IP Library Granted Patent US 9,273,180
Granted Patent B2
US 9,273,180 · App. 14/034,611 · Granted Mar 1, 2016

Polyols from biomass and polymeric products produced therefrom

Inventors: Ramani Narayan (Okemos, MI); Daniel Graiver (Midlan, MI); Elodie Hablot (Lansing, MI); Vahid Sendijarevic (Troy, MI); Siva Rama Krishna Chalasani (East Lansing, MI)
Assignee: Board of Trustees of Michigan State University and Vahid Sendijarevice, joint ownership
C08G63/6854C07C269/00C07C269/04C07C277/08C08G4/00C08G18/3831C08G18/4833C08G18/60C08G18/6446C08G18/6685C08G18/7664C08G71/04C08G2101/0025C08G2101/0083
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Quick Facts
Patent No.
US 9,273,180
App. No.
14/034,611
Granted
Mar 1, 2016
Kind
B2
Abstract

Polyol compositions containing methane linkages derived from amino acids. The polyols are obtained from the reaction of the carbonate with the cadres in the amino acids. Individual amino acids or mixtures of amino acids that are prepared from the hydrolysis of the proteins can be used.

Claims (42)

1. A process of producing polyols, said process comprising:

a. providing a biomass material comprising proteins;

b. hydrolyzing said biomass material to amino acids;

c. condensing said amino acids with a diamine to produce amine terminated monomers;

d. reacting said monomers with a carbonate to provide hydroxyl terminated urethane oligomers.

2. A process of producing polyols as claimed in claim 1 wherein, in addition, there is a step e. of alkoxylating any carbohydrates in the biomass material comprising proteins to produce hydroxyl groups.

3. A product produced by the process of claim 1 .

4. A product produced by the process of claim 2 .

5. A process as claimed in claim 1 wherein the biomass material is a meal produced by the extraction of oil from vegetable seed.

6. A process of producing polyols, said process comprising:

a. providing a material selected from a group consisting essentially of i. proteins, ii. amino acids derived from proteins, and, iii. mixtures of i. and ii.;

b. condensing any amino acids in said proteins or amino acids derived from said proteins with a diamine to produce amine terminated monomers;

c. reacting said monomers with a carbonate to provide hydroxyl terminated urethane oligomers.

7. A product produced by the process of claim 6 .

8. A process of producing polyols as claimed in claim 6 wherein, in addition, said material contains protein and the process further comprises a step d. of alkoxylating carbohydrates in the protein to produce hydroxyl groups.

9. A product produced by the process of claim 8 .

10. A process of producing polyols, the method comprising;

a. removing any carbohydrates from a biomass material comprising proteins;

b. hydrolyzing said biomass material to amino acids;

c. condensing said amino acids with a diamine to produce amine terminated monomers;

d. reacting said monomers with a carbonate to provide hydroxyl terminated urethane oligomers.

11. A product produced by the process of claim 10 .

12. A polyurethane composition produced using the product claimed in claim 3 .

13. A polyurethane composition produced using the product claimed in claim 4 .

14. A polyurethane composition produced using the product claimed in claim 7 .

15. A polyurethane composition produced using the product claimed in claim 9 .

16. A polyurethane composition produced using the product claimed in claim 11 .

17. A polyester composition produced using the product claimed in claim 3 .

18. A polyester composition produced using the product claimed in claim 4 .

19. A polyester composition produced using the product claimed in claim 7 .

20. A polyester composition produced using the product claimed in claim 9 .

21. A polyester composition produced using the product claimed in claim 11 .

22. A polyacetal composition produced using the product claimed in claim 3 .

23. A polyacetal composition produced using the product claimed in claim 4 .

24. A polyacetal composition produced using the product claimed in claim 7 .

25. A polyacetal composition produced using the product claimed in claim 9 .

26. A polyacetal composition produced using the product claimed in claim 11 .

27. The process as claimed in 1 wherein the carbonate is selected from the group consisting essentially of i. ethylene carbonate, ii. propylene carbonate, iii. butylene carbonate, iv. glycerol carbonate, and v. a mixture comprising two or more of i., ii., iii., and iv.

28. The process as claimed in claim 1 , wherein the molar ratio of the carbonate to the monomers ranges between 1:10 to 10:1.

29. The process as claimed in claim 28 , wherein the molar ratio of the carbonate to the monomers ranges between 1:2 to 2:1.

30. A rigid polyurethane foam which has a foam density in the range from 15 to 65 g/l when produced from the polyol from the process as claimed in claim 1 .

31. An insulating rigid foam produced using the product as claimed in claim 3 .

Assignments (5)
CONFIRMATORY LICENSE Recorded Mar 30, 2016
From: MICHIGAN STATE UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 038299/0510 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2016
From: NARAYAN, RAMANI
To: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
Reel/Frame 037583/0518 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2016
From: GRAIVER, DANIEL
To: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
Reel/Frame 037583/0664 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2016
From: BIOPLASTIC POLYMERS AND COMPOSITIES LLC
To: MICHIGAN STATE UNIVERSITY
Reel/Frame 037585/0862 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2014
From: HABLOT, ELODIE; CHALASANI, SIVA RAMA KRISHNA
To: BIOPLASTIC POLYMERS AND COMPOSITES, LLC
Reel/Frame 033512/0340 →
Continuity (2)
Provisional Application 61705114 · Sep 24, 2012
Related Publication 20140171535A1 · Jun 19, 2014