Antifouling materials containing cationic polysiloxanes

• US 8,278,400 B2
• Filed: 04/20/2010
• Issued: 10/02/2012
• Est. Priority Date: 05/09/2005
• Status: Expired due to Fees

• Current Assignee: Ndsu-Research Foundation
• Original Assignee: Ndsu-Research Foundation
• Inventors: Chisholm, Bret Ja, Boudjouk, Philip, Thomas, Johnson, Christianson, David Allen, Stafslien, Shane Jeremy
• Primary Examiner(s): Peng, Kuo-Liang
• Application Number:
  US12/763,818
• Publication Number:
  US 20100204399A1
• Time in Patent Office: 896 Days
• Field of Search: 428/447, 525/474
• US Class Current: 525/474
• CPC Class Codes: B63B 59/04 Preventing hull fouling anti-fouling paints C09D5/16
• CPC Class Codes: C08G 77/385 containing halogens
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C09D 179/02 Polyamines
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: C09D 183/10 Block or graft copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00
• CPC Class Codes: C09D 183/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence
• CPC Class Codes: C09D 5/1675 Polyorganosiloxane-containing compositions
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Polyamine cross-linked polysiloxanes, such as functionalized polysiloxane cross-linked with a polyalkylenepolyamine are described herein. The polyamine cross-linked polysiloxanes may be used in an antifouling composition to prevent biological fouling in marine environments.

Claims

1. A polyamine cross-linked polysiloxane which is prepared by cross linking a copolymer using a polyamine, wherein the copolymer has the formula:

2. The polyamine cross-linked polysiloxane of claim 1 wherein the copolymer has a formula:

3. The polyamine cross-linked polysiloxane of claim 2 wherein m is 0;

p is 0;

R¹, R², R³, R⁵ and R¹⁰ are methyl;

R⁴ is hydrogen or methyl;

R⁷ is hydrogen or methyl; and

R⁶ includes a group represented by the formula;

4. The polyamine cross-linked polysiloxane of claim 2 wherein R¹, R², R³, R⁵ and R¹⁰ are methyl;

R⁴ is hydrogen or methyl;

R⁷ is hydrogen or methyl; and

R⁶ includes a biocidal group.

5. The polyamine cross-linked polysiloxane of claim 2 wherein the polyamine comprises polyalkylenepolyamine having the following formula:

6. The polyamine cross-linked polysiloxane of claim 5, wherein R is ethylene or propylene;

R¹¹ and R¹² are methoxy;

at least one of EC¹ and EC² is —

SiR¹¹R¹²R¹³; and

the polyalkylenepolyamine has an average molecular weight of at least about 500 g/mol.

7. The polyamine cross-linked polysiloxane of claim 5, wherein L¹ is alkylene having 2 to 6 carbon atoms.

8. The polyamine cross-linked polysiloxane of claim 5, wherein EC¹ and EC² are independently H, trialkoxysilylalkyl, or dialkoxyalkylsilylalkyl.

9. The polyamine cross-linked polysiloxane of claim 2, wherein the polyamine comprises bis(dimethylamino)-dimethylsilane.

10. The polyamine cross-linked polysiloxane of claim 1 wherein the polyamine cross-linked polysiloxane further comprises one or more covalently-bound biocidal groups, which are toxic to organisms that cause fouling in an aquatic environment.

11. The polyamine cross-linked polysiloxane of claim 1 wherein the polyamine cross-linked polysiloxane comprises polyalkylenepolyamine subunits, which have an average molecular weight of at least about 500 g/mol.

12. A polymer coating comprising the polyamine cross-linked polysiloxane of claim 1.

13. A method of coating a substrate comprising:

applying a mixture, which includes a polyamine functionalized material and the copolymer having the formula shown in claim 1, to the substrate.

14. The polyamine cross-linked polysiloxane of claim 1 wherein the copolymer has a formula:

15. A polymer coating comprising the polyamine cross-linked polysiloxane of claim 14.

16. The polyamine cross-linked polysiloxane of claim 14, wherein the polyamine comprises bis(dimethylamino)-dimethylsilane.

17. The polyamine cross-linked polysiloxane of claim 1 wherein at least one of R⁶, R⁸, and R⁹ includes a biocidal group.

18. The polyamine cross-linked polysiloxane of claim 1 wherein the polyamine comprises polyalkylenepolyamine having the following formula:

19. The polyamine cross-linked polysiloxane of claim 18 wherein R is ethylene or propylene;

R¹¹ and R¹² are methoxy;

at least one of EC¹ and EC² is —

SiR¹¹R¹²R¹³; and

the polyalkylenepolyamine has an average molecular weight of at least about 500 g/mol.

20. The polyamine cross-linked polysiloxane of claim 1 wherein the copolymer is a random copolymer.

21. The polyamine cross-linked polysiloxane of claim 20, wherein the alkoxysilyl functionalized polyamine includes one or more dialkoxyalkylsilylalkyl groups and/or trialkoxysilylalkyl groups.

22. The polyamine cross-linked polysiloxane of claim 1, wherein the polyamine comprises alkoxysilyl functionalized polyamine with an average molecular weight of at least about 500 g/mol and no more than about 5,000 g/mol.

23. The polyamine cross-linked polysiloxane of claim 1, wherein the polyamine comprises bis(dimethylamino)-dimethylsilane.