Polymerizable compositions for optical articles

• US 20060004166A1
• Filed: 06/28/2005
• Published: 01/05/2006
• Est. Priority Date: 12/30/2003
• Status: Abandoned Application

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Olson, David B., Larson, Randy A., Berg, Brandon T.
• Application Number:
  US11/167,953
• Publication Number:
  US 20060004166A1
• Time in Patent Office: Days
• US Class Current: 526/286
• CPC Class Codes: C08F 222/1025 of aromatic dialcohols
• CPC Class Codes: C08F 222/103 of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
• CPC Class Codes: G02B 6/0053 Prismatic sheet or layer; Brightness enhancement element, sheet or layer
• CPC Class Codes: G02F 1/133507 Films for enhancing the luminance
• CPC Class Codes: G02F 1/133607 the light controlling member including light directing or refracting elements, e.g. prisms or lenses
• CPC Class Codes: Y10T 428/31935 Ester, halide or nitrile of addition polymer

Abstract

Polymerizable compositions particularly useful for brightness enhancing films.

Claims

1. A brightness enhancing film comprising the reaction product of a polymerizable composition consisting essentially of:

a) a first monomer comprising a major portion of 2-propenoic acid, (1-methylethylidene)bis[(2,6-dibromo-4,1-phenylene)oxy(2-hydroxy-3,1-propanediyl)]ester;

b) pentaerythritol tri(meth)acrylate;

c) phenoxyethyl(meth)acrylate; and

d) optionally a photoinitiator.

2. The brightness enhancing film of claim 1 wherein the first monomer is present in the polymerizable composition in an amount of at least 40 wt-%.

3. The brightness enhancing film of claim 1 wherein the first monomer is present in the polymerizable composition in an amount of at least 50 wt-%.

4. The brightness enhancing film of claim 1 wherein the first monomer is present in the polymerizable composition in an amount of at least about 60 wt-%.

5. The brightness enhancing film of claim 1 wherein the pentaerythritol tri(meth)acrylate is present in the polymerizable composition in an amount ranging from about 5 wt-% to about 30 wt-%.

6. The brightness enhancing film of claim 1 wherein the phenoxyethyl(meth)acrylate is present in the polymerizable composition in an up to about 35 wt-%.

7. A brightness enhancing film comprising the reaction product of a polymerizable composition consisting essentially of:

a) a first monomer selected from

i) a monomer comprising a major portion having the structure

wherein R1 is independently hydrogen or methyl,

R2 is independently hydrogen or bromine,

Q is independently O or S, and

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂—

;

ii) a monomer comprising a major portion having the structure

wherein R1 is independently hydrogen or methyl,

R2 is independently hydrogen or bromine,

Q is independently O or S,

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂, and

L is a linking group independently selected from linear or branched C₂-C₁₂ alkyl groups wherein the carbon chain is optionally substituted with one or more oxygen group and/or the carbon atoms are optionally substituted with one or more hydroxyl groups; and

mixtures of i and ii;

b) a crosslinking agent comprising at least three (meth)acrylate functional groups;

c) at least one monofunctional (meth)acrylate diluent; and

d) optionally a photoinitiator.

8. The brightness enhancing film of claim 7 wherein the crosslinking agent is a liquid a ambient temperature.

9. The brightness enhancing film of claim 8 wherein the crosslinking agent is selected from the group consisting pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, and mixtures thereof.

10. The brightness enhancing film of claim 7 wherein the monofunctional (meth)acrylate diluent is a liquid at ambient temperature.

11. The brightness enhancing film of claim 10 wherein the monofunctional (meth)acrylate diluent comprises phenoxyethyl (meth)acrylate, benzyl(meth)acrylate, and mixtures thereof.

12. The brightness enhancing film of claim 7 wherein the first monomer is free of methacrylate functional groups.

13. A brightness enhancing film comprising the reaction product of

a) at least 50 wt-% of one or more first monomers selected from the group consisting of:

i) a monomer comprising a major portion having the structure

wherein R1 is independently hydrogen or methyl,

R2 is independently hydrogen or bromine,

Q is independently O or S, and

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂—

;

ii) a monomer comprising a major portion having the structure

wherein R1 is independently hydrogen or methyl,

R2 is independently hydrogen or bromine,

Q is independently O or S,

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂, and

L is a linking group independently selected from linear or branched C₂-C₁₂ alkyl groups wherein the carbon chain is optionally substituted with one or more oxygen group and/or the carbon atoms are optionally substituted with one or more hydroxyl groups;

and mixtures of i and ii;

b) a crosslinking agent comprising at least three (meth)acrylate functional groups.

14. The brightness enhancing film of claim 13 wherein the first monomer consists of the reaction product of Tetrabromobisphenol A diglycidyl ether and (meth)acrylic acid.

15. The brightness enhancing film of claim 13 wherein the crosslinking agent is a liquid at ambient temperature.

16. The brightness enhancing film of claim 15 wherein the crosslinking agent is selected from the group consisting pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, and mixtures thereof.

17. The brightness enhancing film of claim 13 further comprising at least one monofunctional (meth)acrylate diluent.

18. The brightness enhancing film of claim 17 wherein the diluent is a liquid at room temperature.

19. The brightness enhancing film of claim 18 wherein the monofunctional (meth)acrylate diluent comprises phenoxyethyl(meth)acrylate, benzyl(meth)acrylate, and mixtures thereof.

20. The brightness enhancing film of claim 18 wherein the polymerizable composition is free of methacrylate functional monomer.

21. An article comprising the brightness enhancing film of claim 13 and a second optical film in contact with the brightness enhancing film.

22. The article of claim 21 wherein the second optical film is a diffuser.

23. The article of claim 21 wherein the second optical film is an absorbing polarizer.

24. The article of claim 21 wherein the second optical film is a reflective polarizer.

25. The article of claim 21 wherein the second optical film comprises a prismatic structure.

26. A polymerizable resin composition comprising

a) at least 50 wt-% of one or more first monomers selected from the group consisting of:

i) a monomer comprising a major portion having the structure

wherein R1 is independently hydrogen or methyl,

R2 is independently hydrogen or bromine,

Q is independently O or S, and

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂—

;

ii) a monomer comprising a major portion having the structure

wherein R1 is independently hydrogen or methyl,

R2 is independently hydrogen or bromine,

Q is independently O or S,

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂, and

L is a linking group independently selected from linear or branched C₂-C₁₂ alkyl groups wherein the carbon chain is optionally substituted with one or more oxygen group and/or the carbon atoms are optionally substituted with one or more hydroxyl groups; and

mixtures of i and ii;

b) a crosslinking agent comprising at least three (meth)acrylate functional groups.

27. An optical material comprising the reaction product of claim 26.

28. The optical material of claim 26 wherein the material is a film.

29. The optical material of claim 26 wherein the film comprises a microstructured surface.