High refractive index microreplication resin

• US 20020123589A1
• Filed: 12/21/2000
• Published: 09/05/2002
• Est. Priority Date: 12/21/2000
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Pokorny, Richard J., Olson, David B., Fong, Bettie C.
• Granted Patent: US 6,541,591 B2
• Time in Patent Office: Days
• US Class Current: 526/286
• CPC Class Codes: C08F 220/301 and one oxygen in the alcohol moiety
• CPC Class Codes: C08F 228/02 by a bond to sulfur
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31576 Ester monomer type [polyvinylacetate, etc.]
• CPC Class Codes: Y10T 428/31649 Ester, halide or nitrile of addition polymer
• CPC Class Codes: Y10T 428/31797 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/3188 Next to cellulosic
• CPC Class Codes: Y10T 428/31917 Next to polyene polymer

Abstract

A polymerizable composition that includes a monomer of the formula

wherein X is hydrogen or one or more of methyl, chlorine, bromine or iodine, R¹ is a straight or branched alkyl linking group of 2 to 12 carbon atoms, R² is hydrogen or methyl, and n is 1 to 3; and a monomer of the formula

wherein X₁ and X₂ are each independently hydrogen or one or more of methyl, chlorine, bromine or iodine, and R² is hydrogen or methyl is described having a high index of refraction and being suitable for use in forming an optical product.

Claims

1. A polymerizable composition comprising:

(a) a monomer of the formula

 

wherein X is hydrogen or one or more methyl, chlorine, bromine or iodine,

R¹ is a straight or branched alkyl linking group of 2 to 12 carbon atoms,

R² is hydrogen or methyl, and

n is 0 to 3; and

(b) a monomer of the formula

wherein X₁ and X₂ are each independently hydrogen or one or more methyl, chlorine, bromine or iodine, and

R² is hydrogen or methyl.

2. The composition of claim 1, wherein monomer (a) is of the formula

3. The composition of claim 1, wherein R¹ is a straight or branched linking group of 2 to 8 carbon atoms.

4. The composition of claim 1, wherein n is 1.

5. The composition of claim 1, wherein monomer (a) is of the formula

6. The composition of claim 1, comprising about 20 to 70 weight percent of monomer (a).

7. The composition of claim 1, comprising about 30 to 50 weight percent of monomer (a).

8. The composition of claim 1, wherein monomer (b) is of the formula

9. The composition of claim 1, wherein monomer (b) is of the formula

10. The composition of claim 1, comprising about 10 to 60 weight percent of monomer (b).

11. The composition of claim 1, comprising about 15 to 30 weight percent of monomer (b).

12. The composition of claim 1, wherein an index of refraction of the composition is at least about 1.60.

13. The composition of claim 1, wherein a melting point of the composition is below about 50°

C.

14. The composition of claim 1, wherein the composition is a liquid at room temperature.

15. The composition of claim 1, which further comprises one or more multi-functional comonomers.

16. The composition of claim 15, comprising up to 50 wt-% of one or more multi-functional comonomers.

17. The composition of claim 15, wherein the comonomer has an index of refraction of at least about 1.50.

18. The composition of claim 1, further comprising a photoinitiator.

19. The composition of claim 18, wherein the photoinitiator comprises 2,4,6-trimethylbenzoy diphenyl phosphine oxide.

20. A polymerized material comprising a composition of claim 1.

21. An optical product comprising:

a base; and

an optical layer prepared from the polymerizable composition according to claim 1.

22. The optical product of claim 21, wherein the base is prepared from materials selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, cellulose triacetate, polyether sulfone, polymethyl methacrylate, polyurethane, polyester, polycarbonate, polyvinyl chloride, syndiotactic polystyrene, polyethylene naphthalate, copolymers or blends based on naphthalene dicarboxylic acids, and glass.

23. The optical product of claim 21, wherein the base comprises a polarizer.

24. The optical product of claim 21, wherein the optical layer comprises a microstructure-bearing layer.

25. The optical product of claim 21, wherein the optical product comprises a brightness enhancement film.

26. A lens sheet comprising:

a transparent substrate; and

an optical layer made from the polymerizable composition of claim 1.