IP Library Granted Patent US 6,921,576
Granted Patent B2
US 6,921,576 · App. 10/266,735 · Granted Jul 26, 2005

Active energy ray-curable antistatic coating composition

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Quick Facts
Patent No.
US 6,921,576
App. No.
10/266,735
Granted
Jul 26, 2005
Kind
B2
Abstract

An active energy ray-curable antistatic coating composition contains (A) inorganic oxide fine particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent containing at least a quaternary ammonium salt group-containing polymer, a quaternary ammonium salt group-containing silane coupling agent and/or a hydrolysis condensate of the silane coupling agent, and optionally contains (C) a polyfunctional (meth)acrylate having at least 3 (meth)acryloyl groups in a molecule.

Claims (62)

1. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group, (B) an antistatic agent containing at least one member selected from the group consisting of a quaternary ammonium salt group-containing polymer, a quaternary ammonium salt group-containing silane coupling agent and a hydrolysis condensate of the silane coupling agent, and (C) a polyfunctional (meth)acrylate having at least 3 (meth)acryloyl groups in a molecule.

2. The antistatic coating composition according to claim 1 , wherein the functional group of (A) is a radical-polymerizable functional group.

3. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles treated with a silane coupling agent having at least one polar group selected from the group consisting of a polyalkylene oxide, a carboxylic acid and a carboxylic acid ester or a silane coupling agent having a bulky structure having a polar group having a side chain that has a molecular weight of at least 300 and having a functional group, and (B) an antistatic agent containing at least one member selected from the group consisting of a quaternary ammonium salt group-containing polymer, a quaternary ammonium salt group-containing silane coupling agent and a hydrolysis condensate of the silane coupling agent.

4. The antistatic coating composition according to claim 3 , wherein the silane coupling agent is an organic compound having a functional group as shown in formula (1),

wherein X and Y are respectively independently an oxygen atom, a sulfur atom or an imino group.

5. The antistatic coating composition according to claim 3 , wherein the silane coupling agent is a reaction product of an alkoxysilane compound having an isocyanate group and a hydroxyl group-containing acrylate.

6. The antistatic coating composition according to claim 3 , wherein the silane coupling agent is a reaction product of a mono(meth)acrylic acid ester of α,ω-hydroxy-terminated polyalkylene glycol and an alkoxysilane compound having an isocyanate group.

7. The antistatic coating composition according to claim 3 , wherein the silane coupling agent is a reaction product of an alkoxysilane compound having a mercapto group and an at least difunctional polyfunctional (meth)acrylate.

8. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain silyl ether group having the structure —O—Si—R—S—P, wherein R is a C 2 -C 10 alkylene group which may be branched and P is a polymer unit having at least one (meth)acryloyl group, having a molecular weight of at least 300 and having a functional group, and (B) an antistatic agent containing at least one member selected from the group consisting of a quaternary ammonium salt group-containing polymer, a quaternary ammonium salt group-containing silane coupling agent and a hydrolysis condensate of the silane coupling agent.

9. The antistatic coating composition according to claim 8 , which further comprises (E) an organic solvent in addition to the components (A) and (B).

10. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent containing at least one member selected from the group consisting of a quaternary ammonium salt group-containing polymer, a quaternary ammonium salt group-containing silane coupling agent and a hydrolysis condensate of the silane coupling agent, said fine inorganic particles being prepared by bonding a silica sol and/or a silicate by way of a sulfide bond with a polymer having a (meth)acryloyl bond obtained by a first step of hydrolysis-condensing a mercapto group-containing silane coupling agent and a silica sol and/or a silicate to prepare a mercapto group-containing silica sol and/or silicate, a second step of polymerizing a monomer having an epoxy group and one radical-polymerizable group or copolymerizing the monomer with another monomer having one radical-polymerizable group, in the presence of the mercapto group-containing silica sol and/or silicate prepared in the first step, to prepare a polymer having an epoxy group bonded with the silica sol and/or silicate by way of a sulfide bond, and a third step of adding a compound having a carboxyl group and a (meth)acryloyl group to the polymer prepared in the second step.

11. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent that is a copolymer of (meth)acrylic acid ester, (meth)acrylic acid amide and/or a styrene derivative which has a quaternary ammonium salt group.

12. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent that comprises a quaternary ammonium salt group-containing polymer that has a (meth)acryloyl group on a side chain.

13. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent that comprises a quaternary ammonium salt group-containing polymer that has a polydimethylsiloxane structure on the main chain of the polymer, on the side chain of the polymer or a combination thereof.

14. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent that comprises a copolymer of a quaternary ammonium salt group-containing (meth)acrylic acid ester a copolymer of a quaternary ammonium salt group-containing (meth)acrylic acid amide, or a mixture thereof, that contains an α,ω-dimercaptopolydimethylsiloxane as a copolymerizable component.

15. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group and (B) an antistatic agent that comprises a trialkoxysilyl group and a silane coupling agent that has a molecular weight of at least 400 and that has a urethane group or a thioether group, or a hydrolysis condensate thereof.

16. An active energy ray-curable antistatic coating composition, which comprises:

(A) fine inorganic oxide particles having a side chain having a molecular weight of at least 300 and having a functional group, (B) an antistatic agent containing at least one member selected from the group consisting of a quaternary ammonium salt group-containing polymer, a quaternary ammonium salt group-containing silane coupling agent and a hydrolysis condensate of the silane coupling agent, (C) a polyfunctional (meth)acrylate having at least 3 (meth)acryloyl groups in a molecule and (D) a polymerization initiator.

17. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 1 .

18. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 3 .

19. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 8 .

20. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 10 .

21. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 11 .

22. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 12 .

23. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 13 .

24. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 14 .

25. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 15 .

26. A molded product comprising a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 16 .

27. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 1 .

28. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 3 .

29. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 8 .

30. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 10 .

31. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 11 .

32. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 12 .

33. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 13 .

34. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 14 .

35. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 15 .

36. A resin-made film, sheet or molded product having a film obtained by active energy ray-curing the antistatic coating composition as claimed in claim 16 .

37. A cured film-formed molded product having a cured film formed by a process comprising:

applying the antistatic coating composition as defined in claim 8 onto a substrate surface,

drying the applied composition to form a film,

processing the substrate and/or the film, and then

curing the film by irradiation with active energy rays.

38. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 1 .

39. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 3 .

40. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 8 .

41. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 10 .

42. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 11 .

43. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 12 .

44. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 13 .

45. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 14 .

46. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 15 .

47. An antistatic coating obtained by active energy ray-curing the antistatic coating composition as defined in claim 16 .

Assignments (3)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
MERGER Recorded Sep 4, 2017
From: MITSUBISHI CHEMICAL CORPORATION
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 043750/0207 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2002
From: TERAUCHI, MAKOTO; HOSOKAWA, NORITAKA; HAYAMA, KAZUHIDE
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 013624/0758 →