# US 5,702,645 A · Photochromic chromene derivatives

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,702,645 A
- Document ID: US5702645A
- Status: Granted
- Kind: A
- Application number: 08/550,033
- Filed: 1995-10-30
- Granted: 1997-12-30
- Earliest claimed: 1995-10-30
- Assignees: Vision-Ease Lens, Inc.
- Inventors: Frank J. Hughes
- Web page: https://patentgrep.com/patent/US5702645A

## CPC

- C07D 493/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Described herein are photochromic compounds or a structural isomer of the photochromic compound, the photochromic compounds represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, A, B, C, and D are each selected from the group consisting essentially of hydrogen, a stable organic radical, a heterocyclic group, halogen, a nitrogen-substituted radical, and a nitrogen-substituted ring radical.

## Claims

### Claim 1

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR22## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least one of A, B, C, or D is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 2

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR23## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 or R.sub.8 is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 3

A photochromic compound or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR24## wherein R.sub.1, R.sub.2, R.sub.4 R.sub.5 R.sub.6 R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that R.sub.4 and R.sub.8 are different from each other.

### Claim 4

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR25## wherein R.sub.4, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least one of A, B, C, or D is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 5

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR26## wherein R.sub.4, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 or R.sub.8 is selected from fie group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 6

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR27## wherein R.sub.4, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that R.sub.4 and R.sub.8 are different from each other.

### Claim 7

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR28## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, and R.sub.8 are each individually selected from group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
wherein A, B, C, and D are each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 8

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR29## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, and R.sub.8, are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 or R.sub.8 is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
wherein A, B, C, and D are each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 9

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR30## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, and R.sub.8 are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 and R.sub.8 are different from each other; and
wherein A, B, C, and D arc each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 10

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR31## wherein R.sub.4 and R.sub.8 are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
wherein A, B, C, and D are each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 11

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR32## wherein R.sub.4 and R.sub.8 are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 or R.sub.8 is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
wherein A, B, C, and D are each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 12

A photochromic compound, or a structural isomer of the photochromic compound, the photochromic compound represented by the formula: ##STR33## wherein R.sub.4 and R.sub.8 are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that R.sub.4 and R.sub.8 are different from each other; and
wherein A, B, C, and D am each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino.

### Claim 13

A photochromic composition, the photochromic composition comprising: ##STR34## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least one of A, B, C, or D is selected from the group consisting of alkoxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
at least one structural isomer of: ##STR35##

### Claim 14

A photochromic composition, the photochromic composition comprising: ##STR36## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8 , A, B, C, and D are each individually selected from the group consisting, of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 or R.sub.8 is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino piperidino, and piperazino; and
least one structural isomer of: ##STR37##

### Claim 15

A photochromic composition, the photochromic composition comprising: ##STR38## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that R.sub.4 and R.sub.8 are different from each other; and
at least one structural isomer of: ##STR39##

### Claim 16

A photochromic composition, the photochromic composition comprising: ##STR40## wherein R.sub.4, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least one of A, B, C, or D is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
at least one structural isomer of: ##STR41##

### Claim 17

A photochromic composition, the photochromic composition comprising: ##STR42## wherein R.sub.4, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that at least R.sub.4 or R.sub.8 is selected from the group consisting of alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
at least one structural isomer of: ##STR43##

### Claim 18

A photochromic composition, the photochromic composition comprising: ##STR44## wherein R.sub.4, R.sub.8, A, B, C, and D are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino, provided that R.sub.4 and R.sub.8 are different from each other; and
at least one structural isomer of: ##STR45##

### Claim 19

A photochromic composition, the photochromic composition comprising: ##STR46## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8 are each individually selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
wherein A, B, C, and D are each individually selected from the group consisting of an unsubstituted monovalent aromatic group and a substituted monovalent aromatic group, the substituents of the substituted monovalent aromatic group selected from the group consisting of alkyl, alkoxy, phenyl, naphthyl, cycloalkyl, furyl, alkoyl, alkoyloxy, aroyl, aroyloxy, halogen, amino, dialkyl amino, nitro, morpholino, piperidino, and piperazino; and
at least one structural isomer of: ##STR47##

### Claim 20

A chromene derivative represented by the formula: ##STR48## or, a structural isomer of any of these.