Source: {"pile_set_name": "USPTO Backgrounds"}

The invention is therefore based on the problem of avoiding the described disadvantages entailed in prior art and to provide photochromic compounds which present properties improved over those of the structures described in prior art and which, in the form excited by light, present a bathochromically shifted absorption in the longest wavelength range within the visible part of the spectrum, compared against comparable prior art compounds. Accordingly compounds had to be found which present a further bathochromic shift of their absorption maximums in the visible range by roughly 100 nm, as compared against the known compounds. Furthermore, the absorption band in the longest wavelength range, i.e. the absorption band between the red or infrared part of the light spectrum and the "absorption gap"--i.e. the point of lowest absorption in the range from 400 to 500 nm--should be as broad as possible. Another objective consisted therefore in the provision of compounds displaying absorption characteristics which offers still a 50% absorption in response to very strong obscuration (transmission at .lambda..sub.max &lt;10%) at 700 nm and at least a 10% absorption still at 750 nm.
Moreover, the preferred compounds should not present a distinct basic function because experience had shown that these lenses not only tend to add protons and result in colour distortions in the production of photochromic plastic lenses in mass-dyeing processes but in permanent use also tend to give rise to secondary reactions under the influence of light which result in the loss of the photochromic reaction.
Moreover, the method of producing the new compounds should be improved over conventional methods, with a main emphasis on a simple process control, cautious reaction conditions and sound yields.
The above-explained problem of the invention is solved by the photochromic naphthopyrane-dyes having the general formula (I) ##STR1## wherein R.sub.1 and R.sub.2
are equal or different, independently of each other, and are selected from PA1 or PA1 or PA1 is selected from PA1 or from PA1 or from PA1 are selected, independently of each other, from the group z consisting of (a) and (b), with PA1 or are selected from PA1 or PA1 or PA1 and Y PA1 (1) 6-methoxy-3-(4-methoxyphenyl)-3,13-diphenyl-13-hydroxy-benz[p]-indeno [2,1-f]naphtho[1,2-b]pyrane PA1 (2) 6-methoxy-3-(4-methoxyphenyl)-3-phenyl-13-(2,5-dimethylphenyl)-13-hydroxy- benz[p]indeno[2,1-f]naphtho[1,2-b]pyrane, PA1 (3) 3-(4-diphenyl amino phenyl)-3-phenyl-13-(2,5-dimethylphenyl)-13-hydroxy-benz[p]indeno[2,1-f]na phtho[1,2-b]pyrane, PA1 (4) 3-(4-diphenyl amino phenyl)-6-methoxy-3,13-diphenyl-13-hydroxy-indeno[2,1-f]naphtho-[1,2-b]pyr ane, PA1 (5) 3-(4-diphenyl amino phenyl)6-methoxy-3-phenyl-13-(2,5-dimethylphenyl)-13-hydroxy-indeno[2,1-f] naphtho[1,2-b]pyrane, PA1 (6) 6-methoxy-3-(4-methoxy phenyl)-3-phenyl-13-(2,5-dimethylphenyl)-13-hydroxy-indeno[2,1-f]naphtho[1 ,2-b]pyrane, PA1 (7) 6-methoxy-3-(4-methoxyphenyl)-3-phenyl-13-(1-naphthyl)-13-hydroxy-indeno [ 2,1-f]-naphtho[1,2-b]pyrane, PA1 (8) 6,11-dimethoxy-3-(4-methoxyphenyl)-3-phenyl-13-(2,5-dimethyl phenyl)-13-hydroxy-indeno[2,1-f]naphtho[1,2-b]pyrane, PA1 (9) 3-(4-methoxyphenyl)-3-phenyl-13-(2,5-dimethylphenyl)-13-hydroxy-indeno-[2, 1-f]-naphtho[1,2-b]pyrane, and PA1 (10) 6-methoxy-3-(4-methoxyphenyl)-3-phenyl-13-(3-methyl-2-thienyl)-13-hydroxy- indeno[2,1-f]naphtho[1,2-b]pyrane.
the group f consisting of (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkoxy, chloro and fluoro; PA2 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, with m, n=0, 1 or 2; PA2 two R.sub.1 and/or two R.sub.2 form together, independently of each other, a carbo- or hetero-cyclic ring, selected from benzene, pyridine, pyrazine, pyrimidine, furan and thiophene; PA2 the group g consisting of hydrogen, hydroxy, (C.sub.1 -C.sub.6)-alkyl, (C.sub.5 -C.sub.6)-cyclo-alkyl, (C.sub.1 -C.sub.6)-acyl, (C.sub.1 -C.sub.6)-alkoxy, phenyl, benzyl, mono-substituted phenyl, mono-substituted benzyl, with the aryl substituents being (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy: PA2 mono-chlorine or mono-fluorine substituted phenyl, naphthyl, phenanthryl, pyrenyl, chinolyl, isochinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl or indolyl, each in non-substituted or mono-substituted form, with the substituents being selected from the group consisting of chloro, fluoro, (C.sub.1 -C.sub.6)-alkyl, or (C.sub.1 -C.sub.6)-alkoxy; PA2 di- or tri-substituted phenyl, with the substituents being selected form 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 possibly representing again the X, X'- or R.sub.4 radical of another photochromic pyrane system; PA2 (a) the non-, mono-, di- and tri-substituted aryl groups phenyl and naphthyl; and PA2 (b) the non-, mono-, di- and tri-substituted hetero-cyclic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl and benzothien-3-yl, PA2 and with the substituents in (a) and (b) being selected from PA2 the group h consisting of hydroxy, amino, mono-(C.sub.1 -C.sub.6)-alkyl-amino, 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 PA2 the group (a) consisting of non-basic amines such as non-substituted or substituted di-arylamino, pyrazole, imidazole, indole, pyridine, pyrazoline, imidazoline, pyrroline, phenothiazine, phenoxazine, phenazine, acridine, or carbazole, with the substituents on the non-basic amines being selected from (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, phenyl, fluoro, chloro and bromo; PA2 (c) (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-chloro-alkyl