Described are novel photochromic indeno-fused naphthopyran compounds, examples of which are naphthopyran compounds having a substituted or unsubstituted indeno group, the 2,1 positions of which are fused to the f side of the naphtho portion of the naphthopyran, and certain substituents at the 3-posi
Described are novel photochromic indeno-fused naphthopyran compounds, examples of which are naphthopyran compounds having a substituted or unsubstituted indeno group, the 2,1 positions of which are fused to the f side of the naphtho portion of the naphthopyran, and certain substituents at the 3-position of the pyran ring. Certain substituents may also be present at the number 5, 6, 7, 8, 9, 10, 11, 12, or 13 carbon atoms of the compounds. These compounds may be represented by the following graphic formula: [Figure] Also described are polymeric organic host materials that contain or that are coated with such compounds. Optically clear articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, benzopyrans, and spiro(indoline)type compounds, are also described.
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A naphthopyran compound represented by the following graphic formula: [Figure] wherein, (a) R1 and R2 together form an oxo group, a spiro heterocyclic group having 2 oxygen atoms and from 3 to 6 carbon atoms including the spirocarbon atom, or R1 and R2 are each hydrogen, hydroxy, C1-C6 alkyl, C3-C7
A naphthopyran compound represented by the following graphic formula: [Figure] wherein, (a) R1 and R2 together form an oxo group, a spiro heterocyclic group having 2 oxygen atoms and from 3 to 6 carbon atoms including the spirocarbon atom, or R1 and R2 are each hydrogen, hydroxy, C1-C6 alkyl, C3-C7 cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl, mono-substituted benzyl, chloro, fluoro, the group, －C(O)W, wherein W is hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C1-C6)alkylamino, or di(C1-C6)alkylamino, or R1 and R2 are each the group, －OR5, wherein R5 is C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, the group, －CH(R6)X, wherein R6 is hydrogen or C1-C3 alkyl and X is CN, CF3, or COOR7, and R7 is hydrogen or C1-C3 alkyl, or R5 is the group, －C(O)Y, wherein Y is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, the unsubstituted, mono- or di-substituted aryl groups phenyl or naphthyl, phenoxy, mono- or di-(C1-C6)alkyl substituted phenoxy, mono- or di-(C1-C6)alkoxy substituted phenoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di-(C1-C6)alkyl substituted phenylamino, or mono- or di-(C1-C6)alkoxy substituted phenylamino, each of said phenyl, benzyl and aryl group substituents being C1-C6 alkyl or C1-C6 alkoxy; (b) R3 and R4 are each C1-C6 alkyl, C1－C6 alkoxy, chloro, or fluoro, and m and n are each the integers 0, 1, or 2; (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 aromatic heterocyclic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, said aryl and aromatic heterocyclic substituents in (c)(i) and (ii) being selected from the group consisting of hydroxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, piperidino, morpholino, pyrryl, C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy, chloro and fluoro; (iii) the groups represented by the following graphic formulae: [Figure] 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, C1-C6 alkyl, and C2-C6 acyl; each R8 is C1-C6 alkyl, C1-C6 alkoxy, hydroxy, chloro or fluoro; R9 and R10 are each hydrogen or C1-C6 alkyl; and p is the integer 0, 1, or 2; (iv) C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6) alkoxy(C3-C6)cycloalkyl, mono(C1-C6)alkyl(C3-C6)cycloalkyl, chloro(C3-C6)cycloalkyl and fluoro(C3-C6)cycloalkyl; and (v) the group represented by the following graphic formula: [Figure] wherein X is hydrogen or C1-C4 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 C1-C4 alkyl, C1-C4 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 C3-C12 spiro-monocyclic hydrocarbon rings, saturated C7-C12 spiro-bicyclic hydrocarbon rings, and saturated C7-C12 spiro-tricyclic hydrocarbon rings, each of said fluoren-9-ylidene substituents being selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, fluoro and chloro.
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