Novel aromatic substituted naphthopyrans
AssigneeTransitions Optical, Inc.
InventorJibing Lin
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Abstract
Described are photochromic 2H-naphtho[1,2-] pyrans characterized by having an aromatic substituent in the 5 position. The aromatic group at 5-position of the naphthopyran is a substituted or unsubstituted aryl group or other substituted or unsubstituted aromatic group. These compounds may be represented by the following graphic formula: 1 Also described are polymeric organic host materials that contain or that are coated with such compounds.
Claims22
A naphthopyran of 2H-naphtho[1,2-b]pyran structure, characterized by having in the 5 position, a group, —Ar(R2)n(COOR3)p, wherein:
- (a) Ar is selected from the group consisting of:
- (i) an aryl group consisting of phenyl and naphthyl;
- and
- (ii) an aromatic group consisting of furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl and fluorenyl;
- (b) each R2 is selected from the group consisting of aryl, mono(C1-C6)alkoxyaryl, di(C1-C6)alkoxyaryl, mono(C1-C6)alkylaryl, di(C1-C6)alkylaryl, haloaryl, C3-C7 cycloalkylaryl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C3-C7 cycloalkyloxy(C1-C6)alkyl, C3-C7 cycloalkyloxy(C1-C6)alkoxy, aryl(C1-C6)alkyl, aryl(C1-C6)alkoxy, aryloxy, aryloxy(C1-C6)alkyl, aryloxy(C1-C6)alkoxy, mono- and di(C1-C6)alkylaryl(C1-C6)alkyl, mono- and di(C1-C6)alkoxyaryl(C1-C6)alkyl, mono- and di(C1-C6)alkylaryl(C1-C6)alkoxy, mono- and di(C1-C6)alkoxyaryl(C1-C6)alkoxy, C1-C6 alkyl, C1-C6 bromoalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, and halogen, said halo and halogen being bromo, chloro, fluoro or iodo, and n is the integer 0, 1, 2, or 3;
- and
- (c) each R3 is selected from the group consisting of C1-C4 alkyl, phenyl, mono(C1-C4)alkyl substituted phenyl, mono(C1-C4)alkoxy substituted phenyl, phenyl(C1-C2)alkyl, mono(C1-C4)alkyl substituted phenyl(C1-C2)alkyl, mono(C1-C4)alkoxy substituted phenyl(C1-C2)alkyl, mono(C1-C4)alkoxy(C2-C3)alkyl, and C1-C4 haloalkyl, and p is the integer 0, 1 or 2, the sum of n and p being 0, 1, 2 or 3 and wherein when p is 2, n is 0.
A naphthopyran compound selected from the group consisting of:
- (a) 2,2-diphenyl-5-(2-methoxycarbonylphenyl)-2H-naphtho[1,2-b]pyran;
- (b) 2,2-diphenyl-5-(4-methoxycarbonylphenyl)-2H-naphtho[1,2-b]pyran;
- (c) 2,2-diphenyl-5-(thien-2-yl)-2H-naphtho[1,2-b]pyran;
- (d) 2,2-diphenyl-5-(phenyl)-2H-naphtho[1,2-b]pyran;.
- (e) 2-phenyl, 2-(4-methoxyphenyl)-5-phenyl-2H-naphtho[1,2-b]pyran;
- (f) 2,2-di(4-methoxyphenyl)-5-phenyl-2H-naphtho[1,2-b]pyran;
- (g) 2-phenyl, 2-(4-morpholinophenyl)-5-phenyl-2H-naphtho[1,2-b]pyran;
- (h) 2,2-di(4-methoxyphenyl)-9-methoxy-5-phenyl-2H-naphtho[1,2-b]pyran;
- (i) 2-phenyl, 2-(4-morpholinophenyl)-9-methoxy-5-phenyl-2H- naphtho[1,2-b]pyran;
- (j) 2,2-di(4-methoxyphenyl)-5-(4-methylphenyl)-2H-naphtho[1,2-b]pyran;
- (k) 2-phenyl, 2-(4-methoxyphenyl)-5-(4-methylphenyl)-2H-naphtho[1,2-b]pyran;
- and
- (l) 2,2-di(4-methoxyphenyl)-9-methoxy-5-(4-methylphenyl)-2H-naphtho[1,2-b]pyran.
Dependencies are inferred from the claim text.