Photochromic indeno(2,1-f)naphtho(1,2-b)pyran compounds useful e.g. in photochromic spectacle lenses

摘要

Photochromic indeno(2,1-f)naphtho(1,2-b)pyran derivatives (I) are new. The derivatives are of formula (I). R1, R2 = 1-2 substituents selected from a group E; E = 1-6 carbon (C) alkyl, 1-6 C alkoxy, chloro (Cl) or fluoro (F) or a 5-6 C cycloalkyl, phenyl, benzyl, di-(1-6 C)-alkylamino, dicyclohexylamino, diphenylamino, piperidyl, morpholinyl or pyridyl group; or 2 R1 groups and/or 2 R2 groups = a group completing a benzo, pyrido, pyrazino, pyrimidino, furano or thiopheno ring; m, n = 0, 1 or 2; R4 = G; monochloro- or monofluoro-phenyl; naphthyl, optionally mono-substituted by Cl, F, 1-6 C alkyl or 1-6 C alkoxy; phenanthryl; pyrenyl; (iso)quinolyl, (di)benzofuranyl, (di)benzothienyl, carbazolyl or indolyl attached to the naphthopyran system by a carbocycle; phenyl di- or tri-substituted by Cl, F, 1-6 C alkyl, 1-6 C alkoxy or by a 1-6 C w-phenylalkyl, or 1-6 C w-phenoxyalkyl group, in which the w-phenyl ring may be the X, X' or R4 group of another photochromic pyran system; G = hydrogen (H); hydroxyl (OH); 1-6 C alkyl; 5-6 C cycloalkyl; 1-6 C acyl; 1-6 C alkoxy; a phenyl or benzyl group, optionally mono-substituted by 1-6 C alkyl or 1-6 C alkoxy; Cl; F; X, X' = Z; Z = (a) optionally mono-, di- or tri-substituted phenyl or naphthyl or (b) optionally mono-, di- or tri-substituted pyridyl, furanyl, benzofuran-2- or -3-yl, thienyl, benzothien-2- or -3-yl, in which the substituted are selected from OH, amino, mono- and di-(1-6 C)-alkylamino, piperidino, morpholino, pyrryl, R, Cl and F; (c) R or 3-6 C cycloalkyl, optionally mono-substituted by 1-6 C-alkoxy, Cl or F; R = 1-6 C alkyl, 1-6 C chloroalkyl, 1-6 C fluoroalkyl, 1-6 C alkoxy or mono-(1-6 C)-alkoxy-(1-4 C)-alkyl; or CXX' = saturated 5-10 C monocyclic, 7-12 C bicyclic or 7-12 C tricyclic hydrocarbon ring or fluoren-9-ylidene; or either X or X' = mono- or di-substituted phenyl, substituted in the p-position by phenyl, -(CH2)p-phenyl or -O-(CH2)p-O-phenyl, in which the second phenyl ring is part of a second, not necessarily identical, photochromic diarylpyran; p = 1-6; Y = H, 1-6 C alkyl, 1-6 C acyl or a benzoyl or naphthoyl group, optionally mono-substituted by 1-6 C alkyl or 1-6 C alkoxy; with the proviso that R1, R2 not = E if R4 = G and X, X' = Z.