# US 5,705,102 A · Photochromic spironaphthopyran compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,705,102 A - Document ID: US5705102A - Status: Granted - Kind: A - Application number: 08/454,956 - Filed: 1995-05-31 - Granted: 1998-01-06 - Earliest claimed: 1994-10-28 - Assignees: Vision-Ease Lens, Inc. - Inventors: Frank J. Hughes; Edward A. Travnicek - Web page: https://patentgrep.com/patent/US5705102A ## CPC - G03C 1/685: Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances - C07D 311/96: spiro-condensed with carbocyclic rings or ring systems - G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G) - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract A naphthopyran compound represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are each selected from the group consisting essentially of hydrogen, a stable organic radical, a heterocyclic group, a halogen, a nitrogen-substituted group, and a nitrogen-substituted ring compound and wherein A is a substituted divalent aromatic radical that includes substituents selected from the group consisting essentially of hydrogen and the stable organic radical. ## Claims ### Claim 1 A photochromic article comprising a host material and a photochromic amount of a naphthopyran compound, the naphthopyran compound represented by the formula: ##STR22## wherein, R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are each selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, a heterocyclic group, a halogen, amino, nitro, morpholino, piperidino, and piperazino; and A is a substituted divalent aromatic radical, the substituents of the divalent aromatic radical selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, and cycloalkyl with the proviso that cyclopentyl and cyclohexyl are excluded. ### Claim 2 (depends on 1) The photochromic article of claim 1 wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are each selected from the group consisting of hydrogen, C1-C2 alkyl, methoxy and ethoxy. ### Claim 3 (depends on 2) The photochromic article of claim 2 wherein the substituents of the divalent aromatic radical are selected from the group consisting of hydrogen, phenyl, naphthyl, alkyl, alkoxy, and cycloalkyl. ### Claim 4 (depends on 1) The photochromic article of claim 1 wherein the host material is made of a polymerized organic compound. ### Claim 5 (depends on 4) The photochromic article of claim 4 wherein the polymerized organic compound is selected from the group consisting of polyacrylate, polycarbonate, polyvinyl alcohol, polyvinyl acetate, polyvinyl chloride, polyurethane, cellulose ester, and a polymer of bis-polyol(allyl carbonate) monomer. ### Claim 6 (depends on 1) The photochromic article of claim 1 wherein the naphthopyran compound is present in an amount of from about 0.01 to about 20 percent by weight, based on the weight of the host material. ### Claim 7 (depends on 1) The photochromic article of claim 1 wherein the article is an optical element. ### Claim 8 (depends on 1) The photochromic article of claim 1 wherein the optical element is a lens. ### Claim 9 (depends on 1) The photochromic article of claim 1 wherein the article is a coating for a substrate. ### Claim 10 (depends on 1) The photochromic article of claim 1, the article further comprising one or more additional photochromic compounds, the naphthopyran compound and the additional photochromic compounds having different maximum wavelengths of activation. ### Claim 11 (depends on 1) The photochromic article of claim 1 wherein the naphthopyran compound is selected from the group consisting of: ##STR23## ### Claim 12 (depends on 1) The photochromic article of claim 1 wherein the substituted divalent aromatic radical is selected from the group consisting of: ##STR24## ### Claim 13 (depends on 1) The photochromic article of claim 1 wherein the substituted divalent aromatic radical is represented by the formula: ##STR25## wherein R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16, and R.sub.17 are selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 14 (depends on 1) The photochromic article of claim 1 wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are each selected from the group consisting of furyl, alkoyl, aroyl, aroyloxy, and the heterocyclic group. ### Claim 15 (depends on 1) The photochromic article of claim 1 wherein either the substituents of the divalent aromatic radical are selected from the group consisting of hydrogen, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that the divalent aromatic radical is substituted with at least one substituent selected from the group consisting of alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, and provided that at least one of the substituents of the divalent aromatic radical is substituted with a radical selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy; or the substituents of the divalent aromatic radical are selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that at least one of the substituents of the divalent aromatic radical is substituted with a radical selected from the group consisting of phenyl, naphthyl, cycloalkyl, furyl, alkoyl, aroyl, and aroyloxy. ### Claim 16 (depends on 1) The photochromic article of claim 1 wherein the divalent aromatic radical includes a five-membered ring radical that is attached to the pyran ring of the naphthopyran compound, the substituents of the divalent aromatic radical selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that at least one of the substituents of the divalent aromatic radical is selected from the group consisting of cycloalkyl, furyl, alkoyl, aroyl, and aroyloxy. ### Claim 17 (depends on 16) The photochromic article of claim 16 wherein the five-membered ring radical that is attached to the pyran ring is represented by the formula: ##STR26## wherein: R.sub.11 and R.sub.12 are either selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, or jointly represent a first aromatic ring radical; R.sub.13 and R.sub.14 are either selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, or jointly represent a second aromatic ring radical; and first aromatic ring radical and the second aromatic ring radical having substituents selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 18 (depends on 19) The photochromic article of claim 19 wherein the first aromatic ring radical and the second aromatic ring radical are selected from the group consisting of phenyl and naphthyl. ### Claim 19 (depends on 1) The photochromic article of claim 1 wherein the divalent aromatic radical includes a six-membered ring radical that is attached to the pyran ring of the naphthopyran compound, the substituents of the divalent aromatic radical selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that at least one of the substituents of the divalent aromatic radical is selected from the group consisting of phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 20 (depends on 19) The photochromic article of claim 19 wherein the six-membered ring radical that is attached to the pyran ring is represented by the formula: ##STR27## wherein R.sub.11, R.sub.12, R.sub.13, R.sub.14, and R.sub.15 are selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that any adjacent two of R.sub.11, R.sub.12, R.sub.13, R.sub.14, and R.sub.15 may jointly represent an aromatic ring radical having substituents selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 21 (depends on 20) The photochromic article of claim 20 wherein the substituted aromatic ring radical is selected from the group consisting of phenyl and naphthyl. ### Claim 22 A naphthopyran compound, the naphthopyran compound represented by the formula: ##STR28## wherein, R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are each selected from the group consisting of hydrogen, a heterocyclic group, halogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, amino, nitro, morpholino, piperidino, and piperazino; and A is a substituted divalent aromatic radical, the substituents of the divalent aromatic radical selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, and cycloalkyl with the proviso that cyclopentyl and cyclohexyl are exluded. ### Claim 23 (depends on 22) The naphthopyran compound of claim 22 wherein the naphthopyran compound is selected from the group consisting of: ##STR29## ### Claim 24 (depends on 22) The naphthopyran compound of claim 22 wherein the substituted divalent aromatic radical is selected from the group consisting of: ##STR30## ### Claim 25 (depends on 22) The naphthopyran compound of claim 22 wherein the substituted divalent aromatic radical is represented by the formula: ##STR31## wherein R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16, and R.sub.17 are selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 26 (depends on 22) The naphthopyran compound of claim 22 wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are each selected from the group consisting of furyl, alkoyl, aroyl, aroyloxy, and the heterocyclic group. ### Claim 27 (depends on 22) The naphthopyran compound of claim 22 wherein either the substituents of the divalent aromatic radical are selected from the group consisting of hydrogen, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that the divalent aromatic radical is substituted with at least one substituent selected from the group consisting of alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, and provided that at least one of the substituents of the divalent aromatic radical is substituted with a radical selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy; or the substituents of the divalent aromatic radical are selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that at least one of the substituents of the divalent aromatic radical is substituted with a radical selected from the group consisting of phenyl, naphthyl, cycloalkyl, furyl, alkoyl, aroyl, and aroyloxy. ### Claim 28 (depends on 22) The naphthopyran compound of claim 22 wherein the divalent aromatic radical includes a five-membered ring radical that is attached to the pyran ring of the naphthopyran compound, the substituents of the divalent aromatic radical selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that at least one of the substituents of the divalent aromatic radical is selected from the group consisting of cycloalkyl, furyl, alkoyl, aroyl, and aroyloxy. ### Claim 29 (depends on 28) The naphthopyran compound of claim 28 wherein the five-membered ring radical that is attached to the pyran ring is represented by the formula: ##STR32## wherein: R.sub.11 and R.sub.12 are either selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, or jointly represent a first aromatic ring radical; R.sub.13 and R.sub.14 are either selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, or jointly represent a second aromatic ring radical; and first aromatic ring radical and the second aromatic ring radical having substituents selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 30 (depends on 29) The naphthopyran compound of claim 29 wherein the first aromatic ring radical and the second aromatic ring radical are selected from the group consisting of phenyl and naphthyl. ### Claim 31 (depends on 22) The naphthopyran compound of claim 22 wherein the divalent aromatic radical includes a six-membered ring radical that is attached to the pyran ring of the naphthopyran compound, the substituents of the divalent aromatic radical selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that at least one of the substituents of the divalent aromatic radical is selected from the group consisting of phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 32 (depends on 31) The naphthopyran compound of claim 31 wherein the six-membered ring radical that is attached to the pyran ring is represented by the formula: ##STR33## wherein R.sub.11, R.sub.12, R.sub.13, R.sub.14, and R.sub.15 are selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy, provided that any adjacent two of R.sub.11, R.sub.12, R.sub.13, R.sub.14, and R.sub.15 may jointly represent an aromatic ring radical having substituents selected from the group consisting of hydrogen, alkyl, phenyl, alkoxy, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, and aroyloxy. ### Claim 33 (depends on 31) The naphthopyran compound of claim 31 wherein the aromatic ring radical is selected from the group consisting of phenyl and naphthyl.