Novel photochromic naphthopyrans

Details Novel photochromic naphthopyrans Novel photochromic naphthopyrans

C - Chemistry, Metallurgy

07

D

C07D 311/92 (2006.01) C07D 493/04 (2006.01) G02B 1/00 (2006.01) G02B 5/23 (2006.01)

Patent

CA 2385728

Described are novel photochromic 2H-naphtho[1,2-b]pyran compounds essentially characterized by having two adjacent moderates to strong electron donor substituents at the 8 and 9 positions or a fused heterocyclic group formed by the substituents coming together, weak to moderate electron donors at the 2 position and a rating of at least 80 in the Relative .DELTA.OD at Saturation Test. The compounds also have certain substituents at the 5 position and optionally at the 6 position of the naphtho portion of the compound. These compounds may be represented by graphic formula (I). Also are described polymeric organic host materials that contain or that are coated with such compounds. Optically clear articles such as ophthalmic lenses or adjacent plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, benzopyrans, and spiro (indoline) type compounds, are also described.

La présente invention concerne des composés photochromes 2H-naphto[1,2-b]pyranes essentiellement caractérisés par la présence de deux substituants adjacents, donneurs d'électrons modérés à forts, aux positions 8 et 9 ou de celle d'un groupe hétérocyclique condensé formé par ces deux substituants, avec des donneurs d'électrons modérés à forts en position 2, et une valeur d'au moins 80 de la DELTA DO relative au test de saturation. Les composés peuvent aussi comporter certains substituants en position 5 et éventuellement en position 6 de la partie naphto du composé. Ces composés peuvent être représentés par la formule graphique (I). L'invention concerne aussi des matériaux hôtes, polymères organiques, qui contiennent ou sont recouverts de tels composés. Elle concerne aussi des articles optiquement clairs, tels que des lentilles ophtalmiques ou des supports transparents adjacents souples, qui incorporent les composés naphtopyranes ou des combinaisons de ces composés avec des composés photochromes complémentaires, par exemple, certains autres naphtopyranes, benzopyranes, et composés de type spiro (indoline).

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