# US 2014/0154527 A1 · Chromene compound

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- Number: US 2014/0154527 A1
- Document ID: US20140154527A1
- Status: Published application
- Kind: A1
- Application number: 14/129,069
- Filed: 2012-06-19
- Published: 2014-06-05
- Earliest claimed: 2011-06-23
- Assignees: Tokuyama Corporation
- Inventors: Shinobu Izumi; Kazuhiro Teranishi; Yusuke Daikoku; Mitsuyoshi Sando
- Web page: https://patentgrep.com/patent/US20140154527A1

## CPC

- C09K 9/02: Organic tenebrescent materials
- C07C 39/17: containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol}
- C07C 39/23: polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
- C07C 43/23: containing hydroxy or O-metal groups
- C07C 323/21: with the sulfur atom of the thio group bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
- C07D 295/096: with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 311/92: Naphthopyrans; Hydrogenated naphthopyrans
- C07D 327/04: Five-membered rings
- C07D 497/10: Spiro-condensed systems
- G02B 5/23: Photochromic filters
- C07C 2601/04: with a four-membered ring
- C07C 2601/08: the ring being saturated
- C07C 2601/14: The ring being saturated
- C07C 2601/16: the ring being unsaturated
- C07C 2603/94: containing "free" spiro atoms
- C08L 83/04: Polysiloxanes
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1088: containing oxygen as the only heteroatom
- Y10T 428/31504: Composite [nonstructural laminate]
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A chromene compound having a short fading half period, especially, a short fading half period even at a low temperature in a general-purpose polymer solid matrix. The chromene compound is represented by the following formula (1). wherein R1 is a hydroxyl group or the like, R2 and R3 are each an aryl group or the like, C* is a spiro carbon atom, a spiro ring A represented by the following formula is a saturated hydrocarbon ring having 4 to 12 ring member carbon atoms or the like, and at least one ring member carbon atom constituting the ring A is a group represented by the following formula (4), and X is a divalent group such as arylene group, wherein R7 and R8 are each a cycloalkyl group or the like.

## Claims

### Claim 1

A chromene compound represented by the following formula (1).
wherein R1 is a hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group having a ring member nitrogen atom and bonded to a benzene ring, to which the heterocyclic group bonded via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group, aryl group, heteroaryl group, alkylthio group, cycloalkylthio group, arylthio group, heteroarylthio group or group having a siloxane bond, “a” is an integer of 0 to 4, when “a” is 2 to 4, a plurality of R1's may be the same or different, and two R1's may be bonded together to form a ring, R2 and R3 are each an alkyl group, aryl group, heteroaryl group, group represented by the following formula (2), or group represented by the following formula (3),
wherein R4 is an aryl group or heteroaryl group, R5 is a hydrogen atom, alkyl group or halogen atom, and “m” is an integer of 1 to 3,
wherein R6 is an aryl group or heteroaryl group, and “n” is an integer of 1 to 3.
R2 and R3 may form an aliphatic ring together with carbon atoms to which R2 and R3 bonded, C* is a spiro carbon atom, a spiro ring A represented by the following formula is a saturated hydrocarbon ring or unsaturated hydrocarbon ring having 4 to 12 carbon atoms constituting the ring, and at least one ring member carbon atom constituting the spiro ring A is a group represented by the following formula (4),
wherein R7 and R8 are each an alkyl group having 3 or more carbon atoms, aralkyl group, cycloalkyl group, aryl group or heteroaryl group, and X is a divalent group selected from alkylene group, alkynylene group, cycloalkylene group, arylene group and alkylene-arylene group.

### Claim 2 (depends on 1)

The chromene compound according to claim 1, wherein X is an arylene group in the above formula (1).

### Claim 3 (depends on 1)

The chromene compound according to claim 1 which is represented by the following formula (5).
wherein R1, R2, R3, C*, Spiro ring A and “a” are as defined in the above formula (1), R9 is a hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group having a ring member nitrogen atom and bonded to a benzene ring, to which the heterocyclic group bonded via the nitrogen atom, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group, aryl group, heteroaryl group, alkylthio group, cycloalkylthio group, arylthio group, heteroarylthio group or group having a siloxane bond, “b” is an integer of 0 to 4, when “b” is 2 to 4, a plurality of R9's may be the same or different, and two R9's may be bonded together to form a ring.

### Claim 4 (depends on 1)

A photochromic curable composition comprising the chromene compound of claim 1 and a polymerizable monomer.

### Claim 5 (depends on 1)

A photochromic optical article having a polymer molded product containing the chromene compound of claim 1 dispersed therein as a constituent member.

### Claim 6 (depends on 1)

An optical article having an optical substrate all or part of at least one surface of which is coated with a polymer film comprising the chromene compound of claim 1 dispersed therein as a constituent member.

### Claim 7

A naphthol compound represented by the following formula (6).
wherein R1, X, C*, spiro ring A and “a” are as defined in the above formula (1).