# US 5,349,065 A · Photochromic compound

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- Number: US 5,349,065 A
- Document ID: US5349065A
- Status: Granted
- Kind: A
- Application number: 07/977,882
- Filed: 1992-11-17
- Granted: 1994-09-20
- Earliest claimed: 1989-06-05
- Assignees: Tokuyama Soda Kabushiki Kaisha
- Inventors: Takashi Tanaka; Satoshi Imura; Kenji Tanaka; Yasuji Kida
- Web page: https://patentgrep.com/patent/US5349065A

## CPC

- C07D 407/04: directly linked by a ring-member-to-ring-member bond
- C07D 311/96: spiro-condensed with carbocyclic rings or ring systems
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 491/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C08K 5/1545: Six-membered rings
- C09K 9/02: Organic tenebrescent materials
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A compound represented by the following general formula (II): ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a phenyl group, a benzyl group, a phenethyl group, an alkylamine group having 1 to 4 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms, and ##STR2## represents a nobornylidene group or bicyclo [3,3,1]9-nonylidene group which may have a substituent, and ##STR3## represents a pyridine, quinoline, pyrrole or benzothiophene group which may have a substituent.

## Claims

### Claim 1

A photochromic compound represented by the following general formula (II): ##STR327## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a phenyl group, a benzyl group, a phenethyl group, an alkylamino group having 1 to 4 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms, ##STR328## represents a norbornylidene group or a bicyclo [3.3.1]9-nonylidene group which may be substituted with at least one member selected from the group consisting of a halogen atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogenoalkyl group having 1 to 4 carbon atoms, a phenyl group, a benzyl group, and a dialkylamino group having 2 to 8 carbon atoms, a phenyl group, a benzyl group and a dialkylamino group having 2 to 8 carbon atoms; ##STR329## represents a divalent unsaturated heterocyclic group selected from the group consisting of a pyridine ring, and a quinoline ring, which may be substituted with at least one member selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenyl group, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, and a halogenalkyl group having 1 to 4 carbon atoms.

### Claim 2 (depends on 1)

A compound as set forth in claim 1, wherein ##STR330## represents said norbornylidene group or said bicyclo [3.3.1]9-nonylidene group which may be substituted with 1 to 3 members which can be the same or different, and are selected from the group consisting of a halogen atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogenoalkyl group having 1 to 4 carbon atoms, a phenyl group, a benzyl group, and a dialkylamino group having 2 to 8 carbon atoms.

### Claim 3 (depends on 1)

A compound as set forth in claim 1, wherein ##STR331## represents a divalent unsaturated heterocyclic group selected from the group consisting of a pyridine ring, and a quinoline ring, which may be substituted with up to five members which may be the same or different selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenyl group, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, and a halogenalkyl group having 1 to 4 carbon atoms.

### Claim 4 (depends on 1)

A compound as set forth in claim 1, wherein ##STR332## represents a divalent unsaturated heterocyclic group selected from the group consisting of a pyridine ring, and a quinoline ring, which may be substituted with 1 to 3 members which may be the same or different selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenyl group, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, and a halogenalkyl group having 1 to 4 carbon atoms.

### Claim 5 (depends on 1)

A compound as set forth in claim 1 selected from the group consisting of ##STR333##

### Claim 6 (depends on 1)

A compound as set forth in claim 1 selected from the group consisting of: ##STR334##

### Claim 7 (depends on 1)

A compound as set forth in claim 1, wherein ##STR335## represents a quinoline ring which may be substituted with at least one member selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenyl group, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, and a halogenalkyl group having 1 to 4 carbon atoms.

### Claim 8 (depends on 3)

A compound as set forth in claim 3, wherein ##STR336## represents a quinoline ring which may be substituted with up to five members which may be the same or different selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenyl group, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, and a halogenalkyl group having 1 to 4 carbon atoms.

### Claim 9 (depends on 4)

A compound as set forth in claim 4, wherein ##STR337## represents a quinoline ring which may be substituted with 1 to 3 members which may be the same or different selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenyl group, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, and a halogenalkyl group having 1 to 4 carbon atoms.

### Claim 10 (depends on 7)

A compound according to claim 7 wherein the quinoline ring has one of the following structures: ##STR338##