Functionalized polysiloxane polymers

• US 7,799,434 B2
• Filed: 07/26/2006
• Issued: 09/21/2010
• Est. Priority Date: 07/29/2005
• Status: Expired due to Fees

• Current Assignee: Ndsu-Research Foundation
• Original Assignee: Ndsu-Research Foundation
• Inventors: Ekin, Abdullah, Webster, Dean C.
• Primary Examiner(s): Zimmer; Marc S
• Application Number:
  US11/989,496
• Publication Number:
  US 20090111937A1
• Time in Patent Office: 1,518 Days
• Field of Search: None
• US Class Current: 428/447
• 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 R¹, R², R³, and R⁴ are independently C₁-C₁₀ alkyl.

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

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

and R¹⁵ and R¹⁶ are hydrogen.

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

6. The polyurethane polymer of claim 5 wherein the mixture further comprises a polyol compound.

7. A coating comprising the polyurethane polymer of claim 6.

15. A coating composition comprising a solvent component;

and the polymer of claim 1.

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

L¹ and L² are independently linear or branched alkylene having from 2 to 10 carbon atoms;

R⁸, R¹⁰, R¹², and R¹⁴ are hydrogen;

R¹⁵ and R¹⁶ are hydrogen;

b, e, z and u are independently an integer from 2 to 6;

a, d, y and t are independently an integer from 1 to 10; and

the polymer has a number average molecular weight of about 5,000 to 50,000.

8. A polymer comprising at least one polyester subunit and at least one subunit derived from a polysiloxane terminated with a hydroxy functional carbamate group.

9. The polymer of claim 8 wherein the at least one subunit is derived from a polysiloxane terminated with a hydroxy alkyl functional carbamate group.

10. The polymer of claim 8 wherein the polymer is derived by crosslinking the polysiloxane using an isocyanate functional compound.

11. The polymer of claim 8 wherein the polymer is derived by reacting the polysiloxane with a mixture comprising an isocyanate functional compound and a polyol compound, which includes polyester polyol, polyether polyol, polycarbonate polyol, acrylic polyol or a mixture thereof.

12. A coating comprising the polymer of claim 8.

13. The coating of claim 12 having a water contact angle after immersion in water for 30 days of at least about 90°

.

14. An article having at least one surface comprising the polymeric coating of claim 12.

17. A polymeric coating comprising a polyurethane polymer prepared by reacting a mixture comprising polyol compound;

polyisocyanate; and

hydroxy terminated polysiloxane having a formula;

18. The polymeric coating of claim 17 wherein R¹, R², R³, and R⁴ are methyl;

L¹ and L² are independently linear or branched alkylene having from 2 to 10 carbon atoms;

R¹⁵ and R¹⁶ are hydrogen;

b, e, z and u are independently an integer from 2 to 6; and

a, d, y and t are independently an integer from 1 to 10.

19. The polymeric coating of claim 18 wherein the polyisocyanate comprises isophorone diisocyanate-based polyisocyanate having an isocyanate equivalent weight of about 200 to 500;

hexane diisocyanate-based polyisocyanate having an isocyanate equivalent weight of about 150 to 300;

or a mixture thereof.

20. A polymeric coating prepared by reacting a mixture comprising an isocyanate functional compound;

polyol compound; and

a polysiloxane polymer having a formula;

21. The polymeric coating of claim 20 wherein R¹, R², R³, and R⁴ are methyl;

L¹ and L² are independently linear or branched alkylene having from 2 to 10 carbon atoms;

R⁵ and R⁶ are independently linear or branched hydroxy-substituted alkylene;

R¹⁵ and R¹⁶ are hydrogen; and

the polyisocyanate comprises isophorone diisocyanate-based polyisocyanate, hexane diisocyanate-based polyisocyanate, or a combination thereof.

22. The polymeric coating of claim 21 wherein the polyol compound comprises polycaprolactone polyol;

and R⁵ and R⁶ are independently 2-hydroxyethyl and 1-(hydroxymethyl)-2-hydroxyethyl or a combination thereof.

23. The polymeric coating of claim 21 wherein the polysiloxane polymer has a number average molecular weight of about 5,000 to 50,000.