# US 8,785,556 B2 · Hydrophobic coating compositions and articles coated with said compositions

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,785,556 B2
- Document ID: US8785556B2
- Status: Granted
- Kind: B2
- Application number: 13/459,787
- Filed: 2012-04-30
- Published: 2012-08-23
- Granted: 2014-07-22
- Earliest claimed: 1997-02-03
- Assignees: Cytonix Corporation
- Applicants: James F. Brown
- Inventors: James F. Brown
- Web page: https://patentgrep.com/patent/US8785556B2

## CPC

- C09D 127/18: Homopolymers or copolymers of tetrafluoroethene
- B01L 3/00: Containers or dishes for laboratory use, e.g. laboratory glassware; Droppers
- B01L 3/50: {Containers for the purpose of retaining a material to be analysed, e.g. test tubes (devices for taking samples of blood A61B5/15)}
- C09D 133/16: Homopolymers or copolymers of esters containing halogen atoms
- B01L 2300/166: Suprahydrophobic; Ultraphobic; Lotus-effect
- B05D 5/083: {involving the use of fluoropolymers}
- B05D 7/227: {of containers, cans or the like}
- C08L 27/18: Homopolymers or copolymers or tetrafluoroethene
- C08L 2205/18: Spheres
- Y10S 436/809: Multifield plates or multicontainer arrays
- Y10S 436/81: Tube, bottle, or dipstick
- Y10T 428/13: Hollow or container type article [e.g., tube, vase, etc.]
- Y10T 428/131: Glass, ceramic, or sintered, fused, fired, or calcined metal oxide or metal carbide containing [e.g., porcelain, brick, cement, etc.]
- Y10T 428/1317: Multilayer [continuous layer]
- Y10T 428/1321: Polymer or resin containing [i.e., natural or synthetic]
- Y10T 428/1352: Polymer or resin containing [i.e., natural or synthetic]
- Y10T 428/139: Open-ended, self-supporting conduit, cylinder, or tube-type article
- Y10T 428/24479: including variation in thickness
- Y10T 428/2495: Thickness [relative or absolute]
- Y10T 428/24967: Absolute thicknesses specified
- Y10T 428/24975: No layer or component greater than 5 mils thick
- Y10T 428/3154: Of fluorinated addition polymer from unsaturated monomers
- Y10T 428/31544: Addition polymer is perhalogenated
- Y10T 428/31551: Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T 428/31663: As siloxane, silicone or silane
- Y10T 428/31667: Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
- 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)
- B01L: CHEMICAL OR PHYSICAL LABORATORY APPARATUS FOR GENERAL USE
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Hydrophobic coating compositions are provided as are processes to coat articles with the compositions. Extremely hydrophobic coatings are provided by the compositions. Durable, weatherable and scratch-resistant coatings are provided by compositions comprising a fluorinated component and an adhesion promoter compound. The adhesion promoter compound can include an alkoxy group, a furfuryl-containing ring structure, and a reactive group.

## Claims

### Claim 1

A composition of matter comprising a first reactant, a linkage reactant, and a first functionalized reactant,
the first reactant comprising at least one perfluoroalkyl group or segment and at least two hydroxyl groups,
the linkage reactant being capable of linking the first reactant and the first functionalized reactant by a first reaction mechanism,
the first functionalized reactant comprising a hydroxyl group and three or more inducible reactive groups that are capable of activation by a second reaction mechanism that differs from the first reaction mechanism, wherein each of the three or more inducible reactive groups comprises an acrylate group or a methacrylate group, and
the remainder of the composition comprising optional solvents, catalysts, additives, fluorinated reactants, and other functionalized reactants that are capable of reacting by the second reaction mechanism, wherein
the composition comprises the first reactant in an amount sufficient to form a surface having a surface energy of about 22 dynes/cm or lower at 20° C. after reaction by the first and second reaction mechanisms.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the first reactant comprises one or more trifluoromethyl groups.

### Claim 3 (depends on 2)

The composition of claim 2, wherein
the composition comprises the first reactant in an amount sufficient to form a surface having at least 15 percent trifluoromethyl groups after reaction by the first and second reaction mechanisms.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the linkage reactant comprises isocyanate groups.

### Claim 5 (depends on 1)

The composition of claim 1, further comprising particles having an average particle size diameter of less than about 100 microns.

### Claim 6 (depends on 1)

The composition of claim 1, further comprising particles having an average particle size diameter of about 100 nanometers or less.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the at least one perfluoroalkyl group or segment has a carbon atom chain length of from 3 to about 20 carbon atoms.

### Claim 8 (depends on 1)

A reaction product formed from the composition of claim 1.

### Claim 9 (depends on 8)

An article comprising or coated with the reaction product of claim 8.

### Claim 10

A composition of matter comprising a first reaction product, the first reaction product being a product of a reaction between a first reactant, a linkage reactant, and a first functionalized reactant, wherein
the first reactant comprises at least one perfluoroalkyl group or segment and at least two hydroxyl groups,
the linkage reactant is capable of linking together the first reactant and the first functionalized reactant by a first reaction mechanism,
the first functionalized reactant comprises (i) a hydroxyl group, and (ii) a group comprising at least three acrylate groups or methacrylate groups,
the remainder of the composition comprises optional ingredients selected from solvents, catalysts, additives, fluorinated or organic reactants, other reactants comprising reactive linkage groups, and additional functionalized reactants, and
the first reaction product comprises the first reactant in an amount sufficient to form a surface, upon polymerization of the first reaction product by a second reaction mechanism, having a surface energy of about 22 dynes/cm or lower at 20° C.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the first reactant comprises one or more trifluoromethyl groups.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the first reaction product comprises the first reactant in an amount sufficient to form a surface, upon polymerization of the first reaction product by a second reaction mechanism, having at least 15 percent trifluoromethyl groups.

### Claim 13 (depends on 10)

The composition of claim 10, wherein the linkage reactant comprises isocyanate groups.

### Claim 14 (depends on 10)

The composition of claim 10, further comprising particles having an average particle size diameter of less than about 100 microns.

### Claim 15 (depends on 10)

The composition of claim 10, further comprising particles having an average particle size diameter of about 100 nanometers or less.

### Claim 16 (depends on 10)

The composition of claim 10, wherein the at least one perfluoroalkyl group or segment has a carbon atom chain length of from 3 to about 20 carbon atoms.

### Claim 17 (depends on 10)

A second reaction product formed from the composition of claim 10.

### Claim 18 (depends on 10)

An article comprising or coated with the reaction product of claim 10.