Lignin derivatives and uses thereof
View Patent ↗An article including a lignin derivative, where the lignin derivative includes a moiety derived from an antimicrobial compound. Also provided are methods of inhibiting microbial growth with an article including a lignin derivative.
1. An article comprising a lignin derivative, wherein the lignin derivative comprises a moiety derived from an antimicrobial compound, and the article is a moldable thermoplastic material, and the lignin derivative is represented by Formula IV:
wherein:
R 1 , R 2 , R 4 , and R 5 are each independently H, halo, alkyl, alkenyl, aryl or heteroaryl;
R 3 is OH or SH; and
O-Lignin is a lignin residue derived from a hydroxyl group of lignin.
2. The article of claim 1 , wherein R 1 , R 2 , R 4 , and R 5 are each H and R 3 is OH.
3. An article comprising a lignin derivative, wherein the lignin derivative comprises a moiety derived from an antimicrobial compound, and the article is a moldable thermoplastic material, and the lignin derivative is represented by Formula IIA:
wherein:
R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 are each independently H, halo, alkyl, alkenyl, aryl or heteroaryl;
L is an alkylene moiety or polyalkyleneoxy moiety; and
O-Lignin is a lignin residue derived from a hydroxyl group of lignin.
4. The article of claim 3 , wherein L is —CH 2 CH(OH)CH 2 —.
5. The article of claim 3 , wherein L is —CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 —.
6. The article of claim 3 , wherein R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 are each independently H or chloro.
7. The article of claim 3 , wherein the moiety derived from the antimicrobial compound comprises:
8. The article of claim 3 , wherein the moiety derived from the antimicrobial compound comprises:
9. A method of inhibiting microbial growth, the method comprising: contacting one or more microbes with an article according to claim 1 .
10. The method of claim 9 , wherein the one or more microbes comprise bacteria.
11. The method of claim 9 , wherein the one or more microbes comprise fungi.
12. A method of inhibiting microbial growth, the method comprising: contacting one or more microbes with an article according to claim 3 .
13. A method of forming a lignin derivative, the method comprising:
contacting a lignin-containing material with a compound of Formula VI to form the lignin derivative, wherein the lignin derivative comprises a moiety of Formula IIA:
R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 are each independently H, halo, alkyl, alkenyl, aryl or heteroaryl;
L is an alkylene moiety or polyalkyleneoxy moiety; and
O-Lignin is a lignin residue derived from a hydroxyl group of lignin.
14. The method of claim 13 , further comprising at least partially depolymerizing the lignin.
15. The method of claim 14 , wherein the depolymerizing comprises a hydrogenolysis reaction.
16. The method of claim 15 , wherein the hydrogenolysis reaction is conducted in the presence of a transition metal catalyst.
17. The method of claim 16 , wherein the transition metal catalyst comprises nickel.
18. The method of claim 16 , wherein the transition metal catalyst further comprises a carbene ligand.
19. The method of claim 13 , wherein the contacting is conducted in the presence of a base.
20. The method of claim 19 , wherein the base comprises an alkali metal hydroxide, a carbonate, a secondary amine, an aromatic amine, or a tertiary amine.
21. The method of claim 13 , wherein contacting is conducted in the presence of an acid.
22. The method of claim 21 , wherein the acid comprises hydrochloric acid, sulfuric acid, acetic acid, trifluoroacetic acid, or phosphoric acid.