Curable resin composition, structural adhesive, coating material or fiber reinforced composite material using the same, foam body using the same, laminate using the same, and cured material thereof

Patent metadata

Field	Value
Publication number	US-10100195-B2
Application number	US-201414896295-A
Country	US
Kind code	B2
Filing date	Jun 5, 2014
Priority date	Jun 7, 2013
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The present invention relates to a curable resin composition comprising a polyol (A) having an average hydroxyl value of 200 to 1500 mg KOH/g, a polyisocyanate (B), and polymer fine particles (C), and a curable resin composition comprising a polyol (A), a polyisocyanate (B), and polymer fine particles (C), wherein the polyol (A) comprises a polyester polyol (a2) as an essential component, and the amount of the polyester polyol (a2) is not less than 20 parts by mass per 100 parts by mass of the polyol (A).

First claim

The invention claimed is:

1. A curable resin composition comprising a polyol (A) having an average hydroxyl value of 200 to 1500 mg KOH/g, a polyisocyanate (B), and polymer fine particles (C), wherein the polymer fine particles (C) have a core-shell structure,
the polymer fine particles (C) have one or more core layers selected from the group consisting of a diene rubber, a (meth)acrylate rubber, and an organosiloxane rubber,
the polymer fine particles (C) have a shell layer graft-polymerized on the core layer,
the shell layer is polymerized with a monomer having a hydroxyl group,
the shell layer is further polymerized with one or more monomers selected from the group consisting of an aromatic vinyl monomer, a vinyl cyanide monomer, and a (meth)acrylate monomer,
the content of the monomer having a hydroxyl group is not less than 4% by mass and not more than 60% by mass per a total monomer used in the formation of the shell layer, and
a dispersion of which the polymer fine particles (C) are dispersed in a part of the polyol (A) is added to the curable resin composition.

2. The curable resin composition according to claim 1 , wherein the polyol (A) comprises a polyether polyol (a1).

3. The curable resin composition according to claim 1 , wherein the polyol (A) has the average hydroxyl value of 350 to 1500 mg KOH/g, and the composition further comprises a curing catalyst (D).

4. The curable resin composition according to claim 2 , wherein the amount of the polyether polyol (a1) is not less than 50 parts by mass per 100 parts by mass of the polyol (A).

5. The curable resin composition according to claim 1 , wherein the polyisocyanate (B) is contained in an amount of 2 to 5000 parts by mass per 100 parts by mass of the polyol (A), and the polymer fine particles (C) are contained in an amount of 1 to 100 parts by mass per 100 parts by mass of the polyol (A) and the polyisocyanate (B).

6. The curable resin composition according to claim 1 , wherein the polymer fine particles (C) have the volume average particle diameter of 10 to 2000 nm.

7. The curable resin composition according to claim 1 , wherein the diene rubber is one or more rubbers selected from the group consisting of a butadiene rubber and a butadiene-styrene rubber.

8. The curable resin composition according to claim 2 , wherein the polymer fine particles (C) are dispersed in a state of primary particles in the curable resin composition.

9. The curable resin composition according to claim 1 , wherein the polyol (A) comprises a multifunctional polyol having three or more functional groups.

10. The curable resin composition according to claim 9 , wherein the amount of the multifunctional polyol having three or more functional groups is not less than 20 parts by mass per 100 parts by mass of the polyol (A).

11. The curable resin composition according to claim 1 , wherein the polyisocyanate (B) has a cyclic structure, a linear structure or a branched structure.

12. The curable resin composition according to claim 11 , wherein the polyisocyanate (B) is an aromatic polyisocyanate.

13. The curable resin composition according to claim 1 , wherein the polyisocyanate (B) has 2.1 or more isocyanate groups on the average per one molecule.

14. The curable resin composition according to claim 11 , wherein the polyisocyanate (B) is one or more polyisocyanates selected from the group consisting of an alicyclic polyisocyanate and an aliphatic polyisocyanate.

15. The curable resin composition according to claim 14 , wherein the polyisocyanate (B) is the alicyclic polyisocyanate.

16. The curable resin composition according to claim 1 , wherein a curing catalyst (D) is contained in an amount of 0.001 to 20 parts by mass per 100 parts by mass of the polyol (A) and the polyisocyanate (B).

17. The curable resin composition according to claim 16 , wherein the curing catalyst (D) is an organotin compound.

18. The curable resin composition according to claim 1 , wherein a dehydrating agent (E) is contained in an amount of 0.1 to 30 parts by mass per 100 parts by mass of the polyol (A) and the polyisocyanate (B).

19. The curable resin composition according to claim 1 , wherein a ratio (β/α) of the total molar amount (β) of the isocyanate group of the polyisocyanate (B) to the total molar amount (α) of the hydroxyl group of the polyol (A) is 0.7 to 1.5.

20. The curable resin composition according to claim 1 , comprising a urethane prepolymer obtained from the reaction of the polyol (A) and the polyisocyanate (B).

21. The curable resin composition according to claim 20 , comprising a urethane prepolymer having an isocyanate group obtained from the reaction of the polyol (A) and the polyisocyanate (B) such that an equivalent ratio (NCO/active hydrogen-containing group) of the isocyanate group (NCO) of the polyisocyanate (B) to the active hydrogen-containing group of the polyol (A) is 1.05 to 5.0.

22. A one pack type moisture-curable resin composition comprising the curable resin composition according to claim 21 .

23. A two pack type curable resin composition comprising the curable resin composition according to claim 1 , wherein the composition comprises a first liquid containing a polyisocyanate (B) and a second liquid containing a polyol (A), polymer fine particles (C) and a curing catalyst (D).

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

25. A structural adhesive formed by using the curable resin composition according to claim 1 .

26. A coating material formed by using the curable resin composition according to claim 1 .

27. A laminate obtained by coating the curable resin composition according to claim 1 on a metal or a porous base material, and curing the curable resin composition.

28. A fiber reinforced composite material formed by using the curable resin composition according to claim 1 as a binder of a reinforced fiber.

29. A foam body obtained by expanding the curable resin composition according to claim 1 .

30. The cured product according to claim 24 , wherein the cured product has a glass transition temperature of 75° C. or more.

Assignees

• Kaneka Corp

Inventors

• Okamoto Toshihiko
• Nishimori Shohei

Classifications

• C08G18/4829

  Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08J2375/04

  Polyurethanes · CPC title

• C08G18/4825

  Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08J2419/00

  Characterised by the use of rubbers not provided for in groups C08J2407/00 - C08J2417/00 · CPC title

• C09D175/04

  Polyurethanes · CPC title