Polymerizable organoboron alkyd resin anti fouling coatings

1. A compound which is represented by Formula I, II or III:

wherein:

R 1 and R 2 are independently a group represented by Formula IV:

-E(CH 2 ) n (CH═CH) n′ (CH 2 ) x (CH═CH) x′ (CH 2 ) z CH 3   (IV)

E is —OC(O)—, O, or CH 2 ;

R 3 , each R 5 , and R 7 are independently NR 8 R 9 or a group represented by Formula IV;

R 4 is a group represented by Formula V:

—(CH 2 ) n (CH═CH) n′ (CH 2 ) x (CH═CH) x′ (CH 2 ) z CH 3   (V);

each R 6 is a group represented by Formula IV or Formula V;

R 8 is H or alkyl;

R 9 is H or alkyl;

X is O;

n is from 0 to 16;

n′ is 1, or 2;

x is from 0 to 10;

x′ is 1, or 2;

n′ and x′ are both greater than 0; and

z is from 0 to 16;

provided that:

the sum of (n+2n′+x+2x′+z) is from 6 to 24.

2. The compound of claim 1 , wherein the sum of: n+2n′+x+2x′+z is from 14 to 24.

3. The compound of claim 1 , wherein x is 0.

4. The compound of claim 1 , wherein x is 1.

5. The compound of claim 1 , wherein z is from 1 to 7.

6. The compound of claim 1 , wherein n is from 1 to 16.

7. The compound of claim 1 , wherein E is CH 2 .

8. The compound of claim 1 , wherein E is O.

9. The compound of claim 1 , wherein E is —OC(O).

10. The compound of claim 1 , wherein the compound is represented by Formula I, and R 1 and R 2 are the same, R 3 is NR 8 R 9 , R 8 is C 2 -C 4 alkyl, and R 9 is C 2 -C 4 alkyl.

11. The compound of claim 1 which is represented by Formula I, and R 1 , R 2 , and R 3 are the same.

12. The compound of claim 10 , wherein the group represented by Formula IV comprises a carbon chain designated as 16:3 (n−3); 18:2 (n−6); 18:2 (n−6); 18:2 (n−7); 18:3 (n−3); 18:3 (n−3); 18:3 (n−5); 18:3 (n−5); 18:3 (n−5); 18:3 (n−5); 18:3 (n−6); 18:3 (n−6); 18:3 (n−6); 18:3 (n−6); 18:3 (n−6); 18:4 (n−3); 18:4 (n−3); 18:4 (n−3); 20:2 (n−6); 20:3 (n−3); 20:3 (n−6); 20:3 (n−6); 20:3 (n−9); 20:4 (n−3); 20:4 (n−6); 20:5 (n−3); 20:5 (n−6); 21:5 (n−3); 22:2 (n−6); 22:4 (n−6); 22:5 (n−3); 22:5 (n−6); 22:6 (n−3); 24:4 (n−6); 24:5 (n−3); 24:5 (n−6); or 24:6 (n−3), wherein the number before the colon is the total number of carbon atoms in the group, the number after the colon is the number of unsaturations in the group, and the number in parentheses is the carbon number from a terminal carbon at which the first unsaturation is located, with each unsaturation being separated from the next by a single methylene group.

13. A polymer comprising a polymerization product of the compound of claim 1 .

14. The polymer of claim 13 , wherein the polymerization product is an olefinic polymerization product, a Diels-Alder polymerization product, an oxygen cross-linked polymerization product, or a peroxide cross-linked polymerization product.

15. A coating composition comprising:

polymer of claim 13 ;

a dispersant; and

a medium.

16. An article comprising the coating composition of claim 15 .

17. A process of preparing a compound of claim 1 having a moiety represented by Formula VI:

B—(R 12 )  VI

the process comprising:

contacting a compound represented by Formula VII with a compound having a B-halogen moiety:

ME(CH 2 ) n (CH═CH) n′ (CH 2 ) x (CH═CH) x′ (CH 2 ) z CH 3   (VII):

wherein:

R 12 is a group represented by Formula IV:

-E(CH 2 ) n (CH═CH) n′ (CH 2 ) x (CH═CH) x′ (CH 2 ) z CH 3   (IV)

E is —OC(O)—, O, or CH 2 ;

M is an alkali or alkaline earth metal halide;

n is from 0 to 16;

n′ is 1, or 2;

x is from 0 to 10;

x′ is 1, or 2;

n′ and x′ are both greater than 0; and

z is from 0 to 16;

provided that:

the sum of:

n+2n′+x+2x′+z is from 6 to 24.

18. The process of claim 17 , wherein M is Li, Na, K, MgF, MgBr, or MgCl.

19. A process of preparing a compound of claim 1 having a moiety represented by Formula IX:

B—(R 13 )  IX

the process comprising:

contacting a compound represented by Formula X with a compound having a B-halogen moiety:

HO(CH 2 ) n (CH═CH) n′ (CH 2 ) x (CH═CH) n′ (CH 2 ) z CH 3   (X):

wherein:

R 13 is a group represented by Formula XI:

—O(CH 2 ) n (CH═CH) n′ (CH 2 ) x (CH═CH) x′ (CH 2 ) z CH 3   (XI)

n is from 0 to 16;

n′ is 1, or 2;

x is from 0 to 10;

x′ is 1, or 2;

n′ and x′ are both greater than 0; and

z is from 0 to 16;

provided that:

the sum of:

n+2n′+x+2x′+z is from 6 to 24.