IP Library Granted Patent US 11,220,475
Granted Patent B2
US 11,220,475 · App. 16/722,710 · Granted Jan 11, 2022

Monomers from biomass

Inventors: Mukund P. Sibi (Fargo, ND); Selvakumar Sermadurai (Kyoto, JP); Nicolas Zimmermann (Treillères, FR); Eric Serum (Eau Claire, WI); Gaoyuan Ma (Irvine, CA); Ramkumar Moorthy (Saint Paul, MN); Krystal Kalliokoski (Fargo, ND)
Assignee: NDSU RESEARCH FOUNDATION
C07C57/34C07C57/40C07C59/64C07C59/84C07D307/54C08G63/065C08G63/181
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Quick Facts
Patent No.
US 11,220,475
App. No.
16/722,710
Granted
Jan 11, 2022
Kind
B2
Abstract

Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.

Claims (39)

1. A compound according to formula II:

wherein both G′ and CT′ are independently

and where a is 1, 2 or 3; and b and c are independently 0, 1, 2, or 3.

2. The compound according to claim 1 , wherein at least one of b and c in both G 1 and G 2 are 0.

3. The compound according to claim 1 , wherein only one of b and c in both G 1 and G 2 are 0.

4. The compound according to claim 1 , wherein the structure of G 1 and G 2 are the same.

5. The compound according to claim 1 , wherein the compound of formula II is selected from:

6. A compound according to formula II:

wherein one of G 1 and G 2 is —(CH 2 ) d OH, wherein d is 1, 2, 3, 4 or 5, and the other of G 1 and G 2 is

where a is 1, 2 or 3; and b and c are independently 0, 1, 2, or 3,

—(CH 2 ) d OH where d is 1, 2, 3, 4 or 5, or

—(CH 2 ) e COOH where e is 0, 1, 2, 3, 4 or 5.

7. The compound according to claim 6 , wherein one of G 1 and G 2 is —(CH 2 ) d OH, wherein d is 1, 2, 3, 4 or 5, and the other of G 1 and G 2 is

8. The compound according to claim 6 , wherein the compound of formula II is:

9. A compound according to formula II:

wherein both G 1 and G 2 are independently —(CH 2 ) e COOH where e is 0, 1, 2, 3, 4 or 5,

with the caveat that if both G 1 and G 2 are —(CH 2 ) e COOH and one of e is 2 then the other e is not 0 or 2 and with the caveat that the compound according to formula II is asymmetric.

10. The compound according to claim 9 , wherein the compound of formula II is selected from:

11. The compound according to claim 1 derived from cellulose, hemicellulose or a combination thereof.

12. The compound according to claim 1 derived from fructose, cellulose, hemicellulose or a combination thereof.

13. The compound according to claim 12 , wherein the fructose is dehydrated to form 5-hydroxymethylfurfural (HMF).

14. The compound according to claim 1 , wherein the compound of formula II is polymerized.

15. The compound according to claim 14 , wherein the polymerization comprises free radical polymerization.

16. The compound according to claim 14 , wherein the polymer is a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.

17. The compound according to claim 14 , wherein the polymer can be used as an adhesive, a plastic, a thermoplastic, a gel, a coating, a film, or any combination thereof.

18. The compound according to claim 6 , derived from cellulose, hemicellulose or a combination thereof.

19. The compound according to claim 6 derived from fructose, cellulose, hemicellulose or a combination thereof.

20. The compound according to claim 19 , wherein the fructose is dehydrated to form 5-hydroxymethylfurfural (HMF).

21. The compound according to claim 6 , wherein the compound of formula II is polymerized.

22. The compound according to claim 21 , wherein the polymerization comprises free radical polymerization.

23. The compound according to claim 21 , wherein the polymer is a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.

24. The compound according to claim 21 , wherein the polymer can be used as an adhesive, a plastic, a thermoplastic, a gel, a coating, a film, or any combination thereof.

25. The compound according to claim 9 , derived from cellulose, hemicellulose or a combination thereof.

26. The compound according to claim 9 derived from fructose, cellulose, hemicellulose or a combination thereof.

27. The compound according to claim 26 , wherein the fructose is dehydrated to form 5-hydroxymethylfurfural (HMF).

28. The compound according to claim 9 , wherein the compound of formula II is polymerized.

29. The compound according to claim 28 , wherein the polymerization comprises free radical polymerization.

30. The compound according to claim 28 , wherein the polymer is a nylon, a polyester, a polyurethane, a polyamide, or a combination thereof.

31. The compound according to claim 28 , wherein the polymer can be used as an adhesive, a plastic, a thermoplastic, a gel, a coating, a film, or any combination thereof.

Assignments (4)
CONFIRMATORY LICENSE Recorded May 4, 2022
From: NORTH DAKOTA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 059852/0863 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2021
From: SIBI, MUKUND P.; SERMADURAI, SELVAKUMAR; ZIMMERMANN, NICOLAS; SERUM, ERIC; MA, GAOYUAN; MOORTHY, RAMKUMAR; KALLIOKOSKI, KRYSTAL
To: NORTH DAKOTA STATE UNIVERSITY
Reel/Frame 058740/0328 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2021
From: NORTH DAKOTA STATE UNIVERSITY
To: NDSU RESEARCH FOUNDATION
Reel/Frame 058978/0847 →
CONFIRMATORY LICENSE Recorded Sep 17, 2020
From: NORTH DAKOTA STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 053802/0700 →
Continuity (4)
Division 15502653
Provisional Application 62035197 · Aug 8, 2014
Related Publication 20200140368A1 · May 7, 2020
Related Publication 20210198175A9 · Jul 1, 2021