Optical product prepared from high index of refraction brominated monomers

• US 5,932,626 A
• Filed: 05/09/1997
• Issued: 08/03/1999
• Est. Priority Date: 05/09/1997
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Olson, David B., Fong, Bettie C.
• Primary Examiner(s): Truong, Duc
• Application Number:
  US08/853,998
• Time in Patent Office: 816 Days
• Field of Search: 522/188, 522/187, 522/182, 522/102, 351/159, 526/292.3, 526/296, 359/385, 428/176
• US Class Current: 522/182
• CPC Class Codes: C08F 20/22 Esters containing halogen
• CPC Class Codes: C08F 220/22 Esters containing halogen
• CPC Class Codes: C08L 33/16 Homopolymers or copolymers of esters containing halogen atoms
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: Y10T 428/24645 with folds in parallel planes

Abstract

Described are optical products comprising a base and an optical layer. The optical layer is prepared from a polymerizable composition comprising an alkyl-substituted brominated phenolic ester(meth)acrylate monomer.

Claims

1. An optical product comprising:

a base; and

an optical layer prepared from a polymerizable composition, the polymerizable composition comprising an alkyl-substituted brominated phenolic ester (meth)acrylate monomer of the general formula;

##STR16## wherein x is from 1 to 4, R is --H or --CH₃, and R^A is a straight or branched alkyl.

2. The optical product of claim 1, wherein the brominated monomer has an index of refraction of at least about 1.50.

3. The optical product of claim 1, wherein the brominated monomer has an index of refraction of at least about 1.55.

4. The optical product of claim 1, wherein the brominated monomer has the general formula:

##STR17## wherein x is from 1 to 4, R is --H or --CH₃, and R^A is a straight or branched alkyl having from 1 to 18 carbon atoms.

5. The optical product of claim 4, wherein the brominated monomer has the general formula:

##STR18## wherein R and x are as defined, and wherein R¹ is an alkyl having from 1 to 18 carbon atoms.

6. The optical product of claim 5, wherein R¹ is an alkyl having from about 3 to 4 carbon atoms.

7. The optical product of claim 5, wherein x is 2.

8. The optical product of claim 5, wherein the brominated monomer has the general formula:

##STR19## wherein R¹ is as defined.

9. The optical product of claim 8, wherein the brominated monomer comprises 4,6-dibromo-2-sec-butyl phenyl acrylate.

10. The optical product of claim 8, wherein the brominated monomer comprises 4,6-dibromo-2-tert-butyl phenyl acrylate.

11. The optical product of claim 8, wherein the brominated monomer comprises 4,6-dibromo-2-isopropyl phenyl acrylate.

12. The optical product of claim 4, wherein the brominated monomer has the general formula:

##STR20## and wherein R and x are as defined, and R² is an alkyl having from about 1 to 18 carbons.

13. The optical product of claim 12, wherein R² is an alkyl having from about 8 to 12 carbons.

14. The optical product of claim 12, wherein x is 2.

15. The optical product of claim 12, wherein the brominated monomer has the formula:

##STR21## wherein R² is as defined.

16. The optical product of claim 15, wherein the brominated monomer has the formula:

##STR22##

17. The optical product of claim 15, wherein the brominated monomer has the formula:

18. The optical product of claim 1, wherein the polymerizable composition further comprises a high index of refraction comonomer.

19. The optical product of claim 18, wherein the high index of refraction comonomer has an index of refraction of at least about 1.50.

20. The optical product of claim 18, wherein the high index of refraction comonomer comprises a (meth)acrylate monomer.

21. The optical product of claim 18, wherein the high index of refraction comonomer comprises an aromatic monomer.

22. The optical product of claim 18, wherein the high index of refraction comonomer comprises a brominated aromatic monomer.

23. The optical product of claim 18, wherein the high index of refraction comonomer comprises a brominated aromatic (meth)acrylate comonomer.

24. The optical product of claim 18, wherein the high index of refraction comonomer comprises methyl styrene.

25. The optical product of claim 1, wherein the polymerizable composition comprises from about 25 to 40 parts by weight of the brominated monomer;

and

from about 5 to 15 parts by weight methyl styrene monomer.

26. The optical product of claim 25, wherein the polymerizable composition further comprises from about 45 to 70 parts by weight aromatic (meth)acrylate monomer, such as brominated aromatic (meth)acrylate monomer.

27. The optical product of claim 1, wherein the composition is liquid at room temperature and atmospheric pressure.

28. The optical product of claim 1, wherein the index of refraction of the composition is at least about 1.56.

29. The optical product of claim 1 wherein the base is prepared from materials selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, polyether sulfone, polymethyl methacrylate, polyurethane, polyester, polyvinyl chloride, syndiotactic polystyrene, polyethylene naphthalate, copolymers or blends based on naphthalene dicarboxylic acids, and glass.

30. The optical product of claim 29, wherein the base comprises a polarizer.

31. The optical product of claim 1, wherein the optical layer comprises a microstructure-bearing layer.

32. The optical product of claim 31, wherein the optical product comprises a brightness enhancement film.

33. A backlit flat panel display comprising the brightness enhancement film of claim 31.

34. A liquid crystal display comprising the backlit flat panel display of claim 33.

35. A computer or television comprising the liquid crystal display of claim 34.

36. A microstructure-bearing optical product comprising a base and an optical layer, the optical layer being prepared from a polymerizable composition comprising:

an alkyl-substituted brominated phenolic ester(meth)acrylate monomer;

methyl styrene monomer; and

aromatic (meth)acrylate comonomer.

37. The microstructure-bearing optical product of claim 36, wherein the microstructure-bearing optical product produces a gain of at least 1.59.

38. A method of preparing a microreplication-bearing optical product, comprising the steps of

preparing an polymerizable composition comprising an alkyl-substituted brominated phenolic ester(meth)acrylate monomer, the polymerizable composition being liquid at room temperature;

depositing the polymerizable composition onto a master negative microstructured molding surface in an amount barely sufficient to fill the cavities of the master;

filling the cavities by moving a bead of the composition between a preformed base and the master, at least one of which is flexible; and

curing the composition.

39. A brightness enhancement film comprising

a base;

and

an optical layer prepared from a polymerizable composition, the polymerizable composition comprising an alkyl-substituted brominated phenolic ester (meth)acrylate monomer of the general formula;

##STR23## wherein x is from 1 to 4, R is --H or --CH₃, and R^A is a straight or branched alkyl.