FUNCTIONALISED ANTIFOULING COMPOUNDS AND USE THEREOF

• US 20120301423A1
• Filed: 02/02/2011
• Published: 11/29/2012
• Est. Priority Date: 02/02/2010
• Status: Active Grant

• Current Assignee: Agency For Science Technology and Research (Government of Singapore), Maritime And Port Authority Of Singapore, National University of Singapore
• Original Assignee: Agency For Science Technology and Research (Government of Singapore), Maritime And Port Authority Of Singapore, National University of Singapore
• Inventors: Teo, Serena Lay Ming, Rittschof, Daniel, Chai, Christina Li Lin, Burkett, Brendan Adrian, Lee, Serina Siew Chen, Dickinson, Gary Howard, Hong, Han
• Granted Patent: US 9,169,223 B2
• Time in Patent Office: Days
• US Class Current: 424/78.09
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 37/18 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
• CPC Class Codes: C07C 233/11 with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 235/34 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07D 295/185 from aliphatic carboxylic acids
• CPC Class Codes: C07D 295/192 from aromatic carboxylic acids
• CPC Class Codes: C08F 120/34 Esters containing nitrogen , e.g. N,N-dimethylaminoethyl (meth)acrylate
• CPC Class Codes: C09D 5/14 Paints containing biocides, e.g. fungicides, insecticides or pesticides C09D5/16 takes precedence
• CPC Class Codes: C09D 5/1625 organic
• CPC Class Codes: C09D 5/165 containing hydrolysable groups C09D5/1643 takes precedence
• CPC Class Codes: C09D 5/1668 Vinyl-type polymers

Abstract

The present invention relates to derivatives of α,α-disubstituted amide compounds which comprise a substituted aryl at the α carbon such that the substituent provides a means for attachment or incorporation of the compound to or in a polymer. The provision of such a substituent on the aryl has surprisingly been found not only to permit attachment to or incorporation in a polymer but also retention of useful antifouling activity. In embodiments, the substituent is selected from hydroxyl, ethers, es ters, carboxyls, alkylsilyls and alkenyls. Experiments demonstrate that antifouling activity can be as good or better as the corresponding unsubstituted compound and that polymers functionalised so as to include or be formed from the substituted compound can be used to reduce settlement.

Claims

1. Use of compound of formula (I) or a salt thereof in a method of reducing or preventing fouling:

2. Use according to claim 1, wherein

(i) R³ and R⁴ together form an optionally substituted 6-membered heterocycle which incorporates the nitrogen to which they are attached according to formula (II):

3. Use according to claim 2, wherein in respect of option (i) each of R⁵ and R⁶ is H;

and in respect of option (ii) each of R³ and R⁴ is Me.

4. Use according to claim 1, wherein R¹ is (B) and R² is

5. Use according to claim 1, wherein R¹ is C₄ alkyl or C₆ alkenyl.

6. Use according to claim 1, wherein the compound is a compound of formula (III) or formula (IV)

7. Use according to claim 1, wherein, if present, each R^S1 is independently optionally substituted C₁ to C₃ alkylene, and wherein, if present, each R^S2 is independently selected from optionally substituted C₁ to C₃ alkyl and C₂ to C₃ alkenyl and C₁ to C₃ alkylsilyl-C₁ to C₃ alkylene.

8. Use according to claim 1, wherein R¹ is (B) and R² is

9. Use according to claim 8, wherein at least two of R^A1, R^A2, R^A3, R^A4 and R^A5 are H.

10. Use according to claim 8, wherein at least three of R^A1, R^A2, R^A3, R^A4 and R^A5 are H.

11. Use according to claim 1, wherein the compound is selected from compounds 15.1, 15.2, 15.3, 15.4, 15.5, 15.6, 15.7, 16.1, 16.2, 16.3, 16.4, 16.5, 16.6, 16.7, 16.8, 16.9, 16.10, 16.11, 17.1, 17.2, 17.3, 17.4, 17.5, 17.6, 17.7, 17.8 and 17.9.

12. A polymer comprising at least one repeating unit formed from a compound of formula (I) as defined in claim 1.

13. A polymer according to claim 12, wherein the polymer is selected from a (meth)acrylate polymer and a silicone polymer.

14. A polymer according to claim 13, wherein the polymer is a (meth)acrylate polymer and comprises repeating units derived from one or more of methylmethacrylate (MMA), hydroxyethyl acrylate (HEA) and vinyl pyrrolidinone (VP).

15. A polymer according to claim 12, comprising a pendant group according to formula X

16. An antifouling coating composition comprising a compound or a polymer according to claim 1.

17. Use of a compound, polymer or coating composition according to claim 1 in a method of reducing or preventing fouling.

18. Use according to claim 17, wherein the method of reducing or preventing fouling is a method of reducing or preventing biofilm formation by one or more of bacteria, fungi, algae and protozoans.

19. A compound of formula (I′

) or a salt thereof;

20. A compound according to claim 19 wherein R¹ is C₄ alkyl or C₆ alkenyl.

21. A compound according to claim 19, wherein the compound is a compound of formula (III) or formula (IV)

22. A compound according to claim 19, wherein, if present, each R^S1 is independently optionally substituted C₁ to C₃ alkylene, and wherein, if present, each R^S2 is independently selected from optionally substituted C₁ to C₃ alkyl and C₂ to C₃ alkenyl and C₁ to C₃ alkylsilyl-C₁ to C₃ alkylene.

23. A compound according to claim 19, wherein R² is

24. A compound according to claim 23, wherein at least two of R^A1, R^A2, R^A3, R^A4 and R^A5 are H.

25. A compound according to claim 24, wherein at least three of R^A1, R^A2, R^A3, R^A4 and R^A5 are H.

26. A compound according to claim 19, wherein the compound is selected from compounds 15.1, 15.2, 15.3, 15.4, 15.5, 15.6, 15.7, 16.1, 16.2, 16.3, 16.4, 16.5, 16.6, 16.7, 16.8, 16.9, 16.10, 16.11, 17.1, 17.2, 17.3, 17.4, 17.5, 17.6, 17.7, 17.8 and 17.9.