Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-2025242091-A1
Application number	US-202418825680-A
Country	US
Kind code	A1
Filing date	Sep 5, 2024
Priority date	Jun 5, 2019
Publication date	Jul 31, 2025
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

What is claimed is:

1 .- 32 . (canceled)

33 . 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 a) treating the surface of the device with a heat source for a time sufficient to undergo thermografting of the charged or zwitterion copolymer onto the surface of the device, thereby making the biofouling-resistant medical device; wherein the charged or zwitterion copolymer comprises a phenyl azide-based copolymer; and wherein the charged or zwitterion copolymer has a number-average molecular weight of between about 10,000 and about 250,000.

34 . The method of claim 33 , wherein the time sufficient to undergo thermografting is at least 1 minute.

35 . The method of claim 33 , wherein the time sufficient to undergo thermografting is at most 24 hours.

36 . The method of claim 33 , wherein the heat source provides a grafting temperature between 60° C. and 240° C.

37 . The method of claim 36 , wherein the heat source provides a grafting temperature between 60° C. and 120° C.

38 . The method of claim 33 , wherein the mixture is an aqueous solution or suspension.

39 . The method of claim 33 , wherein the mixture is a non-aqueous solution or suspension.

40 . The method of claim 33 , wherein the thermografting is not affected by the presence of oxygen.

41 . The method of claim 33 , wherein the mixture comprising the charged or zwitterion copolymer has a concentration of between 1 mg/mL and 30 mg/mL.

42 . The method of claim 41 , wherein the mixture comprising the charged or zwitterion copolymer has a concentration of between 1 mg/mL and 15 mg/mL.

43 . The method of claim 33 , wherein the mixture comprising the charged or zwitterion copolymer has a concentration between 0.1 mg/cm 2 to 10 mg/cm 2 of the surface of the device.

44 . The method of claim 33 , wherein the device comprises a carbon-based device or a silicon-based device.

45 . The method of claim 33 , wherein the device comprises a silicon-based device, wherein the silicon-based device comprises a silicon-based polymer moiety.

46 . The method of claim 45 , where the silicon-base polymer moiety comprises polydimethylsiloxane (PDMS).

47 . The method of claim 33 , wherein the biofouling is produced by a bacterium, a virus, and/or a fungus.

48 . The method of claim 33 , wherein the charged or zwitterion copolymer is a compound of
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 91 , R 121 , 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 9 a 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 91 , R 9b , R 9c , R 13a , R 3b , 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.

49 . The method of claim 48 , wherein each of R 1a , R 1b , R 2a , and R 2b is F.

50 . The method of claim 48 , wherein D is —S(═O) 2 O— or —C(═O)O—.

51 . The method of claim 48 , wherein A 1 is —S(═O) 2 — and each A 2 , A 3 , and A 4 is —C(═O)—.

52 . The method of claim 48 , wherein each B 1 , B 2 , and B 3 is independently —O— or —NR 3c —.

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