Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-12109332-B2
Application number	US-202318386896-A
Country	US
Kind code	B2
Filing date	Nov 3, 2023
Priority date	Jun 5, 2019
Publication date	Oct 8, 2024
Grant date	Oct 8, 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

The invention claimed is:

1. A medical device coated with a compound 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 5c , and R 5d 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 CR 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 medical device of claim 1 , wherein each of R 1a , R 1b , R 2a , and R 2b is F.

3. The medical device of claim 1 , wherein D is —S(═O) 2 O − or —C(═O)O − .

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

5. The medical device of claim 1 , wherein each B 1 , B 2 , and B 3 is independently —O— or —NR 3c —.

6. The medical device of claim 1 , wherein the compound has a number-average molecular weight of between about 10,000 and about 250,000.

7. The medical device of claim 1 , wherein the medical device comprises a silicon-based device or a carbon-based device.

8. The medical device of claim 7 , wherein the silicon-based device comprises a siloxane polymer moiety, a sesquisiloxane polymer moiety, a siloxane-silarylene polymer moiety, a silalkylene polymer moiety, a polysilane moiety, a polysilylene moiety, or a polysilazane moiety.

9. The medical device of claim 7 , wherein the carbon-based device comprises a polyolefin moiety, a polyethylene (PE) moiety, a polypropylene (PP) moiety, a polyamide (PA) moiety, a polytetrafluoroethylene (PTFE) moiety, a polyvinylidene fluoride (PVdF) moiety, or a polyvinyl chloride (PVC) moiety.

10. The medical device of claim 7 , wherein the medical device is a silicon-based device comprising a silicon surface.

11. The medical device of claim 10 , wherein the compound is covalently bound to the silicon surface.

12. The medical device of claim 11 , wherein the medical device comprises an implant, an IV, a prosthesis, suturing material, valve, stent, catheter, rod, shunt, scope, a contact lens, tubing, wiring, electrode, clip, fastener, syringe, container, bandage, patch, or a combination thereof.

13. The medical device of claim 12 , wherein the medical device is a catheter.

14. The medical device of claim 13 , wherein the catheter comprises an indwelling catheter, uretic catheter, permeath, or Foley catheter.

15. The medical device of claim 12 , wherein the medical device is a shunt.

16. The medical device of claim 15 , wherein the shunt comprises a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt, a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS), a portacaval shunt, or a vesico-amniotic shunt.

17. The medical device of claim 15 , wherein the shunt is a cerebral shunt.

18. The medical device of claim 12 , wherein the medical device is a stent.

19. The medical device of claim 18 , wherein the stent comprises a coronary stent, a vascular stent, or a biliary stent.

20. The medical device of claim 12 , wherein the scope comprises a scope utilized in an image-guided surgery including endoscopy or laparoscopy.

21. The medical device of claim 1 , wherein the medical device comprises an auditory prosthesis, artificial larynx, an artificial bone, an artificial joint, an artificial organ, dental implants, mammary implants, penile implants, cranio/facial tendons, tendons, ligaments, menisci, or disks.

22. The medical device of claim 21 , wherein the medical device is an auditory prostheses.

23. The medical device of c

Assignees

• Univ California
• Silq Tech Corporation

Inventors

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

Classifications

• C08F220/382

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

• C08F220/30

  containing aromatic rings in the alcohol moiety · CPC title

• C08F220/34

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

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08F2438/01

  Atom Transfer Radical Polymerization [ATRP] or reverse ATRP · CPC title