary ammonium functional group, or a monomer that can be converted to such functional groups, or a combination thereof.

120. The method according to claim 119, wherein the one or more charged monomer residues containing a sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrene sulfonate, vinyl sulfonic acid, 3-sulfopropyl acrylate, 3-sulfopropyl methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

122. The method according to claim 119, wherein the one or more charged monomer residues containing a phosphonate functional group include residues of 11-phosphonowndecylacrylate, vinylphosphonic acid, derivatives of these monomers, salts of these monomers, or combinations thereof.

123. The method according to claim 119, wherein the one or more charged monomer residues containing an imidazolium functional group include residues of 1-allyl-3-methylimidazolium chloride, 1-vinylimidazole, derivatives of these monomers, salts of these monomers, or combinations thereof.

124. The method according to claim 119, wherein the one or more charged monomer residues containing a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide, 2-ethyldimethylammonioethyl methacrylate, 2-(methacryloyloxy)ethyl]trimethylammonium, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

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

127. The method according to claim 125, wherein the one or more uncharged monomer residues composed of a pyrrolidone functional group include a residue of n-vinyl-2-pyrrolidone or a derivative thereof.

128. The method according to claim 125, wherein the one or more uncharged monomer residues composed of acetate functional groups include vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

129. The method according to claim 125, wherein the one or more uncharged monomer residues composed of an ether functional group include tetrahydrofurfuryl acrylate or methacrylate, any acrylate or methacrylate monomer having a polyethylene glycol or polypropylene glycol functional group, 2-ethoxyethyl methacrylate, diethylene glycol butyl ether methacrylate, derivatives of these monomers, or a combination thereof.

130. The method according to claim 117, wherein the one or more amine-reactive monomer residues consist of an epoxy, ketone, anhydride, alkene, or isocyanate functional group, or a combination thereof.

131. The method according to claim 130, wherein the one or more amine-reactive monomer residues composed of epoxy functional groups include glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, allyl glycidyl ether, 4-vinyl-1-cyclohexene 1,2-epoxide, derivatives of these monomers, or combinations thereof.

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

133. The method according to claim 130, wherein the one or more amine-reactive monomer residues composed of an anhydride functional group include n-hydroxysuccinimide-containing monomers, maleic anhydride, derivatives of these monomers, or combinations thereof.

134. The method according to claim 130, wherein the one or more amine-reactive monomer residues composed of an alkene functional group include allyl methacrylate, vinyl methacrylate, derivatives of these monomers, or combinations thereof.

135. The method according to claim 130, wherein the one or more amine-reactive monomer residues composed of isocyanate functional groups include a residue of 2-isocyanatoethyl methacrylate or a derivative thereof.

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

137. The method according to claim 136, wherein the amine-containing crosslinking agent comprises a polyetheramine, or a polymer having a polyether skeleton containing polyethylene oxide, polypropylene oxide, or other ethylene oxide containing one or more nitrogen atoms per molecule, polyoxypropylenediamine, polyoxypropylenetriamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidisole, dicyandiamide, or a combination thereof.

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

139. The method according to claim 138, wherein the water-miscible auxiliary solvent includes 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 according to claim 117, wherein the second component further comprises a carrier solvent.

141. The method according to claim 140, wherein the carrier solvent comprises a water-miscible solvent including water, 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 according to claim 117, 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.

143. The method according to 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 according to claim 142, wherein the mechanical additive comprises one or more of the following: silica nanoparticles, alumina nanoparticles, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, cellulose nanofibers, polyhedral oligomer silsesquioxane (POSS) materials, silsesquioxane materials, silicone materials, fumed silica, polyamide particles, phyllosilicate particles, montmorillonite particles, boehmite particles, epoxy-containing reactive diluents, waxes, or any combination thereof.

145. The method according to claim 142, wherein the coupling agent comprises one or more of (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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

146. The method according to claim 142, wherein the UV absorber comprises one or more of benzophenone, benzotriazole, cyanoacrylate, hydroxyphenyltriazine, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, or any combination thereof.

147. The method according to claim 142, wherein the UV stabilizer comprises one or more hindered amine-based light stabilizers (HALS) activators.

148. The method according to claim 147, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) decandioate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester decandioate, dimethyl succinate polymer containing 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]] or a combination thereof.

149. The method according to claim 142, 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, cetyltrimethylammonium bromide surfactant, dispersant, styrene-maleic acid copolymer, silicone-modified polyacrylate, polyethylene-polypropylene block copolymer surfactant, other commercially available leveling or wetting additives, or a combination thereof.

150. The method according to claim 142, wherein the curing catalyst comprises a catalytic acid or base that supports the crosslinking reaction for forming the crosslinked film.

151. The method according to 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 according to claim 117, wherein the first composition and the second composition are found in amounts sufficient to form a hydrophilic film that cures within 48 hours at 25°C and 0% to 50% relative humidity.

153. The method according to claim 117, wherein the first composition and the second composition are found in amounts sufficient to form a hydrophilic film that is touch-dry after heating at 130°C for 5 minutes.

154. The method according to claim 117, wherein the first composition and the second composition are found in an amount sufficient to have a pot life of more than eight hours.

155. The method according to claim 117, wherein the substrate is sequentially washed with a surfactant, water, acetone, isopropyl alcohol or another alcohol, glass cleaning solution, or a combination of these solutions, or some of these solutions, before pretreatment.

156. The method according to claim 117, wherein the substrate is pre-treated with a surface activation treatment, a primer, an adhesion promoter, or a combination thereof before the application of the anti-fogging coating.

157. The method according to claim 156, wherein the surface activation treatment includes corona treatment, plasma treatment, UV irradiation, ozone exposure, flame activation, exposure to an acid or base, or a combination thereof.

158. The method according to claim 156, wherein the primer or adhesion promoter comprises a silane coupling agent that functionalizes the substrate with an amine, epoxy, thiol, amide, carboxylic acid, or isocyanate functional group.

159. The method according to claim 156, wherein the primer or adhesion promoter comprises (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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or a combination thereof.

160. The method according to claim 117, wherein the substrate includes glass, plastic, polycarbonate, polyethylene terephthalate, poly(methyl methacrylate), poly(ethene-co-tetrafluoroethene), metal, aluminum, ceramic material, or any combination thereof.

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

162. The method according to claim 117, wherein the coating is applied to the substrate by spray coating, needle dispensing, film coating, brush coating, roller coating, dipping coating, blade coating, flow coating, or a combination thereof.

163. A kit for forming a hydrophilic crosslinked film, (A) A first component comprising a first composition comprising at least one prepolymer, wherein the at least one prepolymer comprises (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 containing at least one amine-containing crosslinking agent, Includes, When the hydrophilic crosslinked film is exposed to cloudy conditions for a period longer than 30 seconds, it exhibits a change in haze value of less than 30%. kit.

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

1.

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

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

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

168. The kit according to claim 163, wherein the one or more charged monomer residues include a sulfonate, carboxyl, phosphonate, nitro, imidazolium, guanidinium, or quaternary ammonium functional group, or a monomer that can be converted to such functional groups, or a combination thereof.

169. The kit according to claim 168, wherein the one or more charged monomer residues containing a sulfonate functional group include residues of 2-acrylamido-2-methylpropanesulfonic acid, 4-styrene sulfonate, vinyl sulfonic acid, 3-sulfopropyl acrylate, 3-sulfopropyl methacrylate, derivatives of these monomers, salts of these monomers, or combinations thereof.

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

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

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

173. The kit according to claim 168, wherein the one or more charged monomer residues containing a quaternary ammonium functional group include residues of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide, 2-ethyldimethylammonioethyl 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 include a hydroxyl, pyrrolidone, acetate, or ether functional group, or a combination thereof.

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

176. The kit according to claim 174, wherein the one or more uncharged monomer residues composed of pyrrolidone functional groups include a residue of n-vinyl-2-pyrrolidone or a derivative thereof.

177. The kit according to claim 174, wherein the one or more uncharged monomer residues composed of acetate functional groups include vinyl acetate, diacetone acrylamide, derivatives of these monomers, or combinations thereof.

178. The kit according to claim 174, wherein the one or more uncharged monomer residues composed of an ether functional group include residues of tetrahydrofurfuryl acrylate or methacrylate, any acrylate or methacrylate 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 consist of an epoxy, ketone, anhydride, alkene, or isocyanate functional group, or a combination thereof.

180. The kit according to claim 179, wherein the one or more amine-reactive monomer residues composed of epoxy functional groups include residues of glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, allyl glycidyl ether, 4-vinyl-1-cyclohexene 1,2-epoxide, derivatives of these monomers, or combinations thereof.

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

182. The kit according to claim 179, wherein the one or more amine-reactive monomer residues composed of anhydride functional groups include n-hydroxysuccinimide-containing monomers, maleic anhydride, derivatives of these monomers, or combinations thereof.

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

184. The kit according to claim 179, wherein the one or more amine-reactive monomer residues composed of isocyanate functional groups include a residue of 2-isocyanatoethyl methacrylate or a derivative thereof.

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

186. The kit according to claim 163, wherein the amine-containing crosslinking agent comprises a polyetheramine, or a polymer having a polyether skeleton containing polyethylene oxide, polypropylene oxide, or other ethylene oxide containing 1 to 4 nitrogen atoms per molecule, polyoxypropylenediamine, polyoxypropylenetriamine, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, n-butylaminopropyltrimethoxysilane, n-methylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, imidisole, dicyandiamide, or any combination thereof.

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

188. The kit according to claim 187, wherein the water-miscible auxiliary 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.

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

190. The kit according to claim 189, wherein the carrier solvent comprises a water-miscible solvent including water, 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, 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.

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, ceria nanoparticles, titania nanoparticles, cellulose nanofibers, polyhedral oligomer silsesquioxane (POSS) material, silsesquioxane material, silicone material, fumed silica, polyamide particles, phyllosilicate 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 (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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

195. The kit according to claim 191, wherein the UV absorber comprises one or more of benzophenone, benzotriazole, cyanoacrylate, hydroxyphenyltriazine, zinc nanoparticles, ceria nanoparticles, titania nanoparticles, or any combination thereof.

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

197. The kit according to claim 191, wherein the UV stabilizer comprises bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 1-methyl-10-(1,2,2,6,6-pentamethyl-4-piperidinyl) decandioate, 1,10-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester decandioate, dimethyl succinate polymer containing 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, poly[[6-[(1,1,3,3,-tetramethylbutyl)amino-s-triazine-2,4-diyl][2,2,6,6-tetramethyl-4-piperidyl)imino]]hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]] or a combination thereof.

198. The kit according to claim 191, 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, cetyltrimethylammonium 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 base that supports the crosslinking reaction for forming the crosslinked film.

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

201. The kit according to claim 163, wherein the first composition and the second composition are found in amounts 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 found in amounts sufficient to form a hydrophilic film that is touch-dry after heating at 130°C for 5 minutes.

203. The kit according to claim 163, wherein the first composition and the second composition are found in amounts sufficient to have a pot life of more than eight hours.

204. The kit according to claim 163, comprising an optional third component containing a primer.

205. The kit according to 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 according to claim 204, wherein the primer comprises (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, isocyanatopropyltriethoxysilane, n-methylaminopropyltrimethoxysilane, n-butylaminopropyltrimethoxysilane, bis(3-trimethoxysilylpropyl)amine, (3-triethoxysilyl)propyl succinic anhydride, or any combination thereof.

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