Coating composition and optical mar-resistant tintable coating

Abstract

A coating composition and coating for ophthalmic lenses and other polymeric substrates having a unique combination of excellent solution stability, rapid cure rate, improved mar resistance, rapid dye absorption, and improved receptivity towards antireflective coatings. The coating comprises an abrasion resistant polymer and a dye-absorption-enhancing oligomer. The coating is tinted after curing with a dye to provide light absorbency in the coating.

1 . A coating composition comprising:
 a) at least one organofunctional trialkoxysilane monomer in the amount of from 20 to 80 percent by weight, said trialkylsiloxane monomer having the formula;   
       
         
           
           
               
               
           
         
       
       where R 1 , R 2 , and R 3  are independently selected from alkyl groups of 1 to 8 carbon atoms;
 n is an integer 1 through 6, inclusive, 
 
       and X is selected from the group consisting of glycidyl, acrylate, methacrylate, acrylamide, methacrylamide, N-methylacrylamide, N-methylmethacrylamide, vinyl, and allyl;
 b) water to hydrolyze at least one third of alkoxy groups of the trialkoxysilane monomer; and 
 c) from 1.0 to 25.0 percent by weight at least one oligomeric tintability enhancer. 
 
     
     
         2 . The coating composition of  claim 1  wherein the oligomeric tintability enhancer has a solubility for at least one disperse dye that so that the disperse dye is at least 5× more by weight absorbed into the dye-absorbing enhancer than the same disperse dye is absorbed by a polymer consisting of units derived from the organofunctional trialkoxysilane under dye-tinting absorption conditions of immersion in a hot (95° C.) aqueous solution with at least 0.2% by weight dye/water. 
     
     
         3 . The coating composition of  claim 1  wherein the oligomeric tintability enhancer i selected from the group consisting of polyester polyol, urethane polyol, acrylic polyol, and acrylated polyurethane. 
     
     
         4 . The composition of  claim 2  further comprising:
 d) from 1.0 to 10.0 percent by weight one or more photoinitiators independently selected from the free radical and cationic photoinitiators. 
 
     
     
         5 . The composition of  claim 2  further comprising an organic solvent. 
     
     
         6 . The composition of  claim 3  further comprising one or more surfactants or wetting agents are present ion an amount between 0.1 and 15% by weight of the total composition. 
     
     
         7 . The composition of  claim 2  wherein the trialkoxysilane comprises an epoxy-trialkoxy silane. 
     
     
         8 . The composition of  claim 2  further comprising at least 1% by weight of a diacrylate monomer in the composition. 
     
     
         9 . The composition of  claim 1  wherein the trialkoxysilane is reactive with the oligomeric tintability enhancer during polymerization of the trialkoxysilane. 
     
     
         10 . The composition of  claim 2  wherein the trialkoxysilane is reactive with the oligomeric tintability enhancer during polymerization of the trialkoxysilane. 
     
     
         11 . The composition of  claim 3  wherein the trialkoxysilane is reactive with the oligomeric tintability enhancer during polymerization of the trialkoxysilane. 
     
     
         12 . The composition of  claim 4  wherein the trialkoxysilane is reactive with the oligomeric tintability enhancer during polymerization of the trialkoxysilane. 
     
     
         13 . The composition of  claim 5  wherein the trialkoxysilane is reactive with the oligomeric tintability enhancer during polymerization of the trialkoxysilane. 
     
     
         14 . An ophthalmic lens having an unpolymerized coating on at least one surface of the lens formed from the coating composition of  claim 1 , the polymerized coating having sufficient disperse dye dissolved therein to absorb at least 70% of transmitted light of a wavelength at which the disperse dye has its maximum absorption. 
     
     
         15 . An ophthalmic lens having an unpolymerized coating on at least one surface of the lens formed from the coating composition of  claim 2 , the polymerized coating having sufficient disperse dye dissolved therein to absorb at least 70% of transmitted light of a wavelength at which the disperse dye has its maximum absorption and the lens has a relative transmission of between 95% and 100%. 
     
     
         16 . An ophthalmic lens having an unpolymerized coating on at least one surface of the lens formed from the coating composition of  claim 3 , the polymerized coating having sufficient disperse dye dissolved therein to absorb at least 70% of transmitted light of a wavelength at which the disperse dye has its maximum absorption. 
     
     
         17 . An ophthalmic lens having an unpolymerized coating on at least one surface of the lens formed from the coating composition of  claim 4 , the polymerized coating having sufficient disperse dye dissolved therein to absorb at least 70% of transmitted light of a wavelength at which the disperse dye has its maximum absorption.