Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11807701-B2
Application number	US-202016892980-A
Country	US
Kind code	B2
Filing date	Jun 4, 2020
Priority date	Jun 5, 2019
Publication date	Nov 7, 2023
Grant date	Nov 7, 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

The invention claimed is:

1. A copolymer comprising:
a) a repeating unit of Formula (VII):

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;
each A 1 and A 2 is independently selected from —C(═O)—, —S(═O)—, —S(═O) 2 —, and —S(═O)(═NR 3c )—;
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, 6, 7, and 8; and
s is an integer selected from 1, 2, 3, 4, and 5;
b) a repeating unit of Formula (VIII):

wherein,
A 3 is —C(═O)—, —S(═O)—, —S(═O) 2 —, or —S(═O)(═NR 3c )—;
B 3 is —O— or —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 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;
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 ;
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 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;
p is an integer selected from 1, 2, 3, 4, or 5; and
wherein the repeating unit of Formula (VIII) is charged or zwitterionic; and
c) a repeating unit of Formula (IX):

A 4 is —C(═O)—, —S(═O)—, —S(═O) 2 —, or —S(═O)(═NR 3c )—;
B 4 is —O— or —NR 3c —;
Z 4 is —(CR 6c R 6d ) k —;
E is —CN, —OR 9a , —NR 9a R 9b , —NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 6 fluoroalkyl, —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;
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 ;
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 9b , R 9c , R 13a , R 13b , and R 13c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; and
k is an integer selected from 1, 2, 3, 4, or 5.

2. The copolymer of claim 1 , wherein each R 1a , R 1b , R 2a , and R 2b is F.

3. The copolymer of claim 1 , wherein A 1 is —S(═O) 2 — and each A 2 , A 3 , and A 4 is —C(═O)—.

4. The copolymer of claim 1 , wherein each B 1 , B 2 , and B 3 is independently —O— or —NR 3c —.

5. The copolymer of claim 4 , wherein each R 3c is hydrogen or —CH 3 .

6. The copolymer of claim 1 , wherein D is —S(═O) 2 O − or —C(═O)O − .

7. The copolymer of claim 1 , wherein E is —NR 9a R 9b R 9c+ or —S(═O) 2 OR 9a .

8. The copolymer of claim 7 , wherein each R 9a , R 9b , and R 9c is independently hydrogen or C 1 -C 4 alkyl.

9. The copolymer of claim 1 , wherein each R 3a and R 3b is —CH 3 .

10. The copolymer of claim 1 , wherein each R 3c , R 3d , R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d is hydrogen.

11. The copolymer of claim 1 , wherein each R 11a , R 12a , and R 13a is hydrogen or —CH 3 .

12. The copolymer of claim 1 , wherein each R 11b , R 11c , R 12b , R 12c , R 13b , and R 13c is hydrogen.

13. The copolymer of claim 1 , wherein n is 0, 1, or 2.

14. The copolymer of claim 1 , wherein each s, t, p, and k is independently 1, 2 or 3.

Assignees

• Univ California
• Hydrophilix Inc
• Silq Tech Corporation

Inventors

• Mcverry Brian T
• Rao Ethan
• Kaner Richard B
• He Na

Classifications

• C08F220/30 Primary

  containing aromatic rings in the alcohol moiety · CPC title

• A61L29/085

  Macromolecular materials · CPC title

• C08F220/34

  Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate} · CPC title

• C08F220/382

  and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate · CPC title

• C08F293/005

  using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent · CPC title