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US 5,238,981 AGranted
Photochromic naphthopyrans
AssigneeTransitions Optical, Inc.
InventorDavid B. Knowles
Life of this patent
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Abstract
Described are novel reversible photochromic naphthopyran compounds substituted at the number eight carbon atom on the naphtho portion of the naphthopyran ring with, for example, a methoxy group. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds are also described.
Claims22
A naphthopyran represented by the following graphic formula:
- ##STR15## wherein R.sub.5 and R.sub.9 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkyl, R.sub.8 is selected from the group consisting of halogen, C.sub.1 -C.sub.5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C.sub.1 -C.sub.5)alkylamino, and LO-, wherein L is a C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.9 aryl(C.sub.1 -C.sub.3)alkyl, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, and B and B' are each selected from the group consisting of the unsubstituted or substituted aryl groups phenyl and naphthyl, said aryl group substituents each being selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl, di(C.sub.1 -C.sub.5)alkylamino, and halogen, said halogen and halo substituents being selected from the group consisting of fluorine, chlorine and bromine, provided that at least one of B and B' is a substituted or unsubstituted phenyl.
A naphthopyran represented by the following graphic formula:
- ##STR16## wherein R.sub.5 and R.sub.9 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkyl, R.sub.8 is selected from the group consisting of halogen, C.sub.1 -C.sub.5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C.sub.1 -C.sub.5)alkylamino, and LO-, wherein L is a C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.9 aryl(C.sub.1 -C.sub.3)alkyl, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, and B and B' are the phenyl groups represented respectively by the following graphic formulae:
- ##STR17## wherein Y.sub.1 is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, fluoro and chloro, Z.sub.1 is selected from the group consisting of hydrogen and Y.sub.1, each Y.sub.2 and Z.sub.2 are selected from the group consisting of C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, cyano, hydroxy, halogen, acrylyl, methacrylyl, acryloxy (C.sub.1 -C.sub.4) alkyl and methacryloxy (C.sub.1 -C.sub.4) alkyl, and a and b are each integers of from 0 to 2.
A naphthopyran selected from the group consisting of:
- (a) 8-methoxy-3,3,-diphenyl-3H-naphtho[2,1-b]pyran,
- (b) 8-methoxy-3-(2-fluorophenyl)-3-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran,
- (c) 8-methoxy-3-phenyl-3-(4-methylphenyl)-3H-naphtho[2,1-b]pyran,
- (d) 8-methoxy-3-phenyl-3-(4-trifluoromethyl)-3H-naphtho[2,1-b]pyran,
- (e) 8-methoxy-3-(2-fluorophenyl)-3-(4-methylphenyl)-3H-naphtho[2,1-b]pyran,
- (f) 8-methoxy-3-(4-dimethylaminophenyl)-3-(phenyl)-3H-naphtho[2,1-b]pyran, and
- (g) 8-acetoxy-3,3-diphenyl-3H-naphtho[2,1-b]pyran.
4 more elements
A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula:
- ##STR18## wherein R.sub.5 and R.sub.9 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkyl, R.sub.8 is selected from the group consisting of halogen, C.sub.1 -C.sub.5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C.sub.1 -C.sub.5)alkylamino, and LO-, wherein L is a C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.9 aryl(C.sub.1 -C.sub.3)alkyl, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, and B and B' are each selected from the group consisting of the unsubstituted or substituted aryl groups phenyl and naphthyl, said aryl group substituents each being selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl, di(C.sub.1 -C.sub.5)alkylamino, and halogen, said halogen and halo substituents being selected from the group consisting of fluorine, chlorine and bromine, provided that at least one of B and B' is a substituted or unsubstituted phenyl.
A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran represented by the following graphic formula:
- ##STR19## wherein R.sub.5 and R.sub.9 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkyl, R.sub.8 is selected from the group consisting of halogen, C.sub.1 -C.sub.5 acyloxy, benzoyloxy, methoxybenzoyloxy, di(C.sub.1 -C.sub.5)alkylamino, and LO-, wherein L is a C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.9 aryl(C.sub.1 -C.sub.3)alkyl, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.1 -C.sub.4 alkyl substituted C.sub.5 -C.sub.7 cycloalkyl, and B and B' are the phenyl groups represented respectively by the following graphic formulae:
- ##STR20## wherein Y.sub.1 is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, fluoro and chloro, Z.sub.1 is selected from the group consisting of hydrogen and Y.sub.1, each Y.sub.2 and Z.sub.2 are selected from the group consisting of C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, cyano, hydroxy, halogen, acrylyl, methacrylyl, acryloxy (C.sub.1 -C.sub.4) alkyl and methacryloxy (C.sub.1 -C.sub.4) alkyl, and a and b are each integers of from 0 to 2.
Dependencies are inferred from the claim text.