Photochromic benzopyrano-fused naphthopyrans

A naphthopyran compound represented by the following:

• ##STR16## wherein, (a) R.sub.1 and R.sub.2 together form an oxo group or R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allyl, phenyl, mono- or di-substituted phenyl, benzyl or mono-substituted benzyl, each of said phenyl and benzyl group substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy;
• (b) each R.sub.3 and R.sub.4 are selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, chloro and fluoro, and m and n are each the integer 0, 1 or 2;
• and
• (c) B and B' are each selected from the group consisting of:
• (i) the unsubstituted, mono-, di-, and tri-substituted aryl groups, phenyl and naphthyl;
• (ii) the unsubstituted, mono- and di-substituted heteroaromatic groups, pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, and fluorenyl, each of said aryl and heteroaromatic substituents in (d) (i) and (ii) being selected from the group consisting of hydroxy, aryl, mono(C.sub.1 -C.sub.6)alkoxyaryl, di(C.sub.1 -C.sub.6)alkoxyaryl, mono(C.sub.1 -C.sub.6)alkylaryl, di(C.sub.1 -C.sub.6)alkylaryl, chloroaryl, fluoroaryl, C.sub.3 -C.sub.7 cycloalkylaryl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyloxy, C.sub.3 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.6)alkyl, C.sub.3 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.6)alkoxy, aryl(C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.6)alkoxy, aryloxy, aryloxy(C.sub.1 -C.sub.6)alkyl, aryloxy(C.sub.1 -C.sub.6)alkoxy, mono- and di-(C.sub.1 -C.sub.6)alkylaryl(C.sub.1 -C.sub.6)alkyl, mono- and di-(C.sub.1 -C.sub.6)alkoxyaryl(C.sub.1 -C.sub.6)alkyl, mono- and di-(C.sub.1 -C.sub.6)alkylaryl(C.sub.1 -C.sub.6)alkoxy, mono- and di-(C.sub.1 -C.sub.6)alkoxyaryl(C.sub.1 -C.sub.6)alkoxy, amino, mono(C.sub.1 -C.sub.6)alkylamino, di(C.sub.1 -C.sub.6)alkylamino, diarylamino, piperazino, N-(C.sub.1 -C.sub.6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.6 alkoxy, mono(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.4)alkyl, acryloxy, methacryloxy, bromo, chloro and fluoro, said aryl group being phenyl or naphthyl;
• (iii) the unsubstituted or mono-substituted groups diarylamino, pyrazolyl, imidazolyl, indolyl, pyridyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, said aryl group being phenyl or naphthyl, each of said substituents being 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;
• (iv) para-substituted phenyl wherein said para substituent is the linking group, --(CH.sub.2).sub.t -- or --O--(CH.sub.2).sub.t --, wherein t is the integer 1, 2, 3, 4, 5 or 6, said linking group being connected to an aryl group, which is a segment of another photochromic naphthopyran;
• (v) the groups represented by the following graphic formulae:
• ##STR17## wherein A is carbon or oxygen and D is oxygen or substituted nitrogen, provided that when D is substituted nitrogen, A is carbon, said nitrogen substituents being selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, and C.sub.2 -C.sub.6 acyl;
• each R.sub.5 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxy, chloro or fluoro;
• R.sub.6 and R.sub.7 are each hydrogen or C.sub.1 -C.sub.6 alkyl;
• and p is the integer 0, 1, or 2;
• (vi) C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, 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, mono(C.sub.1 -C.sub.6)alkyl(C.sub.3 -C.sub.6)cycloalkyl, chloro(C.sub.3 -C.sub.6)cycloalkyl, fluoro(C.sub.3 -C.sub.6)cycloalkyl and C.sub.4 -C.sub.12 bicycloalkyl;
• and
• (vii) the group represented by the following graphic formula:
• ##STR18## wherein L is hydrogen or C.sub.1 -C.sub.4 alkyl and M is selected from the unsubstituted, mono-, and di-substituted members of the group consisting of naphthyl, phenyl, furanyl, and thienyl, each of said group substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoro, or chloro;
• or
• (e) B and B' taken together form fluoren-9-ylidene, mono-, or di-substituted fluoren-9-ylidene or a member selected from the group consisting of saturated C.sub.3 -C.sub.12 spiro-monocyclic hydrocarbon rings, saturated C.sub.7 -C.sub.12 spiro-bicyclic hydrocarbon rings, and saturated C.sub.7 -C.sub.12 spiro-tricyclic hydrocarbon rings, each of said fluoren-9-ylidene substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoro and chloro.