# US 11,111,392 B2 · Optical device with antistatic property

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- Number: US 11,111,392 B2
- Document ID: US11111392B2
- Status: Granted
- Kind: B2
- Application number: 15/728,321
- Filed: 2017-10-09
- Published: 2018-02-01
- Granted: 2021-09-07
- Earliest claimed: 2009-10-30
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Thomas P. Klun; Brandt K. Carter; Michael K. Gerlach; Mahfuza B. Ali; Mark J. Pellerite; Thomas M. Snyder; William M. Lamanna
- Web page: https://patentgrep.com/patent/US11111392B2

## CPC

- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C08F 220/301: {and one oxygen in the alcohol moiety}
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- C08F 222/103: {of trialcohols, e.g. trimethylolpropane tri(meth)acrylate}
- C08F 222/104: {of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate}
- C08F 222/408: {substituted imides comprising other heteroatoms}
- Y10T 428/24355: Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
- Y10T 428/269: including synthetic resin or polymer layer or component
- Y10T 428/31504: Composite [nonstructural laminate]
- Y10T 428/31609: Particulate metal or metal compound-containing
- Y10T 428/31721: Of polyimide
- Y10T 428/31931: Polyene monomer-containing
- Y10T 428/31935: Ester, halide or nitrile of addition polymer
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

An optical device having a first optical member, a second optical member, and an antistatic layer disposed between the first optical member and the second optical member wherein the antistatic layer contains the reaction product of a mixture comprising at least one polymerizable onium salt having an anion and at least one non-onium polymerizable monomer, oligomer, or polymer.

## Claims

### Claim 1

An optical device comprising a first optical member having a front surface, a second optical member, and an antistatic layer disposed between the first optical member and the second optical member wherein the first optical member, the second optical member, and the antistatic layer define an optical path such that light incident to the front surface of the first optical member will pass through each of the first optical member, the second optical member, and the antistatic layer;
wherein the antistatic layer is transparent and has a glass transition temperature of 20° C. or less and is the reaction product of a reaction mixture consisting essentially of photo-initiator, 2 to 90 wt. % of at least one polymerizable onium salt having a fluoroorganic anion, at least one non-onium polymerizable multifunctional (meth)acrylate monomer or oligomer and optionally at least one polymerizable monofunctional (meth)acrylate monomer or oligomer, wherein the onium salt has the formula:
(R1)a-bG+[(CH2)qDR2]bX−
wherein:
each R1 comprises independently an alkyl, alicyclic, aryl, alkalicyclic, alkaryl, alicyclicalkyl, aralicyclic, or alicyclicaryl moiety, wherein such moiety may comprise one or more heteroatoms such as for example, nitrogen, oxygen, or sulfur, or may comprise phosphorus, or a halogen; R1 may be cyclic or aromatic and include G+in the cycle;
G is nitrogen, sulfur, or phosphorus;
a is 3 where G is sulfur and a is 4 where G is nitrogen or phosphorous;
b is an integer of 1 to 3 where G is sulfur and b is an integer of 1 to 4 where G is nitrogen or phosphorus;
q is an integer from 1 to 4;
D is oxygen, sulfur, or NR wherein R is H or a lower alkyl of 1 to 4 carbon atoms;
R2 is a (meth)acryl; and
X−is a fluoroorganic anion which is a methide or an imide.

### Claim 2 (depends on 1)

The optical device of claim 1 wherein the onium salt is a quaternary ammonium salt.

### Claim 3 (depends on 1)

The optical device of claim 1 wherein the onium salt is selected from the group consisting of ammonium salts, sulfonium salts, and phosphonium salts.

### Claim 4 (depends on 1)

The optical device of claim 1 wherein the polymerizable multifunctional (meth)acrylate monomer or oligomer is independently selected from the group consisting of multifunctional (meth)acrylate monomers bearing alkoxylated moieties and polyurethane multi-acrylates and the polymerizable monofunctional (meth)acrylate monomer or oligomer is a monofunctional (meth)acrylate monomer bearing alkoxylated moieties.

### Claim 5 (depends on 4)

The optical device of claim 4 wherein the alkoxylated moieties are ethoxylated moieties.

### Claim 6 (depends on 1)

The optical device of claim 1 wherein the at least one non-onium polymerizable multifunctional (meth)acrylate monomer or oligomer or the optional at least one non-onium polymerizable monofunctional monomer or oligomer comprises a mixture of at least two polymerizable compounds.

### Claim 7 (depends on 1)

The optical device of claim 1 wherein the at least one non-onium polymerizable multifunctional (meth)acrylate monomer or oligomer comprises a mixture of an aliphatic urethane diacrylate and an ethoxylated phenoxy ethyl acrylate.

### Claim 8 (depends on 1)

The optical device of claim 1 wherein X−is C(SO2CF3)3 or −N(SO2CF3)2.

### Claim 9 (depends on 1)

The optical device of claim 1 wherein the at least one polymerizable onium salt comprises from 2 to 50% by weight of the reaction mixture.

### Claim 10 (depends on 1)

The optical device of claim 1 wherein the glass transition temperature of the antistatic layer is less than 10° C.

### Claim 11 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is affixed to at least one of the first optical member and the second optical member.

### Claim 12 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is affixed to both the first optical member and the second optical member.

### Claim 13 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is affixed to at least one of the first optical member and the second optical member via an intervening layer.

### Claim 14 (depends on 13)

The optical device of claim 13 wherein the antistatic layer is affixed to both the first optical member via an intervening layer, and the second optical member via an intervening layer.

### Claim 15 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is affixed to either the first optical member or the second optical member, and is also affixed to the remaining optical member via an intervening layer.

### Claim 16 (depends on 1)

The optical device of claim 1 exhibiting a charge decay time of less than 10 seconds.

### Claim 17 (depends on 1)

The optical device of claim 1 exhibiting a charge decay time of less than 5 seconds.

### Claim 18 (depends on 1)

The optical device of claim 1 exhibiting a charge decay time of less than 2 seconds.

### Claim 19 (depends on 1)

The optical device of claim 1 wherein the first optical member and the second optical member are independently selected from the group consisting of optical base films, multilayer optical films, diffuse reflecting polarizer films, prismatic brightness enhancement films, arrays of prismatic optical features, arrays of lenticular optical features, and beaded gain diffuser films.

### Claim 20 (depends on 19)

The optical device of claim 19 wherein the first optical member comprises an optical base film and the second optical member comprises an array of prismatic optical features.

### Claim 21 (depends on 19)

The optical device of claim 19 wherein the first optical member comprises a multilayer optical film and the second optical member comprises a prismatic brightness enhancement film.

### Claim 22 (depends on 19)

The optical device of claim 19 wherein the multilayer optical film is a polarizer.

### Claim 23 (depends on 19)

The optical device of claim 19 wherein the first optical member comprises a multilayer optical film and the second optical member comprises an array of prismatic optical features.

### Claim 24 (depends on 23)

The optical device of claim 23 having an Optical Gain greater than 2.0.

### Claim 25 (depends on 1)

The optical device of claim 1 wherein the first optical member comprises an optical base film and the second optical member comprises a prismatic brightness enhancement film.

### Claim 26 (depends on 25)

The optical device of claim 25 having an Optical Gain greater than 1.6.

### Claim 27 (depends on 1)

The optical device of claim 1 wherein the antistatic layer has a surface texture on one or both sides.

### Claim 28 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is greater than 0.25 micron thick.

### Claim 29 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is greater than 0.5 micron thick.

### Claim 30 (depends on 1)

The optical device of claim 1 wherein the antistatic layer is greater than 1 micron thick.

### Claim 31 (depends on 1)

The optical device of claim 1 wherein the charge decay time is lower than that for an optical device which lacks the second optical member but is otherwise identical in all respects.

### Claim 32 (depends on 1)

The optical device of claim 1 wherein the charge decay time is lower than that for an optical device which lacks the antistatic layer but is otherwise identical in all respects.

### Claim 33

An optical device comprising a first optical member having a front surface, a second optical member, and an antistatic layer disposed between the first optical member and the second optical member wherein the first optical member, the second optical member, and the antistatic layer define an optical path such that light incident to the front surface of the first optical member will pass through each of the first optical member, the second optical member, and the antistatic layer;
wherein the antistatic layer is transparent and has a glass transition temperature of 20° C. or less and is the reaction product of a reaction mixture consisting essentially of 2 to 90 wt. % of at least one polymerizable onium salt having a fluoroorganic anion, at least one non-onium polymerizable multifunctional (meth)acrylate monomer or oligomer and optionally at least one polymerizable monofunctional (meth)acrylate monomer or oligomer, wherein the onium salt has the formula:
(R1)a-bG+[(CH2)qDR2]bX−
wherein:
each R1 comprises independently an alkyl, alicyclic, aryl, alkalicyclic, alkaryl, alicyclicalkyl, aralicyclic, or alicyclicaryl moiety, wherein such moiety may comprise one or more heteroatoms such as for example, nitrogen, oxygen, or sulfur, or may comprise phosphorus, or a halogen; le may be cyclic or aromatic and include G+in the cycle;
G is nitrogen, sulfur, or phosphorus;
a is 3 where G is sulfur and a is 4 where G is nitrogen or phosphorus;
b is an integer of 1 to 3 where G is sulfur and b is an integer of 1 to 4 where G is nitrogen or phosphorus;
q is an integer from 1 to 4;
D is oxygen, sulfur, or NR wherein R is H or a lower alkyl of 1 to 4 carbon atoms;
Re is a (meth)acryl; and
X−is a fluoroorganic anion which is a methide or an imide.