Curing-type coating-agent composition

Patent metadata

Field	Value
Publication number	US-9403990-B2
Application number	US-201214343323-A
Country	US
Kind code	B2
Filing date	Aug 27, 2012
Priority date	Sep 6, 2011
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

A curing-type coating-agent composition according to the present invention contains: Component (A) (e.g., an isocyanuric ring-containing urethane (meth)acrylate compound) in an amount of from 20 to 80 parts by mass; Component (B) (e.g., an isocyanuric ring-containing tri(meth)acrylate compound free from any urethane bond) in an amount of from 10 to 70 parts by mass; Component (C-1) (e.g., a reaction compound between a colloidal silica and an alkoxysilane compound having a maleimide group) in amount of from 1 to 35 parts by mass, or Component (C-2) (e.g., a specific organosilicon compound) in an amount of from 5 to 35 parts by mass; a radical-polymerization initiator serving as Component (D) in an amount of from 0.1 to 10 parts by mass; an ultraviolet absorber serving as Component (E) in an amount of from 1 to 12 parts by mass; and an organic solvent serving as Component (F) in an amount of from 10 to 1,000 parts by mass; with respect to a sum of the Component (A), the Component (B), and the Component (C-1) or the Component (C-2) being taken as 100 parts by mass. The aforementioned composition demonstrates excellent wear resistance and weatherability as a coating agent for plastic substrate, or the like, which is employed outside.

First claim

The invention claimed is:

1. A curable coating-agent composition being characterized in that:
the curable coating-agent composition contains:
Component (A) in an amount of from 20 to 80 parts by mass;
Component (B) in an amount of from 10 to 70 parts by mass;
Component (C-1) in an amount of from 1 to 35 parts by mass;
a radical-polymerization initiator serving as Component (D) in an amount of from 0.1 to 10 parts by mass;
an ultraviolet absorber serving as Component (E) in an amount of from 1 to 12 parts by mass; and
an organic solvent serving as Component (F) in an amount of from 10 to 1,000 parts by mass;
with respect to a sum of the Component (A), the Component (B) and the Component (C-1) being taken as 100 parts by mass:

wherein Component (A) is an isocyanuric ring-containing urethane (meth)acrylate compound being expressed by following Formula (1):

in Formula (1), each of R 1 , R 2 and R 3 is a divalent organic group whose number of carbon atoms is from 2 to 10 independently; and each of R 4 , R 5 and R 6 is a hydrogen atom, or a methyl group independently;
wherein Component (B) is an isocyanuric ring-containing tri(meth)acrylate compound being free from any urethane bond that is expressed by following Formula (2):

in Formula (2), each of R 7 , R 8 and R 9 is a divalent organic group whose number of carbon atoms is from 2 to 10 independently; each of R 10 , R 11 and R 12 is a hydrogen atom, or a methyl group independently; each of n 1 , n 2 and n 3 is a number of from 1 to 3 independently; and n 1 +n 2 +n 3 =from 3 to 9:
wherein Component (C-1) is an involatile component formed by reacting an alkoxysilane compound (c1) according to Formula (3), with a colloidal silica (c2), wherein a mass ratio of (c1) to (c2) is 9:1 to 1:9;

in Formula (3), R 13 is a hydrogen atom, or a monovalent organic group; R 14 is a divalent hydrocarbon whose number of carbon atoms is from 1 to 6; and “z” is a positive number of from 0.1 or more to 3 or less; wherein when “z” is less than 3, the alkoxysilane compound (c1) is a condensate, and R 13 may be two or more different groups.

2. The curable coating-agent composition as set forth in claim 1 , wherein said Compound (E) includes a benzotriazole-based ultraviolet absorber having a (meth)acryloyl group.

3. The curable coating-agent composition as set forth in claim 1 , wherein said colloidal silica (c2) has an average primary particle diameter of from 1 to 100 nm.

4. The curable coating-agent composition as set forth in claim 1 , wherein R 1 , R 2 and R 3 are a tetramethylene group, respectively; and R 4 , R 5 and R 6 are a hydrogen atom, respectively in Formula (1) for said Component (A).

5. The curable coating-agent composition as set forth in claim 1 , wherein R 7 , R 8 and R 9 are an ethylene group, respectively; R 10 , R 11 and R 12 are a hydrogen atom, respectively; n 1 , n 2 and n 3 are 1, respectively; and n 1 +n 2 +n 3 =3 in Formula (2) for said Component (B).

6. The curable coating-agent composition as set forth in claim 1 further containing a hindered amine-based light stabilizer serving as Component (G) in an amount of from 0.05 to 1.5 parts by mass with respect to a sum of said Component (A), said Component (B) and said Component (C-1) being taken as 100 parts by mass.

7. The curable coating-agent composition as set forth in claim 1 further containing a silicone-based and/or fluorine-based surface modifier serving as Component (H) in an amount of from 0.01 to 1.0 part by mass with respect to a sum of said Component (A), said Component (B) and said Component (C-1) being taken as 100 parts by mass.

8. The curable coating-agent composition as set forth in claim 1 , wherein said Component (D) is a photo radical-polymerization initiator.

9. The curable coating-agent composition as set forth in claim 1 , wherein said Component (C-1) is an involatile component in reaction products obtained by means of a production process that includes:
a step of adding an aminopropyltrialkoxysilane to a carboxylic acid anhydride having a double bond that is expressed by following Formula (6), thereby turning them into an amic acid;
a step of turning said amic acid into a maleimide group by means of subjecting said amic acid to ring closing by heating, and subjecting an alkoxyl group to a hydrolytic condensation reaction with use of water that generates in the ring-closing reaction, thereby obtaining an alkoxysilane compound (c1) being expressed by said Formula (3); and
a step of reacting the obtained (c1) with the colloidal silica (c2) whose average primary particle diameter is from 1 to 100 nm by heating them in the presence of an organic solvent including water:

Assignees

• Takashima Hiroaki
• Kumagai Kyoko
• Hayashi Hidetaka
• Mitsuoka Tetsuya
• Ueda Naoharu
• Muramatsu Hisashi
• Inata Kazumasa
• Fujita Takeshi
• Sanai Yasuyuki
• Okazaki Eiichi
• Yoneda Satoshi
• Furuta Naomasa
• Toyota Jidoshokki Kk
• Toagosei Co Ltd

Inventors

• Takashima Hiroaki
• Kumagai Kyoko
• Hayashi Hidetaka
• Mitsuoka Tetsuya
• Ueda Naoharu
• Muramatsu Hisashi
• Inata Kazumasa
• Fujita Takeshi
• Sanai Yasuyuki
• Okazaki Eiichi
• Yoneda Satoshi
• Furuta Naomasa

Classifications

• C09D7/1233

  Chemistry & Metallurgy · mapped topic

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/673

  containing two or more acrylate or alkylacrylate ester groups · CPC title