Benzotriazole compound, light absorber, and resin composition

Patent metadata

Field	Value
Publication number	US-12486239-B2
Application number	US-202017760991-A
Country	US
Kind code	B2
Filing date	Sep 18, 2020
Priority date	Sep 18, 2019
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

Provided is a benzotriazole compound represented by Formula (1). In Formula (1), R 1 to R 4 represent substituents. In Formula (1), n1 represents an integer from 0 to 4, and n2 represents an integer from 0 to 3.

First claim

The invention claimed is:

1 . A benzotriazole compound represented by the following Formula (1):

wherein, in Formula (1), each R 1 independently represents an unsubstituted alkyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a structure represented by Formula (2), wherein the unsubstituted alkyl group is selected from the group consisting of an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, a 1-methylpentyl group, a 4-methyl-2-pentyl group, a 2-ethylbutyl group, an n-heptyl group, a 1-methylhexyl group, an n-octyl group, 1-methylheptyl group, and a 2-ethylhexyl group;
wherein, in Formula (1), each R 2 independently represents a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a carboxylic acid ester group, a sulfonic acid ester group, or a structure represented by the following Formula (2);
wherein, in Formula (1), in a case in which a plurality of R 1 is present, each of the plurality of R 1 may be the same or different, or may be bonded to each other to form a ring;
wherein, in Formula (1), in a case in which a plurality of R 2 is present, each of the plurality of R 2 may be the same or different, or may be bonded to each other to form a ring;
wherein, in Formula (1), each R 3 independently represents a hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted arylcarbonyl group; and
R 4 independently represents a substituted or unsubstituted alkyl group a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylcarbonyl group, or a substituted or unsubstituted arylcarbonyl group,
and R 3 and R 4 may be bonded to each other to form ring; and
wherein, in Formula (1), R 1 is contained in at least one of the 5-position or 6-position of the benzotriazole ring; and
wherein, in Formula (1), n1 represents an integer from 1 to 4, and n2 represents an integer from 0 to 3: and;

wherein, in Formula (2), R 5 represents a linear or branched alkylene group, an arylene group, or a divalent group in which an alkylene group and an arylene group are bonded to each other, and the alkylene group, the arylene group, and the divalent group in which an alkylene group and an arylene group are bonded to each other may contain an oxygen atom;
wherein, in Formula (2), * represents a binding position, and n3 represents an integer from 0 to 3; and
wherein, in Formula (2), X represents a structure represented by the following Formula (X1) or a structure represented by the following Formula (X2):

wherein, in Formula (X1) and Formula (X2), each of R 6 and R 7 independently represents a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a carboxylic acid ester group, or a sulfonic acid ester group;
wherein, in Formula (X1) and Formula (X2), in a case in which a plurality of R 6 is present, each of the plurality of R 6 may be the same or different, or may be bonded to each other to form a ring;
wherein, in Formula (X1) and Formula (X2), in a case in which a plurality of R 7 is present, each of the plurality of R 7 may be the same or different, or may be bonded to each other to form a ring;
wherein, in Formula (X1) and Formula (X2), each of R 8 and R 9 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, or a substituted or unsubstituted carbamoyl group, and R 8 and R 9 may be bonded to each other to form a ring, where * represents a binding position;
wherein, in Formula (X1), m1 represents an integer from 0 to 3, and m2 represents an integer from 0 to 3; and
wherein, in Formula (X2), m3 represents an integer from 0 to 4, and m4 represents an integer from 0 to 2.

2 . The benzotriazole compound according to claim 1 , wherein R 4 is a substituted or unsubstituted alkylcarbonyl group, or a substituted or unsubstituted arylcarbonyl group.

3 . The benzotriazole compound according to claim 1 , wherein R 3 is a hydrogen atom and R 4 is a substituted or unsubstituted alkylcarbonyl group.

4 . The benzotriazole compound according to claim 1 , wherein R 1 is a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a structure represented by Formula (2).

5 . The benzotriazole compound according to claim 1 , having a maximum absorption wavelength of from 330 nm to 430 nm.

6 . A light absorber containing the benzotriazole compound according to claim 1 .

7 . A resin composition, comprising:
(A) a thermoplastic resin or a thermosetting resin; and (B) the benzotriazole compound according to claim 1 .

8 . The resin composition according to claim 7 , wherein a content of the benzotriazole compound is from 500 ppm to 9000 ppm with respect to a total mass of the resin composition.

9 . The resin composition according to claim 7 , wherein a* is from −9 to 1 and b* is from −1 to 19 in a CIE 1976 (L*, a*, b*) color space in a case in which the resin composition is measured at a thickness of 2 mm.

10 . The resin composition according to claim 7 , wherein:
the thermoplastic resin is at least one selected from a polycarbonate resin, a polyamide resin, an acrylic resin, or a polyester resin, and the thermosetting resin is at least one selected from a polyurethane resin, a polythiourethane resin, or an allyldiglycol carbonate resin.

11 . The benzotriazole according to claim 1 , wherein Ri 1 is a substituted or unsubstituted arylthio group, R 3 is a hydrogen atom, and R 4 is a substituted or unsubstituted alkylcarbonyl group.

Assignees

• Mitsui Chemicals Inc
• Yamamoto Chemicals Inc

Inventors

• Kawaguchi Masaru
• Ito Shinsuke
• Totani Yoshiyuki
• Matsui Yusuke
• Kumagae Yojirou
• Kakio Daisuke
• Sawano Bunji
• Naruse Hiroshi
• Yamaguchi Ryoji

Classifications

• C08K5/3475

  condensed with carbocyclic rings · CPC title

• G02C7/10

  Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses · CPC title

• G02B5/22

  Absorbing filters {(G02B5/201 - G02B5/208 take precedence)} · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C09K3/00

  Materials not provided for elsewhere · CPC title