Photocurable composition

• US 20040029044A1
• Filed: 08/08/2002
• Published: 02/12/2004
• Est. Priority Date: 08/08/2002
• Status: Abandoned Application

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Severance, Richard L., Ylitalo, Caroline M., Elliott, Peter T.
• Application Number:
  US10/214,619
• Publication Number:
  US 20040029044A1
• Time in Patent Office: Days
• US Class Current: 430/281.1
• CPC Class Codes: C08F 22/40 Imides, e.g. cyclic imides
• CPC Class Codes: C08F 222/40 Imides, e.g. cyclic imides
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

Abstract

A photocurable composition comprises: at least one free-radically polymerizable material, at least one benzophenone derivative, at least one acylphosphine oxide, and at least one maleimide having the formula:

wherein

each R² independently represents a divalent organic group or a covalent bond, and

n is 1, 2, or 3.

The photocurable composition may be applied to substrate and cured by exposure to actinic radiation.

Claims

1. A photocurable composition comprising:

at least one free-radically polymerizable material;

at least one benzophenone derivative;

at least one acylphosphine oxide; and

at least one maleimide having the formula;

wherein

each R² independently represents a divalent organic group or a covalent bond, and

n is 1, 2, or 3.

2. The photocurable composition of claim 1, wherein R² is alkylene, phenylene, or a covalent bond.

3. The photocurable composition of claim 1, wherein n is 1 or 2.

4. The photocurable composition of claim 1, wherein the at least one polymerizable material is present in an amount of from about 30 percent by weight to about 95 percent by weight, based on the total weight of the polymerizable material.

5. The photocurable composition of claim 1, wherein the at least one polymerizable material is present in an amount of from about 50 percent by weight to about 90 percent by weight, based on the total weight of the polymerizable material.

6. The photocurable composition of claim 1, wherein the at least one polymerizable material comprises at least one of an acrylate monomer or a methacrylate monomer.

7. The photocurable composition of claim 1, wherein the benzophenone derivative is benzophenone.

8. The photocurable composition of claim 1, wherein the at least one acylphosphine oxide comprises at least one of 2,4,6-trimethylbenzoyldiphenylphosphine oxide or bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide.

9. The photocurable composition of claim 1, wherein the at least one maleimide comprises at least one of N-methylmaleimide or 1,1′

-(methylenedi-4,1-phenylene)bismaleimide.

10. The photocurable composition of claim 1, wherein the combined amount of benzophenone derivative, acylphosphine oxide, and maleimide is in a range of from about 3 percent by weight to about 12 percent by weight, based on the combined weight of polymerizable material, benzophenone derivative, acylphosphine oxide, and maleimide.

11. The photocurable composition of claim 1, wherein the combined amount of benzophenone derivative, acylphosphine oxide, and maleimide is in a range of from about 4 percent by weight to about 10 percent by weight, based on the combined weight of polymerizable material, benzophenone derivative, acylphosphine oxide, and maleimide.

12. The photocurable composition of claim 1, wherein the weight ratio of benzophenone derivative to acylphosphine oxide is in a range of from about 1:

5 to about 10;

1.

13. The photocurable composition of claim 1, wherein the amount of maleimide is in a range of from about 0.01 percent by weight to about 5 percent by weight, based on the combined weight of polymerizable material, benzophenone derivative, acylphosphine oxide, and maleimide.

14. The photocurable composition of claim 1, further comprising solvent.

15. The photocurable composition of claim 1, wherein the viscosity is less than or equal to about 35 milliPascal-seconds at 80°

C.

16. The photocurable composition of claim 1, further comprising colorant.

17. The photocurable composition of claim 16, further comprising solvent.

18. The photocurable composition of claim 16, wherein the viscosity is less than or equal to about 35 milliPascal-seconds at 80°

C.

19. A method for applying a photocurable composition to a substrate comprising:

providing a substrate;

providing a photocurable composition comprising;

at least one free-radically polymerizable material;

at least one benzophenone derivative;

at least one acylphosphine oxide; and

at least one maleimide having the formula;

wherein

each R² independently represents a divalent organic group or a covalent bond, and

n is 1, 2, or 3; and

applying the photocurable composition to the substrate.

20. The method of claim 19, further comprising exposing the photocurable composition to actinic radiation.

21. The method of claim 19, wherein applying comprises printing.

22. The method of claim 19, wherein applying comprises a method selected from the group consisting of screen printing, flexographic printing, and ink jet printing.

23. The method of claim 19, wherein applying comprises ink jet printing.

24. The method of claim 19, wherein the photocurable composition further comprises colorant.

25. The method of claim 24, further comprising exposing the photocurable composition to actinic radiation.

26. The method of claim 24, wherein applying comprises printing.

27. The method of claim 24, wherein applying comprises a method selected from the group consisting of screen printing, flexographic printing, and ink jet printing.

28. The method of claim 24, wherein applying comprises ink jet printing.

29. The method of claim 25, wherein the actinic radiation is supplied by a medium pressure mercury lamp.

30. The method of claim 24, wherein the substrate comprises woven fabric.

31. The method of claim 24, wherein the substrate comprises non-woven fabric.

32. The method of claim 24, wherein the substrate is retroreflective.

33. The method of claim 24, wherein the substrate comprises a polymeric film.

34. The method of claim 24, wherein the substrate is selected from the group consisting of paper, vinyl film, and retroreflective sheeting.

35. The method of claim 24, wherein the substrate comprises a multilayer polyolefin based film.

36. An article comprising a substrate having thereon a reaction product of a photocurable composition comprising:

at least one free-radically polymerizable material;

at least one benzophenone derivative;

at least one acylphosphine oxide; and

at least one maleimide having the formula;

wherein

each R² independently represents a divalent organic group or a covalent bond, and

n is 1, 2, or 3.

37. The article of claim 36, wherein the photocurable composition further comprises colorant.

38. The article of claim 36, wherein the substrate comprises woven fabric.

39. The article of claim 36, wherein the substrate comprises non-woven fabric.

40. The article of claim 36, wherein the substrate is retroreflective.

41. The article of claim 36, wherein the substrate comprises a polymeric film.

42. The article of claim 36, wherein the substrate is selected from the group consisting of paper, vinyl film, and retroreflective sheeting.

43. The article of claim 36, wherein the substrate comprises a multilayer polyolefin based film.