Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-2024141084-A1
Application number	US-202318386896-A
Country	US
Kind code	A1
Filing date	Nov 3, 2023
Priority date	Jun 5, 2019
Publication date	May 2, 2024
Grant date	—

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

1 - 30 . (canceled)

31 . 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 5c , 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.

32 . The medical device of claim 31 , wherein each of R 1a , R 1b , R 2a , and R 2b is F.

33 . The medical device of claim 31 , wherein D is —S(═O) 2 O − or —C(═O)O − .

34 . The medical device of claim 31 , wherein A 1 is —S(═O) 2 — and each A 2 , A 3 , and A 4 is —C(═O)—.

35 . The medical device of claim 31 , wherein each B 1 , B 2 , and B 3 is independently —O— or —NR 3c —.

36 . The medical device of claim 31 , wherein the compound has a number-average molecular weight of between about 10,000 and about 250,000.

37 . The medical device of claim 31 , wherein the medical device comprises a silicon-based device or a carbon-based device.

38 . The medical device of claim 37 , 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.

39 . The medical device of claim 37 , 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.

40 . The medical device of claim 37 , wherein the medical device is a silicon-based device comprising a silicon surface.

41 . The medical device of claim 40 , wherein the compound is covalently bound to the silicon surface.

42 . The medical device of claim 41 , 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.

43 . The medical device of claim 42 , wherein the medical device is a catheter.

44 . The medical device of claim 43 , wherein the catheter comprises an indwelling catheter, uretic catheter, permcath, or Foley catheter.

45 . The medical device of claim 42 , wherein the medical device is a shunt.

46 . The medical device of claim 45 , 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.

47 . The medical device of claim 45 , wherein the shunt is a cerebral shunt.

48 . The medical device of claim 42 , wherein the medical device is a stent.

49 . The medical device of claim 48 , wherein the stent comprises a coronary stent, a vascular stent, or a biliary stent.

50 . The medical device of claim 42 , wherein the scope comprises a scope utilized in an image-guided surgery including endoscopy or laparoscopy.

51 . The medical device of claim 31 , 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.

52 . The medical device of claim 51 , wherein the medical device is

Assignees

• Univ California
• Silq Tech Corporation

Inventors

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

Classifications

• C08F220/34 Primary

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

• A61L29/085

  Macromolecular materials · CPC title

• C08F220/30

  containing aromatic rings in the alcohol moiety · 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