# US 2023/0056474 A1 · Ice-Shedding and Smudge-Repellant Coating

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- Number: US 2023/0056474 A1
- Document ID: US20230056474A1
- Status: Published application
- Kind: A1
- Application number: 17/798,647
- Filed: 2021-02-12
- Published: 2023-02-23
- Earliest claimed: 2020-02-14
- Assignees: Queen's University at Kingston
- Applicants: Queen's University at Kingston
- Inventors: Guojun Liu; Alexander Newell Harper
- Web page: https://patentgrep.com/patent/US20230056474A1

## CPC

- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C08F 220/1808: {C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate}
- C08F 290/068: {Polysiloxanes}
- C08G 18/2865: {Compounds having only one primary or secondary amino group; Ammonia}
- C08G 18/6229: {Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols}
- C08G 18/6295: {Polymers of silicium containing compounds having carbon-to-carbon double bonds}
- C08G 18/638: {characterised by the use of compounds having carbon-to-carbon double bonds other than styrene and/or olefinic nitriles}
- C08G 18/73: acyclic
- C08G 18/808: {Monoamines}
- C09D 5/1625: {organic}
- C09D 5/1637: {Macromolecular compounds}
- C09D 5/1693: {as part of a multilayer system}
- C09D 7/20: Diluents or solvents
- C09D 133/10: Homopolymers or copolymers of methacrylic acid esters
- C09D 151/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09D 175/04: Polyurethanes
- C09K 3/18: for application to surfaces to minimize adherence of ice, mist or water thereto (rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30); Thawing or antifreeze materials for application to surfaces (used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A coating that is able to shed accumulated material (such as ice) that includes a crosslinkable copolymer with hydrogen bonding moieties and liquid-like side chains, and an oil (or other non-aqueous liquid) that is compatible with the side-chains and that resides in the crosslinked coating and on the surface of the coating together with the side-chains that are on the external surface. Methods may use the coating for de-icing, shedding of marine organisms, and smudge-repellency.

## Claims

### Claim 1

A coating that sheds accumulated material, comprising:
a coating precursor that comprises a crosslinkable copolymer comprising hydrogen bonding moieties and liquid-like side chains that are compatible with a selected non-aqueous liquid; and 0.2-30 vol % of the selected non-aqueous liquid,
wherein when the coating is crosslinked, at least a portion of the liquid-like side-chains and the non-aqueous liquid are present at the surface of the coating.

### Claim 2 (depends on 1)

The coating of claim 1, wherein the copolymer comprises polyurethane, epoxy, polymethacrylate, polymer/inorganic hybrid coating, rubber, or polyacrylate,

### Claim 3 (depends on 1)

The coating of claim 1, wherein hydrogen bonding moieties comprise acrylamide, urea, urethane, ureidopyridinone, hydroxyl, carboxyl, amino, pyridine, nucleic bases, or any combination thereof.

### Claim 4 (depends on 1)

The coating of claim 1, wherein the non-aqueous liquid is ethylene glycol, glycerol, ionic liquid, oligo(ethylene glycol), or oil.

### Claim 5

(canceled)

### Claim 6 (depends on 4)

The coating of claim 4, wherein the oil comprises cooking oil, canola oil, vegetable oil, poly(dialkyl siloxane), perfluorinated polyether, poly(alkyl acrylates), polyisobutylene, any polymer that is a liquid down to −40° C., poly(diphenyl siloxane), poly(methylphenyl siloxane), polyisobutylene, poly(alkyl methacrylate), poly(alkyl acrylate), poly(alkyl styrene), perfluorinated polyether, poly(diethyl siloxane), hexadecane, sunflower oil, canola oil, cotton seed oil, or a combination thereof.

### Claim 7 (depends on 4, 5, 6)

The coating of claim 4 to 6, wherein the oil is a low-surface-tension oil.

### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7)

The coating of claim 1 to 7, wherein the liquid-like side chains and the non-aqueous liquid are the same.

### Claim 9 (depends on 1)

The coating of claim 1, wherein the liquid-like side chains and the non-aqueous liquid are different.

### Claim 10 (depends on 1)

The coating of claim 1, wherein accumulated material comprises ice, marine organisms, bacteria, blood, biofluids, proteins, smudges, and/or stains.

### Claim 11

(canceled)

### Claim 12 (depends on 1)

The coating of claim 1, wherein the non-aqueous liquid is ethylene glycol and the liquid-like side chains are poly(ethylene glycol).

### Claim 13

(canceled)

### Claim 14 (depends on 1)

The coating of claim 1, further comprising a crosslinker.

### Claim 15

(canceled)

### Claim 16

A method for shedding accumulated material, comprising:
applying a coating precursor to a substrate to form a crosslinked coating, wherein the coating precursor comprises a crosslinkable copolymer comprising hydrogen bonding moieties and liquid-like side chains that are compatible (miscible) with a selected non-aqueous liquid;
adding 0.2-30 vol % of the selected non-aqueous liquid either to the coating precursor or to the crosslinked coating;
wherein accumulated material on the coating readily sheds.

### Claim at position 17

-39. (canceled)

### Claim 40 (depends on 1)

The coating of claim 1, comprising P(EHMA-s-HEMA), P(EHMA-s-HEMA)-g-PDMS, P(EHMA-s-HEMA)-based polyurethane, P(EHMA-s-HEMA)-g-PDMS-based polyurethane, P(EHMA-s-MMA-s-HEMA), P(EHMA-s-MMA-s-HEMA)-based polyurethane, P(EHMA-s-MMA-s-HEMA)-g-PDMS, P(EHMA-s-MMA-s-HEMA)-g-PDMS-based polyurethane, or any combination thereof, wherein EHMA is 2-ethylhexyl methacrylate; HEMA is 2-hydroxyethyl methacrylate; and PDMS is poly(dimethyl siloxane).

### Claim 41 (depends on 1)

The coating of claim 1, comprising a lubricated bilayer coating.

### Claim 42 (depends on 41)

The coating of claim 41, wherein the coating comprises a copolymer that comprises a first and a second polyol, wherein the second polyol comprises a small fraction of fluorinated moieties and comprises a lower molar fraction of hydroxyl groups than the first polyol.

### Claim 43 (depends on 42)

The coating of claim 42, wherein the first polyol is P(EHMA80%/o-s-HEMA20%) and the second polyol is P(EHMA93%/o-s-HEMA3%/o-s-FHEMA4%), where EHMA denotes EHMA is 2-ethylhexyl methacrylate; HEMA denotes 2-hydroxyethyl methacrylate; FHEMA denotes 2-(perfluorohexyl) ethyl methacrylate), and subscripts denote molar fractions of monomers in the copolymer.

### Claim 44 (depends on 41)

The coating of claim 41, comprising P(EHMA-s-HEMA)-g-PDMS, wherein EHMA is 2-ethylhexyl methacrylate; HEMA is 2-hydroxyethyl methacrylate; and
PDMS is poly(dimethyl siloxane).

### Claim 45

(canceled)

### Claim 46 (depends on 41)

The coating of claim 41, wherein the lubricant is PDMS-UPy, wherein PDMS is poly(dimethyl siloxane); and
UPy is ureidopyrimidinone.

### Claim 47 (depends on 39)

The coating of claim 39, comprising a mixture of HDIT and UPy-NCO referred to as PU-H0, PU-H50, PU-H75, and PU-H100 wherein 0, 50, 75, and 100 are an amount on the percentile scale of isocyanate groups contributed by UPy-NCO.

### Claim at position 26

-50. (canceled)

### Claim 51

P(EHMA-s-HEMA)-g-PDMS.

### Claim at position 28

-57. (canceled)