Materials and methods for light adjustable ophthalmic devices

An ophthalmic device made by a free radical polymerization of a reactive monomer mixture comprising:

• a) a compound having the chemical structure depicted in Formula I:
• wherein Pg is a polymerizable group, L is a linking group, X is O or NH, R1 is a substituent with at least one double bond capable of undergoing an intramolecular [2+2]cycloaddition reaction with the coumarin double bond in the 3-4 position to form a multi-ring structure including one cyclobutane ring, and R2 is independently at each occurrence hydrogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 thioalkyl group, a C3-C7 cycloalkyl group, phenyl, benzyl, halo, hydroxy, amino, or NR3R4, wherein R3 and R4 are independently hydrogen or a C1-C6 alkyl group;
• b) one or more monomers suitable for making the ophthalmic device;
• c) a cross-linking agent;
• and
• d) a free radical initiator.

An ophthalmic device made by a free radical polymerization of a reactive monomer mixture comprising:

• a) 3,7-dimethyloct-6-en-1-yl 7-((6-(acryloyloxy)hexyl)oxy)-2-oxo-2H-chromene-3-carboxylate, having the chemical structure shown in Formula II:
• b) 4-hydroxybutyl acrylate;
• c) N-butyl acrylate;
• d) ethyl methacrylate;
• e) ethylene glycol dimethacrylate;
• and
• f) azobisisobutyronitrile;
• wherein the concentration of Formula II in the reactive monomer mixture is between 20 and 35 weight percent;
• wherein the concentration of 4-hydroxybutyl acrylate in the reactive monomer mixture is between 15 and 20 weight percent;
• wherein the concentration of N-butyl acrylate in the reactive monomer mixture is between 5 and 20 weight percent;
• wherein the concentration of ethyl methacrylate in the reactive monomer mixture is between 25 and 45 weight percent;
• wherein the concentration of ethylene glycol dimethacrylate in the reactive monomer mixture is between 1 and 3 weight percent;
• and wherein the concentration of azobisisobutyronitrile in the reactive monomer mixture is between 1 and 3 weight percent.