US 11,807,701 B2
Biofouling resistant coatings and methods of making and using the same
Brian T. McVerry, Laguna Hills, CA (US); Ethan Rao, Venice, CA (US); Richard B. Kaner, Los Angeles, CA (US); and Na He, Los Angeles, CA (US)
Assigned to The Regents of the University of California, Oakland, CA (US); and Silq Technologies Corporation, Los Angeles, CA (US)
Filed by The Regents of the University of California, Oakland, CA (US); and Hydrophilix, Inc., Los Angeles, CA (US)
Filed on Jun. 4, 2020, as Appl. No. 16/892,980.
Claims priority of provisional application 62/857,725, filed on Jun. 5, 2019.
Prior Publication US 2020/0385506 A1, Dec. 10, 2020
Int. Cl. C08F 220/34 (2006.01); C08F 220/30 (2006.01); C08F 293/00 (2006.01); C09D 153/00 (2006.01); A61L 29/08 (2006.01); C09D 5/00 (2006.01); C08F 220/38 (2006.01)
CPC C08F 220/30 (2013.01) [A61L 29/085 (2013.01); C08F 220/34 (2013.01); C08F 220/382 (2020.02); C08F 293/005 (2013.01); C09D 5/00 (2013.01); C09D 153/00 (2013.01); A61L 2420/02 (2013.01); C08F 2438/01 (2013.01)] 14 Claims
OG exemplary drawing
 
1. A copolymer comprising:
a) a repeating unit of Formula (VII):

OG Complex Work Unit Chemistry
wherein
each R1a and R1b is independently selected from hydrogen and halogen;
each R2a and R2b is independently selected from halogen, —CN, and optionally substituted C1-C6 fluoroalkyl;
each A1 and A2 is independently selected from —C(═O)—, —S(═O)—, —S(═O)2—, and —S(═O)(═NR3c)—;
each B1 and B2 is independently selected from —O— and —NR3c—;
Z1 is —(CR6cR6d)s—;
each R4c, R4d, R5d, R5e, R6c, and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O)2—;
each R9a, R11a, R11b, and R11c is independently selected from hydrogen, optionally substituted C1-C4 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):

OG Complex Work Unit Chemistry
wherein,
A3 is —C(═O)—, —S(═O)—, —S(═O)2—, or —S(═O)(═NR3c)—;
B3 is —O— or —NR3c—;
D is —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
Z2 is —(CR6cR6d)t—;
Z3 is —(CR6cR6d)p—;
each R3a and R3b is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted benzyl;
each R6c and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O)2—;
each R9a, R12a, R12b, and R12c is independently selected from hydrogen, optionally substituted C1-C4 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):

OG Complex Work Unit Chemistry
A4 is —C(═O)—, —S(═O)—, —S(═O)2—, or —S(═O)(═NR3c)—;
B4 is —O— or —NR3c—;
Z4 is —(CR6cR6d)k—;
E is —CN, —OR9a, —NR9aR9b, —NR9aR9bR9c+, optionally substituted C1-C4 alkyl, optionally substituted C1-C6 fluoroalkyl, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
each R6c, and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O)2—;
each R9a, R9b, R9c, R13a, R13b, and R13c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl; and
k is an integer selected from 1, 2, 3, 4, or 5.