Curable resin composition, cured product thereof, laminate, and method for producing laminate

Patent metadata

Field	Value
Publication number	US-9487682-B2
Application number	US-201214009417-A
Country	US
Kind code	B2
Filing date	Apr 5, 2012
Priority date	Apr 5, 2011
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

This curable resin composition comprises (A) a polymerizable (meth)acrylic-based monomer, (B) a thiourea compound component, and (C) a peroxide component having a structure of formula (1), and may have (D) a (meth) acrylic-based polymer component as an optional component. (In formula (1), R is a C1-15 hydrocarbon group.) In the curable resin composition, preferably, the content of the (A) component is 5-100 mass % and the content of the (D) component is 0-95 mass % relative to the total mass of the (A) component and the (D) component.

First claim

The invention claimed is:

1. A curable resin composition comprising:
(A) a polymerizable (meth)acrylic-based monomer component;
(B) a thiourea compound component; and
(C) a peroxide component having a structure of the following formula (1),
wherein the composition may contain (D) a (meth)acrylic-based polymer component as an optional component,

wherein R in the formula (1) is a hydrocarbon group with a carbon number of 1 to 15.

2. The curable resin composition according to claim 1 , wherein
a content of the (A) component is 5 to 100 mass %, and
a content of the (D) component is 0 to 95 mass %,
relative to the total mass of the (A) component and the (D) component.

3. The curable resin composition according to claim 1 , wherein
a content of the (A) component is 80 to 100 mass %, and
a content of the (D) component is 0 to 20 mass %,
relative to the total mass of the (A) component and the (D) component.

4. The curable resin composition according to claim 1 , wherein
a content of the (A) component is 80 to 98 mass %, and
a content of the (D) component is 2 to 20 mass %,
relative to the total mass of the (A) component and the (D) component.

5. The curable resin composition according to claim 1 ,
wherein the (B) component is at least one compound selected from the group consisting of thiourea, ethylene thiourea, N,N′-dimethyl thiourea, N,N′-diethyl thiourea, N,N′-dipropyl thiourea, N,N′-di-n-butyl thiourea, N,N′-dilauryl thiourea, N,N′-diphenyl thiourea, trimethyl thiourea, 1-acetyl-2-thiourea and 1-benzoyl-2-thiourea; and
wherein the (C) component is at least one compound selected from the group consisting of t-hexylperoxy isopropyl monocarbonate, t-butylperoxy isopropyl monocarbonate, t-butylperoxy 2-ethylhexyl monocarbonate, t-butylperoxy allyl monocarbonate and 1,6-bis(t-butylperoxy carbonyloxy)hexane.

6. The curable resin composition according to claim 1 , comprising:
0.05 to 5 parts by mass of the (C) component; and
0.1 to 10 parts by mass of the (D) components,

relative to a total of 100 parts by mass of the (A) component and the (D) component.

7. The curable resin composition according to claim 6 ,
wherein the (B) component is at least one compound selected from the group consisting of thiourea, ethylene thiourea, N,N′-dimethyl thiourea, N,N′-diethyl thiourea, N,N′-dipropyl thiourea, N,N′-di-n-butyl thiourea, N,N′-dilauryl thiourea, N,N′-diphenyl thiourea, trimethyl thiourea, 1-acetyl-2-thiourea and 1-benzoyl-2-thiourea; and
wherein the (C) component is at least one compound selected from the group consisting of t-hexylperoxy isopropyl monocarbonate, t-butylperoxy isopropyl monocarbonate, t-butylperoxy 2-ethylhexyl monocarbonate, t-butylperoxy allyl monocarbonate and 1,6-bis(t-butylperoxy carbonyloxy)hexane.

8. A cured product obtained by curing the curable resin composition according to claim 1 .

9. A cured product obtained by curing the curable resin composition according to claim 5 .

10. A cured product obtained by curing the curable resin composition according to claim 6 .

11. A cured product obtained by curing the curable resin composition according to claim 7 .

12. A laminate comprising a layer consisting of the cured product according to claim 8 between two substrates.

13. A laminate comprising a layer consisting of the cured product according to claim 9 between two substrates.

14. A laminate comprising a layer consisting of the cured product according to claim 10 between two substrates.

15. A laminate comprising a layer consisting of the cured product according to claim 11 between two substrates.

16. A method for producing the laminate according to claim 12 , comprising:
pouring the curable resin composition according to claim 1 between two opposing substrates; and
curing the curable resin composition.

17. A method for producing the laminate according to claim 13 , comprising:
pouring the curable resin composition according to claim 5 between two opposing substrates; and
curing the curable resin composition.

18. A method for producing the laminate according to claim 14 , comprising:
pouring the curable resin composition according to claim 6 between two opposing substrates; and
curing the composition.

19. A method for producing the laminate according to claim 15 , comprising:
pouring the curable resin composition according to claim 7 between two opposing substrates; and
curing the curable resin composition.

Assignees

• Matsumura Kazunari
• Mitsubishi Rayon Co

Inventors

• Matsumura Kazunari

Classifications

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C09J135/02 Primary

  Homopolymers or copolymers of esters (C09J135/06, C09J135/08 take precedence) · CPC title

• B32B7/14

  applied in spaced arrangements, e.g. in stripes · CPC title

• C08F265/06

  Polymerisation of acrylate or methacrylate esters on to polymers thereof · CPC title