IP Library Granted Patent US 7,569,619
Granted Patent B2
US 7,569,619 · App. 11/123,041 · Granted Aug 4, 2009

Radiation-curable resin composition and cured product thereof

Assignee: Mitsubishi Chemical Corporation
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Quick Facts
Patent No.
US 7,569,619
App. No.
11/123,041
Granted
Aug 4, 2009
Kind
B2
Abstract

A radiation-curable resin composition comprising an inorganic component containing a silica particle composed of a hydrolyzate of an oligomer of an alkoxysilane and a monomer and/or an oligomer thereof, wherein viscosity at 25° C. is from 1,000 to 10,000 centipoises.

Claims (36)

1. A radiation-curable resin composition, comprising:

(i) an inorganic component comprising silica particles obtained by hydrolyzing a mixture consisting of an oligomer of an alkoxysilane and a solvent, and

(ii) a monomer having a radiation-curable functional group, an oligomer having a radiation-curable functional group, or both said monomer and said oligomer,

wherein the solvent is present in an amount of 5% by weight or less based on the total weight of the radiation-curable resin composition,

wherein the viscosity of the radiation curable composition at 25° C. is from 1,000 to 10,000 centipoises, and

wherein the silica particle has a number average particle size of 50 nm or less,

and wherein a cured product of the composition has a light transmittance of 80% or more at an optical path length of 0.1 mm at 550 nm.

2. The radiation-curable resin composition according to claim 1 , wherein surface tension of the composition at 25° C. is 40 mN/m or less.

3. The radiation-curable resin composition according to claim 1 , which comprises a silica particle composed of a hydrolyzate of an oligomer of an alkoxysilane as the inorganic component, the silica particle being surface-treated with a compound selected from the group consisting of a silane coupling agent, a hydrolyzate of a silane coupling agent, and a condensate thereof.

4. The radiation-curable resin composition according to claim 1 , wherein at least one and the oligomer of the monomer has a group capable of forming an intramolecular hydrogen bond or an intermolecular hydrogen bond.

5. The radiation-curable resin composition according to claim 1 , wherein at least one of the monomer and the oligomer contains a urethane bond or a hydroxyalkylene group.

6. The radiation-curable resin composition according to claim 5 , wherein at least one of the monomer and the oligomer having a radiation-curable group and containing a urethane bond or a hydroxyalkylene group, has an acid group.

7. The radiation-curable resin composition according to claim 6 , wherein the content of the acid group is from 0.1×10 −4 eq/g to 13×10 −4 eq/g.

8. The radiation-curable resin composition according to claim 6 , wherein the acid group is a carboxyl group.

9. The radiation-curable resin composition according to claim 5 , wherein the radiation-curable group is a (meth)acryloyl group.

10. The radiation-curable resin composition according to claim 1 , wherein at least one of the monomer and the oligomer is a compound having no aromatic ring.

11. The radiation-curable resin composition according to claim 1 , wherein the composition does not contain any solvent.

12. The radiation-curable resin composition according to claim 1 , wherein the silica particle is treated with a silane coupling agent having a radiation-curable group.

13. The radiation-curable resin composition according to claim 12 , wherein the silane coupling agent is at least one selected from the group consisting of epoxy cyclohexylethyltrimethoxysilane, glycidoxypropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, acryloxypropyltrimethoxysilane, methacryloxypropyltrimethoxysilane, mercaptopropyltrimethoxysilane, and mercaptopropyltriethoxysilane.

14. The radiation-curable resin composition according to claim 12 , wherein the silica particle treated with the silane coupling agent includes an Si—O—Si bond between the silane coupling agent and the silica particle.

15. The radiation-curable resin composition according to claim 1 , wherein the monomer and/or the oligomer has a (meth)acryloyl group and a urethane bond.

16. The radiation-curable resin composition of claim 1 , wherein the inorganic component is present in an amount of 5% by weight or more.

17. The radiation-curable resin composition of claim 1 , wherein the silica particles have a number average particle size of 40 nm or less.

18. The radiation-curable resin composition of claim 1 , wherein the silica particles have a number average particle size of 30 nm or less.

19. The radiation-curable resin composition of claim 1 , wherein the silica particles have a number average particle size of 15 nm or less.

20. The radiation-curable resin composition of claim 1 , wherein the silica particles have a number average particle size of 12 nm or less.

21. A radiation-cured resin composition obtained by radiation-curing the radiation-curable resin composition according to claim 1 .

22. The radiation-cured resin composition according to claim 21 , in the form of a film having a thickness of from 20 to 500 μm.

23. The radiation-curable resin composition of claim 1 , wherein a radiation cured film of the radiation-curable resin composition having a thickness of 1 mm has a minimum transparency of 83% at 550 nm.

24. The radiation-curable resin composition of claim 1 , wherein a radiation cured film of the radiation-curable resin composition having a thickness of 1 mm has a minimum transparency of 85% at 550 nm.

25. The radiation-curable resin composition of claim 1 , wherein the solvent is at least one selected from the group consisting of an alcohol, a glycol, a hydrocarbon, an ester, a ketone, and an ether.

26. The radiation-curable resin composition according to claim 1 , wherein the solvent is at least one of an alcohol and a ketone.

27. The radiation-curable resin composition according to claim 1 , wherein the alcohol is at least one selected from the group consisting of methanol, ethanol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, octanol, n-propyl alcohol, and acetylacetone alcohol.

28. The radiation-curable resin composition according to claim 1 , wherein the silica particles are obtained by hydrolyzing the oligomer of an alkoxysilane with from 0.3 to 1 equivalents of water based on the mol number of alkoxy groups of the oligomer of an alkoxysilane.

29. A radiation-cured resin film having a thickness of 85 μm or greater obtained by radiation-curing the radiation-curable resin composition according to claim 1 .

30. A radiation-cured resin film having a thickness of 100±15 μm obtained by radiation-curing the radiation-curable resin composition according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2005
From: ESAKI, AKIRA; MATSUDA, OSAMU
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 016859/0421 →
Priority Claims (2)
JP 2002-325706 · Nov 8, 2002 · national
JP 2003-179251 · Jun 24, 2003 · national
Continuity (2)
Continuation PCTJP031419300 · Nov 7, 2003
Related Publication 20050267230A1 · Dec 1, 2005