Chromene compound, curable composition comprising the compound, and optical article including a cured body of the curable composition

Patent metadata

Field	Value
Publication number	US-11401276-B2
Application number	US-201816629277-A
Country	US
Kind code	B2
Filing date	Jul 11, 2018
Priority date	Jul 14, 2017
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

A chromene compound having at least one indenonaphthopyran moiety which has a group forming a spiro ring together with the 13-position carbon atom and further an oligomer chain group selected from a polyalkylene oxide oligomer chain group having at least three recurring units and a polyester oligomer chain group having at least three recurring units, represented by the following formula and having reduced matrix dependence:wherein R1 and R2 are each a group which may have an oligomer chain group, the ring Z bonded to the 13-position carbon atom of the chromene compound is a Spiro ring group, and R3 and R4 are each an aryl group or heteroaryl group which may have an oligomer chain group.Preferably, the chromene compound has at least one oligomer chain group in the molecule.

First claim

The invention claimed is:

1. A chromene compound having an indenonaphthopyran moiety, wherein the indenonaphthopyran moiety has a spiro ring formed together with the 13-position carbon atom at the 13-position and an oligomer chain group selected from the group consisting of a polyalkylene oxide oligomer chain group having at least three recurring units and a polyester oligomer chain group having at least three recurring units, and wherein
the chromene compound, which is represented by the following formula (1):

wherein R 1 and R 2 are each independently the oligomer chain group, hydroxyl group, alkyl group, haloalkyl group, cycloalkyl group which may have a substituent, alkoxy group, amino group, substituted amino group, heterocyclic group which may have a substituent, cyano group, halogen atom, alkylthio group, arylthio group which may have a substituent, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group, alkoxycarbonyl group, aralkyl group which may have a substituent, aralkoxy group which may have a substituent, aryloxy group which may have a substituent, aryl group which may have a substituent, heteroaryl group which may have a substituent, thiol group, alkoxyalkylthio group, haloalkylthio group or cycloalkylthio group which may have a substituent, “a” is an integer of 0 to 4, “b” is an integer of 0 to 4, when “a” is 2 to 4, a plurality of R 1 's may be the same or different, when “b” is 2 to 4, a plurality of R 2 's may be the same or different, when “a” is 2 to 4 and adjacent R 1 's are existent, two adjacent R 1 's may form together with two carbon atoms bonded to these R 1 's a ring which may include an oxygen atom, carbon atom, sulfur atom or nitrogen atom, and further the ring may have a substituent, when “b” is 2 to 4 and adjacent R 2 's are existent, two adjacent R 2 's may form together with two carbon atoms bonded to these R 2 's a ring which may include an oxygen atom, carbon atom, sulfur atom or nitrogen atom, and further the ring may have a substituent; R 3 and R 4 are each independently the oligomer chain group, an aryl group which may have a substituent, or heteroaryl group which may have a substituent and at least one of R 3 and R 4 is the oligomer chain group, the aryl group having the oligomer chain group, or the heteroaryl group having the oligomer chain group; the spiro ring Z represented by the following formula (Z) and bonded to the 13-position of the chromene compound together with the 13-position carbon atom is an aliphatic ring which may have a substituent and has 3 to 20 carbon atoms constituting the ring together with the 13-position carbon atom, condensed polycyclic ring obtained by condensing an aromatic ring or aromatic heterocyclic ring which may have a substituent to the aliphatic ring, heterocyclic ring which may have a substituent and has 3 to 20 atoms constituting the ring together with the 13-position carbon atom, or condensed polycyclic ring obtained by condensing an aromatic ring or aromatic heterocyclic ring which may have a substituent to the heterocyclic ring; and the substituent of each of the groups which may have a substituent may be the oligomer chain group to ensure that the chromene compound has at least one oligomer chain group in the molecule

2. The chromene compound according to claim 1 , wherein the spiro ring Z represented by the formula (Z) is a ring selected from cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclononane ring, cyclodecane ring, cycloundecane ring, cyclododecane ring and spirodicyclohexane ring, the ring may have 1 to 10 alkyl groups with 1 to 3 carbon atoms or 1 to 10 cycloalkyl groups with 5 to 7 carbon atoms as substituents, or the ring is a ring to which a cycloalkyl group having 5 to 7 carbon atoms may be condensed.

3. The chromene compound according to claim 1 , wherein the spiro ring Z represented by the formula (Z) is a ring selected from the following formulas:

wherein carbon atoms having bonds shown by a dotted line are the 13-position carbon atoms.

4. The chromene compound according to claim 1 , which is represented by the following formula (2):

wherein R 1 , R 2 , “a”, “b” and spiro ring Z are as defined in the formula (1); R 100 and R 101 are each independently the oligomer chain group, hydrogen atom, hydroxyl group, alkyl group having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 8 carbon atoms, alkoxy group having 1 to 6 carbon atoms, amino group, substituted amino group, heterocyclic group which may have a substituent, cyano group, halogen atom, alkylthio group having 1 to 6 carbon atoms, arylthio group having 6 to 10 carbon atoms which may have a substituent, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group having 2 to 7 carbon atoms, alkoxycarbonyl group having 2 to 7 carbon atoms, aralkyl group having 7 to 11 carbon atoms which may have a substituent, aralkoxy group having 7 to 11 carbon atoms which may have a substituent, aryloxy group having 6 to 12 carbon atoms which may have a substituent, aryl group having 6 to 12 carbon atoms which may have a substituent, heteroaryl group having 3 to 12 carbon atoms which may have a substituent, thiol group, alkoxyalkylthio group having 2 to 9 carbon atoms, haloalkylthio group having 1 to 6 carbon atoms or cycloalkylthio group having 3 to 8 carbon atoms, and R 100 and R 101 may form a ring represented by the following formula (3) together;

in the above formula, two asterisk marks represent 6-position or 7-position carbon atom, and either one or both of X and Y are sulfur atoms, methylene groups, oxygen atoms or groups represented by the following formula (4):

in the above formula, R 7 is the oligomer chain group, hydrogen atom, hydroxyl group, alkyl group having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 8 carbon atoms, alkoxy group having 1 to 6 carbon atoms, aryl group having 6 to 12 carbon atoms which may have a substituent or heteroaryl group having 3 to 12 carbon atoms which may have a substituents;
R 5 and R 6 are each independently the oligomer chain group, hydroxyl group, alkyl group having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 8 carbon atoms, alkoxy group having 1 to 6 carbon atoms, amino group, substituted amino group, heterocyclic group which may have a substituent, cyano group, nitro group, formyl group, hydroxycarbonyl group, alkylcarbonyl group having 2 to 7 carbon atoms, alkoxycarbonyl group having 2 to 7 carbon atoms, halogen atom, aralkyl group having 7 to 11 carbon atoms which may have a substituent, aralkoxy group having 7 to 11 carbon atoms which may have a substituent, aryl group having 6 to 12 carbon atoms which may have a substituent, thiol group, alkylthio group having 1 to 6 carbon atoms, alkoxyalkylthio group having 2 to 9 carbon atoms, haloalkylthio group having 1 to 6 carbon atoms, cycloalkylthio group having 3 to 8 carbon atoms, or arylthio group having 6 to 10 carbon atoms which may have a substituent, and R 5 and R 6 may form an aliphatic ring which may have a substituent together with carbon atoms bonded thereto

Assignees

• Tokuyama Corp

Inventors

• Miyazaki Masayuki
• Takenaka Junji

Classifications

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C07D497/10 Primary

  Spiro-condensed systems · CPC title

• C08G65/26

  from cyclic ethers and other compounds · CPC title

• C09K9/02

  Organic tenebrescent materials · CPC title

• G02B5/23

  Photochromic filters · CPC title