Photochromic naphtopyrane colorants, method for the production and use thereof, photochromic object

A photochromic naphthopyran dye corresponding to formula (I):

• ##STR6## wherein R.sub.1 and R.sub.2 are each independently selected from the group f consisting of (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy, chloro and fluoro;
• or
• the group consisting of hydrogen, (C.sub.1 -C.sub.6)-cyclo-alkyl, phenyl, benzyl, dialkyl-(C.sub.1 -C.sub.6)-amino, dicyclo-hexylamino, diphenylamino, piperidyl, morpholinyl and pyridyl;
• and
• m and n each independently represent 0, 1 or 2;
• or
• two groups R.sub.1 and/or two groups R.sub.2 form together, independently of each other, a carbocyclic or heterocyclic ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, furan and thiophene;
• R.sub.4 is selected from
• the group g consisting of hydrogen, hydroxy, (C.sub.1 -C.sub.6)-alkyl, (C.sub.5 -C.sub.6)-cycloalkyl, (C.sub.1 -C.sub.6)-acyl, (C.sub.1 -C.sub.6)-alkoxy, phenyl, benzyl, phenyl mono-substituted with (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy, and benzyl mono-substituted with (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy;
• or from
• mono-chloro or mono-fluoro substituted phenyl, naphthyl, phenanthryl, pyrenyl, chinolyl, isochinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl, each unsubstituted or mono-substituted with a substituent selected from the group consisting of chloro, fluoro, (C.sub.1 -C.sub.6)-alkyl, and (C.sub.1 -C.sub.6)-alkoxy;
• or from
• phenyl di- or tri-substituted with substituents selected from the group consisting of chloro, fluoro, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy, (C.sub.1 -C.sub.6)-.omega.-phenylalkyl and (C.sub.1 -C.sub.6)-.omega.-phenoxy-alkyl with the phenyl ring at the .omega.-position optionally representing the X, X' or R.sub.4 radical of another photochromic pyran system;
• X and X' are each independently selected from
• the group z consisting of (a) and (b), wherein
• (a) consists of the un-, mono-, di- and tri-substituted aryl groups phenyl and naphthyl;
• and
• (b) consists of the un-, mono-, di- and tri-substituted heterocyclic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl and benzothien-3-yl,
• the substituents in (a) and (b) being selected from:
• the group h consisting of hydroxy, amino, mono-(C.sub.1 -C.sub.6)-alkylamino, di-(C.sub.1 -C.sub.6)-alkylamino, piperidino, morpholino, pyrryl;
• -(C.sub.1 -C.sub.6)-alkyl, -(C.sub.1 -C.sub.6)-chloro-alkyl, -(C.sub.1 -C.sub.6)-fluoro-alkyl, -(C.sub.1 -C.sub.6)-alkoxy, mono-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, chloro and fluoro;
• or
• the group a consisting of non-basic amines selected from the group consisting of unsubstituted or substituted diarylamino, pyrazole, imidazole, indole, pyridine, pyrazoline, imidazoline, pyrroline, phenothiazine, phenoxazine, phenazine, acridine, or carbazole, wherein the substituents on the substituted non-basic amines are selected from the group consisting of (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, phenyl, fluoro, chloro and bromo;
• or X and X' are selected from
• (c) (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-chloroalkyl, (C.sub.1 -C.sub.6)-fluoroalkyl, mono-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, mono-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.3 -C.sub.6)-cycloalkyl, chloro-(C.sub.3 -C.sub.6)-cycloalkyl, and fluoro-(C.sub.3 -C.sub.6)-cycloalkyl;
• or
• X and X' together with the carbon atom at the junction with the pyran form a saturated C.sub.5 -C.sub.10 -monocyclic, C.sub.7 -C.sub.12 -bicyclic or C.sub.7 -C.sub.12 -tricyclic hydrocarbon ring or a fluorene-9-ylidene;
• or
• either X or X' is mono- or di-substituted phenyl which is substituted in the position para to the connection site with -phenyl, --(CH.sub.2).sub.p -phenyl or --O--(CH.sub.2).sub.p --O-phenyl substituent, wherein p represents an integer from 1 to 6, and the ring of the substituent group forms part of a second photochromic pyran;
• and
• Y is selected from the group consisting of
• hydrogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-acyl, unsubstituted benzoyl, unsubstituted naphthoyl, benzoyl mono-substituted with (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy, and naphthoyl mono-substituted with (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy;
• with the proviso that R.sub.1 and R.sub.2 are not from the group f if R.sub.4 is from the group g, and X and X' are from the group z, and the members of the group z are unsubstituted or are substituted with substituents from the group h.