Lignin derivatives having polycations and uses thereof
View Patent ↗A lignin derivative including one or more polycations is provided and an article including such a lignin derivative is also provided. Methods of inhibiting microbial growth with an article including such a lignin derivative are further provided.
1. A lignin derivative represented by the Formula I:
wherein:
G is absent or a polymeric group;
R 1 is an alkylene, (alkyleneamino) q , (alkyleneoxy) q , (alkyleneoxyarylene) q , or (alkyleneoxyarylene)alkylene(aryleneoxyalkylene) q moiety, wherein q is from 1 to 10;
R 2 is H or alkyl;
R 3 is a polycation; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion of a biomass, pulping of lignocellulosics, hydrogenolysis of lignin, the acid-catalyzed or base-catalyzed treatment of lignin, or combination of two or more thereof.
2. The lignin derivative of claim 1 , wherein the lignin derivative is thermoplastic.
3. The lignin derivative of claim 1 , wherein G comprises a group selected from a polyacrylate, polyalkylacrylate, polymethacrylate, polyacrylamide, polyolefin, polyepoxide, polyurethane, and polyurea.
4. The lignin derivative of claim 1 , wherein G is absent.
5. The lignin derivative of claim 1 , wherein Lignin-OGR 1 — is a group of formula:
wherein:
R 4 is H, alkyl, alkenyl, alkynyl, alkoxy, ester, or CN;
R 5 is H or alkyl;
R 6 is H or alkyl; and
n is from 1 to 1000.
6. The lignin derivative of claim 5 , wherein R 2 , R 4 , R 5 , and R 6 is each independently H or C 1 -C 4 alkyl.
7. The lignin derivative of claim 1 , wherein R 1 is
8. The lignin derivative of claim 1 , wherein R 3 is a polypeptide having at least one or more amino acid residues selected from lysine, histidine, arginine, tryptophan, ornithine, 2,4-diaminobutyric acid, and 2,3-diaminopropionic acid, and wherein at least one basic residue of the polypeptide is protonated.
9. The lignin derivative of claim 1 , wherein R 3 is selected from poly(methylene-co-guanidine), poly-L-lysine, ε-poly-L-lysine, poly-L-ornithine, poly-L-arginine, poly-L-histidine, poly-L-tryptophan, poly-2,4-diaminobutyric acid, poly-2,3-diaminopropionic acid, and a protamine.
10. The lignin derivative of claim 1 , wherein R 3 is poly(methylene-co-guanidine) or s-poly-L-lysine.
11. An article comprising a lignin derivative represented by Formula I:
wherein:
G is absent or a polymeric group;
R 1 is an alkylene, (alkyleneamino) q , (alkyleneoxy) q , (alkyleneoxyarylene) q , or (alkyleneoxyarylene)alkylene(aryleneoxyalkylene) q moiety, wherein q is from 1 to 10;
R 2 is H or alkyl;
R 3 is a polycation; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion of a biomass, pulping of lignocellulosics, hydrogenolysis of lignin, the acid-catalyzed or base-catalyzed treatment of lignin, or combination of two or more thereof;
wherein the article is a packaging, pharmaceutical, cosmetic, perfume, thermoplastic, garment, paper product, drywall, medical equipment, or toy.
12. The article of claim 11 , wherein G is absent.
13. The article of claim 11 , wherein Lignin-OGR 1 — is a group of formula:
wherein:
R 4 is H, alkyl, alkenyl, alkynyl, alkoxy, ester, or CN;
R 5 is H or alkyl;
R 6 is H or alkyl;
n is from 1 to 1000; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion of a biomass, pulping of lignocellulosics, hydrogenolysis of lignin, the acid-catalyzed or base-catalyzed treatment of lignin, or combination of two or more thereof.
14. The article of claim 11 , wherein G comprises a group selected from a polyacrylate, polyalkylacrylate, polymethacrylate, polyacrylamide, polyolefin, polyepoxide, polyurethane, and polyurea.
15. A method of inhibiting microbial growth, the method comprising: contacting one or more microbes with an article comprising a lignin derivative, wherein the lignin derivative is represented by Formula I:
wherein:
G is absent or a polymeric group;
R 1 is an alkylene, (alkyleneamino) q , (alkyleneoxy) q , (alkyleneoxyarylene) q , or (alkyleneoxyarylene)alkylene(aryleneoxyalkylene) q moiety, wherein q is from 1 to 10;
R 2 is H or alkyl;
R 3 is a polycation; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion of a biomass, pulping of lignocellulosics, hydrogenolysis of lignin, the acid-catalyzed or base-catalyzed treatment of lignin, or combination of two or more thereof.
16. The method of claim 15 , wherein the one or more microbes comprise bacteria or fungi.
17. The method of claim 15 , wherein G is absent.
18. The method of claim 15 , wherein Lignin-OGR 1 — is a group of formula:
wherein:
R 4 is H, alkyl, alkenyl, alkynyl, alkoxy, ester, or CN;
R 5 is H or alkyl;
R 6 is H or alkyl;
n is from 1 to 1000; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion, pulping, pre-treatment of biomass, hydrogenolysis, acid-catalyzed treatment, base-catalyzed treatment, or combination of two or more thereof.
19. A method of coating an article with a lignin derivative, wherein the method comprises contacting an article with one or more groups of Formula I:
wherein:
G is absent or a polymeric group;
R 1 is an alkylene, (alkyleneamino) q , (alkyleneoxy) q , (alkyleneoxyarylene or (alkyleneoxyarylene)alkylene(aryleneoxyalkylene) q moiety, wherein q is from 1 to 10;
R 2 is H or alkyl;
R 3 is a polycation; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion of a biomass, pulping of lignocellulosics, hydrogenolysis of lignin, the acid-catalyzed or base-catalyzed treatment of lignin, or combination of two or more thereof.
20. The method of claim 19 , wherein the article is a packaging, pharmaceutical, cosmetic, perfume, thermoplastic, garment, paper product, drywall, medical equipment, or toy.
21. The method of claim 19 , wherein Lignin-OGR 1 — is a group of formula:
wherein:
R 4 is H, alkyl, alkenyl, alkynyl, alkoxy, ester, or CN;
R 5 is H or alkyl;
R 6 is H or alkyl;
n is from 1 to 1000; and
the Lignin is a lignin product derived from a process comprising extraction of finely ground wood, acidic dioxane extraction of wood, steam explosion, dilute acid hydrolysis, ammonia fiber expansion of a biomass, pulping of lignocellulosics, hydrogenolysis of lignin, the acid-catalyzed or base-catalyzed treatment of lignin, or combination of two or more thereof.
22. The lignin derivative of claim 1 , wherein the lignin is derived from hydrogenolysis of lignin, the acid-catalyzed treatment of lignin, or the base-catalyzed treatment of lignin.