Polymer and polymer-derived particles comprising polyfurfuryl alcohol and methods thereof

Patent metadata

Field	Value
Publication number	US-12006399-B1
Application number	US-202217650111-A
Country	US
Kind code	B1
Filing date	Feb 7, 2022
Priority date	Feb 10, 2021
Publication date	Jun 11, 2024
Grant date	Jun 11, 2024

Abstract

Aspects relate to a method of particle fabrication, comprising mixing at least one stabilizing compound with an aqueous solution to produce a first mixture, mixing furfuryl alcohol, a derivative of furfuryl alcohol, or a mixture thereof, into the first mixture to produce a second mixture, heating the second mixture, mixing a surfactant comprising an acid moiety (e.g., an alkylbenzene sulfonic acid) and the second mixture to produce a third mixture, initiating a polycondensation reaction of the furfuryl alcohol, the derivative of the furfuryl alcohol, or the mixture thereof, in the third mixture to produce polymer (or polymer-derived) particles comprising polyfurfuryl alcohol, and (optionally) defining or modifying the glass transition temperature of the polymer or polymer-derived particles comprising polyfurfuryl alcohol.

First claim

The invention claimed is:

1. A method of particle fabrication, comprising:
mixing at least one stabilizing compound with an aqueous solution to produce a first mixture;
mixing furfuryl alcohol, a derivative of furfuryl alcohol, or a mixture thereof, into the first mixture to produce a second mixture;
heating the second mixture;
mixing a surfactant comprising an acid moiety and the second mixture to produce a third mixture; and
initiating a polycondensation reaction of the furfuryl alcohol, the derivative of the furfuryl alcohol, or the mixture thereof, in the third mixture to produce polymer or polymer-derived particles comprising polyfurfuryl alcohol.

2. The method of claim 1 , further comprising:
defining or modifying a glass transition temperature of the polymer or polymer-derived particles comprising the polyfurfuryl alcohol.

3. The method of claim 2 ,
wherein, prior to the modifying, the glass transition temperature of the polymer or polymer-derived particles comprising the polyfurfuryl alcohol is in the range between about 20° C. to 90° C., and
wherein the modifying increases the glass transition temperature of the polymer or polymer-derived particles comprising the polyfurfuryl alcohol to above about 100° C.

4. The method of claim 2 ,
wherein, prior to the modifying, the glass transition temperature of the polymer or polymer-derived particles comprising the polyfurfuryl alcohol is in the range between about 40° C. to 200° C., and
wherein the modifying eliminates the glass transition temperature of the polymer or polymer-derived particles comprising the polyfurfuryl alcohol such that a glass transition of the polymer or polymer-derived particles comprising the polyfurfuryl alcohol does not occur.

5. The method of claim 2 ,
wherein the polymer or polymer-derived particles are produced as polymer or polymer-derived particle droplets, and
wherein the glass transition temperature is modified by curing and at least partially solidifying the polymer or polymer-derived particle droplets.

6. The method of claim 1 , wherein the surfactant comprises alkylbenzene sulfonic acid.

7. The method of claim 1 , wherein the first mixture comprises the at least one stabilizing compound at a concentration of about 0.0001 wt. % to about 50.0000 wt. % of the first mixture.

8. The method of claim 1 , wherein the at least one stabilizing compound comprises polyvinylpyrrolidone, a polyvinyl alcohol, a tri-block copolymer derived from polypropylene and polyethylene, gum acacia, polyvinyl acetate, polyacrylonitrile, or a combination thereof.

9. The method of claim 8 , where the at least one stabilizing compound comprises the polyvinyl alcohol.

10. The method of claim 9 , wherein a percent hydrolysis of the polyvinyl alcohol is in the range between about 40% to about 99%.

11. The method of claim 9 , where a viscosity of a 4 wt. % solution of the polyvinyl alcohol at 20° C. is in the range between about 3 mPa·s to about 200 mPa·s.

12. The method of claim 1 ,
wherein the first mixture is a solution with the at least one stabilizing compound being dissolved into the aqueous solution, or,
wherein the first mixture is a suspension with the at least one stabilizing compound being dispersed into the aqueous solution.

13. The method of claim 1 , wherein the second mixture comprises the furfuryl alcohol, the derivative of furfuryl alcohol, or the mixture thereof, at a concentration of about 0.0001 wt. % to about 80.0000 wt. % of the second mixture.

14. The method of claim 1 , wherein the second mixture comprises a heterogeneous solution of the at least one stabilizing compound, the aqueous solution, and the furfuryl alcohol, the derivative of furfuryl alcohol, or the mixture thereof.

15. The method of claim 14 , wherein the heating induces a transition of the second mixture from the heterogenous solution to a homogeneous solution of the at least one stabilizing compound, the aqueous solution, and the furfuryl alcohol, the derivative of furfuryl alcohol, or the mixture thereof, with an aqueous phase and a hydrophobic emulsion phase.

16. The method of claim 1 , wherein the second mixture comprises a homogenous solution of the at least one stabilizing compound, the aqueous solution, and the furfuryl alcohol, the derivative of furfuryl alcohol, or the mixture thereof, with an aqueous phase and a hydrophobic emulsion phase.

17. The method of claim 16 , wherein the heating induces a transition of the second mixture from the homogenous solution to a heterogeneous solution of the at least one stabilizing compound, the aqueous solution, and the furfuryl alcohol, the derivative of furfuryl alcohol, or the mixture thereof.

18. The method of claim 1 , wherein the heating heats the second mixture to a temperature between about 30° C. and about 100° C.

19. The method of claim 1 , wherein the surfactant is mixed into the second mixture as a neat liquid or as part of another aqueous solution.

20. The method of claim 1 , wherein the third mixture comprises the surfactant at a concentration of about 0.001 wt. % to about 30.0000 wt. % of the third mixture.

21. The method of claim 1 , wherein the surfactant is mixed into the second mixture at a first temperature that is less than a second temperature of the second mixture.

22. The method of claim 1 , wherein the surfactant is mixed into the second mixture at a first temperature that is greater than a second temperature of the second mixture.

23. The method of claim 1 , wherein the surfactant is mixed into the second mixture at the same temperature as the second mixture.

24. The method of claim 1 , wherein the polymer or polymer-derived particles exhibit a spherical shape, a near-spherical shape, or a spheroidal shape, or a combination thereof.

25. The method of claim 1 , wherein the polymer or polymer-derived particles comprise an average particle size between about 100 nanometers to about 100 microns.

Assignees

• Sila Nanotechnologies Inc

Inventors

• Lachman Eric
• Yushin Gleb
• Ingle Nicholas
• Fevre Mareva
• Foxly Emma
• Werth Nicholas
• Gurbuz Elif

Classifications

• C08G65/36 Primary

  Furfuryl alcohol · CPC title

• H01M4/62

  Selection of inactive substances as ingredients for active masses, e.g. binders, fillers · CPC title

• H01M4/622

  being polymers · CPC title

• C08L71/14 Primary

  Furfuryl alcohol polymers · CPC title