Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-2020385506-A1
Application number	US-202016892980-A
Country	US
Kind code	A1
Filing date	Jun 4, 2020
Priority date	Jun 5, 2019
Publication date	Dec 10, 2020
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 . 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 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.

15 . A medical device coated with a compound of claim 1 .

16 . A biofouling-resistant medical device, wherein a surface of the medical device is coated with a compound of claim 1 .

17 . The biofouling-resistant medical device of claim 16 , 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, or a combination thereof.

18 . The biofouling-resistant medical device of claim 17 , wherein the medical device is a catheter.

19 . The biofouling-resistant medical device of claim 16 , wherein the biofouling is produced by a bacterium, a virus, and/or a fungus.

20 . A method of making a biofouling-resistant medical device, comprising:
a) contacting a surface of a device with a mixture comprising a charged or zwitterion copolymer; and b) treating the surface of the device of step a) with a heat source for a time sufficient to undergo thermografting of the copolymer onto the surface of the device, thereby making the biofouling-resistant device; wherein the charged or zwitterion copolymer comprises a phenyl azide-based copolymer;
and wherein the charged or zwitterion copolymer having a number-average molecular weight of between about 10,000 and about 250,000.

21 .- 30 . (canceled)

Assignees

• Univ California
• Hydrophilix Inc

Inventors

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

Classifications

• C09D133/14

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

• C09D5/1668 Primary

  Vinyl-type polymers · CPC title

• C08F220/585

  and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS] · CPC title

• C08F220/385

  and containing nitrogen · CPC title

• C08F220/285 Primary

  and containing a polyether chain in the alcohol moiety · CPC title