# US 11,441,049 B2 · Zwitterionic copolymer coatings and related methods

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- Number: US 11,441,049 B2
- Document ID: US11441049B2
- Status: Granted
- Kind: B2
- Application number: 17/435,654
- Filed: 2020-03-13
- Published: 2022-02-10
- Granted: 2022-09-13
- Earliest claimed: 2019-03-14
- Assignees: University of Washington
- Applicants: University of Washington
- Inventors: Shaoyi Jiang; Xiaojie Lin; Jonathan Himmelfarb; Buddy D. Ratner
- Web page: https://patentgrep.com/patent/US11441049B2

## CPC

- C09D 133/26: Homopolymers or copolymers of acrylamide or methacrylamide
- A61L 29/041: {obtained by reactions only involving carbon-to-carbon unsaturated bonds}
- A61L 29/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 29/085: {Macromolecular materials}
- A61L 29/141: {Plasticizers}
- A61L 29/145: {Hydrogels or hydrocolloids}
- C08J 3/28: Treatment by wave energy or particle radiation
- C08J 2333/26: Homopolymers or copolymers of acrylamide or methacrylamide
- C08L 2312/06: by radiation
- 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)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Zwitterionic carboxybetaine copolymers and their use in coatings to impart non-fouling and functionality to surfaces, particularly surfaces of blood-contacting medical devices.

## Claims

### Claim 1

A method for inhibiting or preventing leaching of a plasticizer from a surface of a substrate, comprising:
(a) coating at least a portion of a surface of a substrate with a composition comprising a copolymer to provide a coated surface, the copolymer comprising first repeating units and second repeating units, wherein each of the first repeating units comprises a pendant zwitterionic group, and wherein each of the second repeating units comprises a pendant photoreactive group effective for crosslinking the copolymer on a surface, to provide a coated surface; and
(b) irradiating the coated surface with ultraviolet light effective to crosslink the copolymer on the surface, thereby providing a coated surface effective for inhibiting or preventing leaching of a plasticizer from the surface;
wherein the copolymer has formula (III):
wherein
R1 and R2 are independently —(CH2)xH, where x is an integer from 0 to 20;
R3 and R4 are independently (CH2)xH, where x is an integer from 0 to 20;
X is O or NH;
Y is O or NH;
n is an integer from 1 to 20;
m is an integer from 1 to 20;
a is from about 0.10 to about 0.90 mole percent;
b is about 0.10 to about 0.90 mole percent;
a+b is 1.0; and
* represents the copolymer terminal groups.

### Claim 2 (depends on 1)

The method of claim 1, wherein the surface is a blood-contacting surface.

### Claim 3 (depends on 1)

The method of claim 1, wherein the substrate is polyurethane tubing, polysulfone dialysis membrane, or hydrocarbon-based membrane container.

### Claim 4 (depends on 1)

The method of claim 1, wherein coating the surface with the composition comprises dipping the surface into the composition.

### Claim 5 (depends on 1)

The method of claim 1, wherein coating at least a portion of the surface comprises spraying, spinning, brushing, or rolling the composition onto the surface.

### Claim 6 (depends on 1)

The method of claim 1, wherein the surface is a hydrocarbon-based surface.

### Claim 7 (depends on 1)

The method of claim 1, wherein the surface is a cellulose, cellulose acetate, polyolefin, polyester, polycarbonate, polyurethane (PU), polysulfone (PSF), poly(ether sulfone) (PES), polyamide, polyacrylic, polyimide, aromatic polyester, polyethylene (PE), polypropylene (PP), polystyrene (PS), poly(ethylene terephthalate) (PET), polyvinyl chloride (PVC), poly(dimethyl siloxane) (PMDS), poly(vinylidiene fluoride) (PVDF), poly(lactic acid) (PLA), or poly(methyl methacrylate) (PMMA) surface.

### Claim 8 (depends on 1)

The method of claim 1, wherein the surface is a polyvinyl chloride surface or a polyurethane surface.

### Claim 9 (depends on 1)

The method of claim 1, wherein the surface is the surface of polyvinyl chloride tubing or polyurethane tubing.

### Claim 10 (depends on 1)

The method of claim 1, wherein the copolymer further comprises third repeating units, wherein each of the third repeating units comprises a pendant hydrophobic group effective for adsorbing the copolymer to the plastic surface.

### Claim 11 (depends on 1)

The method of claim 1, wherein m is 1 or 2.

### Claim 12 (depends on 1)

The method of claim 1, wherein a is from about 0.70 to about 0.90 mole percent.

### Claim 13 (depends on 1)

The method of claim 1, wherein a is about 0.80 mole percent.

### Claim 14 (depends on 1)

The method of claim 1, wherein b is about 0.10 to about 0.30 mole percent.

### Claim 15 (depends on 1)

The method of claim 1, wherein b is about 0.20 mole percent.
