Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-12121634-B2
Application number	US-202217989281-A
Country	US
Kind code	B2
Filing date	Nov 17, 2022
Priority date	Dec 1, 2017
Publication date	Oct 22, 2024
Grant date	Oct 22, 2024

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 compound comprising: 1) a monomer having the structure:

and
2) a zwitterionic monomer having the structure of formula (V):

wherein
A 3 is independently selected from —C(═O)—, —S(═O)—, —S(═O) 2 —, and —S(═O)(═NR 3c )—;
B 3 is independently selected from —O— and —NR 3c —;
D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;
Z 2 is —(CR 6c R 6d ) t —;
Z 3 is —(CR 6c R 6d ) p —;
each R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;
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;
each 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 ;
X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;
each R 9a , R 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;
t is an integer selected from 1, 2, 3, 4, or 5; and
p is an integer selected from 1, 2, 3, 4, or 5.

2. The compound of claim 1 , wherein each R 6c and R 6d is independently selected from hydrogen and —CH 3 .

3. The compound of claim 1 , wherein the zwitterionic monomer having the structure of formula (V) comprises sulfobetaine.

4. The compound of claim 1 , wherein the zwitterionic monomer having the structure of formula (V) is

5. The compound of claim 1 , wherein the compound comprises perfluorophenylazide methacrylate-co-sulfobetaine methacrylate.

6. The compound of claim 1 , wherein the compound is a random copolymer.

7. A biofouling resistant coating comprising the compound of claim 1 .

8. The biofouling resistant coating of claim 7 , wherein the biofouling resistant coating is grafted to a surface of a medical device.

9. A medical device having a surface grafted with the compound of claim 1 .

10. The medical device of claim 9 , 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.

11. The medical device of claim 10 , wherein the medical device comprises the tubing.

12. The medical device of claim 9 , wherein the medical device exhibits reduced bacterial cell adhesion.

Assignees

• Univ California
• Silq Tech Corporation

Inventors

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

Classifications

• C08J7/056

  Forming hydrophilic coatings · CPC title

• C08F220/387

  and containing nitrogen and oxygen · CPC title

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• C08J2433/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08J2383/04

  Polysiloxanes · CPC title