Glycidyl ether based optical coating compositions

Abstract

A combination comprising a substrate and cured coating composition formed of the hydrolysis product of an epoxy functional alkoxy silane in combination with one or more monoaromatic (mono- or di) glycidyl ethers, the cured coating providing improved adhesion as compared to previous known UV curable coatings. The coating composition includes at least one monoaromatic di- or monoglycidyl ethers, and most preferably includes resorcinol diglycidyl ether.

1 . A combination comprising a substrate having a cured coating formed by the application of ultraviolet radiation to an organofunctional silane composition that comprises a monoaromatic mono- or diglycidyl ether, wherein the cured coating exhibits acceptable adhesion resistance, as determined by crosshatch adhesion testing under conditions of deionized water and humidity testing. 
     
     
         2 . A combination according to  claim 1 , wherein the cured coating also exhibits acceptable adhesion resistance, as determined by crosshatch adhesion testing under conditions of QUV testing. 
     
     
         3 . A combination according to  claim 1  wherein the monoaromatic glyciidyl ether is selected from the group consisting of
 a) 1,3-benzenediol-2,2′-[oxybis(methylene)]dioxirane (“RDGE”); 
 b) o-cresyl glycidyl ether; 2-[(2-methylphenoxy)methyl]oxirane; 
 c) 2-[(4-tert-butylphenoxy)methyl]oxirane; 
 d) 2-(phenoxymethyl)oxirane; 
 e) 2-[(4-nonylphenoxy)methyl]oxirane); 
 f) 1,4-bis(glycidyloxy) benzene); 
 
       and combinations thereof. 
     
     
         4 . A combination according to  claim 3 , wherein the monoaromatic glycidyl ether comprises RDGE. 
     
     
         5 . A combination according to  claim 1 , wherein the substrate is selected from the group consisting of polycarbonate and high index substrates. 
     
     
         6 . A combination according to  claim 5 , wherein the substrate comprises a high index substrate. 
     
     
         7 . A combination according to  claim 1 , wherein the silane composition comprises:
 a) a partially hydrolyzed alkoxy-functional silane, selected from the group consisting of epoxy-, vinyl- and acryloxy-functional alkoxysilanes,   b) a substantially non-hydrolyzed alkoxy-functional silane,   c) an ethylenically unsaturated monomer,   d) a cationic photoinitiator, and   e) a free radical initiator.   
     
     
         8 . A combination according to  claim 7 , wherein the substrate is selected from the group consisting of polycarbonate and high index substrates. 
     
     
         9 . A combination according to  claim 8 , wherein the composition comprises RDGE as the glycidyl ether. 
     
     
         10 . A combination according to  claim 1  wherein the composition consists essentially of RDGE as the ether, the substrate comprises a high index substrate, and the cured coating exhibits acceptable adhesion resistance, as determined by crosshatch adhesion testing under conditions of QUV testing. 
     
     
         11 . A method of coating a composition upon the surface of a polymeric material, the method comprising the steps of:
 a) providing an organofunctional silane composition and substrate,   b) coating and curing the composition to provide a combination according to  claim 1 .   
     
     
         12 . A method according to  claim 11 , wherein the cured coating also exhibits acceptable adhesion resistance, as determined by crosshatch adhesion testing under conditions of QUV testing. 
     
     
         13 . A method according to  claim 11  wherein the monoaromatic glyciidyl ether is selected from the group consisting of
 a) 1,3-benzenediol-2,2′-[oxybis(methylene)]dioxirane (“RDGE”); 
 b) o-cresyl glycidyl ether; 2-[(2-methylphenoxy)methyl]oxirane; 
 c) 2-[(4-tert-butylphenoxy)methyl]oxirane; 
 d) 2-(phenoxymethyl)oxirane; 
 e) 2-[(4-nonylphenoxy)methyl]oxirane); 
 f) 1,4-bis(glycidyloxy) benzene); 
 
       and combinations thereof. 
     
     
         14 . A method according to  claim 13 , wherein the monoaromatic glycidyl ether comprises RDGE. 
     
     
         15 . A method according to  claim 11 , wherein the substrate is selected from the group consisting of polycarbonate and high index substrates. 
     
     
         16 . A method according to  claim 15 , wherein the substrate comprises a high index substrate. 
     
     
         17 . A method according to  claim 11 , wherein the silane composition comprises:
 a) a partially hydrolyzed alkoxy-functional silane, selected from the group consisting of epoxy-, vinyl- and acryloxy-functional alkoxysilanes,   b) a substantially non-hydrolyzed alkoxy-functional silane,   c) an ethylenically unsaturated monomer,   d) a cationic photoinitiator, and   e) a free radical initiator.   
     
     
         18 . A method according to  claim 17 , wherein the substrate is selected from the group consisting of polycarbonate and high index substrates. 
     
     
         19 . A method according to  claim 18 , wherein the composition comprises RDGE as the glycidyl ether. 
     
     
         20 . A method according to  claim 11  wherein the composition consists essentially of RDGE as the ether, the substrate comprises a high index substrate, and the cured coating exhibits acceptable adhesion resistance, as determined by crosshatch adhesion testing under conditions of QUV testing.