Compositions for articles comprising replicated microstructures

• US 20060128853A1
• Filed: 10/25/2005
• Published: 06/15/2006
• Est. Priority Date: 12/13/2004
• Status: Abandoned Application

• Current Assignee: Sabic Innovative Plastics IP BV (Government of Saudi Arabia)
• Original Assignee: General Electric Company
• Inventors: Olson, Daniel Robert
• Application Number:
  US11/257,576
• Publication Number:
  US 20060128853A1
• Time in Patent Office: Days
• US Class Current: 524/261
• CPC Class Codes: C08F 220/10 Esters
• CPC Class Codes: C08F 222/1025 of aromatic dialcohols
• CPC Class Codes: C09D 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

Abstract

The present invention provides novel curable compositions useful in the preparation of light management films and other optical articles. The curable compositions comprise (a) at least one silicone-containing surfactant, (b) at least one a multifunctional (meth)acrylate having structure I; (c) at least one nanoparticulate filler; and in certain embodiments, (d) at least one monofunctional (meth)acrylate. The curable compositions may be cured to provide the corresponding cured compositions and articles made therefrom.

Claims

1. A curable composition comprising:

(a) at least one silicone containing surfactant, wherein the surfactant is present in a range corresponding to from about 0.01 to about 5 weight percent based upon the total weight of the composition;

(b) at least one multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S, or Se;

n is at least 2; and

R² is a polyvalent aromatic radical; and

(c) at least one nanoparticulate filler.

2. A curable composition comprising:

(a) at least one silicone containing surfactant, wherein the surfactant is present in a range corresponding to from about 0.01 to about 5 weight percent based upon the total weight of the composition;

(b) a multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S, or Se;

n is at least 2; and

R² is a polyvalent aromatic radical; and

(c) at least one nanoparticulate filler; and

(d) at least one monofunctional (meth)acrylate.

3. The curable composition according to claim 2, wherein said nanoparticulate filler comprises at least one nanoparticulate metal oxide selected from the group consisting of silica, zirconia, titania, ceria, alumina, antimony oxide, and mixtures thereof.

4. The curable composition according to claim 2, wherein said nanoparticulate filler comprises antimony oxide.

5. The curable composition according to claim 2, wherein said nanoparticulate filler comprises at least one organic functional group.

6. The curable composition according to claim 5, wherein said at least one organic functional group is selected from the group consisting of aliphatic radicals, cycloaliphatic radicals, and aromatic radicals.

7. The curable composition according to claim 5, wherein said at least one organic functional group comprises at least one (meth)acryloyloxy group.

8. The curable composition according to claim 2, wherein R² is a divalent aromatic radical having structure III

9. The curable composition according to claim 2, wherein the multifunctional (meth)acrylate comprises at least one di(meth)acrylate having structure IV

10. The curable composition according to claim 2, wherein said silicone-containing surfactant comprises a polyalkyleneoxide modified polydimethylsiloxane having structure V

11. The curable composition according to claim 2, wherein said at least one silicone-containing surfactant is present in an amount corresponding to from about 0.1 to about 1 weight percent based upon the total weight of the composition.

12. The curable composition according to claim 2, wherein said multifunctional (meth)acrylate I is present in an amount corresponding to from about 30 to about 80 weight percent of the total weight of the composition, and said monofunctional (meth)acrylate is present in an amount corresponding to from about 20 to about 70 weight percent of the total weight of the composition.

13. The curable composition according to claim 2, wherein said at least one monofunctional (meth)acrylate is selected from the group consisting of methyl acrylate, methyl (meth)acrylate, and arylether (meth)acrylate monomers having structure VI

14. The curable composition according to claim 2, wherein said at least one monofunctional (meth)acrylate comprises phenylthioethyl (meth)acrylate VII

15. The curable composition according to claim 2, wherein said at least one monofunctional (meth)acrylate comprises naphthylthioethyl (meth)acrylate VIII

16. The curable composition according to claim 2, further comprising at least one polymerization initiator.

17. A curable composition comprising:

(a) at least one silicone-containing surfactant, said at least one silicone-containing surfactant being present in an amount corresponding to from about 0.1 to about 1 weight percent based upon the total weight of the composition;

(b) a multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S, or Se;

n is 2; and

R² is a divalent aromatic radical;

(c) at least one nanoparticulate filler; and

(d) at least one monofunctional (meth)acrylate having structure VI

wherein R¹⁰ is hydrogen or methyl;

X² and X³ are independently in each instance O, S, or Se;

R¹¹ is a divalent C₁-C₂₀ aliphatic radical, a divalent C₃-C₂₀ cycloaliphatic radical, or a divalent C₃-C₂₀ aromatic radical; and

Ar is monovalent C₃-C₂₀ aromatic radical.

18. The curable composition according to claim 17, further comprising an aliphatic acid having structure II

19. The curable composition according to claim 18, wherein said aliphatic acid comprises at least one fatty acid selected from the group consisting of myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and eicosanoic acid.

20. The curable composition according to claim 17, wherein said multifunctional (meth)acrylate comprises a di(meth)acrylate having structure IV

21. A curable composition comprising:

(a) at least one silicone-containing surfactant, said at least one silicone-containing surfactant being present in an amount corresponding to from about 0.1 to about 1 weight percent based upon the total weight of the composition;

(b) a multifunctional (meth)acrylate represented by the structure IV

wherein R¹ is hydrogen or methyl, and U is a bond, an oxygen atom, a sulfur atom, a selenium atom, an SO₂ group, an SO group, a CO group, a C₁-C₂₀ aliphatic radical, C₃-C₂₀ cycloaliphatic radical, or a C₃-C₂₀ aromatic radical;

(c) at least one nanoparticulate filler comprising antimony oxide and at least one meth(acryloyloxy) group; and

(d) at least one monofunctional (meth)acrylate having structure VI

wherein R¹⁰ is hydrogen or methyl;

X² and X³ are independently in each instance O, S, or Se;

R¹¹ is a divalent C₁-C₂₀ aliphatic radical, a divalent C₃-C₂₀ cycloaliphatic radical, or a divalent C₃-C₂₀ aromatic radical; and

Ar is monovalent C₃-C₂₀ aromatic radical.

22. A cured composition comprising:

(a) at least one silicone-containing surfactant, said at least one silicone-containing surfactant being present in an amount corresponding to from about 0.1 to about 5 weight percent based upon the total weight of the composition;

(b) structural units derived from at least one multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S, or Se;

n is at least 2; and

R² is a polyvalent aromatic radical; and

(c) at least one nanoparticulate filler; and

(d) structural units derived from at least one monofunctional (meth)acrylate.

23. The cured composition according to claim 22, wherein R² is a divalent aromatic radical having structure III

24. The cured composition according to claim 22, wherein the multifunctional (meth)acrylate comprises at least one di(meth)acrylate having structure IV

25. The cured composition according to claim 22, wherein said silicone-containing surfactant comprises a polyalkyleneoxide modified polydimethylsiloxane having structure V

26. The cured composition according to claim 22, wherein said at least one silicone-containing surfactant is present in an amount corresponding to from about 0.1 to about 1 weight percent based upon the total weight of the composition.

27. The cured composition according to claim 22, wherein said strucrural units derived from the at least one multifunctional (meth)acrylate I are present in an amount corresponding to from about 50 to about 80 weight percent of the total weight of the cured composition, and said structural units derived from at least one monofunctional (meth)acrylate are present in an amount corresponding to from about 20 to about 50 weight percent of the total weight of the cured composition.

28. The cured composition according to claim 22, wherein said at least one monofunctional (meth)acrylate is selected from the group consisting of methyl acrylate, methyl (meth)acrylate, and arylether (meth)acrylate monomers having structure VI

29. The cured composition according to claim 22, wherein said at least one monofunctional (meth)acrylate comprises phenylthioethyl (meth)acrylate VII

30. The cured composition according to claim 22, wherein said at least one monofunctional (meth)acrylate comprises naphthylthioethyl (meth)acrylate VIII

31. An article comprising a cured composition, said cured composiiton comprising:

(a) at least one silicone containing surfactant, wherein the surfactant is present in a range corresponding to from about 0.01 to about 5 weight percent based upon the total weight of the composition;

(b) structural units derived from at least one multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S, or Se;

n is at least 2; and

R² is a polyvalent aromatic radical; and

(c) at least one nanoparticulate filler; and

(d) structural units derived from at least one monofunctional (meth)acrylate.

32. The article according to claim 31, said article comprising at least one surface microstructure.

33. The article according to claim 32 which is a brightness enhancement film.

34. An article comprising a cured composition, said cured composiiton comprising:

(a) at least one silicone containing surfactant, wherein the surfactant is present in a range corresponding to from about 0.01 to about 1 weight percent based upon the total weight of the composition;

(b) structural units derived from at least one multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S or Se;

n is at least 2; and

R² is a polyvalent aromatic radical;

(c) at least one nanoparticulate filler; and

(d) structural units derived from at least one monofunctional (meth)acrylate having structure VI

(e) wherein R¹⁰ is hydrogen or methyl;

X² and X³ are independently in each instance O, S, or Se;

R¹¹ is a divalent C₁-C₂₀ aliphatic radical, a divalent C₃C₂₀ cycloaliphatic radical, or a divalent C₃-C₂₀ aromatic radical; and

Ar is monovalent C₃-C₂₀ aromatic radical.

35. The article according to claim 34, said article being a multilayer article comprising a substrate selected from the group consisting of glass, and thermoplastic materials.

36. The article according to claim 34, wherein said article comprises at least one surface microstructure.

37. A cured composition comprising:

(a) at least one silicone containing surfactant, wherein the surfactant is present in a range corresponding to from about 0.01 to about 5 weight percent based upon the total weight of the composition;

(b) structural units derived from at least one multifunctional (meth)acrylate represented by the structure I

wherein R¹ is hydrogen or methyl;

X¹ is O, S, or Se;

n is at least 2; and

R² is a polyvalent aromatic radical; and

(c) at least one nanoparticulate filler.