Polyurethane-based photochromic optical materials

A photochromic composition, comprising:

• a polyurethane prepolymer comprising the reaction product of:
• an aromatic, aliphatic or cycloaliphatic isocyanate having the formula R1(NCY)x, where x is greater than or equal to 2, Y is O or S, and R1 is selected from the group consisting of:
• alkylene, arylene, hydrocarbon and substituted hydrocarbon containing one or more aryl-NCY and/or one or more alkyl-NCY bonds;
• and
• a compound having an active hydrogen containing group having the formula (XH)yR2(WH)z, where y+z is greater than or equal to 2, X is O, S, NH, NR3 or COO, W is O, S, NH, NR3 or COO, and R2 is selected from the group consisting of alkylene, arylene polyester, polyether, hydrocarbon and substituted hydrocarbon having 2 to 200 carbon atoms;
• a polysilsequioxane;
• a monomer having the formula
• where y+z is greater than or equal to 1, X is O, S, NH, NR3 or COO, W is O, S, NH, NR3 or COO, w+v is greater than or equal to 1, R5 and R6 are the same or different unsaturated groups, and R4 is selected from the group consisting of alkylene, arylene, polyester, polyether, hydrocarbon and substituted hydrocarbon having from 2 to 200 carbon atoms;
• and
• a photochromic compound.

A method of making a photochromic article, comprising the steps of:

• providing an isocyanate, a compound having an active hydrogen containing group, a monomer that has both an active hydrogen containing group and an unsaturated group, a polysilsequioxane and a photochromic compound;
• combining the photochromic compound with the isocyanate or the compound having an active hydrogen containing group or the monomer that has both an active hydrogen containing group and an unsaturated group;
• combining the isocyanate and the compound having an active hydrogen containing group to form a polyurethane prepolymer;
• combining the monomer with the polyurethane prepolymer to form a urethane resin;
• and
• combining the polysilsequioxane with the urethane resin, and
• polymerizing the mixture to form the article.

A method of making a photochromic article, comprising the steps of:

• providing an isocyanate, a compound having an active hydrogen containing group, a monomer that has both an active hydrogen containing group and an unsaturated group, a polysilsequioxane, a photochromic compound and a photochromic promoter;
• combining the isocyanate and the compound having an active hydrogen containing group to form a polyurethane prepolymer;
• combining the monomer with the polyurethane prepolymer to form a urethane resin;
• combining the photochromic compound with the photochromic promoter;
• combining the photochromic compound, the photochromic promoter and polysilsequioxane with the urethane resin, and polymerizing the mixture to form the article.