WO2024197150A1 - Coatings comprising cationic curing materials - Google Patents

Coatings comprising cationic curing materials Download PDF

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Publication number
WO2024197150A1
WO2024197150A1 PCT/US2024/020917 US2024020917W WO2024197150A1 WO 2024197150 A1 WO2024197150 A1 WO 2024197150A1 US 2024020917 W US2024020917 W US 2024020917W WO 2024197150 A1 WO2024197150 A1 WO 2024197150A1
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coating composition
oil
coating
combinations
acetate
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PCT/US2024/020917
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French (fr)
Inventor
Matthew H. STRIEWING
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Swimc LLC
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Swimc LLC
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Application filed by Swimc LLC filed Critical Swimc LLC
Priority to EP24720960.4A priority Critical patent/EP4683974A1/en
Priority to CN202480020802.0A priority patent/CN120858147A/en
Publication of WO2024197150A1 publication Critical patent/WO2024197150A1/en
Priority to MX2025011171A priority patent/MX2025011171A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes

Definitions

  • the present disclosure relates generally to a coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
  • a method of preparing the coating and an article containing the coating are also disclosed.
  • UV curing also known as radical UV curing
  • UV curing is a standard curing process that has been used in the coatings industry. Although this UV curing process may occur with exposure to sunlight, some portions of the coating may not fully cure such as shaded areas or areas with only indirect light. Further, exterior conditions may change frequently, which could delay or disrupt the radical UV curing process.
  • many interior coatings may be cured by UV light, but a lack of access to proper UV curing equipment may prevent such a coating from being fully cured. These interior coatings also may not have exposure to an adequate UV light source, e.g., a window, reducing their ability to fully cure as well.
  • oxygen inhibition during the typical radical UV curing process may lead to poor surface cure.
  • the free radical polymerization of radical UV cure coatings is succeptable to oxygen inhibition since oxygen may come into contact with the coating surface and then terminate the reaction. This can lead to insufficent cure on the surface, or with extremely thin films, preventing cure. Further, there may be other issues such as toxcitity, skin irritation, and odor for customers using radical UV curing products.
  • cationic curing may be used instead of radical UV curing.
  • Cationic curing chemistry is a UV -initiated cationic polymerization. Although exposure of a coating to sunlight may start the cationic curable process, continuous exposure to UV light is not required to fully cure. Cationic curing is also not inhibited by oxygen, allowing curing to occur after it has been initiated by UV.
  • cationic curing is used in ink and 3D printing applications, curing conditions must be tightly controlled or they may not be adequately cured. For example, cationic curing may be terminated, delayed, or disrupted by the presence of moisture, which may frequently occur in exterior applications or other applications where moisture cannot be controlled.
  • solvent-based coatings are oil-based coatings which cure through oxidative crosslinking.
  • oil-based coatings are often easier to apply over substrates like wood than water-based coatings. Oil-based coatings penetrate the wood, reducing lap marks and future peeling.
  • oil-based coatings take longer to dry than water-based coatings and contain higher VOC’s. Further, they are more prone to act as a food source for mold, mildew, and algae.
  • long oil alkyd resin has been used for high solids coatings, especially wood stains.
  • its product performance suffers from slow dry times and tackiness.
  • water reducible alkyd technology had been developed to achieve low VOC target, but the high polarity of the alkyd resin reduces its performance properties, including weatherability.
  • water-based coatings generally provide improved UV resistance and color retention. Although water-based coatings have improved drying time and mold, mildew, and algae resistance over oil-based coatings, they are more difficult to apply. Since they have more difficulty in penetrating substrates like wood, they also have a potential for peeling if the coating is overapplied.
  • the coating composition may comprise at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
  • Also described is a method of preparing the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
  • An article containing the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible is also described.
  • FIG. 1 illustrates a panel coated with a conventionally cured coating and the coating composition described herein comprising a cationic curing material, which has been subjected to outdoor weathering conditions.
  • FIG. 2 illustrates a panel coated with a conventionally cured coating and the coating composition described herein comprising a cationic curing material, which has been subjected to outdoor weathering conditions.
  • FIG. 3 illustrates a wood panel coated with the coating composition described herein comprising a cationic curing material and cured in comparison to an untreated board for water resistance.
  • the word “exemplary” means “serving as an example, instance, or illustration.”
  • the embodiments described herein are not limiting, but rather exemplary only. It should be understood that the described embodiments are not necessarily to be construed as preferred or advantageous over other embodiments. Moreover, the term “embodiment(s)” does not require that all embodiments include the discussed feature, advantage, or mode of operation.
  • the present disclosure relates generally to coatings that provide advantageous improvements over current coatings. It has been discovered that the use of a particular coating composition comprising at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible can surprisingly lead to preferred performance properties when used in a coating, namely improved weatherability, wear resistance, adhesion, dry time and tackiness, application, cure time, reduced odor, lower toxicity, reduced skin irritation, and mold, mildew, and algae resistance while having decreased VOC’s and without sacrificing other performance properties as well as other advantages.
  • the coating composition comprising at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible may have improved properties over typical coatings that are either UV curing or cationic curing.
  • the coating composition described herein comprising at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible may have certain improved properties over many solvent-based coatings or water-based coatings as well as traditional coatings utilizing radical UV curing.
  • the ability to cationic cure and chain transfer with hydroxyl groups such as those hydroxyl groups in cellulose and lignin of wood may provide a method to covalently bond the coating composition to a substrate and provide improved adhesion and performance.
  • Applications using both UV cure and cationic cure can be formulated with photoinitiators which will decompose in normal sunlight, allowing for ambient initiation of the reaction.
  • the photoinitiators for cationic cure do not decompose to form free radicals, but instead form a strong Bronsted acid.
  • anhydrous hydrophobic means a material for a coating composition which is both substantially free of water, preferably a material in which water is present at a content of less than or equal to 2% by weight, relative to the total weight of the composition and will not substantially interact with water.
  • “Cationic” describes the portion of the initiator that is the conjugate base to the Bronsted acid and refers to the portion of the molecule that absorbs the radition to initiate cure.
  • the free radicals generated by radical UV cure photoinitiators may have a relatively short half life (typically seconds), so the curing mechanism requires constant UV exposure to keep generating new free radicals in order to drive cure to completion.
  • the Bronsted acid in cationic cure has a longer half life, typically hours to days, allowing it to persist in the coating and drive the curing.
  • UV cationic cure chemistry may be used for exterior coatings products in outdoor conditions while radical UV cure product would be prevented from curing completely in areas without an adequate UV source such as shadowed and dark areas.
  • UV cationic cure would also provide a more consistent and uniform curing over UV radical curing since products would not be affected by shadows from clouds, trees and other plants, or structures during different conditions throughout the day.
  • the Bronsted acid may catalyze the cationic cure resins through a ring opening reaction, potentially leading to lower shrinkage and increased adhesion of the coating. Table 1 below further highlights benefits of using cationic curing over radical UV curing.
  • UV cationic curing reaction shows the polymerization process in which a ring opening reaction occurs.
  • the cationic reaction mechanism may be protected from the water or moisture that may occur in certain enviroments, especially an exterior environment, by creating an anhydrous or substantially anhydrous environment, thus providing a coating composition not subject to oxygen or water inhibition of cure. Since it is also hydrophobic, there is a reduced exposure to water as well.
  • the coating composition described herein is a UV cationic curing coating.
  • the coating composition described herein cures when UV initiates the cationic curing reaction but is not required to sustain it.
  • at least one anhydrous hydrophobic material and at least one cationic curing material may copolymerize with each other.
  • at least one anhydrous hydrophobic material may cure, either in addition to the UV and cationic cure or separately from these cure methods, by oxidative drying.
  • the coating composition described herein comprises at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible. If at least one anhydrous hydrophobic material and at least one cationic curing material are not fully miscible or substantially miscible, then the anhydrous hydrophobic material(s) and cationic curing material(s) may be adjusted to ensure compatibility such that they are substantially miscible. Adjustments to ensure compatibility may be done through material choices of the coatings composition.
  • At least one anhydrous hydrophobic material of the coating composition described herein comprises at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, at least one oil, at least one solvent, or combinations thereof.
  • at least one anhydrous hydrophobic material may be substantially miscible in a solvent-based coating.
  • at least one anhydrous hydrophobic material may be substantially miscible in a water-based coating.
  • at least one anhydrous hydrophobic material of the coating composition may at least partially penetrate into a substrate.
  • At least one anhydrous hydrophobic material may create an anhydrous hydrophobic environment that may protect the cationic curing material in the coating composition from reaction inhibition with water.
  • the coating composition described herein may be cured in exterior conditions or conditions in which moisture may not be controlled.
  • At least one alkyd resin may comprise various oil lengths.
  • at least one alkyd resin may be derived from a biobased source such as plant oils.
  • at least one solution polymer comprises at least one: acrylic polyol, acrylic, alkyd, oil modified urethane, acrylic modified alkyd, or combinations thereof.
  • Typical solvents used for solution polymerization may include but are not limited to water, ethanol, a mixture of water and ethanol, ethyl ether, benzene, and benzyl alcohol. Solvents used in solution polymerization may be removed during processing of the solution polymer.
  • the acrylic portion of at least one solvent-based acrylic may comprise alkyl (meth)acrylates and vinyl monomers, such as but not limited to, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-/i-/t-butyl (meth)acrylate, 2- ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether, 2-(acetoacetoxy)ethyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, diacetone acrylamide, acrylamide, meth
  • the alkyl methacrylate polymers may be those prepared from a range of C12 to C22 alkyl methacrylates.
  • Some preferred monomers include styrene, methyl methacrylate, methacrylic acid, hydroxyethyl acrylate, acetoacetoxyethyl methacrylate, butyl acrylate, butyl methacrylate, or combinations thereof. Others are also contemplated.
  • the at least one oil is a conjugated oil.
  • the conjugated oil comprises linseed oil, castor oil, soybean oil, sunflower oil, safflower oil, tall oil, nahar oil, tobacco seed oil, coconut oil, rubber seed oil, karanja oil, lesquerella oil, tung oil, or combinations thereof.
  • Other oils are also contemplated.
  • the at least one solvent comprises a non-drying oil.
  • the at least one solvent comprises mineral spirits, butyl acetate, n-butyl propionate, di ethylene glycol monoethyl acetate, ethylene glycol monobutyl ether acetate, ethyl 3- ethoxy propionate, ethyl acetate, 2-ethylhexyl acetate, isobutyl acetate, isobutyl isobutyrate, isopropyl Acetate, methyl acetate, methyl n-amyl ketone, methyl isoamyl ketone, methyl propyl ketone, propylene glycol monomethyl ether acetate, propyl acetate, n-propyl propionate, or combinations thereof.
  • Other solvents are also contemplated.
  • the at least one cationic curing material comprises at least one cationic photoinitiator, at least one acid catalyst, or combinations thereof. At least one cationic curing material may be initiated by UV. However, the use of at least one anhydrous hydrophobic material may substantially reduce or prevent the termination of the cationic reaction by water.
  • the coating composition described herein is substantially immiscible with water. In one embodiment, the coating composition described herein is completely immiscible with water.
  • the coating composition described herein comprises at least one cationic photoinitiator.
  • the cationic photoinitiator may be subjected to UV to
  • at least one cationic photointiator comprises triphenylsulfonium, diaryliodonium, diazonium salts, diaryliodonium salts, ferrocenium salts, triarylsulfonium salt, alkylsulfonium salt, iron arene salt, sulfonyloxyketone, triarylsiloxysiloxane, or combinations thereof.
  • at least one cationic photointiator comprises various other metallocene compounds.
  • At least one cationic photoinitiator comprises Bis-(4-t-butylphenyl)-Iodonium hexafluorophosphate.
  • at least one cationic photointiator may be sensitized with at least one UV photoinitiator in order to achieve initiation of the UV cure and aid in the UV cationic curing reaction.
  • Other cationic photoinitiators are also contemplated.
  • the coating composition described herein comprises at least one acid catalyst.
  • at least one acid catalyst comprises sulfuric acid, sulfonic acid, hydrochloric acid, organic sulfonic acid, ferric sulfate, hydrofluoric acid, phosphoric acid, toluenesulfonic acid, polystyrene sulfonate, heteropoly acids, zeolites, acetic acid, or combinations thereof.
  • Other acid catalysts are also contemplated.
  • a 2K system for the coating composition may be provided with the use of at least one acid catalyst.
  • the coating composition described herein further comprises at least one polymer, at least one reactive diluent, at least one non-reactive diluent, at least one solvent, at least one drier, at least one colorant, at least one pigment, at least one surfactant, at least one dispersant, at least one wax, at least one anti-skinning agent, at least one defoamer, at least one fungicide, at least one biocide, at least one mildewcide, at least one thickener, or combinations thereof.
  • additives may include but are not limited to polymers or polymer dispersions, leveling agents, antisettling agents, pH buffers, corrosion inhibitors, driers, anti-skinning agents, anti-cratering agents, anti-sag agents, heat stabilizers, UV absorbers/inhibitors, HAUS (hindered amine light stabilizers), antioxidants, wetting agents, flow agents, and the like, and various combinations thereof as needed for a particular application.
  • Other additives are also contemplated.
  • the coating composition described herein further comprises UV radical materials.
  • the UV radical materials in the coating composition may provide a cationic/radical UV hybrid cure.
  • the coating composition described herein further comprises at least one epoxy.
  • the epoxy may react within the UV cationic curing process.
  • the use of an epoxy with at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, or combinations thereof may provide certain advantages with a hybrid system. These advantages may include slower curing time than at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, or combinations thereof if such slower curing time is desired.
  • at least one epoxy may be derived from a biobased source such as soybean oil.
  • the coating composition described herein further comprising epoxy may include at least one polyol, including but not limited to acrylic polyols, polyester polyol, or combinations thereof, as the cationic cure mechanism chain transfers with hydroxyl groups.
  • the addition of at least one polyol may allow adjustments with the hardness of the film of the coating composition described herein.
  • the at least one anhydrous hydrophobic material is part of an interpenetrating polymer network (IPN).
  • IPN interpenetrating polymer network
  • having an IPN may result in additional performance improvements.
  • the IPN described may be provided through free radical polymerization (as in radical UV cure), oxidative crosslinking, or combinations thereof. Other polymerizations and crosslinking mechanisms are also contemplated.
  • the coating composition described herein further comprises at least one dual functional material.
  • This dual functional material acts to cure in a different mechanism than IPN.
  • at least one dual functional material comprises: 1) a cyclic ether or hydroxyl with an unsaturated alkene, 2) a cyclic ether with an acrylate, or 3) combinations thereof.
  • the dual functional material described may be provided through free radical polymerization (as in radical UV cure), oxidative crosslinking, or combinations thereof.
  • the dual functional material may be provided using both free radical polymerization of acrylates (as in radical UV cure) and oxidative crosslinking of alkyds. Other polymerizations and crosslinking mechanisms are also contemplated.
  • the coating composition described herein may provide for the formulation of coatings that lower VOC’s.
  • the VOC’s of the coating composition described herein are 500 g/1 or less as measured by ASTM D3960.
  • the coating composition described herein has a Volatile Organic Compound (VOC) as measured by ASTM D3960 of less than 250 g/1.
  • the coating composition described herein can have Volatile Organic Compound (VOC) as measured by ASTM D3960 of less than 450 g/1, less than 400 g/1, less than 350 g/1, less than 300 g/1, less than 275 g/1, less than 225 g/1, less than 200 g/1, less than 175 g/1, less than 150 g/1, less than 125 g/1, less than 100 g/1, less than 75 g/1, less than 50 g/1, and less than 25 g/1. Lower and higher levels of VOC’s are also contemplated.
  • VOC Volatile Organic Compound
  • the coating composition described herein has a volatile organic compound content of less than about 250 g/L according to EPA M24.
  • the coating composition described herein can have Volatile Organic Compound (VOC) as measured by EPA M24 of less than 225 g/1, less than 200 g/1, less than 175 g/1, less than 150 g/1, less than 125 g/1, less than 100 g/1, less than 75 g/1, less than 50 g/1, and less than 25 g/1.
  • VOC Volatile Organic Compound
  • the coating composition described herein may provide for the formulation of coatings that contain higher solids.
  • the coating composition described herein is a wood stain. In many embodiments, the coating composition is a clear coating, a semi-transparent coating, a semi-solid coating, or a solid color coating. In one embodiment, the coating composition described herein is a semi-sheer or lightly tinted wood stain. In one embodiment, the coating composition described herein is a semi-transparent wood stain. In one embodiment, the coating composition described herein is a solid color wood stain. In another embodiment, the coating composition described herein is a clear coat. In other embodiments, the coating composition described herein is a primer. In yet other embodiments, the coating composition described herein is a basecoat. In some other embodiments, the coating composition described herein is a topcoat.
  • the coating composition described herein is a one-part system. In other embodiments, the coating composition described herein is a two-part system. [0043] Also described herein is a method of preparing the coating described herein comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
  • At least one substrate is wood, metal, glass, plastic, paper, leather, fabric, ceramic, concrete, composites, or combinations thereof. In one embodiment, at least one substrate is a previously coated substrate.
  • At least partially applying the coating may be achieved by brush, roller, spray (air atomized, airless, high-volume low pressure (HVLP), and electrostatic), pad, dip coating, roll coating, spin coating, flow coating, curtain coating, centrifugal coating, continuous coating, and autodeposition.
  • spray air atomized, airless, high-volume low pressure (HVLP), and electrostatic
  • pad dip coating, roll coating, spin coating, flow coating, curtain coating, centrifugal coating, continuous coating, and autodeposition.
  • an article comprising the coating composition described herein is also disclosed.
  • the article comprises the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
  • an article may comprise: 1) a substrate having at least one surface; and 2) the coating composition described herein.
  • the substrate is wood, metal, glass, plastic, paper, leather, fabric, ceramic, concrete, composites, or combinations thereof.
  • the substrate is a previously coated substrate.
  • the previously coated substrate may be a substrate that is covered by a waterborne coating or a solvent-based coating.
  • the previously coated substrate comprises one coating. In yet another embodiment, the previously coated substrate comprises at least one additional coating. In many embodiments, at least one additional coating may comprise a solvent borne or a waterborne coating. In one embodiment, at least one additional coating may be different from the coating composition described herein. In another embodiment, at least one additional coating may be the same as the coating composition described herein.
  • FIG. 1 details a photograph of a panel coated with a conventional UV cured coating and the coating composition described herein comprising a cationic curing material.
  • the panel shown in FIG. 1 has been subjected to outdoor weathering conditions with multiple freeze-thaw cycles, namely northeast Ohio, over the period of a year.
  • the conventional UV cured solvent-borne coating (shown as B) and the coating composition described herein comprising a cationic curing material (shown as A) are differentiated after one year. Although they had a similar and non-distinguishable appearance to each other prior to outdoor weathering, the cationic coating composition is now clearly showing less wear and color inconsistencies than the conventional UV cured coating after one year of outdoor exposure.
  • FIG. 2 also details photographs of panels coated with a conventional alkyd based exterior wood stain and the coating composition described herein comprising a cationic curing material.
  • the panels shown in FIG. 2 has been subjected to outdoor weathering conditions with multiple freeze-thaw cycles, namely northeast Ohio, over the period of a year.
  • the conventional alkyd based exterior wood stain (shown as D) and the coating composition described herein comprising a cationic curing material shown prior to outdoor weathering. However, they are differentiated after one year of outdoor exposure.
  • the cationic coating composition (shown as E) is now clearly showing less wear and color inconsistencies than the conventional alkyd based exterior wood stain (shown as F) after one year of outdoor exposure. Further, the conventional alkyd based exterior wood stain (shown as F) has signs of both fading and flaking as compared to the cationic coating composition (shown as E). The conventional alkyd based exterior wood stain (shown as F) has significant color change when compared to how it looked before exposure (shown as D), namely a graying in color.
  • FIG. 3 provides a wood panel coated with the coating composition described herein comprising a cationic curing material (shown as G) in comparison to an untreated wood substrate for water resistance (shown as H).
  • the coating composition described herein comprising a cationic curing material may provide both penetration into a wood substrate and water resistance properties whereas water penetrates into the untreated wood substrate (shown as H).
  • Embodiment 1 A coating composition comprising: at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
  • Embodiment 2 An embodiment of Embodiment 1, wherein at least one anhydrous hydrophobic material comprises at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, at least one oil, at least one solvent, or combinations thereof.
  • Embodiment 3 An embodiment of Embodiment 2, wherein the at least one solution polymer comprises at least one: acrylic polyol, acrylic, alkyd, oil modified urethane, acrylic modified alkyd, or combinations thereof.
  • Embodiment 4 An embodiment of Embodiment 2, wherein the at least one oil is a conjugated oil.
  • Embodiment 5 An embodiment of Embodiment 4, wherein the conjugated oil comprises linseed oil, castor oil, soybean oil, sunflower oil, safflower oil, tall oil, nahar oil, tobacco seed oil, coconut oil, rubber seed oil, karanja oil, lesquerella oil, tung oil, or combinations thereof.
  • the conjugated oil comprises linseed oil, castor oil, soybean oil, sunflower oil, safflower oil, tall oil, nahar oil, tobacco seed oil, coconut oil, rubber seed oil, karanja oil, lesquerella oil, tung oil, or combinations thereof.
  • Embodiment 6 An embodiment of Embodiment 2, wherein the at least one solvent comprises mineral spirits, butyl acetate, n-butyl propionate, diethylene glycol monoethyl acetate, ethylene glycol monobutyl ether acetate, ethyl 3 -ethoxypropionate, ethyl acetate, 2-ethylhexyl acetate, isobutyl acetate, isobutyl isobutyrate, isopropyl Acetate, methyl acetate, methyl n-amyl ketone, methyl isoamyl ketone, methyl propyl ketone, propylene glycol monomethyl ether acetate, propyl acetate, n-propyl propionate, or combinations thereof.
  • the at least one solvent comprises mineral spirits, butyl acetate, n-butyl propionate, diethylene glycol monoethyl acetate, ethylene glycol monobutyl
  • Embodiment 7 An embodiment of any of Embodiments 1-6, wherein the at least one cationic curing material comprises at least one cationic photoinitiator, at least one acid catalyst, or combinations thereof.
  • Embodiment 8 An embodiment of any of Embodiments 1-7, wherein the coating composition is substantially immiscible with water.
  • Embodiment 9 An embodiment of any of Embodiments 1-8, wherein the coating composition further comprises at least one polymer, at least one reactive diluent, at least one non- reactive diluent, at least one solvent, at least one drier, at least one colorant, at least one pigment, at least one surfactant, at least one dispersant, at least one wax, at least one anti-skinning agent, at least one defoamer, at least one fungicide, at least one biocide, at least one mildewcide, at least one thickener, or combinations thereof.
  • the coating composition further comprises at least one polymer, at least one reactive diluent, at least one non- reactive diluent, at least one solvent, at least one drier, at least one colorant, at least one pigment, at least one surfactant, at least one dispersant, at least one wax, at least one anti-skinning agent, at least one defoamer, at least one fungicide, at least one biocide
  • Embodiment 10 An embodiment of any of Embodiments 1-9, wherein the at least one anhydrous hydrophobic material is part of an interpenetrating polymer network (IPN).
  • IPN interpenetrating polymer network
  • Embodiment 11 An embodiment of any of Embodiments 1-9 further comprising at least one dual functional material.
  • Embodiment 12 An embodiment of Embodiment 11, wherein at least one dual functional material comprises a cyclic ether or hydroxyl with an unsaturated alkene, a cyclic ether with an acrylate, or combinations thereof.
  • Embodiment 13 An embodiment of any of Embodiments 1-12, wherein the coating composition is a wood stain.
  • Embodiment 14 An embodiment of any of Embodiments 1-12, wherein the coating composition is a clear coating, a semi-transparent coating, a semi-solid coating, or a solid color coating.
  • Embodiment 15 An embodiment of any of Embodiments 1-14, wherein the coating composition is a one-part system.
  • Embodiment 16 An embodiment of any of Embodiments 1-14, wherein the coating composition is a two-part system.
  • Embodiment 17 A method of preparing the coating composition of any of Embodiments 1-16.
  • Embodiment 18 A method of at least partially applying the coating composition of any of Embodiments 1-16 to at least one substrate.
  • Embodiment 19 An embodiment of Embodiment 18, wherein at least one substrate is wood, metal, glass, plastic, paper, leather, fabric, ceramic, concrete, composites, or combinations thereof.
  • Embodiment 20 An embodiment of Embodiment 18, wherein at least one substrate is a previously coated substrate.
  • Embodiment 21 An article comprising the coating composition of any of Embodiments 1- 16.

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Abstract

The present application relates to a coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible. Also described is a method of preparing the coating composition and an article containing the coating composition described herein.

Description

COATINGS COMPRISING CATIONIC CURING MATERIALS
FIELD
[001] The present disclosure relates generally to a coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible. A method of preparing the coating and an article containing the coating are also disclosed.
BACKGROUND
[002] More recently, clearcoats and stains, both waterborne and solvent borne, have been used in numerous applications, including but not limited to applications in general industrial, building materials, homes and businesses, wood, composites, and other goods that may be coated.
[003] Many of these coatings are used in exterior applications and are cured by ultraviolet (UV) curing process. UV curing, also known as radical UV curing, is a standard curing process that has been used in the coatings industry. Although this UV curing process may occur with exposure to sunlight, some portions of the coating may not fully cure such as shaded areas or areas with only indirect light. Further, exterior conditions may change frequently, which could delay or disrupt the radical UV curing process. Also, many interior coatings may be cured by UV light, but a lack of access to proper UV curing equipment may prevent such a coating from being fully cured. These interior coatings also may not have exposure to an adequate UV light source, e.g., a window, reducing their ability to fully cure as well. Additionally, oxygen inhibition during the typical radical UV curing process may lead to poor surface cure. Specifically, the free radical polymerization of radical UV cure coatings is succeptable to oxygen inhibition since oxygen may come into contact with the coating surface and then terminate the reaction. This can lead to insufficent cure on the surface, or with extremely thin films, preventing cure. Further, there may be other issues such as toxcitity, skin irritation, and odor for customers using radical UV curing products.
[004] Alternatively, cationic curing may be used instead of radical UV curing. Cationic curing chemistry is a UV -initiated cationic polymerization. Although exposure of a coating to sunlight may start the cationic curable process, continuous exposure to UV light is not required to fully cure. Cationic curing is also not inhibited by oxygen, allowing curing to occur after it has been initiated by UV. Although cationic curing is used in ink and 3D printing applications, curing conditions must be tightly controlled or they may not be adequately cured. For example, cationic curing may be terminated, delayed, or disrupted by the presence of moisture, which may frequently occur in exterior applications or other applications where moisture cannot be controlled. These disadvantages have led to limit the use of cationic curing in coatings, especially with exterior products and with curing conditions that cannot be controlled.
[005] Additionally, consumers must choose between solvent-based coatings and water-based coatings. Often, these solvent-based coatings are oil-based coatings which cure through oxidative crosslinking. Typically, oil-based coatings are often easier to apply over substrates like wood than water-based coatings. Oil-based coatings penetrate the wood, reducing lap marks and future peeling. However, oil-based coatings take longer to dry than water-based coatings and contain higher VOC’s. Further, they are more prone to act as a food source for mold, mildew, and algae. For example, long oil alkyd resin has been used for high solids coatings, especially wood stains. However, its product performance suffers from slow dry times and tackiness. In order to overcome these challenges, water reducible alkyd technology had been developed to achieve low VOC target, but the high polarity of the alkyd resin reduces its performance properties, including weatherability.
[006] Alternatively, water-based coatings generally provide improved UV resistance and color retention. Although water-based coatings have improved drying time and mold, mildew, and algae resistance over oil-based coatings, they are more difficult to apply. Since they have more difficulty in penetrating substrates like wood, they also have a potential for peeling if the coating is overapplied.
[007] Consumers have increasingly demanded particular performance requirements for such coatings, especially exterior wood coatings, where curing may be consistent and minimally affected by varying external conditions. Consumers are continually looking for coatings that exhibit these properties such as weatherability, wear resistance, adhesion, application, cure time, and mold, mildew, and algae resistance without sacrificing other performance properties. In view of these challenges with many conventional coatings, the need therefore remains for improved coatings that can provide weatherability, wear resistance, adhesion, and other improved properties as well as other advantages after curing.
SUMMARY
[008] The embodiments of what is described herein are not intended to be exhaustive or to limit what is provided in the claimed subject matter and disclosed in the detailed description. Rather, the embodiments are chosen and described so that others skilled in the art may appreciate and understand the principles and practices of what is provided in the claimed subject matter.
[009] A coating and methods of preparing are shown and described. The coating composition may comprise at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
[0010] Also described is a method of preparing the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible. An article containing the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible is also described.
[0011] To the accomplishment of the foregoing and related ends, the following description set forth certain illustrative aspects and implementations. These are indicative of a few of the various ways in which one or more aspects may be employed. Other aspects, advantages and novel features of the disclosure will become apparent from the following detailed description when considered.
BRIEF DESCRIPTION OF THE DRAWINGS
[0012] The preferred embodiment of which will be described in detail in the specification and illustrated in the accompanying drawings which form a part hereof, and wherein: [0013] FIG. 1 illustrates a panel coated with a conventionally cured coating and the coating composition described herein comprising a cationic curing material, which has been subjected to outdoor weathering conditions.
[0014] FIG. 2 illustrates a panel coated with a conventionally cured coating and the coating composition described herein comprising a cationic curing material, which has been subjected to outdoor weathering conditions.
[0015] FIG. 3 illustrates a wood panel coated with the coating composition described herein comprising a cationic curing material and cured in comparison to an untreated board for water resistance.
DETAILED DESCRIPTION
[0016] Aspects of what is described herein are disclosed in the following description related to specific embodiments. Alternative embodiments may be devised without departing from the scope of what is described herein. Additionally, well-known embodiments of what is described herein may not be described in detail or will be omitted so as to not obscure the relevant details of what is described herein. Further, to facilitate an understanding of the description, discussion of several terms used herein follows.
[0017] As used herein, the word “exemplary” means “serving as an example, instance, or illustration.” The embodiments described herein are not limiting, but rather exemplary only. It should be understood that the described embodiments are not necessarily to be construed as preferred or advantageous over other embodiments. Moreover, the term “embodiment(s)” does not require that all embodiments include the discussed feature, advantage, or mode of operation.
[0018] The present disclosure relates generally to coatings that provide advantageous improvements over current coatings. It has been discovered that the use of a particular coating composition comprising at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible can surprisingly lead to preferred performance properties when used in a coating, namely improved weatherability, wear resistance, adhesion, dry time and tackiness, application, cure time, reduced odor, lower toxicity, reduced skin irritation, and mold, mildew, and algae resistance while having decreased VOC’s and without sacrificing other performance properties as well as other advantages. In particular, the coating composition comprising at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible may have improved properties over typical coatings that are either UV curing or cationic curing. Further, the coating composition described herein comprising at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible may have certain improved properties over many solvent-based coatings or water-based coatings as well as traditional coatings utilizing radical UV curing. By combining at least one anhydrous hydrophobic material with at least one cationic curing material, many issues with typical cationic curing may be substantially overcome.
[0019] Although not to be bound by theory, the ability to cationic cure and chain transfer with hydroxyl groups such as those hydroxyl groups in cellulose and lignin of wood may provide a method to covalently bond the coating composition to a substrate and provide improved adhesion and performance. Applications using both UV cure and cationic cure can be formulated with photoinitiators which will decompose in normal sunlight, allowing for ambient initiation of the reaction. However, the photoinitiators for cationic cure do not decompose to form free radicals, but instead form a strong Bronsted acid. The term “anhydrous hydrophobic” means a material for a coating composition which is both substantially free of water, preferably a material in which water is present at a content of less than or equal to 2% by weight, relative to the total weight of the composition and will not substantially interact with water. “Cationic” describes the portion of the initiator that is the conjugate base to the Bronsted acid and refers to the portion of the molecule that absorbs the radition to initiate cure. The free radicals generated by radical UV cure photoinitiators may have a relatively short half life (typically seconds), so the curing mechanism requires constant UV exposure to keep generating new free radicals in order to drive cure to completion. Unlike the free radicals, the Bronsted acid in cationic cure has a longer half life, typically hours to days, allowing it to persist in the coating and drive the curing. As such, UV cationic cure chemistry may be used for exterior coatings products in outdoor conditions while radical UV cure product would be prevented from curing completely in areas without an adequate UV source such as shadowed and dark areas. UV cationic cure would also provide a more consistent and uniform curing over UV radical curing since products would not be affected by shadows from clouds, trees and other plants, or structures during different conditions throughout the day. Further, the Bronsted acid may catalyze the cationic cure resins through a ring opening reaction, potentially leading to lower shrinkage and increased adhesion of the coating. Table 1 below further highlights benefits of using cationic curing over radical UV curing.
Table I: Radcure Chemistry - Free Radical vs. Cationic
Figure imgf000008_0002
From: Verschueren, Kris and Kaur, Balwant '‘Cycloaliphatic Epoxide Resins for Cationic UV-Cure”
(Conference Proceedings of RADTECH ASIA '99. Radiation Curing: the technology for the next millenium)
[0020] The UV cationic curing reaction provided below shows the polymerization process in which a ring opening reaction occurs.
Figure imgf000008_0001
[0021] With the coating composition described herein, the cationic reaction mechanism may be protected from the water or moisture that may occur in certain enviroments, especially an exterior environment, by creating an anhydrous or substantially anhydrous environment, thus providing a coating composition not subject to oxygen or water inhibition of cure. Since it is also hydrophobic, there is a reduced exposure to water as well.
[0022] The coating composition described herein is a UV cationic curing coating. The coating composition described herein cures when UV initiates the cationic curing reaction but is not required to sustain it. Further, in some embodiments, at least one anhydrous hydrophobic material and at least one cationic curing material may copolymerize with each other. Additionally, at least one anhydrous hydrophobic material may cure, either in addition to the UV and cationic cure or separately from these cure methods, by oxidative drying.
[0023] In many embodiments, the coating composition described herein comprises at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible. If at least one anhydrous hydrophobic material and at least one cationic curing material are not fully miscible or substantially miscible, then the anhydrous hydrophobic material(s) and cationic curing material(s) may be adjusted to ensure compatibility such that they are substantially miscible. Adjustments to ensure compatibility may be done through material choices of the coatings composition.
[0024] Further, in many embodiments, at least one anhydrous hydrophobic material of the coating composition described herein comprises at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, at least one oil, at least one solvent, or combinations thereof. In many embodiments, at least one anhydrous hydrophobic material may be substantially miscible in a solvent-based coating. In some embodiments, at least one anhydrous hydrophobic material may be substantially miscible in a water-based coating. In many embodiments, at least one anhydrous hydrophobic material of the coating composition may at least partially penetrate into a substrate. Not to be bound by theory, at least one anhydrous hydrophobic material may create an anhydrous hydrophobic environment that may protect the cationic curing material in the coating composition from reaction inhibition with water. By inhibiting or preventing the reaction with water, the coating composition described herein may be cured in exterior conditions or conditions in which moisture may not be controlled.
[0025] In many embodiments, at least one alkyd resin may comprise various oil lengths. In some embodiments, at least one alkyd resin may be derived from a biobased source such as plant oils. [0026] In many embodiments, at least one solution polymer comprises at least one: acrylic polyol, acrylic, alkyd, oil modified urethane, acrylic modified alkyd, or combinations thereof. Typical solvents used for solution polymerization may include but are not limited to water, ethanol, a mixture of water and ethanol, ethyl ether, benzene, and benzyl alcohol. Solvents used in solution polymerization may be removed during processing of the solution polymer.
[0027] In some embodiments, the acrylic portion of at least one solvent-based acrylic may comprise alkyl (meth)acrylates and vinyl monomers, such as but not limited to, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-/i-/t-butyl (meth)acrylate, 2- ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether, 2-(acetoacetoxy)ethyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, diacetone acrylamide, acrylamide, methacrylamide, methylol (meth)acrylamide, styrene, a-methyl styrene, vinyl toluene, vinyl acetate, vinyl propionate, allyl methacrylate, or combinations thereof. In some embodiments, the alkyl methacrylate polymers may be those prepared from a range of C12 to C22 alkyl methacrylates. Some preferred monomers include styrene, methyl methacrylate, methacrylic acid, hydroxyethyl acrylate, acetoacetoxyethyl methacrylate, butyl acrylate, butyl methacrylate, or combinations thereof. Others are also contemplated.
[0028] In many embodiments, the at least one oil is a conjugated oil. In some embodiments, the conjugated oil comprises linseed oil, castor oil, soybean oil, sunflower oil, safflower oil, tall oil, nahar oil, tobacco seed oil, coconut oil, rubber seed oil, karanja oil, lesquerella oil, tung oil, or combinations thereof. Other oils are also contemplated.
[0029] In many embodiments, the at least one solvent comprises a non-drying oil. In some embodiments, the at least one solvent comprises mineral spirits, butyl acetate, n-butyl propionate, di ethylene glycol monoethyl acetate, ethylene glycol monobutyl ether acetate, ethyl 3- ethoxy propionate, ethyl acetate, 2-ethylhexyl acetate, isobutyl acetate, isobutyl isobutyrate, isopropyl Acetate, methyl acetate, methyl n-amyl ketone, methyl isoamyl ketone, methyl propyl ketone, propylene glycol monomethyl ether acetate, propyl acetate, n-propyl propionate, or combinations thereof. Other solvents are also contemplated.
[0030] In many embodiments, the at least one cationic curing material comprises at least one cationic photoinitiator, at least one acid catalyst, or combinations thereof. At least one cationic curing material may be initiated by UV. However, the use of at least one anhydrous hydrophobic material may substantially reduce or prevent the termination of the cationic reaction by water. In many embodiments, the coating composition described herein is substantially immiscible with water. In one embodiment, the coating composition described herein is completely immiscible with water.
[0031] In some embodiments, the coating composition described herein comprises at least one cationic photoinitiator. The cationic photoinitiator may be subjected to UV to In one embodiment, at least one cationic photointiator comprises triphenylsulfonium, diaryliodonium, diazonium salts, diaryliodonium salts, ferrocenium salts, triarylsulfonium salt, alkylsulfonium salt, iron arene salt, sulfonyloxyketone, triarylsiloxysiloxane, or combinations thereof. In other embodiments, at least one cationic photointiator comprises various other metallocene compounds. In another embodiment, at least one cationic photoinitiator comprises Bis-(4-t-butylphenyl)-Iodonium hexafluorophosphate. In yet another embodiment, at least one cationic photointiator may be sensitized with at least one UV photoinitiator in order to achieve initiation of the UV cure and aid in the UV cationic curing reaction. Other cationic photoinitiators are also contemplated.
[0032] In some embodiments, the coating composition described herein comprises at least one acid catalyst. In many embodiments, at least one acid catalyst comprises sulfuric acid, sulfonic acid, hydrochloric acid, organic sulfonic acid, ferric sulfate, hydrofluoric acid, phosphoric acid, toluenesulfonic acid, polystyrene sulfonate, heteropoly acids, zeolites, acetic acid, or combinations thereof. Other acid catalysts are also contemplated. In some embodiments, a 2K system for the coating composition may be provided with the use of at least one acid catalyst.
[0033] Additionally, various additives as used herein refer to a general category of components or other raw materials that may be added to the compositions herein to promote various properties. In many embodiments, the coating composition described herein further comprises at least one polymer, at least one reactive diluent, at least one non-reactive diluent, at least one solvent, at least one drier, at least one colorant, at least one pigment, at least one surfactant, at least one dispersant, at least one wax, at least one anti-skinning agent, at least one defoamer, at least one fungicide, at least one biocide, at least one mildewcide, at least one thickener, or combinations thereof. Other additives may include but are not limited to polymers or polymer dispersions, leveling agents, antisettling agents, pH buffers, corrosion inhibitors, driers, anti-skinning agents, anti-cratering agents, anti-sag agents, heat stabilizers, UV absorbers/inhibitors, HAUS (hindered amine light stabilizers), antioxidants, wetting agents, flow agents, and the like, and various combinations thereof as needed for a particular application. Other additives are also contemplated.
[0034] In one embodiment, the coating composition described herein further comprises UV radical materials. The UV radical materials in the coating composition may provide a cationic/radical UV hybrid cure.
[0035] In other embodiments, the coating composition described herein further comprises at least one epoxy. The epoxy may react within the UV cationic curing process. The use of an epoxy with at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, or combinations thereof may provide certain advantages with a hybrid system. These advantages may include slower curing time than at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, or combinations thereof if such slower curing time is desired. In some embodiments, at least one epoxy may be derived from a biobased source such as soybean oil. Further, in many embodiments, the coating composition described herein further comprising epoxy may include at least one polyol, including but not limited to acrylic polyols, polyester polyol, or combinations thereof, as the cationic cure mechanism chain transfers with hydroxyl groups. The addition of at least one polyol may allow adjustments with the hardness of the film of the coating composition described herein.
[0036] In some embodiments, the at least one anhydrous hydrophobic material is part of an interpenetrating polymer network (IPN). In many embodiments, having an IPN may result in additional performance improvements. In one embodiment, the IPN described may be provided through free radical polymerization (as in radical UV cure), oxidative crosslinking, or combinations thereof. Other polymerizations and crosslinking mechanisms are also contemplated.
[0037] In some embodiments, the coating composition described herein further comprises at least one dual functional material. This dual functional material acts to cure in a different mechanism than IPN. In some embodiments, at least one dual functional material comprises: 1) a cyclic ether or hydroxyl with an unsaturated alkene, 2) a cyclic ether with an acrylate, or 3) combinations thereof. In one embodiment, the dual functional material described may be provided through free radical polymerization (as in radical UV cure), oxidative crosslinking, or combinations thereof. For example, the dual functional material may be provided using both free radical polymerization of acrylates (as in radical UV cure) and oxidative crosslinking of alkyds. Other polymerizations and crosslinking mechanisms are also contemplated.
[0038] In many embodiments, the coating composition described herein may provide for the formulation of coatings that lower VOC’s. In many embodiments, the VOC’s of the coating composition described herein are 500 g/1 or less as measured by ASTM D3960. In some embodiments, the coating composition described herein has a Volatile Organic Compound (VOC) as measured by ASTM D3960 of less than 250 g/1. In other embodiments, the coating composition described herein can have Volatile Organic Compound (VOC) as measured by ASTM D3960 of less than 450 g/1, less than 400 g/1, less than 350 g/1, less than 300 g/1, less than 275 g/1, less than 225 g/1, less than 200 g/1, less than 175 g/1, less than 150 g/1, less than 125 g/1, less than 100 g/1, less than 75 g/1, less than 50 g/1, and less than 25 g/1. Lower and higher levels of VOC’s are also contemplated.
[0039] In many embodiments, the coating composition described herein has a volatile organic compound content of less than about 250 g/L according to EPA M24. In other embodiments, the coating composition described herein can have Volatile Organic Compound (VOC) as measured by EPA M24 of less than 225 g/1, less than 200 g/1, less than 175 g/1, less than 150 g/1, less than 125 g/1, less than 100 g/1, less than 75 g/1, less than 50 g/1, and less than 25 g/1. Lower and higher levels of VOC’s are also contemplated.
[0040] In many embodiments, the coating composition described herein may provide for the formulation of coatings that contain higher solids.
[0041] In many embodiments, the coating composition described herein is a wood stain. In many embodiments, the coating composition is a clear coating, a semi-transparent coating, a semi-solid coating, or a solid color coating. In one embodiment, the coating composition described herein is a semi-sheer or lightly tinted wood stain. In one embodiment, the coating composition described herein is a semi-transparent wood stain. In one embodiment, the coating composition described herein is a solid color wood stain. In another embodiment, the coating composition described herein is a clear coat. In other embodiments, the coating composition described herein is a primer. In yet other embodiments, the coating composition described herein is a basecoat. In some other embodiments, the coating composition described herein is a topcoat.
[0042] In many embodiments, the coating composition described herein is a one-part system. In other embodiments, the coating composition described herein is a two-part system. [0043] Also described herein is a method of preparing the coating described herein comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
[0044] Further described is a method of at least partially applying the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible to at least one substrate. In many embodiments, at least one substrate is wood, metal, glass, plastic, paper, leather, fabric, ceramic, concrete, composites, or combinations thereof. In one embodiment, at least one substrate is a previously coated substrate. In many embodiments, at least partially applying the coating may be achieved by brush, roller, spray (air atomized, airless, high-volume low pressure (HVLP), and electrostatic), pad, dip coating, roll coating, spin coating, flow coating, curtain coating, centrifugal coating, continuous coating, and autodeposition. Other application methods are also contemplated.
[0045] In many embodiments, an article comprising the coating composition described herein is also disclosed. The article comprises the coating composition comprising at least one anhydrous hydrophobic material and at least one cationic curing material, wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible. In some embodiments, an article may comprise: 1) a substrate having at least one surface; and 2) the coating composition described herein. In some embodiments, the substrate is wood, metal, glass, plastic, paper, leather, fabric, ceramic, concrete, composites, or combinations thereof. In other embodiments, the substrate is a previously coated substrate. The previously coated substrate may be a substrate that is covered by a waterborne coating or a solvent-based coating. In many embodiments, the previously coated substrate comprises one coating. In yet another embodiment, the previously coated substrate comprises at least one additional coating. In many embodiments, at least one additional coating may comprise a solvent borne or a waterborne coating. In one embodiment, at least one additional coating may be different from the coating composition described herein. In another embodiment, at least one additional coating may be the same as the coating composition described herein.
[0046] FIG. 1 details a photograph of a panel coated with a conventional UV cured coating and the coating composition described herein comprising a cationic curing material. The panel shown in FIG. 1 has been subjected to outdoor weathering conditions with multiple freeze-thaw cycles, namely northeast Ohio, over the period of a year. From the photograph, the conventional UV cured solvent-borne coating (shown as B) and the coating composition described herein comprising a cationic curing material (shown as A) are differentiated after one year. Although they had a similar and non-distinguishable appearance to each other prior to outdoor weathering, the cationic coating composition is now clearly showing less wear and color inconsistencies than the conventional UV cured coating after one year of outdoor exposure.
[0047] FIG. 2 also details photographs of panels coated with a conventional alkyd based exterior wood stain and the coating composition described herein comprising a cationic curing material. The panels shown in FIG. 2 has been subjected to outdoor weathering conditions with multiple freeze-thaw cycles, namely northeast Ohio, over the period of a year. From the photograph, the conventional alkyd based exterior wood stain (shown as D) and the coating composition described herein comprising a cationic curing material (shown as C) are shown prior to outdoor weathering. However, they are differentiated after one year of outdoor exposure. Although they had a similar and non-distinguishable appearance to each other prior to outdoor weathering, the cationic coating composition (shown as E) is now clearly showing less wear and color inconsistencies than the conventional alkyd based exterior wood stain (shown as F) after one year of outdoor exposure. Further, the conventional alkyd based exterior wood stain (shown as F) has signs of both fading and flaking as compared to the cationic coating composition (shown as E). The conventional alkyd based exterior wood stain (shown as F) has significant color change when compared to how it looked before exposure (shown as D), namely a graying in color.
[0048] FIG. 3 provides a wood panel coated with the coating composition described herein comprising a cationic curing material (shown as G) in comparison to an untreated wood substrate for water resistance (shown as H). The coating composition described herein comprising a cationic curing material may provide both penetration into a wood substrate and water resistance properties whereas water penetrates into the untreated wood substrate (shown as H).
Embodiments
[0049] The following embodiments are contemplated. All combinations of features and embodiments are contemplated. [0050] Embodiment 1 : A coating composition comprising: at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
[0051] Embodiment 2: An embodiment of Embodiment 1, wherein at least one anhydrous hydrophobic material comprises at least one alkyd resin, at least one solution polymer, at least one solvent-based acrylic, at least one urethane, at least one oil, at least one solvent, or combinations thereof.
[0052] Embodiment 3: An embodiment of Embodiment 2, wherein the at least one solution polymer comprises at least one: acrylic polyol, acrylic, alkyd, oil modified urethane, acrylic modified alkyd, or combinations thereof.
[0053] Embodiment 4: An embodiment of Embodiment 2, wherein the at least one oil is a conjugated oil.
[0054] Embodiment 5: An embodiment of Embodiment 4, wherein the conjugated oil comprises linseed oil, castor oil, soybean oil, sunflower oil, safflower oil, tall oil, nahar oil, tobacco seed oil, coconut oil, rubber seed oil, karanja oil, lesquerella oil, tung oil, or combinations thereof.
[0055] Embodiment 6: An embodiment of Embodiment 2, wherein the at least one solvent comprises mineral spirits, butyl acetate, n-butyl propionate, diethylene glycol monoethyl acetate, ethylene glycol monobutyl ether acetate, ethyl 3 -ethoxypropionate, ethyl acetate, 2-ethylhexyl acetate, isobutyl acetate, isobutyl isobutyrate, isopropyl Acetate, methyl acetate, methyl n-amyl ketone, methyl isoamyl ketone, methyl propyl ketone, propylene glycol monomethyl ether acetate, propyl acetate, n-propyl propionate, or combinations thereof.
[0056] Embodiment 7: An embodiment of any of Embodiments 1-6, wherein the at least one cationic curing material comprises at least one cationic photoinitiator, at least one acid catalyst, or combinations thereof.
[0057] Embodiment 8: An embodiment of any of Embodiments 1-7, wherein the coating composition is substantially immiscible with water.
[0058] Embodiment 9: An embodiment of any of Embodiments 1-8, wherein the coating composition further comprises at least one polymer, at least one reactive diluent, at least one non- reactive diluent, at least one solvent, at least one drier, at least one colorant, at least one pigment, at least one surfactant, at least one dispersant, at least one wax, at least one anti-skinning agent, at least one defoamer, at least one fungicide, at least one biocide, at least one mildewcide, at least one thickener, or combinations thereof.
[0059] Embodiment 10: An embodiment of any of Embodiments 1-9, wherein the at least one anhydrous hydrophobic material is part of an interpenetrating polymer network (IPN).
[0060] Embodiment 11 : An embodiment of any of Embodiments 1-9 further comprising at least one dual functional material.
[0061] Embodiment 12: An embodiment of Embodiment 11, wherein at least one dual functional material comprises a cyclic ether or hydroxyl with an unsaturated alkene, a cyclic ether with an acrylate, or combinations thereof.
[0062] Embodiment 13: An embodiment of any of Embodiments 1-12, wherein the coating composition is a wood stain.
[0063] Embodiment 14: An embodiment of any of Embodiments 1-12, wherein the coating composition is a clear coating, a semi-transparent coating, a semi-solid coating, or a solid color coating.
[0064] Embodiment 15: An embodiment of any of Embodiments 1-14, wherein the coating composition is a one-part system.
[0065] Embodiment 16: An embodiment of any of Embodiments 1-14, wherein the coating composition is a two-part system.
[0066] Embodiment 17: A method of preparing the coating composition of any of Embodiments 1-16.
[0067] Embodiment 18: A method of at least partially applying the coating composition of any of Embodiments 1-16 to at least one substrate.
[0068] Embodiment 19: An embodiment of Embodiment 18, wherein at least one substrate is wood, metal, glass, plastic, paper, leather, fabric, ceramic, concrete, composites, or combinations thereof.
[0069] Embodiment 20: An embodiment of Embodiment 18, wherein at least one substrate is a previously coated substrate.
[0070] Embodiment 21 : An article comprising the coating composition of any of Embodiments 1- 16.
[0071] What has been described above includes examples of the claimed subject matter. All details and any described modifications in connection with the Background and Detailed Description are within the spirit and scope of the claimed subject matter will be readily apparent to those of skill in the art. In addition, it should be understood that aspects of the claimed subject matter and portions of various embodiments and various features recited below and/or in the appended claims may be combined or interchanged either in whole or in part. In the foregoing descriptions of the various embodiments, those embodiments which refer to another embodiment may be appropriately combined with other embodiments as will be appreciated by one of skill in the art. Furthermore, those of ordinary skill in the art will appreciate that the foregoing description is by way of example only, and is not intended to limit the claimed subject matter, realizing that many further combinations and permutations of the claimed subject matter are possible. It is, of course, not possible to describe every conceivable combination of components or methodologies for purposes of describing the claimed subject matter, but one of ordinary skill in the art may recognize. Accordingly, the claimed subject matter is intended to embrace all such alterations, modifications and variations that fall within the spirit and scope of the appended claims. Furthermore, to the extent that the term “includes” is used in either the detailed description or the claims, such term is intended to be inclusive in a manner similar to the term “comprising” as “comprising” is interpreted when employed as a transitional word in a claim.

Claims

What is claimed is:
1. A coating composition comprising: at least one anhydrous hydrophobic material; and at least one cationic curing material; wherein at least one anhydrous hydrophobic material and at least one cationic curing material are substantially miscible.
2. The coating composition of Claim 1, wherein at least one anhydrous hydrophobic material comprises at least one alkyd resin, at least one solution polymer, at least one solventbased acrylic, at least one urethane, at least one oil, at least one solvent, or combinations thereof.
3. The coating composition of Claim 2, wherein the at least one solution polymer comprises at least one: acrylic polyol, acrylic, alkyd, oil modified urethane, acrylic modified alkyd, or combinations thereof.
4. The coating composition of Claim 2, wherein the at least one oil is a conjugated oil.
5. The coating composition of Claim 4, wherein the conjugated oil comprises linseed oil, castor oil, soybean oil, sunflower oil, safflower oil, tall oil, nahar oil, tobacco seed oil, coconut oil, rubber seed oil, karanja oil, lesquerella oil, tung oil, or combinations thereof.
6. The coating composition of Claim 2, wherein the at least one solvent comprises mineral spirits, butyl acetate, n-butyl propionate, diethylene glycol monoethyl acetate, ethylene glycol monobutyl ether acetate, ethyl 3 -ethoxypropionate, ethyl acetate, 2-ethylhexyl acetate, isobutyl acetate, isobutyl isobutyrate, isopropyl acetate, methyl acetate, methyl n-amyl ketone, methyl isoamyl ketone, methyl propyl ketone, propylene glycol monomethyl ether acetate, propyl acetate, n-propyl propionate, or combinations thereof.
7. The coating composition of any of Claims 1-6, wherein the at least one cationic curing material comprises at least one cationic photoinitiator, at least one acid catalyst, or combinations thereof.
8. The coating composition of any of Claims 1-7, wherein the coating composition is substantially immiscible with water.
9. The coating composition of any of Claims 1-8, wherein the coating composition further comprises at least one polymer, at least one reactive diluent, at least one non-reactive diluent, at least one solvent, at least one drier, at least one colorant, at least one pigment, at least one surfactant, at least one dispersant, at least one wax, at least one anti-skinning agent, at least one defoamer, at least one fungicide, at least one biocide, at least one mildewcide, at least one thickener, or combinations thereof.
10. The coating composition of any of Claims 1-9, wherein the at least one anhydrous hydrophobic material is part of an interpenetrating polymer network (IPN).
11. The coating composition of any of Claims 1-9 further comprising at least one dual functional material.
12. The coating composition of Claim 11, wherein at least one dual functional material comprises a cyclic ether or hydroxyl with an unsaturated alkene, a cyclic ether with an acrylate, or combinations thereof.
13. The coating composition of any of claims 1-12, wherein the coating composition is a wood stain.
14. The coating composition of any of claims 1-13, wherein the coating composition is a clear coating, a semi-transparent coating, a semi-solid coating, or a solid color coating.
15. The coating composition of any of claims 1-14, wherein the coating composition is a one- part system.
16. The coating composition of any of claims 1-14, wherein the coating composition is a two-part system.
17. A method of preparing the coating composition of any of claims 1-16.
18. A method of at least partially applying the coating composition of any of claims 1-16 to at least one substrate.
19. The method of claim 18, wherein at least one substrate is wood, metal, glass, plastic, paper, -leather, fabric, ceramic, concrete, composites, or combinations thereof.
20. The method of claim 18, wherein at least one substrate is a previously coated substrate.
21. An article comprising the coating composition of any of claims 1-16.
PCT/US2024/020917 2023-03-23 2024-03-21 Coatings comprising cationic curing materials Ceased WO2024197150A1 (en)

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EP24720960.4A EP4683974A1 (en) 2023-03-23 2024-03-21 Coatings comprising cationic curing materials
CN202480020802.0A CN120858147A (en) 2023-03-23 2024-03-21 Coatings containing cationic curing materials
MX2025011171A MX2025011171A (en) 2023-03-23 2025-09-22 Coatings comprising cationic curing materials

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US202363491867P 2023-03-23 2023-03-23
US63/491,867 2023-03-23

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009155115A2 (en) * 2008-05-30 2009-12-23 Reactive Surfaces, Ltd. Coatings and surface treatments having active enzymes and peptides
US20100210745A1 (en) * 2002-09-09 2010-08-19 Reactive Surfaces, Ltd. Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes
US20100233146A1 (en) * 2002-09-09 2010-09-16 Reactive Surfaces, Ltd. Coatings and Surface Treatments Having Active Enzymes and Peptides
US20110240064A1 (en) * 2002-09-09 2011-10-06 Reactive Surfaces, Ltd. Polymeric Coatings Incorporating Bioactive Enzymes for Cleaning a Surface
US20110250626A1 (en) * 2002-09-09 2011-10-13 Reactive Surfaces, Ltd. Visual Assays for Coatings Incorporating Bioactive Enzymes for Catalytic Functions
US20120097194A1 (en) * 2002-09-09 2012-04-26 Reactive Surfaces, Ltd. Polymeric Coatings Incorporating Bioactive Enzymes for Catalytic Function

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100210745A1 (en) * 2002-09-09 2010-08-19 Reactive Surfaces, Ltd. Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes
US20100233146A1 (en) * 2002-09-09 2010-09-16 Reactive Surfaces, Ltd. Coatings and Surface Treatments Having Active Enzymes and Peptides
US20110240064A1 (en) * 2002-09-09 2011-10-06 Reactive Surfaces, Ltd. Polymeric Coatings Incorporating Bioactive Enzymes for Cleaning a Surface
US20110250626A1 (en) * 2002-09-09 2011-10-13 Reactive Surfaces, Ltd. Visual Assays for Coatings Incorporating Bioactive Enzymes for Catalytic Functions
US20120097194A1 (en) * 2002-09-09 2012-04-26 Reactive Surfaces, Ltd. Polymeric Coatings Incorporating Bioactive Enzymes for Catalytic Function
WO2009155115A2 (en) * 2008-05-30 2009-12-23 Reactive Surfaces, Ltd. Coatings and surface treatments having active enzymes and peptides

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CN120858147A (en) 2025-10-28
EP4683974A1 (en) 2026-01-28

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