IP Library › Granted Patent US 12,209,165
Granted Patent B2
US 12,209,165 · App. 18/209,884 · Granted Jan 28, 2025

Polyamides, and methods of producing thereof

Inventors: Han Lee (Chicago, IL); Sadesh H. Sookraj (Rochester, NY); Alexander Tseitlin (Rochester, NY)
Assignee: Novomer, Inc.
C08G69/22C08G69/16
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Quick Facts
Patent No.
US 12,209,165
App. No.
18/209,884
Granted
Jan 28, 2025
Kind
B2
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.

Claims (27)

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%.

Assignments (2)
CHANGE OF NAME Recorded Mar 24, 2026
From: NMER WINDDOWN, INC.
To: NOVOMER LLC
Reel/Frame 075187/0876 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2023
From: LEE, HAN; SOOKRAJ, SADESH H.; TSEITLIN, ALEXANDER
To: NOVOMER, INC.
Reel/Frame 063957/0351 →
Continuity (3)
Continuation 16494635
Provisional Application 62473008 · Mar 17, 2017
Related Publication 20230340199A1 · Oct 26, 2023
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