Compositions comprising lignin

• US 9,963,555 B2
• Filed: 12/21/2015
• Issued: 05/08/2018
• 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:
  US14/976,796
• Publication Number:
  US 20160108182A1
• Time in Patent Office: 869 Days
• 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

wherein said phenol substitute is a composition produced by a two stage process, said two stage process comprising;

a first stage comprising;

providing a mixture comprising lignocellulosic biomass and water; and

heating said mixture to a first temperature of about 130°

C. to about 250°

C. and maintaining said first temperature for a period of about 0.5 min to about 5 hours, thereby producing a first solids fraction and a first liquid fraction; and

a second stage comprising;

subjecting said first solids fraction obtained from said first stage to a supercritical or near-critical fluid under a pressure of about 40 bar to about 300 bar;

wherein said supercritical or near-critical fluid comprises water;

wherein said supercritical or near-critical fluid is at a temperature of about 374°

C. to about 600°

C.;

wherein said subjecting step elevates said first solids fraction to a second temperature of about 250°

C. to about 450°

C.;

wherein said first solids fraction is maintained at said second temperature for a period of about 0.05 sec to about 10 sec, thereby producing a second solids fraction and a second liquid fraction; and

wherein said composition comprises said second solids fraction.

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 first stage employs a pressure of about 4 bar to about 100 bar.

4. The phenolic resin of claim 1,

wherein said second stage employs a pressure of about 40 bar to about 260.

5. The phenolic resin of claim 1,

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

6. The phenolic resin of claim 1,

wherein said second stage employs supercritical water.

7. The phenolic resin of claim 1,

wherein said composition is prepared without the addition of acid.

8. 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;

or

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.

9. The phenolic resin of claim 1,

wherein said first stage employs a digester and a steam explosion unit.

19. Plywood or a particle board comprising the phenolic resin of claim 1.

21. The phenolic resin of claim 1,

wherein said second stage employs a pressure of about 230 bar to about 300 bar.

10. A phenol formaldehyde resin comprising:

a reaction product of phenol and formaldehyde; and

an extender, wherein said extender comprises;

lignin; and

wherein said extender is a composition produced by a two stage process, said two stage process comprising;

a first stage comprising;

providing a mixture comprising lignocellulosic biomass and water; and

heating said mixture to a first temperature of about 130°

C. to about 250°

C. and maintain said first temperature for a period of about 0.5 min to about 5 hours, thereby producing a first solids fraction and a first liquid fraction; and

a second stage comprising;

subjecting said first solids obtained from said first stage to a supercritical or near-critical fluid under a pressure of about 40 bar to about 300 bar;

wherein said supercritical or near-critical fluid comprises water;

wherein said supercritical or near-critical fluid is at a temperature of about 374°

C. to about 600°

C.;

wherein said subjecting step elevates said first solids fraction to a second temperature of about 250°

C. to about 450°

C.;

wherein said first solids fraction is maintained at said second temperature for a period of about 0.05 sec to about 10 sec, thereby producing a second solids fraction and a second liquid fraction; and

wherein said composition comprises said second solids fraction.

11. The phenol formaldehyde resin of claim 10,

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

12. The phenol formaldehyde resin of claim 10,

wherein said first stage employs a pressure of about 4 bar to about 100 bar.

13. The phenol formaldehyde resin of claim 10,

wherein said second stage employs a pressure of about 40 bar to about 260 bar.

14. The phenol formaldehyde resin of claim 10,

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

15. The phenol formaldehyde resin of claim 10,

wherein said second stage employs supercritical water.

16. The phenol formaldehyde resin of claim 10,

wherein said composition is prepared without the addition of acid.

17. The phenol formaldehyde resin of claim 10,

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;

or

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.

18. The phenol formaldehyde resin of claim 10,

wherein said first stage employs a digester and a steam explosion unit.

20. Plywood or a particle board comprising the phenol formaldehyde resin of claim 10.

22. The phenol formaldehyde resin of claim 10,

wherein said second stage employs a pressure of about 230 bar to about 300 bar.