Marine coatings
Marine coatings including cationic polymers hydrolyzable to nonfouling zwitterionic polymers, coated marine surfaces, and methods for making and using the marine coatings.
1. A marine substrate, comprising a polymer coating, wherein the polymer has the formula:
PB-(L 1 -N + (R a )(R b )-L 2 -A(=O)−OR c ) n (X − ) n
wherein
PB is a polymer backbone;
N + is a cationic center;
R a and R b are independently selected from hydrogen, alkyl, and aryl;
A(=O)—OR c is a hydrolyzable group, wherein A is selected from the group consisting of C, S, SO, P, or PO, and R c is an alkyl, aryl, acyl, or silyl group that may be further substituted with one or more substituents;
L 1 is a linker that covalently couples the cationic center to the polymer backbone;
L 2 is a linker that covalently couples the cationic center to the hydrolyzable group; X— is a counter ion associated with the cationic center; and n is an integer from about 10 to about 10,000.
2. The marine substrate of claim 1 , wherein the counter ion is a hydrophobic organic counter ion.
3. The marine substrate of claim 1 , wherein the counter ion is selected from the group consisting of C1-C20 carboxylates and C1-C20 alkylsulfonates.
4. The marine substrate of claim 1 , wherein the counter ion is biologically active.
5. The marine substrate of claim 1 , wherein the counter ion is selected from the group consisting of an antimicrobial, an antibacterial, and an antifungal agents.
6. The marine substrate of claim 1 , wherein the counter ion is salicylate.
7. The marine substrate of claim 1 , wherein the hydrolyzable group releases a hydrophobic organic group on hydrolysis.
8. The marine substrate of claim 1 , wherein the hydrolyzable group releases a C1-C20 carboxylate on hydrolysis.
9. The marine substrate of claim 1 , wherein R a and R b are independently selected from the group consisting of C1-C10 straight chain and branched alkyl groups.
10. The marine substrate of claim 1 , wherein L 1 is selected from the group consisting of —C(═O)O—(CH 2 ) n — and —C(═O)NH—(CH 2 ) n —, wherein n is an integer from 1 to 20.
11. The marine substrate of claim 1 , wherein L 2 is —(CH 2 ) n —, where n is an integer from 1 to 20.
12. The marine substrate of claim 1 , wherein A is selected from the group consisting of C, SO, and PO.
13. The marine substrate of claim 1 , wherein R c is C1-C20 alkyl.
14. The marine substrate of claim 1 , wherein X— is selected from the group consisting of halide, carboxylate, alkylsulfonate, sulfate, nitrate, perchlorate, tetrafluoroborate, hexafluorophosphate, trifluoromethylsulfonate, bis(trifluoromethylsulfonyl)amide, lactate, and salicylate.
15. The marine substrate of claim 1 , wherein the marine substrate is a vessel hull.
16. The marine substrate of claim 1 , wherein the marine substrate is a propeller, periscope of sensor.
17. The marine substrate of claim 1 , wherein the marine substrate is a bridge.
18. The marine substrate of claim 1 , wherein the marine substrate is a fish net.
19. A method for treating a surface of a marine substrate, comprising applying a polymer coating, wherein the polymer has the formula:
PB-(L 1 -N + (R a )(R b )-L 2 -A(=O)—OR c ) n (X − ) x
wherein
PB is a polymer backbone;
N + is a cationic center;
R a and R b are independently selected from hydrogen, alkyl, and aryl;
A(=O)—OR c is a hydrolyzable group, wherein A is selected from the group consisting of C, S, SO, P, or PO, and R c is an alkyl, aryl, acyl, or silyl group that may be further substituted with one or more substituents;
L 1 is a linker that covalently couples the cationic center to the polymer backbone;
L 2 is a linker that covalently couples the cationic center to the hydrolyzable group; X— is a counter ion associated with the cationic center; and n is an integer from about 10 to about 10,000.
20. The method of claim 19 , wherein applying the coating comprises spraying the coating.
21. The method of claim 19 , wherein applying the coating comprises painting the coating.
22. The method of claim 19 , wherein the substrate is a vessel hull or marine structure.