# US 10,767,056 B2 · Coating composition including a salt having a silsesquioxane anion

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- Number: US 10,767,056 B2
- Document ID: US10767056B2
- Status: Granted
- Kind: B2
- Application number: 16/332,303
- Filed: 2017-10-30
- Published: 2019-08-01
- Granted: 2020-09-08
- Earliest claimed: 2016-11-04
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Hyeok Jeong; Cheol Hee Lee; Jin Kyu Lee
- Web page: https://patentgrep.com/patent/US10767056B2

## CPC

- C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
- C08J 5/18: Manufacture of films or sheets
- C08K 5/544: containing nitrogen
- C08L 33/06: of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- 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}
- C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)}
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 133/06: of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- G02B 1/14: Protective coatings, e.g. hard coatings
- G02B 1/16: having an anti-static effect, e.g. electrically conducting coatings
- G02F 1/1333: Constructional arrangements; {Manufacturing methods}(G02F1/135, G02F1/136 take precedence)
- 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)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## Abstract

A coating composition having excellent anti-static properties and suitable for use as anti-static hard coating films. The coating composition comprises a radical polymerizable binder and a salt based on an anion including a cage-shaped frame. The anti-static hard coating film formed using the coating composition has excellent anti-static properties, abrasion resistance and moist heat resistance. Such film may be used for an optical laminate a display device, and the like.

## Claims

### Claim 1

A coating composition comprising:
a radically polymerizable binder; and
a salt having a polysilsesquioxane anion containing at least two units represented by Formula 1 below and a radically polymerizable cation:
[RSiO3/2] [Formula 1]
wherein R is a hydroxyl group, a thiol group, an oxygen anion (—O−) or a sulfur anion (—S−) and R in at least one unit of the at least two units of Formula 1 is an oxygen anion (—O−) or a sulfur anion (—S−).

### Claim 2 (depends on 1)

The coating composition according to claim 1, wherein the anion further comprises a unit represented by Formula 2 below:
[R2SiO2/2] [Formula 2]
wherein R is a hydroxyl group, a thiol group, an oxygen anion (—O−) or a sulfur anion (—S−).

### Claim 3 (depends on 1)

The coating composition according to claim 1, wherein the polysilsesquioxane anion has a molecular weight in a range of 500 to 2500.

### Claim 4 (depends on 1)

The coating composition according to claim 1, wherein the radically polymerizable cation is represented by Formula 3 below:
wherein each R1 to R4 is independently hydrogen, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloyloxyalkyl group or a methacryloyloxyalkyl group, and at least one of R1 to R4 is an alkenyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloyloxyalkyl group or a methacryloyloxyalkyl group.

### Claim 5 (depends on 1)

The coating composition according to claim 1, wherein the salt is contained in an amount of 7 to 45 parts by weight relative to 100 parts by weight of the binder.

### Claim 6 (depends on 1)

The coating composition according to claim 1, wherein the radically polymerizable binder is an acrylate compound.

### Claim 7 (depends on 1)

The coating composition according to claim 1, wherein the radically polymerizable binder is a multifunctional acrylate compound.

### Claim 8 (depends on 7)

The coating composition according to claim 7, wherein the multifunctional acrylate compound is a trifunctional or higher acrylate.

### Claim 9

A film comprising a coating layer which comprises a radically polymerizable binder; radically polymerizable cations; and polysilsesquioxane anions containing at least two units of Formula 1 below:
[RSiO3/2] [Formula 1]
wherein R is a hydroxyl group, a thiol group, an oxygen anion (—O−) or a sulfur anion (—S−) and R in at least one of the at least two units of Formula 1 is an oxygen anion (—O−) or a sulfur anion (—S−).

### Claim 10 (depends on 9)

The film according to claim 9, wherein the coating layer comprises a polymeric material obtained by polymerizing the radically polymerizable binder and the radically polymerizable cations.

### Claim 11 (depends on 9)

The film according to claim 9, wherein the film has a surface resistance in a range of 1×108 to 9×1010Ω/□.

### Claim 12 (depends on 9)

The film according to claim 9, wherein the film has a haze of 1% or less.

### Claim 13 (depends on 9)

The film according to claim 9, wherein the film has a transmittance of 90% or more.

### Claim 14 (depends on 9)

An optical laminate comprising the film of claim 9.

### Claim 15 (depends on 9, 14)

A display device comprising the film of claim 9 or the optical laminate of claim 14.