Polyols from biomass and polymeric products produced therefrom

Patent metadata

Field	Value
Publication number	US-9273180-B2
Application number	US-201314034611-A
Country	US
Kind code	B2
Filing date	Sep 24, 2013
Priority date	Sep 24, 2012
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

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.

First claim

What is claimed is:

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 .

Assignees

• Narayan Ramani
• Graiver Daniel
• Hablot Elodie
• Sendijarevic Vahid
• Chalasani Siva Rama Krishna
• Univ Michigan State

Inventors

• Narayan Ramani
• Graiver Daniel
• Hablot Elodie
• Sendijarevic Vahid
• Chalasani Siva Rama Krishna

Classifications

• C07C269/00

  Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups [IMAGE cpc-sch-C07C-0964.gif], the nitrogen atom not being part of nitro or nitroso groups · CPC title

• C08G18/60

  Polyamides or polyester-amides · CPC title

• C08G71/04

  Polyurethanes · CPC title

• C08G18/6685

  with compounds of group C08G18/3225 or polyamines of C08G18/38 · CPC title

• C08G18/4833

  Polyethers containing oxyethylene units · CPC title