Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11541153-B2
Application number	US-202016924523-A
Country	US
Kind code	B2
Filing date	Jul 9, 2020
Priority date	Dec 1, 2017
Publication date	Jan 3, 2023
Grant date	Jan 3, 2023

Abstract

Disclosed herein are compositions to use in biofouling-resistant coatings, biofouling-resistant coatings, methods of making biofouling-resistant coatings, biofouling-resistant devices, and methods of making biofouling-resistant devices.

First claim

What is claimed is:

1. A phenyl azide-based copolymer comprising a compound of formula (IV):

wherein
each R 1a and R 1b is independently selected from hydrogen and halogen;
each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;
A 1 is —S(═O) 2 —;
A 2 is —C(═O)—;
each B 1 and B 2 is independently selected from —O— and —NR 3c —;
Z 1 is —(CR 6c R 6d ) s —); each R 4c , R 4d , R 5d , R 5e , R 6c and R 6d is independently selected from hydrogen, halogen, —CN, —OR 9a , optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;
each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X-, optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;
each R 9a , R 11a , R 11b , and R 11c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;
n is an integer selected from 0, 1, 2, 3, 4, 5, and 6; and
s is an integer selected from 1, 2, 3, 4, and 5.

2. The phenyl azide-based copolymer of claim 1 , wherein R 1a and R 1b are each F.

3. The phenyl azide-based copolymer of claim 1 , wherein R 2a and R 2b are each F.

4. The phenyl azide-based copolymer of claim 1 , wherein B 1 and B 2 are each —NR 3c —; and wherein R 3c in —NR 3c — is hydrogen or —CH 3 .

5. The phenyl azide-based copolymer of claim 4 , wherein R 3c in —NR 3c — is hydrogen.

6. The phenyl azide-based copolymer of claim 1 , wherein each R 6c and R 6d is independently selected from hydrogen and -CH 3 .

7. The phenyl azide-based copolymer of claim 1 , wherein each R 5d and R 5e is hydrogen and n is 0.

8. The phenyl azide-based copolymer of claim 1 , wherein R 11a is hydrogen or —CH 3 .

9. The phenyl azide-based copolymer of claim 1 , wherein each R 11b and R 11c is hydrogen.

10. The phenyl azide-based copolymer of claim 1 , wherein the phenyl azide-based copolymer comprises a monomer comprising sulfobetaine.

11. The phenyl azide-based copolymer of claim 10 , wherein the monomer is sulfobetaine methacrylate.

12. The phenyl azide-based copolymer of claim 11 , wherein the phenyl azide-based copolymer is formed from a reaction of the sulfobetaine methacrylate and the compound of formula (IV).

13. The phenyl azide-based copolymer of claim 1 , wherein the phenyl azide-based copolymer comprises sulfobetaine methacrylate-co-perfluorophenylazide methacrylate.

14. The phenyl azide-based copolymer of claim 1 , wherein the phenyl azide-based copolymer consists of sulfobetaine methacrylate-co-perfluorophenylazide methacrylate.

15. A biofouling resistant coating comprising the phenyl azide-based copolymer of claim 1 .

16. The biofouling resistant coating of claim 15 , wherein the biofouling resistant coating is configured to be coated onto a medical device.

17. A medical device coated with a compound that has the structure of the phenyl azide-based copolymer of claim 1 .

18. The medical device of claim 17 , wherein the medical device comprises an implant, an IV, a prosthesis, a suturing material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, a tubing, a wiring, an electrode, a clip, a fastener, a syringe, a container for storage of one or more other medical devices, or a combination thereof.

19. The medical device of claim 18 , wherein the medical device comprises the tubing.

Assignees

• Univ California
• Silq Tech Corporation

Inventors

• Kaner Richard B
• Chen Dayong
• Mcverry Brian T
• Rao Ethan
• Polasko Alexandra L

Classifications

• A61L29/085

  Macromolecular materials · CPC title

• C08J7/056

  Forming hydrophilic coatings · CPC title

• A61L31/10 Primary

  Macromolecular materials · CPC title

• A61L27/34

  Macromolecular materials · CPC title

• A61L2420/02

  Methods for coating medical devices · CPC title