IP Library › Granted Patent US 11,591,287
Granted Patent B2
US 11,591,287 · App. 16/619,699 · Granted Feb 28, 2023

Antifouling zwitterionic polymer coating and reverse coating method

Inventors: Zhiqiang Cao (Troy, MI); Wei Wang (Detroit, MI)
Assignee: Wayne State University
C07C229/22A61K31/337A61K35/76A61K38/28A61K39/001106A61K39/39A61K47/543A61K47/544A61K47/58A61K47/6909A61K47/6915A61K47/6921B32B7/12B32B27/08C07C227/16C08F120/36C08G81/027C09D5/1668C09D5/1693C09D133/14C09D133/26B32B2307/7145C12N15/86
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Quick Facts
Patent No.
US 11,591,287
App. No.
16/619,699
Granted
Feb 28, 2023
Kind
B2
Abstract

Compositions are provided according to aspects of the present invention that include a hydrogel and a liner, wherein a surface of the hydrogel dissociably-engages a surface of the liner. Compositions are provided according to aspects of the present invention that include a hydrogel and a hydrophobic glue, wherein at least a portion of the gel network of the hydrogel is occupied by the hydrophobic glue. Reverse coaling processes and articles of manufacture made by reverse coating processes are provided according to aspects of the present invention. Compositions are provided according to aspects of the present invention that include a hydrogel and a substrate, wherein: the hydrogel comprises a polymer network; the substrate comprises a surface comprising a polymer network; and the polymer network of the hydrogel and the polymer network of the surface are entangled.

Claims (29)

1. A composition comprising a hydrophilic hydrogel element and a substrate, wherein:

the hydrophilic hydrogel element comprises a polymer network or a continuous phase, wherein:

the hydrophilic hydrogel element comprises a polymer having a structure of formula II

R 1 , R 2 , and R 3 are each independently selected from hydrogen, alkyl, and aryl groups;

L 1 is a linker that covalently couples the polymer sidechain to the polymer backbone;

X − is a counter ion associated with the cationic center;

M + is a metal ion, an ammonium ion, or an organic ion;

L 3 is a linker that covalently couples two polymer backbones;

n is an integer in the range of 2 to about 100,000;

m is a positive non-zero integer; and

m/n is in the range of 0.1%-99.9%;

the substrate comprises a surface comprising a polymer network or a continuous phase; and

the polymer network or the continuous phase of the hydrophilic hydrogel element and the polymer network or the continuous phase of the surface are entangled, wherein the entanglement is physical in nature and the polymer network or the continuous phase of the hydrophilic hydrogel element and the polymer network or the continuous phase of the surface of the substrate cannot be disentangled without breaking covalent, ionic, or hydrogen bonds of either the polymer network or the continuous phase of the hydrogel or the covalent, ionic, or hydrogen bonds of polymer network or the covalent, ionic, hydrogen, metallic or van der Waals bonds of continuous phase of the surface of the substrate; and

the porosity of the hydrophilic hydrogel element is greater than the porosity of the substrate.

2. The composition of claim 1 , wherein the surface of the substrate comprises a material selected from the group consisting of: agarose, crosslinked alginate, crosslinked or non-crosslinked poly-hydroxyethyl-methacrylate (PHEMA), crosslinked or non-crosslinked poly-N-(2-Hydroxypropyl) methacrylamide (PHPMA), polydimethylsiloxane (PDMS), crosslinked or non-crossliked polystyrene (PS), crosslinked silicone hydrogel, polyurethane (PU), silicone rubber, epoxy, epoxy-coated steel, glass, ceramic, plastic, metal, membrane materials, a derivative of any of the foregoing, and a combination of any two or more of the foregoing.

3. The composition of claim 1 , wherein the hydrophilic hydrogel element comprises a crosslinked or non-crosslinked polymer.

4. The composition of claim 1 , wherein the hydrophilic hydrogel element further comprises one or more of crosslinked poly-acrylic acid, crosslinked poly(vinyl alcohol), non-crosslinked poly(vinyl alcohol), crosslinked poly(vinylpyrrolidone), non-crosslinked poly(vinylpyrrolidone), silicone-containing hydrogel, crosslinked polyacrylamide, crosslinked poly-(N-isopropyl-acrylamide), non-crosslinked poly-(N-isopropyl-acrylamide), crosslinked poly-methyl-methacrylate, poly-hydroxyethyl-methacrylate (PHEMA), crosslinked polyethylene glycol (PEG), crosslinked poly(ethylene glycol) methacrylate (PEGMA), crosslinked poly(ethylene glycol) diacrylate (PEGDA), polypropylene glycol, crosslinked zwitterionic poly-(sulfobetaine methacrylate) (PSBMA), crosslinked zwitterionic 2-methacryloyloxyethyl phosphorylcholine (PMPC), crosslinked zwitterionic poly-carboxybetaine methacrylate (PCBMA), crosslinked zwitterionic poly-carboxybetaine acrylamide (PCBAA), non-crosslinked zwitterionic PCBAA, crosslinked alginate, crosslinked chitosan, gelatin, collagen, fibrin, agarose, hyaluronic acid, cellulose, polypeptides, or a derivative of one or more of the foregoing.

5. The composition of claim 1 , wherein:

R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, fluorine, trifluoromethyl, C 1 -C 6 alkyl, and C 6 -C 12 aryl groups;

L 1 is —C(═O)O—(CH 2 ) z - or —C(═O)NH—(CH 2 ) z -; and

z is an integer from 1 to 20.

6. A device, comprising the hydrophilic hydrogel element of claim 1 , wherein a surface of the device is at least partially covered by the hydrophilic hydrogel element.

7. The device of claim 6 , wherein the device is a medical device.

8. The medical device of claim 7 , wherein the medical device is an implantable medical device or a surgical instrument.

9. The medical device of claim 8 , wherein the medical device is a blood or tissue contacting device.

10. The medical device of claim 8 , wherein the medical device is a stent, artificial blood vessel, catheter, tubing, or dialysis device.

11. A water-immersible device, comprising the hydrophilic hydrogel element of claim 1 , wherein a surface of the water-immersible device is at least partially covered by the hydrophilic hydrogel element.

12. The water-immersible device of claim 11 , wherein the water-immersible device is a component of a watercraft, dock, lock, dam, water-treatment plant, underwater cable, offshore drill, or offshore well, or an instrument or tool for operating or maintaining any one of the foregoing.

13. The water-immersible device of claim 12 , wherein the water-immersible device is the hull of a watercraft.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2020
From: CAO, ZHIQIANG; WANG, WEI
To: WAYNE STATE UNIVERSITY
Reel/Frame 051504/0109 →
Continuity (4)
Provisional Application 62623844 · Jan 30, 2018
Provisional Application 62573431 · Oct 17, 2017
Provisional Application 62515704 · Jun 6, 2017
Related Publication 20200181426A1 · Jun 11, 2020