Functionalized Polysiloxane Polymers

• US 20090111937A1
• Filed: 07/26/2006
• Published: 04/30/2009
• Est. Priority Date: 07/29/2005
• Status: Active Grant

• Current Assignee: Ndsu-Research Foundation
• Original Assignee: Ndsu-Research Foundation
• Inventors: Ekin, Abdullah, Webster, Dean C.
• Granted Patent: US 7,799,434 B2
• Time in Patent Office: Days
• US Class Current: 524/588
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/452 containing nitrogen-containing sequences
• CPC Class Codes: C08G 77/455 containing polyamide, polyesteramide or polyimide sequences
• CPC Class Codes: C09D 5/1675 Polyorganosiloxane-containing compositions
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Polysiloxanes terminated with one or more hydroxy functional carbamate groups are provided. The polymers may have the formula (I) wherein R¹, R², R³, and R⁴ are independently hydrogen, C₁-C₁₀ alkyl, C₁-C₁₀ fluoro-substituted alkyl; cyclopentyl, cyclohexyl, benzyl, toluoyl, xylyl and/or phenyl; R⁵ and R⁶ are linking groups; R¹⁵ and R¹⁶ are independently hydrogen, C₁-C₁₀ alkyl, cyclopentyl, cyclohexyl, benzyl, toluoyl, xylyl or phenyl; and L¹ and L² are linking groups. Typically, x is such that the polymer has a molecular weight of about 1,000 to 100,000. Other polymeric materials produced by reacting with an isocyanate functional compound or a lactone and coating compositions containing such polymeric materials are also provided.

Claims

1. A polymer having the formula:

2. The polymer of claim 1 wherein R⁵ and R⁶ are independently linear or branched hydroxy-substituted alkylene or a combination thereof.

3. The polymer of claim 2 wherein R⁵ and R⁶ are hydroxypropylene.

4. The polymer of claim 1 wherein R¹, R², R³, and R⁴ are independently C₁-C₁₀ alkyl, C₁-C₁₀ fluoro-substituted alkyl, cyclopentyl, cyclohexyl, benzyl, toluoyl, xylyl or phenyl.

5. The polymer of claim 1 wherein L¹ and L² are independently linear or branched alkylene having from 2 to 10 carbon atoms.

6. The polymer of claim 1 wherein

R⁵ has the formula

HO—

R⁷

and R⁶ has the formula

R⁸—

OH

wherein R⁷ and R⁸ are independently linear or branched alkylene;

linear or branched hydroxy-substituted alkylene;

linear or branched vinyl-substituted alkylene;

or a combination thereof.

7. The polymer of claim 1 wherein R¹, R², R³, and R⁴ are methyl;

and R¹⁵ and R¹⁶ are hydrogen.

8. The polymer of claim 1 wherein

R⁵ has the formula

9. A polymer prepared by reacting a mixture comprising the polymer of claim 1 and an isocyanate functional compound.

10. The polymer of claim 9 wherein the mixture further comprises a polyol compound.

11. A coating comprising the polymer of claim 10.

21. A coating composition comprising a solvent component;

and the polymer of claim 1.

12. A polymer including at least one subunit derived from a polysiloxane terminated with a hydroxy functional carbamate group.

13. The polymer of claim 12 wherein the subunit is derived from a polysiloxane terminated with a hydroxy alkyl functional carbamate group.

14. The polymer of claim 12 wherein the polymer is derived by crosslinking the polysiloxane using an isocyanate functional compound.

15. The polymer of claim 12 wherein the polymer comprises at least one polyester subunit.

16. The polymer of claim 12 wherein the polymer comprises at least one polyurethane subunit.

17. A coating comprising the polymer of claim 12.

18. The coating of claim 17 having a water contact angle after immersion in water for 30 days of at least about 90°

.

19. The coating of claim 17 having a water contact angle after immersion in water for 30 days of no more than about 30 N.

20. An article having at least one surface comprising the polymeric coating of claim 17.