UV curable hydrophilic coatings
View Patent ↗UV curing hydrophilic coating compositions and methods to make and use the compositions are disclosed. The compositions include about 40 wt. percent to about 95 wt. percent of a vinyl ether compound, an epoxide compound, a compound with vinyl ether and epoxy functional groups, or any combination thereof; about 0.1 wt. percent to about 40 wt. percent of at least one polar diluent; about 40 wt. percent or less of at least one non-polar diluent; and about 0.5 wt. percent to about 12 wt. percent of at least one photoinitiator.
1. A hydrophilic coating composition comprising:
about 40 wt. percent to about 95 wt. percent of a vinyl ether compound, an epoxide compound, a compound with vinyl ether and epoxy functional groups, or any combination thereof, wherein:
the vinyl ether compound is selected from the group consisting of a polyether vinyl ether, a polyacrylate vinyl ether, a polyester vinyl ether, a polycarbonate vinyl ether, a polybutadiene vinyl ether, a polyisopropylene vinyl ether, a polyurethane vinyl ether, a polyimide vinyl ether, a polyamide vinyl ether, a polyphosphazene vinyl ether, a siloxane vinyl ether, or any combination thereof,
the epoxide compound is selected from the group consisting of neopentylglycol di(4-methyl-3,4-epoxycyclohexanecarboxylate), 4-benzyloxymethylcyclohexane oxide, 1,2-epoxy-3-phenoxypropane, epoxidized 1,2,3-tris(1-propenoxy)propane, benzyl 3,4-epoxycyclohexylmethyl ether, 3,4-epoxycyclohexylcarboxaldehyde dibenzyl acetal, or any combination thereof, and
the compound with vinyl ether and epoxy functional groups is selected from the group consisting of 2-methylvinyl 3′,4′-epoxycyclohexylmethyl ether, 2-methylvinyl 3′,4′-epoxy-6′-methylcyclohexylmethyl ether, 2-methylvinyl 3′-methyl-3′,4′-epoxycyclohexyl-dimethylmethyl ether, 2-methylvinyl 5′,6-epoxy-2′-norbomylmethyl ether, or any combination thereof;
about 0.1 wt. percent to about 40 wt. percent of at least one polar diluent, wherein the at least one polar diluent is a low molecular weight vinyl ether monomer with at least one polar functional group, a low molecular weight epoxide monomer with at least one polar functional group, or any combination thereof;
about 40 wt. percent or less of at least one non-polar diluent;
about 0.5 wt. percent to about 12 wt. percent of at least one photoinitiator; and
about 2 wt. percent to about 10 wt. percent of a pigment, and
wherein the hydrophilic coating composition is configured to have polar groups covering about 1 percent to about 10 percent of a coated surface after being cured.
2. The hydrophilic coating composition of claim 1 , wherein the at least one polar diluent is 1,4-butanediol mono vinylether, ethylene glycol mono vinyl ether, diethylene glycol mono vinyl ether, 4-(hydroxylmethyl)cyclohexylmethyl vinyl ether, glycidol, N-vinyl pyrrolidone, N-vinyl caprolactam, vinyl imidazole, vinyl methyacetamide, or any combination thereof.
3. The hydrophilic coating composition of claim 1 , wherein the at least one non-polar diluent is cyclohexene oxide, 1,2-epoxyhexane, 1,2-epoxyoctane, 1,2-epoxydecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, epichlorohydrin, styrene oxide, ethyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, t-butyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 1,4-butanediol divinylether, epichlorohydrin, styrene oxide, or any combination thereof.
4. The hydrophilic coating composition of claim 1 , wherein the at least one photoinitiator is a cationic photoinitiator selected from the group consisting of a diaryliodonium salt, a triarylsulphonium salt, a triarylselenonium salt, a dialkylphenacylsulphonium salt, an aryloxydiarylsulphoxonium salt, a dialylphenacylsulphoxonium salt, or any combination thereof.
5. The hydrophilic coating composition of claim 1 , wherein the at least one photoinitiator is a cationic photoinitiator selected from the group consisting of (4-noctyloxyphenyl)phenyliodonium hexafluoroantimonate, (4-n-undecyloxyphenyl)phenyliodonium hexafluoroantimonate, bis(4-dodecylphenyl)iodonium hexafluoroantimonate, iodonium (4-methylphenyl) [4-(2-methylpropyl) phenyl]-hexafluorophosphate(1-), tris(4-alkylphenyl)sulfonium hexafluorophosphate, or any combination thereof.
6. The hydrophilic coating composition of claim 1 , wherein the polar group on the coated surface is an amide, a carboxyl, a carbonyl, a hydroxyl, or any combination thereof.
7. The hydrophilic coating composition of claim 1 , further comprising a filler present from about 2 wt. percent to about 40 wt. percent.
8. The hydrophilic coating composition of claim 1 , further comprising at least one of a coalescing agent, a rheology modifier, a plasticizer, a surfactant, or any combination thereof.
9. The hydrophilic coating composition of claim 1 , wherein the hydrophilic coating composition does not comprise a solvent.
10. The hydrophilic coating composition of claim 1 , wherein the hydrophilic coating composition does not comprise a volatile solvent.
11. The hydrophilic coating composition of claim 1 , wherein the hydrophilic coating is a decorative coating, an industrial coating, a protective coating, a self-cleaning coating, or any combination thereof.
12. The hydrophilic coating composition of claim 1 , wherein the hydrophilic coating is curable by UV radiation.
13. The hydrophilic coating composition of claim 12 , wherein the UV radiation has a wavelength of about 200 nanometers to about 400 nanometers.
14. The hydrophilic coating composition of claim 1 , wherein the hydrophilic coating is configured to produce a hydrophilic surface upon curing, and wherein the hydrophilic surface has a water contact angle of less than 20°.
15. A method of to modify a surface to a hydrophilic surface, the method comprising:
applying a coating composition to the surface to form a coated surface, wherein the coating composition comprises:
about 40 wt. percent to about 95 wt. percent of a vinyl ether compound, an epoxide compound, a compound with vinyl ether and epoxy functional groups, or any combination thereof, wherein:
the vinyl ether compound is selected from the group consisting of a polyether vinyl ether, a polyacrylate vinyl ether, a polyester vinyl ether, a polycarbonate vinyl ether, a polybutadiene vinyl ether, a polyisopropylene vinyl ether, a polyurethane vinyl ether, a polyimide vinyl ether, a polyamide vinyl ether, a polyphosphazene vinyl ether, a siloxane vinyl ether, or any combination thereof,
the epoxide compound is selected from the group consisting of neopentylglycol di(4-methyl-3,4-epoxycyclohexanecarboxylate), 4-benzyloxymethyl cyclohexane oxide, 1,2-epoxy-3-phenoxypropane, epoxidized 1,2,3-tris(1-propenoxy)propane, benzyl 3,4-epoxycyclohexylmethyl ether, 3,4-epoxycyclohexylcarboxaldehyde dibenzyl acetal, or any combination thereof, and
the compound with vinyl ether and epoxy functional groups is selected from the group consisting of 2-methylvinyl 3′,4′-epoxycyclohexylmethyl ether, 2-methylvinyl 3′,4′-epoxy-6′-methylcyclohexylmethyl ether, 2-methylvinyl 3′-methyl-3′,4′-epoxycyclohexyl-dimethylmethyl ether, 2-methylvinyl 5′,6-epoxy-2′-norbomylmethyl ether, or any combination thereof;
about 0.1 wt. percent to about 40 wt. percent of at least one polar diluent, wherein the at least one polar diluent is low molecular weight vinyl ether monomer with at least one polar functional group, a low molecular weight epoxide monomer with at least one polar functional group, or any combination thereof; about 40 wt. percent or less of at least one non-polar diluent;
about 0.5 wt. percent to about 12 wt. percent of at least one photoinitiator; and
about 2 wt. percent to about 10 wt. percent of a pigment; and
exposing the coated surface to UV light to cure the coating composition,
wherein the cured coating composition has polar groups covering about 1 percent to about 10 percent of the coated surface, and wherein the cured coating composition has a water contact angle of less than 20°.
16. The method of claim 15 , wherein applying the coating composition comprises:
applying the coating composition comprising about 40 wt. percent to about 95 wt. percent of a vinyl ether compound or an epoxide compound, a compound with vinyl ether and epoxy functional groups, or a combination thereof,
about 0.1 wt. percent to about 40 wt. percent of at least one polar diluent, wherein the at least one polar diluent is low molecular weight vinyl ether monomer with at least one polar functional group, a low molecular weight epoxide monomer with at least one polar functional group, or any combination thereof,
about 40 wt. percent or less of at least one non-polar diluent,
about 0.5 wt. percent to about 12 wt. percent of at least one photoinitiator selected from the group consisting of diaryliodonium salt, a triarylsulphonium salt, a triarylselenonium salt, a dialkylphenacylsulphonium salt, an aryloxydiarylsulphoxonium salt, a dialylphenacylsulphoxonium salt, or any combination thereof, and
about 2 wt. percent to about 10 wt. percent of a pigment.
17. The method of claim 15 , wherein applying the coating composition further comprises about 2 wt. percent to about 40 wt. percent of a filler.
18. The method of claim 15 , wherein applying the coating composition to the surface comprises brushing, spraying, spreading, or rolling on the surface.
19. The method of claim 15 , wherein applying the coating composition to the surface comprises applying the coating composition to a hydrophobic surface.
20. The method of claim 15 , wherein exposing the coated surface to UV light comprises exposing the coated surface to UV light of about 200 nanometers to about 400 nanometers for about 5 minutes to about 5 hours.
21. A coated article, comprising:
a substrate; and
a coating disposed on at least one surface of the substrate, wherein the coating comprises about 40 wt. percent to about 95 wt. percent of a vinyl ether compound, an epoxide compound, a compound with vinyl ether and epoxy functional groups, or any combination thereof, wherein:
the vinyl ether compound is selected from the group consisting of a polyether vinyl ether, a polyacrylate vinyl ether, a polyester vinyl ether, a polycarbonate vinyl ether, a polybutadiene vinyl ether, a polyisopropylene vinyl ether, a polyurethane vinyl ether, a polyimide vinyl ether, a polyamide vinyl ether, a polyphosphazene vinyl ether, a siloxane vinyl ether, or any combination thereof,
the epoxide compound is selected from the group consisting of neopentylglycol di(4-methyl-3,4-epoxycyclohexanecarboxylate), 4-benzyloxymethylcyclohexane oxide, 1,2-epoxy-3-phenoxypropane, epoxidized 1,2,3-tris(1-propenoxy)propane, benzyl 3,4-epoxycyclohexylmethyl ether, 3,4-epoxycyclohexylcarboxaldehyde dibenzyl acetal, or any combination thereof, and
the compound with vinyl ether and epoxy functional groups is selected from the group consisting of 2-methylvinyl 3′,4′-epoxycyclohexylmethyl ether, 2-methylvinyl 3′,4′-epoxy-6′-methylcyclohexylmethyl ether, 2-methylvinyl 3′-methyl-3′,4′-epoxycyclohexyl-dimethylmethyl ether, 2-methylvinyl 5′,6-epoxy-2′-norbomylmethyl ether, or any combination thereof;
about 0.1 wt. percent to about 40 wt. percent of at least one polar diluent, wherein the at least one polar diluent is low molecular weight vinyl ether monomer with at least one polar functional group, a low molecular weight epoxide monomer with at least one polar functional group, or any combination thereof;
about 40 wt. percent or less of at least one non-polar diluent;
about 0.5 wt. percent to about 12 wt. percent of at least one photoinitiator; and
about 2 wt. percent to about 10 wt. percent of a pigment, and
wherein the coating is configured to have polar groups that cover about 1 percent to about 10 percent of a coated surface after being cured.
22. The coated article of claim 21 , wherein the at least one photoinitiator is a cationic photoinitiator selected from the group consisting of a diaryliodonium salt, a triarylsulphonium salt, a triarylselenonium salt, a dialkylphenacylsulphonium salt, an aryloxydiarylsulphoxonium salt, a dialylphenacylsulphoxonium salt, or any combination thereof.
23. The coated article of claim 21 , wherein the coating is configured to produce a hydrophilic surface upon the curing, wherein the hydrophilic surface has a water contact angle of less than 20°.