Compositions comprising lignin

• US 9,255,188 B2
• Filed: 10/08/2013
• Issued: 02/09/2016
• Est. Priority Date: 12/30/2011
• Status: Active Grant

• Current Assignee: Renmatix, Inc.
• Original Assignee: Renmatix, Inc.
• Inventors: Kilambi, Srinivas, Kadam, Kiran L.
• Primary Examiner(s): Heincer, Liam J
• Application Number:
  US14/048,935
• Publication Number:
  US 20140039144A1
• Time in Patent Office: 854 Days
• US Class Current: 1/1
• CPC Class Codes: C07G 1/00 Lignin; Lignin derivatives
• CPC Class Codes: C08G 16/0293 with natural products, oils, bitumens, residues
• CPC Class Codes: C08G 8/20 with polyhydric phenols
• CPC Class Codes: C08H 6/00 Macromolecular compounds derived from lignin, e.g. tannins, humic acids

Abstract

Compositions comprising lignin and low levels of undesirable impurities, such as compounds containing sulfur, nitrogen, or metals, are disclosed.

Claims

1. A phenolic resin:

wherein at least a portion of said phenolic resin is produced by a reaction with a phenol substitute;

wherein said phenol substitute comprises;

lignin; and

less than about 2000 mg in total per kg of said lignin of elements;

wherein said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.

2. The phenolic resin of claim 1,

wherein said lignin has an average particle size less than about 500 microns.

3. The phenolic resin of claim 1,

wherein said lignin has a bulk density of less than about 0.35 g/cc.

4. The phenolic resin of claim 1,

wherein said phenol substitute is substantially free of organic solvent.

5. The phenolic resin of claim 1,

wherein said phenol substitute comprises less than about 700 mg of calcium per kg of said lignin.

6. The phenolic resin of claim 1,

wherein said phenol substitute comprises less than about 525 mg of iron per kg of said lignin.

7. The phenolic resin of claim 1,

wherein said phenol substitute comprises less than about 150 mg of sulfur per kg of said lignin.

8. The phenolic resin of claim 1,

wherein said phenol substitute comprises less than about 20 g of ash per kg of said lignin.

9. The phenolic resin of claim 1,

wherein said phenol substitute comprises less than about 2000 mg of nitrogen per kg of said lignin.

10. The phenolic resin of claim 1,

wherein said phenol substitute has a weight ratio of the total mass of hydrogen and nitrogen to carbon of less than about 0.110.

11. The phenolic resin of claim 1,

wherein said lignin is present in said phenol substitute at a level of at least 30% by weight, based on the total weight of said phenol substitute, as measured by pyrolysis molecular beam mass spectrometry.

12. The phenolic resin of claim 1,

wherein said lignin is present in said phenol substitute in an amount greater than about 50 wt. %, based on the weight of said phenol substitute, as measured by NREL procedures.

13. The phenolic resin of claim 1,

wherein a weight ratio of syringyl monolignol to guaiacyl monolignol is about 2.0 to about 3.0, as measured by pyrolysis molecular beam mass spectrometry.

14. The phenolic resin of claim 1,

wherein said phenol substitute is a solid residue remaining after extracting lignocellulosic biomass using a two stage process, said two stage process comprising:

a first stage, wherein the lignocellulosic biomass is treated at a temperature of about 130°

C. to about 250°

C. for about 0.5 min to about 5 hours; and

a second stage, wherein solids obtained from said first stage are treated at a temperature of about 250°

C. to about 450°

C. for about 0.1 sec to about 3 min.

15. A phenol formaldehyde resin comprising:

a reaction product of phenol and formaldehyde; and

an extender, wherein said extender comprises;

lignin; and

less than about 2000 mg in total per kg of said lignin of elements;

wherein said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.

16. The phenol formaldehyde resin of claim 15,

wherein said lignin has an average particle size less than about 500 microns.

17. The phenol formaldehyde resin of claim 15,

wherein said lignin has a bulk density of less than about 0.35 g/cc.

18. The phenol formaldehyde resin of claim 15,

wherein said extender is substantially free of organic solvent.

19. The phenol formaldehyde resin of claim 15,

wherein said extender comprises less than about 700 mg of calcium per kg of said lignin.

20. The phenol formaldehyde resin of claim 15,

wherein said extender comprises less than about 525 mg of iron per kg of said lignin.

21. The phenol formaldehyde resin of claim 15,

wherein said extender comprises less than about 150 mg of sulfur per kg of said lignin.

22. The phenol formaldehyde resin of claim 15,

wherein said extender comprises less than about 20 g of ash per kg of said lignin.

23. The phenol formaldehyde resin of claim 15,

wherein said extender comprises less than about 2000 mg of nitrogen per kg of said lignin.

24. The phenol formaldehyde resin of claim 15,

wherein said extender has a weight ratio of the total mass of hydrogen and nitrogen to carbon of less than about 0.110.

25. The phenol formaldehyde resin of claim 15,

wherein said lignin is present in said extender at a level of at least 30% by weight, based on the total weight of said extender, as measured by pyrolysis molecular beam mass spectrometry.

26. The phenol formaldehyde resin of claim 15,

wherein said lignin is present in said extender in an amount greater than about 50 wt. %, based on the weight of said extender, as measured by NREL procedures.

27. The phenol formaldehyde resin of claim 15,

wherein a weight ratio of syringyl monolignol to guaiacyl monolignol is about 2.0 to about 3.0, as measured by pyrolysis molecular beam mass spectrometry.

28. The phenol formaldehyde resin of claim 15,

wherein said extender is a solid residue remaining after extracting lignocellulosic biomass using a two stage process, said two stage process comprising:

a first stage, wherein the lignocellulosic biomass is treated at a temperature of about 130°

C. to about 250°

C. for about 0.5 min to about 5 hours; and

a second stage, wherein solids obtained from said first stage are treated at a temperature of about 250°

C. to about 450°

C. for about 0.1 sec to about 3 min.

29. A particle board comprising the phenol formaldehyde resin of claim 15.

30. Plywood comprising the phenol formaldehyde resin of claim 15.