The Plessey Company Plc

John Whittall

Harry G Heller

Stephen N Oliver

Clive Trundle

Jack Brettle

Martin W Baskerville

A series of novel photochromic spiropyrans are disclosed in which a spiro-adamantane group is introduced into the 2-position of the benzopyran or naphthopyran ring. The spiropyran compounds of the invention exhibit heliochromic properties, i.e. they color in sunlight and fade rapidly at ambient temperatures in the absence of U.V. light, making them good candidates for use in the manufacture of sunglasses. The invention includes lenses which darken in sunlight and incorporate the novel spiropyrans and a process for the preparation of the spiropyran compounds.

Photochromic spiropyran compounds

Photoreactive plastics lenses are disclosed which are coated or impregnated with an adamantane 2-spiro-benzo or naphthopyran and with a blue coloring photochromic benzo- or naphthopyran having a nitrogen containing substituent in the 2-position in the pyran ring. The lenses darken in sunlight and fade rapidly at ambient temperatures in the dark or in white light which does not contain a U.V. component. The combination of the yellow/orange coloring adamantane 2-spiro pyran compound with the purple/blue coloring pyran gives a desired brown/grey coloration in the sunlight-darkened lens. The invention includes novel blue-coloring pyran compounds in which the nitrogen-containing substituent in the 2-position is a phenyl group having an amino or substituted amino or nitrogen-containing heterocyclic substituent in the ortho- or para-position of the phenyl group. The basic chromene structure and the suffix N will be used to distinguish the blue-coloring pyran compounds having a nitrogen-containing substituent, namely: ##STR1##

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Caerphilly, United Kingdom

John Whittall