Described are novel photochromic indeno-fused naphthopyran compounds having certain substituents at the 2-position of the pyran ring and an alkoxy group at the number 6 carbon atom. Certain other substituents may also optionally be present at the number 5, 7, 8, 9, 10, 11, 12 or 13 carbon atoms of t
Described are novel photochromic indeno-fused naphthopyran compounds having certain substituents at the 2-position of the pyran ring and an alkoxy group at the number 6 carbon atom. Certain other substituents may also optionally be present at the number 5, 7, 8, 9, 10, 11, 12 or 13 carbon atoms of the compounds. These compounds may be represented by the following graphic formula: [ STR 1 ] Also described are certain novel indeno-fused naphthols which are used to make the novel naphthopyran compounds. Further described are polymeric organic host materials that contain or that are coated with the novel naphthopyran compounds, or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, benzopyrans, and spiro(indoline)type compounds.
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[ We claim:] [1.] A naphthopyran compound represented by the following graphic formula: [ STR 16 ] wherein, (a) R.sub.1 is C.sub.1 -C.sub.6 alkoxy;(b) each R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, chloro, or fluoro, and n is the integer 0, 1, or 2;(c) each R.sub.3 is C.sub.1 -C.su
[ We claim:] [1.] A naphthopyran compound represented by the following graphic formula: [ STR 16 ] wherein, (a) R.sub.1 is C.sub.1 -C.sub.6 alkoxy;(b) each R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, chloro, or fluoro, and n is the integer 0, 1, or 2;(c) each R.sub.3 is C.sub.1 -C.sub.6 alkyl, chloro or fluoro, and m is the integer 0, 1 or 2;(d) R.sub.4 and R.sub.5 together form an oxo group, or R.sub.4 and R.sub.5 are each hydrogen, hydroxy, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl, mono-substituted benzyl, or R.sub.4 and R.sub.5 are each the group, --OR.sub.6, wherein R.sub.6 is C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.3 -C.sub.7 cycloalkyl, mono(C.sub.1 -C.sub.4)alkyl substituted C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl or allyl, each of said phenyl and benzyl group substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; and(e) 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, said aryl and heteroaromatic substituents in (e)(i) and (ii) being selected from the group 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 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, chloro and fluoro;(iii) the groups represented by the following graphic formulae: [ STR 17 ] 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.7 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxy, chloro or fluoro; R.sub.8 and R.sub.9 are each hydrogen or C.sub.1 -C.sub.6 alkyl; and p is the integer 0, 1, or 2;(iv) 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 and fluoro(C.sub.3 -C.sub.6)cyclo-alkyl; and(v) the group represented by the following graphic formula: [ STR 18 ] wherein Q is hydrogen or C.sub.1 -C.sub.4 alkyl and Z 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(vi) 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.
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