Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-2020338240-A1
Application number	US-202016924523-A
Country	US
Kind code	A1
Filing date	Jul 9, 2020
Priority date	Dec 1, 2017
Publication date	Oct 29, 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 - 30 . (canceled)

31 . A phenyl azide-based copolymer comprising a compound of Formula (IV):

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, and 6; and
s is an integer selected from 1, 2, 3, 4, and 5.

32 . The phenyl azide-based copolymer of claim 31 , wherein R 1a and R 1b are each F.

33 . The phenyl azide-based copolymer of claim 31 , wherein R 2a and R 2b are each F.

34 . The phenyl azide-based copolymer of claim 31 , wherein A 1 is —S(═O) 2 — and A 2 is —C(═O)—.

35 . The phenyl azide-based copolymer of claim 31 , wherein B 1 and B 2 are each —NR 3c —; and wherein R 3c in —NR 3c — is hydrogen or —CH 3 .

36 . The phenyl azide-based copolymer of claim 35 , wherein R 3c in —NR 3c — is hydrogen or —CH 3 .

37 . The phenyl azide-based copolymer of claim 31 , wherein each R 6c and R 6d is independently selected from hydrogen and —CH 3 .

38 . The phenyl azide-based copolymer of claim 31 , wherein each R 5d and R 5e is hydrogen and n is 0.

39 . The phenyl azide-based copolymer of claim 31 , wherein R 11a is hydrogen or —CH 3 .

40 . The phenyl azide-based copolymer of claim 31 , wherein each R 11b and R 11c is hydrogen.

41 . A biofouling-resistant coating comprising a compound of Formula (I):

wherein
A is selected from —C(═O)—, —S(═O)—, —S(═O) 2 —, and —S(═O)(—NR 3 )—;
L is selected from —OQ, —NR 3 Q, and —N(R 3 ) 2 Q + ;
Q is a structure represented by a formula:

Z is selected from —CR 6a R 6b —, —C(═O)—, —C(═NH)—, and —C(═NH)NR 7 —;
m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;
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 R 3 is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X-optionally substituted C 1 -C 4 alkyl, optionally substituted aryl, and —X-optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;
each R 4a , R 4b , R 5a , R 5c , R 6a , and R 6b is independently selected from hydrogen, halogen, —CN, —OR 9 , optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted aryl, —NR 8a R 8b , —NR 8a R 8b R 8c+ , —S(═O) 2 O, —S(═O) 2 OR 9 , —C(═O)O − , and —C(═O)OR 9 ;

R 5b is —NR 10a R 10b or —NR 10a R 10b R 10c+ ;
each R 7 , R 8a , R 8b , R 8c , and R 9 is independently selected from hydrogen and optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;
each R 10a and R 10c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, optionally substituted aryl, -(optionally substituted C1-C8alkylene)S(═O) 2 O − , -(optionally substituted C 1 -C 8 alkylene)S(═O) 2 OH, -(optionally substituted C 1 -C 8 alkylene)C(═O)O − , and -(optionally substituted C 1 -C 8 alkylene)C(═O)OH; and
R 10b is —C(═O)—C 2 -C 6 alkenyl, S(═O)—C 2 -C 6 alkenyl, or —S(═O) 2 —C 2 -C 6 alkenyl.

42 . The biofouling-resistant coating of claim 41 , wherein the compound has the following structure:

43 . The biofouling-resistant coating of claim 42 , wherein R 1a , R 1b , R 2a , and R 2b are each F.

44 . The biofouling-resistant coating of claim 43 , wherein Z is —CR 6a R 6b — and each R 6a and R 6b in —CR 6a R 6b — is hydrogen.

45 . The biofouling-resistant coating of claim 44 , wherein m is 0, 1, 2, or 3.

46 . The biofouling-resistant coating of claim 44 , wherein m is 0.

47 . The biofouling-resistant coating of claim 41 , wherein R 5a is hydrogen; R 5b is —NR 10a R 10b ; and R 5c is hydrogen.

48 . The biofouling-resistant coating of claim 41 , wherein the compound has the structure of Formula (Ia) or Formula (Ib):

49 . The biofouling-resistant coating of claim 41 , wherein R 10a is hydrogen.

50 . The biofouling-resistant coating of claim 41 , wherein R 3 is hydrogen.

Assignees

• Univ California
• Hydrophilix Inc

Inventors

• Kaner Richard B
• Chen Dayong
• Mcverry Brian T
• Rao Ethan
• Polasko Alexandra L

Classifications

• A61L17/005 Primary

  containing a biologically active substance, e.g. a medicament or a biocide · CPC title

• C08F220/387

  and containing nitrogen and oxygen · CPC title

• C08J7/056

  Forming hydrophilic coatings · CPC title

• A61L17/145

  Coating · CPC title

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title