Photo-curable coating composition and coated article

Patent metadata

Field	Value
Publication number	US-9850386-B2
Application number	US-201514746359-A
Country	US
Kind code	B2
Filing date	Jun 22, 2015
Priority date	Jun 23, 2014
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A photo-curable coating composition comprising (1) a polyfunctional (meth)acrylic monomer, (2) a photopolymerization initiator, and (3) a specific hydroxyphenyltriazine base UV absorber has high mar resistance and long-term weather resistance.

First claim

The invention claimed is:

1. A coated article comprising a substrate which is coated with a photo-curable coating composition directly or via another layer,
wherein the photo-curable coating composition comprises (1) a polyfunctional (meth)acrylic monomer, (2) a photopolymerization initiator, and (3) a hydroxyphenyltriazine base UV absorber having the general formula (1):

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

wherein * designates a bonding site, r is 0 or 1, R 1 , R 2 and R 3 are each independently hydrogen, or hydroxyl, C1-C20 alkyl, C4-C12 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C4-C12 cycloalkoxy, C2-C20 alkenyloxy, C7-C20 aralkyl, halogen, —C≡N, C1-C5 haloalkyl, —SO 2 R′, —SO 3 H, —SO 3 M wherein M is an alkali metal, —COOR′, —CONHR′, —CONR′R″, —OCOOR′, —OCOR′, —OCONHR′, (meth)acrylamino, (meth)acryloxy group, optionally substituted C6-C12 aryl or optionally substituted C3-C12 heteroaryl group, wherein R′ and R″ are independently hydrogen, C1-C20 alkyl, C4-C12 cycloalkyl, optionally substituted C6-C12 aryl or optionally substituted C3-C12 heteroaryl group,
X is a divalent, straight or branched, saturated hydrocarbon residue which may be separated by at least one atom selected from oxygen, nitrogen, sulfur, and phosphorus,
T is a urethane group: —O—(C═O)—NH—,
Q is a divalent, straight or branched, saturated hydrocarbon residue which may be separated by at least one oxygen, and
P is a (meth)acryloxy group.

2. The coated article of claim 1 wherein X has the general formula (3) or (4):

wherein *1 bonds to oxygen in formula (1), *2 bonds to T in formula (1), and *3 bonds to T in formula (1) directly or through a divalent, straight or branched, saturated hydrocarbon group which may be separated by at least one atom selected from oxygen, nitrogen, sulfur, and phosphorus, and Q has the general formula (5):

wherein *4 bonds to T in formula (1) and *5 bonds to P in formula (1).

3. The coated article of claim 2 , wherein R 1 , R 2 and R 3 in formula (1) are each independently hydrogen or methyl, X is formula (3), and Q is formula (5).

4. The coated article of claim 1 , wherein the polyfunctional (meth)acrylic monomer is at least one monomer selected from the group consisting of dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tris(2-(meth)acryloxyalkyl)isocyanurate, polyurethane poly(meth)acrylate having at least 5 (meth)acrylic groups in the molecule, and polyester poly(meth)acrylate having at least 5 (meth)acrylic groups in the molecule.

5. The coated article of claim 1 , wherein the photo-curable coating composition further comprises colloidal silica surface treated with a (meth)acrylic functional alkoxysilane.

6. The coated article of claim 1 , wherein the photo-curable coating composition further comprises at least one member selected from the group consisting of:
(i) hindered amine photostabilizers,
(ii) metal oxide fine particles other than colloidal silica surface treated with a (meth)acrylic functional alkoxysilane, and
(iii) UV absorbers other than the hydroxyphenyltriazine base UV absorber having the general formula (1).

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

Assignees

• Shinetsu Chemical Co

Inventors

• Higuchi Koichi
• Aoki Yukimasa

Classifications

• C08K9/06

  with silicon-containing compounds · CPC title

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08F220/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C08K5/3492

  Triazines · CPC title

• C09D7/1241

  Chemistry & Metallurgy · mapped topic