Radiation-curable resin composition and cured product thereof

• US 7,569,619 B2
• Filed: 05/06/2005
• Issued: 08/04/2009
• Est. Priority Date: 11/08/2002
• Status: Expired due to Fees

• Current Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Inventors: Matsuda, Osamu, Esaki, Akira
• Primary Examiner(s): Berman; Susan W
• Application Number:
  US11/123,041
• Publication Number:
  US 20050267230A1
• Time in Patent Office: 1,551 Days
• Field of Search: 522/25, 522/79, 522/80, 522/83, 522/172, 524/858, 524/847
• US Class Current: 522/79
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 292/00 Macromolecular compounds obtained by polymerising monomers on to inorganic materials
• CPC Class Codes: C08F 299/00 Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
• CPC Class Codes: C08F 299/08 from polysiloxanes
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/6674 with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/6692 with compounds of group C08G18/34
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08K 9/06 with silicon-containing compounds
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 51/10 grafted on to inorganic materials
• CPC Class Codes: C08L 75/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: G11B 2007/24312 group 14 elements (e.g. Si, Ge, Sn)
• CPC Class Codes: G11B 2007/24314 group 15 elements (e.g. Sb, Bi)
• CPC Class Codes: G11B 2007/24316 group 16 elements (i.e. chalcogenides, Se, Te)
• CPC Class Codes: G11B 7/2534 polycarbonates [PC]
• CPC Class Codes: G11B 7/2542 consisting essentially of organic resins
• CPC Class Codes: G11B 7/2545 : containing inorganic fillers, e.g. particles or fibres
• CPC Class Codes: G11B 7/266 : Sputtering or spin-coating layers sputtering in general C23C14/24; spin-coating in general B05D1/005

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

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<sup>−

4</sup> eq/g to 13×

10<sup>−

4</sup> 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 μ

m.

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 μ

m 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 μ

m obtained by radiation-curing the radiation-curable resin composition according to claim 1.