IP Library › Granted Patent US 12,415,878
Granted Patent B2
US 12,415,878 · App. 18/485,652 · Granted Sep 16, 2025

Benzyl (meth)acrylate monomers suitable for microstructured optical films

Inventors: Bryan V. Hunt (Anoka, MN); Kyle J. Lindstrom (Houlton, WI); Maureen C. Nelson (West St. Paul, MN)
Assignee: 3M Innovative Properties Company
C08F220/1812C08J7/16C09D133/06G02B1/04
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Quick Facts
Patent No.
US 12,415,878
App. No.
18/485,652
Granted
Sep 16, 2025
Kind
B2
Abstract

Presently described are optical films comprising a polymerized (e.g. microstructured) surface that comprises the reaction product of a polymerizable resin composition and polymerizable resin compositions that comprise nanoparticles; at least one first monomer comprising at least two (meth)acrylate groups; and at least one second (meth)acrylate monomer having the structure wherein at least one R1 comprises an aromatic substituent, t is an integer from 1 to 4, and R2 is hydrogen or methyl.

Claims (20)

1. An optical film comprising a polymerized microstructured surface that comprises the reaction product of a polymerizable resin composition comprising

at least one first non-aromatic monomer comprising at least two (meth)acrylate groups, wherein the first non-aromatic monomer(s) is present in an amount up to 30 wt. %; and

zirconia nanoparticles wherein the amount of zirconia nanoparticles ranges from 10 wt. % to 70 wt. %;

at least one second (meth)acrylate monomer having the structure

wherein at least one R1 comprises an aromatic substituent selected from the group consisting of

t is 1, and

R2 is hydrogen

wherein the second (meth)acrylate monomer(s) is present in an amount of at least 10 wt. % and the amounts are based on the total polymerizable resin composition inclusive of the zirconia nanoparticles.

2. The optical film of claim 1 wherein the second monomer has a viscosity of less than 100 cps at 25° C.

3. The optical film of claim 1 wherein the first monomer comprising at least two (meth)acrylate groups has a molecular weight of at least 350 g/mole.

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

5. The optical film of claim 1 wherein the zirconia nanoparticles have a refractive index of at least 1.60.

6. The optical film of claim 5 wherein the polymerizable resin comprises 30 to 60 wt.-% zirconia nanoparticles.

7. The optical film of claim 1 wherein the optical film is a brightness enhancing film.

8. The optical film of claim 7 wherein the brightness enhancing film has a single sheet relative gain of at least 1.75.

9. The optical film of claim 1 wherein the at least first non-aromatic monomer is selected from 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol monoacrylate monomethacrylate, ethylene glycol diacrylate, alkoxylated aliphatic diacrylate, alkoxylated cyclohexane dimethanol diacrylate, alkoxylated hexanediol diacrylate, alkoxylated neopentyl glycol diacrylate, caprolactone modified neopentylglycol hydroxypivalate diacrylate, caprolactone modified neopentylglycol hydroxypivalate diacrylate, cyclohexanedimethanol diacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, tetraethylene glycol diacrylate, tricyclodecanedimethanol diacrylate, triethylene glycol diacrylate, and tripropylene glycol diacrylate.

10. The optical film of claim 1 wherein the at least first non-aromatic monomer comprises at least three (meth)acrylate groups.

11. The optical film of claim 10 wherein the at least first non-aromatic monomer is selected from pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane tri(methacrylate), dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, trimethylolpropane ethoxylate tri(meth)acrylate, glyceryl tri(meth)acrylate, pentaerythritol propoxylate tri(meth)acrylate, and ditrimethylolpropane tetra(meth)acrylate.

12. The optical film of claim 1 wherein the polymerizable resin comprises other monofunctional diluents in combination with the second (meth)acrylate monomer.

13. The optical film of claim 1 wherein the second (meth)acrylate monomer is 3-phenoxy benzyl acrylate.

Continuity (4)
Continuation 15841028 · Dec 13, 2017
Division 13985058
Provisional Application 61485853 · May 13, 2011
Related Publication 20240084061A1 · Mar 14, 2024
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