Radiation-curable resin composition and cured product thereof

• US 20050267230A1
• Filed: 05/06/2005
• Published: 12/01/2005
• Est. Priority Date: 11/08/2002
• Status: Active Grant

• Current Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Inventors: Matsuda, Osamu, Esaki, Akira
• Granted Patent: US 7,569,619 B2
• Time in Patent Office: Days
• US Class Current: 522/172
• 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 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.

2. The radiation-curable resin composition according to claim 1, 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.

3. The radiation-curable resin composition according to claim 1, wherein surface tension of the composition at 25°

C. is 40 mN/m or less.

4. 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.

5. The radiation-curable resin composition according to claim 1, wherein the inorganic component having a particle size larger than 30 nm is 1% by weight or less in the composition.

6. The radiation-curable resin composition according to claim 1, wherein the monomer and/or the oligomer thereof is a monomer having a group capable of forming an intramolecular hydrogen bond or an intermolecular hydrogen bond and/or an oligomer thereof.

7. The radiation-curable resin composition according to claim 1, wherein the monomer and/or the oligomer thereof comprises a monomer having a radiation-curable group and containing a urethane bond or a hydroxyalkylne group and/or an oligomer thereof.

8. The radiation-curable resin composition according to claim 7, wherein the monomer having a radiation-curable group and containing a urethane bond or a hydroxyalkylene group and/or the oligomer thereof has an acid group.

9. The radiation-curable resin composition according to claim 7, wherein the content of the acid group derived from the monomer having a radiation-curable group and/or the oligomer thereof in the composition is from 0.1×

10<sup>−

4</sup> eq/g to 13×

10<sup>−

4</sup> eq/g.

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

11. The radiation-curable resin composition according to claim 7, wherein the radiation-curable group is a (meth)acryloyl group.

22. The radiation-curable resin composition according to claim 1, wherein the monomer and/or the oligomer thereof is a compound having no aromatic ring.

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

24. A process for producing the radiation-curable resin composition according to claim 1, wherein the following steps are successively conducted:

a step of synthesizing a silica particle by hydrolysis of an oligomer of an alkoxysilane at a temperature of 10 to 100°

C. in a liquid medium;

a step of protecting the surface of the silica particle;

a step of mixing the monomer and/or the oligomer thereof; and

a step of removing a solvent at a temperature of 10 to 75°

C.

26. A cured product obtainable by curing the curable resin composition according to claim 1.

27. The cured product according to claim 26, which is used for an optical material.

28. A laminate having a layer composed of the cured product according to claim 26.

30. An optical recording medium having a layer composed of the cured product according to claim 26.

12. A radiation-curable resin composition comprising a silica particle composed of a hydrolyzate of an oligomer of an alkoxysilane, a monomer containing a urethane bond or a hydroxyalkylene group and/or an oligomer thereof, and a silane coupling agent.

13. The radiation-curable resin composition according to claim 12, wherein the monomer and/or the oligomer thereof further have an acid group.

14. The radiation-curable resin composition according to claim 13, wherein the content of the acid group derived from the monomer having a radiation-curable group and/or the oligomer thereof in the composition is from 0.1×

10<sup>−

4</sup> eq/g to 13×

10<sup>−

4</sup> eq/g.

15. The radiation-curable resin composition according to claim 13, wherein the acid group is a carboxyl group.

16. The radiation-curable resin composition according to claim 12, wherein the monomer and/or the oligomer thereof further has a (meth)acryloyl group.

17. A radiation-curable resin composition comprising a silica particle and a monomer containing a urethane bond or a hydroxyalkylene group and/or an oligomer thereof,

wherein the monomer and/or the oligomer thereof have an acid group.

18. The radiation-curable resin composition according to claim 17, wherein the silica particle is obtained by hydrolysis of an oligomer of an alkoxysilane.

19. The radiation-curable resin composition according to claim 17, wherein the content of the acid group derived from the monomer having a radiation-curable group and/or the oligomer thereof in the composition is from 0.1×

10<sup>−

4</sup> eq/g to 13×

10<sup>−

4</sup> eq/g.

20. The radiation-curable resin composition according to claim 17, wherein the acid group is a carboxyl group.

21. The radiation-curable resin composition according to claim 17, wherein the monomer containing a urethane bond or a hydroxyalkylene group and/or the oligomer thereof further has a (meth)acryloyl group.

25. A radiation-curable resin composition, wherein a cured product obtainable by irradiation at a radiation intensity of 0.1 to 3 J/cm² has the following physical properties a) and b):

a) a surface hardness is HB or higher, and

b) after a laminate obtained by forming a cured product layer having a film thickness of 100±

15 μ

m on a substrate material made of polycarbonate having a thickness of 1.2±

0.2 mm is placed under an environment of 80°

C. and 85% RH for 100 hours, it is retained that a ratio of adhered area to the adherent material is 50% of initial adhered area.

29. An optical recording medium having a protective layer having a surface hardness of HB or higher and a thickness of 20 μ

m or more,

wherein it is retained that a ratio of adhered area of a substrate or a substrate having a laminate to the protective layer after placed under an environment of 80°

C. and 85% RH for 100 hours is 50% or more of initial adhered area.