Photochromic naphthopyran compounds
AssigneeTransitions Optical, Inc.
InventorBarry VanGemert
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Abstract
Described are novel reversible photochromic naphthopyran compounds, examples of which are 3-aryl-3-arylalkenyl naphthopyrans. 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 or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
Claims16
A naphthopyran compound represented by the following graphic formula:
- ##STR3## wherein R.sub.1 and R.sub.2 are each selected from the group consisting of C.sub.1 -C.sub.5 acyloxy, benzoyloxy, C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl, mono- or di-substituted phenyl, C.sub.1 -C.sub.4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C.sub.1 -C.sub.4) alkyl, methacryloxy (C.sub.1 -C.sub.4) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, chloro and bromo, a and b are each integers of from 0 to 2, X is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl, and Y and Z are each selected from the group consisting of substituted and unsubstituted naphthyl, furyl, thienyl and phenyl, said substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 alkoxy, chloro and fluoro.
A photochromic article comprising a polymerized organic host material and a photochromic amount of a naphthopyran compound represented by the following graphic formula:
- ##STR4## wherein R.sub.1 and R.sub.2 are each selected from the group consisting of C.sub.1 -C.sub.5 acyloxy, benzoyloxy, C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl, mono- or di-substituted phenyl, C.sub.1 -C.sub.4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C.sub.1 -C.sub.4) alkyl, methacryloxy (C.sub.1 -C.sub.4) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, chloro and bromo, a and b are each integers of from 0 to 2, X is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl, and Y and Z are each selected from the group consisting of substituted and unsubstituted naphthyl, furyl, thienyl and phenyl, said substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, chloro and fluoro.
A photochromic article comprising a solid transparent polymerized organic host material and a photochromic amount of each of (a) a first photochromic substance selected from the group consisting of spiro(indoline)naphthoxazines, spiro(indoline)pyrido benzoxazines, and spiro(indoline)benzoxazines, and (b) a naphthopyran compound represented by the following graphic formula:
- ##STR5## wherein R.sub.1 and R.sub.2 are each selected from the group consisting of C.sub.1 -C.sub.5 acyloxy, benzoyloxy, C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl, mono- or di-substituted phenyl, C.sub.1 -C.sub.4 alkoxy, halogen, acrylyl, methacrylyl, acryloxy (C.sub.1 -C.sub.4) alkyl, methacryloxy (C.sub.1 -C.sub.4) alkyl, furyl and thienyl, said phenyl substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, chloro and bromo, a and b are each integers of from 0 to 2, the sum of a and b being not more than 2, X is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl, and Y and Z are each selected from the group consisting of substituted and unsubstituted naphthyl, furyl, thienyl and phenyl, said substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, chloro and fluoro.
Dependencies are inferred from the claim text.