Fluorinated networks for anti-fouling surfaces

Patent metadata

Field	Value
Publication number	US-10745586-B2
Application number	US-201715671639-A
Country	US
Kind code	B2
Filing date	Aug 8, 2017
Priority date	Aug 8, 2017
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

According to one or more embodiments, a method of making an antifouling coating includes forming a polythioaminal polymer by reacting a fluorinated primary amine with an aldehyde to form an intermediate imine, and then reacting the intermediate imine with a dithiol. The method further includes depositing the polythioaminal on a substrate, and increasing a temperature of the polythioaminal deposited on the substrate to crosslink the polythioaminal and increase a contact angle of the substrate with crosslinked polythioaminal.

First claim

What is claimed is:

1. A method of making an antifouling coating, the method comprising:
forming a poly(thioaminal) polymer by reacting a fluorinated primary amine with an aldehyde to form an intermediate imine, and then reacting the intermediate imine with a dithiol;
depositing the poly(thioaminal) on a substrate; and
increasing a temperature of the poly(thioaminal) deposited on the substrate to crosslink the poly(thioaminal) and increase a contact angle of the substrate with crosslinked poly(thioaminal).

2. The method of claim 1 , where the fluorinated primary amine is a diamine.

3. The method of claim 1 , where the fluorinated primary amine comprises at least one aromatic ring.

4. The method of claim 1 , where the fluorinated primary amine is a dianiline.

5. The method of claim 1 , wherein depositing the poly(thioaminal) on the substrate is by spin-coating.

6. The method of claim 1 , where the aldehyde is paraformaldehyde.

7. The method of claim 1 , where the dithiol is 1,6-hexanedithiol.

8. The method of claim 1 , where the polythioaminal is a linear polymer.

9. A method of making a hydrophobic antifouling coating, the method comprising:
forming a linear poly(thioaminal) polymer by reacting a fluorinated dianiline derivative with a paraformaldehyde to form an intermediate imine, and then reacting the intermediate imine with a dithiol;
disposing the linear poly(thioaminal) polymer on a surface of a substrate; and
increasing a temperature of the linear poly(thioaminal) polymer to crosslink the linear poly(thioaminal) polymer and increase a contact angle of the substrate with crosslinked poly(thioaminal).

10. The method of claim 9 , where the substrate is a surface of a medical device.

11. The method of claim 10 , where the medical device is an implantable medical device.

12. The method of claim 9 , where the contact angle is at least 100°.

13. The method of claim 9 , where the temperature is increased to at least 100° C.

14. The method of claim 9 , where the dithiol is 1,6-hexanedithiol.

15. A method of making a hydrophobic coating on a surface of a medical device, the method comprising:
forming a poly(thioaminal) polymer by reacting a fluorinated aniline with an aldehyde to form an intermediate imine, and then reacting the intermediate imine with a dithiol;
depositing the poly(thioaminal) polymer on a surface of the medical device; and
increasing a temperature of the poly(thioaminal) polymer to increase a contact angle of the poly(thioaminal) polymer with the surface of the medical device.

16. The method of claim 15 , wherein the aldehyde is paraformaldehyde.

17. The method of claim 15 , wherein forming the poly(thioaminal) polymer forms a linear polymer.

18. The method of claim 17 , wherein increasing the temperature of the poly(thioaminal) polymer induces crosslinking by forming substitutions at nitrogen groups.

19. The method of claim 15 , wherein a polydispersity index (PDI) of the poly(thioaminal) polymer is about 2.

20. The method of claim 19 , wherein increasing the temperature increases the PDI of the poly(thioaminal) polymer.

Assignees

• IBM
• Agency Science Tech & Res
• Agency For Science Tech

Inventors

• Cahan Amos
• Ding Xin
• Fevre Mareva B
• Hedrick James L
• Liang zhen chang
• Park Nathaniel H
• Van Kessel Theodore G
• Wojtecki Rudy J
• Yang Yi Yan

Classifications

• B05D5/083

  involving the use of fluoropolymers · CPC title

• C09D5/1662

  Synthetic film-forming substance · CPC title

• A61L2300/404

  Biocides, antimicrobial agents, antiseptic agents · CPC title

• A61L29/085

  Macromolecular materials · CPC title

• A61L27/34

  Macromolecular materials · CPC title