# US 10,865,327 B2 · Tintable abrasion resistant compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,865,327 B2 - Document ID: US10865327B2 - Status: Granted - Kind: B2 - Application number: 16/293,007 - Filed: 2019-03-05 - Published: 2020-01-02 - Granted: 2020-12-15 - Earliest claimed: 2018-06-29 - Applicants: Polymer Technology, Inc. - Inventors: Gerald Treadway - Web page: https://patentgrep.com/patent/US10865327B2 ## CPC - C09D 183/10: Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00) - B05D 3/067: {Curing or cross-linking the coating} - C08G 77/04: Polysiloxanes - C08G 77/442: containing vinyl polymer sequences - C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} - C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 - C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes - C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) - G02B 1/12: by surface treatment, e.g. by irradiation - G02B 1/14: Protective coatings, e.g. hard coatings - B05D 2201/02: Polymeric substrate - B05D 2518/10: Silicon-containing polymers - C08G 77/14: containing silicon bound to oxygen-containing groups - C08G 2150/00: Compositions for coatings - C09D: COATING 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 (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS ## Abstract A coating composition with a stable shelf-life for forming a transparent coating upon eyeglass lenses or other substrates having improved abrasion resistance and tintability. The composition comprising a silicone-based binder component, a curing agent component, and being substantially free of volatiles. The binder component comprises the partial hydrolysis product of an epoxy-functional alkoxysilane, a polyglycidylether, and an acrylic monomer. The curing agent component comprises a cationic photoinitiator and a free radical photoinitiator. ## Claims ### Claim 1 A copolymer coating comprising a copolymer comprising monomer units from: a) 3-glycidyloxypropyltrimethoxysilane having a weight percent of 53.6 to 71.6 based on the total weight of the copolymer coating, wherein 30% to 40% of the methoxy groups of the trimethoxysilane moieties of 3-glycidyloxypropyltrimethoxysilane in the copolymer coating have been hydrolyzed to form silanols; and b) hexanediol diacrylate having a weight percent of 14.3 to 24.9 based on the total weight of the copolymer coating; wherein the copolymer coating was cured with a curing energy of 0.1 mJ to 0.5 mJ. ### Claim 2 (depends on 1) The copolymer coating of claim 1 wherein the copolymer coating has a Bayer abrasion ratio of at least 2.0. ### Claim 3 (depends on 2) The copolymer coating of claim 2 wherein the cured copolymer coating has an ASTM D3359 adhesion test value of at least 4 B for a polycarbonate substrate. ### Claim 4 (depends on 2) The copolymer coating of claim 2 wherein the copolymer coating was cured with a curing energy of 0.3 mJ to 0.5 mJ. ### Claim 5 (depends on 4) The copolymer coating of claim 4 wherein the copolymer coating was cured with a curing energy of 0.3 mJ to 0.4 mJ. ### Claim 6 (depends on 1) The copolymer coating of claim 1 wherein the copolymer coating is a tinted copolymer coating. ### Claim 7 (depends on 6) The copolymer coating of claim 6 wherein the tinted copolymer coating has a total light transmission of 10% to 90%. ### Claim 8 (depends on 6) The copolymer coating of claim 6 wherein the copolymer further comprises copolymerized monomer units from one or more ethers. ### Claim 9 (depends on 8) The copolymer coating of claim 8 wherein the one or more ethers is cyclohexanedimethanol diglycidyl ether, trimethylolpropane triglycidyl ether, xylene dioxetane (XDO), dioxetanyl ether (DOX), or a combination thereof. ### Claim 10 (depends on 9) The copolymer coating of claim 9 wherein the one or more ethers is dioxetanyl ether (DOX). ### Claim 11 (depends on 1) The copolymer coating of claim 1 wherein the copolymer further comprises copolymerized monomer units from one other acrylate wherein the one other acrylate has three or more acryloyl groups. ### Claim 12 (depends on 11) The copolymer coating of claim 11 wherein the one other acrylate is tris[2-(acryloyloxy)ethyl] isocyanurate. ### Claim 13 (depends on 1) A method for forming the copolymer coating according to claim 1, comprising: a) partially hydrolyzing an aqueous solution of 3-glycidyloxypropyltrimethoxysilane by heating the 3-glycidyloxypropyltrimethoxysilane with a catalytic amount of mineral acid to form a partially hydrolyzed product; b) removing at least about 95% of volatiles; and c) mixing the partially hydrolyzed product with i) hexanediol diacrylate, ii) a cationic initiator, and iii) a radical initiator, wherein a stable coating composition is thereby formed; wherein a change in viscosity of the stable coating composition after 14 days is less than about 10 cps; d) coating a surface of a substrate with the stable coating composition; e) curing the coated surface with a curing energy of 0.1 mJ to 0.5 mJ of UV light to form the copolymer coating; and e) optionally tinting the copolymer coating in a heated solution of a dye; wherein 3-glycidyloxypropyltrimethoxysilane has a weight percent of 53.6 to 71.6 based on the total weight of the copolymer coating and 30% to 40% of the methoxy groups of the trimethoxysilane moieties of 3-glycidyloxypropyltrimethoxysilane in the copolymer coating have been hydrolyzed to form silanols; and hexanediol diacrylate has a weight percent of 14.3 to 24.9 based on the total weight of the copolymer coating; wherein the copolymer coating forms a mar resistant surface on the substrate and the mar resistant surface has a Bayer abrasion ratio of at least about 1.0. ### Claim 14 (depends on 13) The method of claim 13 comprising tinting the copolymer coating wherein the copolymer further comprises copolymerized monomer units from one or more vinyl ethers, one or more allyl ethers, one or more diglycidyl ethers, one or more triglycidyl ethers, one or more oxetanyl ethers, or a combination thereof. ### Claim 15 (depends on 14) The method of claim 14 wherein one of the one or more diglycidyl ethers is cyclohexanedimethanol diglycidyl ether; one of the one or more triglycidyl ethers is trimethylolpropane triglycidyl ether; one of the one or more oxetanyl ethers is a xylene dioxetane (XDO), dioxetanyl ether (DOX), or a combination thereof. ### Claim 16 (depends on 13) The method of claim 13 further comprising mixing the partially hydrolyzed product with tris[2-(acryloyloxy)ethyl] isocyanurate. ### Claim 17 (depends on 13) The method of claim 13 wherein the stable coating composition further comprises a surface additive. ### Claim 18 (depends on 13) The method of claim 13 wherein the substrate is polycarbonate, the mar resistant surface has a coating thickness of about 3 microns to about 6 microns, and/or the mar resistant surface has a boiling water resistance value of about 5 B. ### Claim 19 (depends on 13) The method of claim 13 further comprising mixing the partially hydrolyzed product with a polyether modified polydimethylsiloxane, and the cationic initiator is triphenylsulfonium hexafluoroantimonate, and the radical initiator is 2-hydroxy-2-methy-1-phenylpropan-1-one. ### Claim 20 (depends on 13) The method of claim 13 wherein the curing energy is 0.3 mJ to 0.5 mJ. ### Claim 21 (depends on 13) The method of claim 13 wherein the curing energy is 0.3 mJ to 0.4 mJ.