Polyamides, and methods of producing thereof

Patent metadata

Field	Value
Publication number	US-12209165-B2
Application number	US-202318209884-A
Country	US
Kind code	B2
Filing date	Jun 14, 2023
Priority date	Mar 17, 2017
Publication date	Jan 28, 2025
Grant date	Jan 28, 2025

Abstract

Provided are methods of producing polyamides from beta-lactones. The polyamides include bio-based polyamides that may be obtained, either in part or completely, from renewable sources.

First claim

What is claimed is:

1. A method, comprising:
contacting an alkylene oxide and carbon monoxide to form a beta lactone compound;
contacting the beta-lactone compound and a nitrogen-containing compound to form a beta hydroxy amide compound;
contacting the beta hydroxy amide compound and one or more weak bases to form a polyamide.

2. The method of claim 1 , wherein the nitrogen-containing compound comprises a primary amine.

3. The method of claim 2 , wherein the primary amine has a formula of R-NH 2 , and wherein R comprises H, methyl, ethyl, propyl, or butyl.

4. The method of claim 3 , wherein the primary amine comprises ammonia.

5. The method of claim 2 , wherein the primary amine is anhydrous.

6. The method of claim 1 , wherein the nitrogen-containing compound comprises a primary amine having a formula of R-NH 2 that is anhydrous, wherein R comprises H, methyl, ethyl, propyl, or butyl.

7. The method of claim 1 , wherein the nitrogen-containing compound comprises anhydrous ammonia.

8. The method of claim 1 , wherein the nitrogen-containing compound has a biocontent of greater than 0%.

9. The method of claim 1 , wherein the alkylene oxide and/or carbon monoxide has a biocontent of greater than 0%.

10. The method of claim 1 , wherein the polyamide comprises repeating units of formula

or a salt thereof, and wherein R 1a , R 1b , R 1c , R 1d and R 2 is independently H or alkyl.

11. The method of claim 1 , wherein the alkylene oxide, carbon monoxide, and nitrogen-containing compound are at least partially obtained from renewable feedstocks.

12. The method of claim 1 , wherein one or more weak bases have a pK b value between 7.2 and 10.4.

13. The method of claim 1 , wherein the one or more weak bases comprise a carbonate salt or a bicarbonate salt, or a combination thereof.

14. The method of claim 1 , wherein the one or more weak bases comprise sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, sodium bicarbonate, potassium bicarbonate, calcium bicarbonate, or magnesium bicarbonate or any combinations thereof.

15. The method of claim 1 , wherein the beta lactone compound comprises beta propiolactone.

16. The method of claim 1 , wherein the alkylene oxide comprises ethylene oxide.

17. A method, comprising:
contacting ethylene oxide and carbon monoxide to form beta propiolactone;
contacting the beta propiolactone and a primary amine to form 3-hydroxy propanamide;
contacting the 3-hydroxy propanamide and one or more weak bases to form a polyamide.

18. The method of claim 17 , wherein the primary amine comprises a compound of the formula R-N (H) 2 that is anhydrous, and wherein R comprises H or alkyl.

19. The method of claim 18 , wherein the primary amine comprises anhydrous ammonia.

20. The method of claim 17 , wherein either or both of the ethylene oxide and/or carbon monoxide has a biocontent greater than 0%.

Assignees

• Novomer Inc

Inventors

• Lee Han
• Sookraj Sadesh H
• Tseitlin Alexander

Classifications

• C08G69/16

  Preparatory processes · CPC title

• C08G69/22 Primary

  Beta-lactams · CPC title

• C08G69/08 Primary

  derived from amino-carboxylic acids · CPC title

• C08G69/04 Primary

  Preparatory processes · CPC title