Reactive UV absorber, making method, coating composition, and coated article

Patent metadata

Field	Value
Publication number	US-9873675-B2
Application number	US-201715442242-A
Country	US
Kind code	B2
Filing date	Feb 24, 2017
Priority date	Apr 1, 2013
Publication date	Jan 23, 2018
Grant date	Jan 23, 2018

Abstract

Novel UV absorbers of benzotriazine type having a plurality of (meth)acryloxy groups have a UV absorbing capacity and a high solubility in multifunctional (meth)acrylate. By combining the (meth)acrylic functional UV absorber with various binder precursors such as photo-curable multifunctional (meth)acrylate, there are obtained coating compositions having improved crosslinking density, UV absorbing capacity, anti-bleeding property, and shelf stability.

First claim

The invention claimed is:

1. A coated article comprising
a substrate, and
a cured coating of a coating composition coated on the substrate directly or via at least one other layer,
wherein said coating composition comprises a reactive UV absorber and a binder precursor,
wherein said reactive UV absorber has the general formula (1):

wherein Y 1 and Y 2 are each independently a substituent group of the general formula (2):

wherein * stands for a bonding site, r is 0 or 1, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, —C═N, C 1 -C 5 haloalkyl, —SO 2 R′, —SO 3 H, —SO 3 M (M=alkali metal), —COOR′, —CONHR′, —CONR′R″, —OCOOR′, —OCOR′, —OCONHR′, (meth)acrylamino, (meth)acryloxy, optionally substituted C 6 -C 12 aryl and optionally substituted C 3 -C 12 heteroaryl, wherein R′ and R″ are each independently hydrogen, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, optionally substituted C 6 -C 12 aryl or optionally substituted C 3 -C 12 heteroaryl,
X is a group having the general formula (3) or (4):

wherein *1 bonds to the oxygen in formula (1), *2 bonds to T in formula (1), *3 each independently is hydrogen or bonds to T in formula (1) directly or via a divalent, linear or branched, saturated hydrocarbon group which may be separated by at least one element of oxygen, nitrogen, sulfur, and phosphor, at least one *3 bonds to T directly or via a divalent, linear or branched, saturated hydrocarbon group which may be separated by at least one element of oxygen, nitrogen, sulfur, and phosphor,
T is a urethane group —O—(C═O)—NH—,
Q is a group having the general formula (5) or (6):

wherein *4 bonds to T in formula (1), and *5 bonds to P in formula (1),
P is (meth)acryloxy,
m is 1 or 2, and n is an integer of 1 to 3, with the proviso that m and n are not equal to 1 at the same time.

2. The coated article of claim 1 , wherein the substrate is made of an organic resin or wood.

3. The coated article of claim 1 wherein in formula (1), R 1 , R 2 and R 3 are each independently hydrogen or methyl, X is a group of formula (3), Q is a group of formula (6), m is 2, and n is 1.

Assignees

• Shinetsu Chemical Co

Inventors

• Higuchi Koichi
• Aoki Yukimasa

Classifications

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• C08J2433/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08K5/3492

  Triazines · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• Y10T428/31551

  Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.] · CPC title