ORTHO-BENZYLPHENOL MONO(METH)ACRYLATE MONOMERS SUITABLE FOR MICROSTRUCTURED OPTICAL FILMS

• US 20090275720A1
• Filed: 04/30/2008
• Published: 11/05/2009
• Est. Priority Date: 04/30/2008
• Status: Abandoned Application

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Lindstrom, Kyle J., Hunt, Bryan V.
• Application Number:
  US12/112,425
• Publication Number:
  US 20090275720A1
• Time in Patent Office: Days
• US Class Current: 526/320
• CPC Class Codes: C08F 220/30 containing aromatic rings in the alcohol moiety
• CPC Class Codes: C08F 220/301 and one oxygen in the alcohol moiety
• CPC Class Codes: C08K 5/105 with phenols

Abstract

Optical films having a polymerized microstructured surface and polymerizable resin compositions are described comprising at least one ortho-benzylphenol mono(meth)acrylate monomer.

Claims

1. An optical film comprising a polymerized microstructured surface that comprises the reaction product of a polymerizable resin composition comprising at least one ortho-benzylphenol mono(meth)acrylate monomer having the structure

wherein

t is 0 or t ranges from 1 to 4 and R is independently a C1-C6 alkyl group,

L is a C2-C12 alkyl group optionally substituted with one or more hydroxyl groups;

n ranges from 0 to 10; and

R1 is H or CH₃.

2. The optical film according to claim 1 wherein the ortho-benzylphenol monomer has a refractive index of at least 1.54.

3. The optical film of claim 1 wherein t is 0.

4. The optical film of claim 1 wherein t ranges from 1 to 4 and R is independently a C1-C3 alkyl group.

5. The optical film of claim 4 wherein n is at least 1.

6. The optical film of claim 5 wherein L is a C2-C3 alkyl group optionally substituted with one or more hydroxyl groups.

7. The optical film of claim 1 wherein the ortho-benzylphenol mono(meth)acrylate monomer has a viscosity of less than 80 cps at 25°

C.

8. The optical film of claim 1 wherein the ortho-benzylphenol monomer has the structure

9. The optical film of claim 1 wherein the ortho-benzylphenol monomer has the structure

10. The optical film of claim 1 wherein the polymerizable resin composition comprises 25 wt-% to 75 wt-% of one or more aromatic monomers or oligomers having at least two aromatic groups and at least two (meth)acrylate groups.

11. The optical film of claim 10 wherein the aromatic monomer or oligomer having at least two aromatic groups and at least two polymerizable (meth)acrylate groups has a molecular weight of at least 350 g/mole.

12. The optical film of claim 11 wherein the aromatic monomer or oligomer has the structure

wherein R1 is independently hydrogen or methyl;

Z is independently —

C(CH₃)₂—

, —

CH₂—

, —

C(O)—

, —

S—

, —

S(O)—

, or —

S(O)₂—

;

Q is independently O or S;

L is independently a C₂-C₆ alkyl group optionally substituted with one or more hydroxy groups; and

and n ranges from 0 to 10.

13. The optical film of claim 11 wherein the aromatic monomer or oligomer has the structure

wherein each R1 is independently H or methyl;

each R2 is independently Br;

m ranges from 0 to 4;

each Q is independently O or S;

n ranges from 0 to 10;

L is independently a C2 to C12 alkyl group optionally substituted with one or more hydroxyl groups;

z is an aromatic ring; and

t is independently 0 or 1.

14. The optical film of claim 1 wherein the polymerizable resin composition is non-halogenated.

15. The optical film of claim 1 wherein the polymerizable resin is free of urethane (meth)acrylate monomers and oligomers.

16. The optical film of claim 1 wherein the polymerizable resin comprises less than 5 wt-% of triphenyl (meth)acrylate monomer.

17. The optical film of claim 1 wherein the optical film is a brightness enhancing film having a single sheet gain of at least 1.59.

18. The optical film of claim 1 wherein the polymerizable resin composition comprises inorganic nanoparticles.

19. An optical film having a polymerized microstructured surface that comprises the reaction product of a polymerizable resin composition comprising at least one ortho-benzylphenol mono(meth)acrylate monomers having a viscosity of less than 80 cps at 25°

C.

20. The optical film of claim 19 wherein the ortho-benzylphenol mono(meth)acrylate has the structure

wherein

R is independently a substituent,

t ranges from 0 to 4;

L is a C2-C12 alkyl group optionally substituted with one or more hydroxyl groups;

n ranges from 0 to 10; and

R1 is H or CH₃.

21. A polymerizable resin composition comprising at least one ortho-benzylphenol mono(meth)acrylate monomers having a viscosity of less than 80 cps at 25°

C.

22. The polymerizable resin composition of claim 21 wherein the ortho-benzylphenol mono(meth)acrylate has the structure

wherein

R is independently a substituent,

t ranges from 0 to 4;

L is a C2-C12 alkyl group optionally substituted with one or more hydroxyl groups;

n ranges from 0 to 10; and

R1 is H or CH₃.

23. An article comprising the reaction product of a polymerizable resin composition comprising the resin composition of claim 21.