Photochromic compounds: Chemistry and application in ophthalmic lenses

Abstract

The preparation of a commercially acceptable plastic photochromic ophthalmic lens requires the incorporation of a number of properties - a neutral activated color, reasonable activation and fade rates, good lifetime, etc.. In this paper we will concentrate on approaches to finding photochromic systems with relatively neutral colors and acceptable rates of activation and fade. The indolino spironaphthoxazines and related compounds have been known for over 25 years. While offering good photochromic properties with regard to kinetics and photostability, they suffer from the fact that the visible absorption bands of the activated, or open, forms have narrow band widths. Also, without difficult to achieve substitution patterns, the absorption bands appear within a relatively narrow range of wavelengths. Partial neutralization of the activated color of the naphthoxazines was achieved through the use of indolino spirobenzoxazines. The open forms within this family exhibited broad absorption bands but the photochromic activity of each of the members was moderate to low. Enhancement of the photochromic activity was possible with triplet sensitization but at the expense of reduced lifetime. True color neutralization was achieved by coupling pyridobenzoxazines with members of a completely different family of photochromic compounds, the naphtliopyrans.