TY - JOUR
T1 - Synthetic lignin-like and degradable nanocarriers
AU - Beckers, Sebastian J.
AU - Fischer, Jochen
AU - Wurm, Frederik R.
N1 - Publisher Copyright:
© 2021 The Royal Society of Chemistry.
PY - 2021/8/28
Y1 - 2021/8/28
N2 - Lignin is a highly abundant biopolymer that is a by-product formed during paper manufacturing. Lignin is degraded by certain lignase-producing fungi and is relatively stable towards hydrolysis, which makes it an attractive material for diverse applications ranging from packaging to agrochemical delivery. However, a major challenge that hinders the large-scale use of lignin is its ill-defined chemical structure as a crosslinked copolymer with a variable comonomer composition, which results in strong batch-to-batch variations. To eradicate such a structural heterogeneity, herein, we synthesized two lignin-like monomers, comprising linkages found in native lignin, i.e., phenylcoumaran and β-O-4-aryl ether, and used them for the preparation of lignin-like nanocarriers by interfacial crosslinking in an inverse miniemulsion. The lignin-like monomers are accessible by a 2- or 4-step synthesis starting from bio-based compounds and can be prepared on a multigram scale. They carry hydroxyl groups, which reacted with toluene diisocyanate to produce lignin-like polyurethane nanocarriers with diameters between 200 and 400 nm. The nanocarriers might be used for the encapsulation of fungicides and for plant protection, as the lignin-like structure allowed the degradation by lignase-producing fungi, which are the cause of many plant diseases. Therefore, the dispersions might be of interest as a degradable drug delivery system, e.g. in advanced plant protection, or as synthetic alternatives to natural lignin.
AB - Lignin is a highly abundant biopolymer that is a by-product formed during paper manufacturing. Lignin is degraded by certain lignase-producing fungi and is relatively stable towards hydrolysis, which makes it an attractive material for diverse applications ranging from packaging to agrochemical delivery. However, a major challenge that hinders the large-scale use of lignin is its ill-defined chemical structure as a crosslinked copolymer with a variable comonomer composition, which results in strong batch-to-batch variations. To eradicate such a structural heterogeneity, herein, we synthesized two lignin-like monomers, comprising linkages found in native lignin, i.e., phenylcoumaran and β-O-4-aryl ether, and used them for the preparation of lignin-like nanocarriers by interfacial crosslinking in an inverse miniemulsion. The lignin-like monomers are accessible by a 2- or 4-step synthesis starting from bio-based compounds and can be prepared on a multigram scale. They carry hydroxyl groups, which reacted with toluene diisocyanate to produce lignin-like polyurethane nanocarriers with diameters between 200 and 400 nm. The nanocarriers might be used for the encapsulation of fungicides and for plant protection, as the lignin-like structure allowed the degradation by lignase-producing fungi, which are the cause of many plant diseases. Therefore, the dispersions might be of interest as a degradable drug delivery system, e.g. in advanced plant protection, or as synthetic alternatives to natural lignin.
UR - http://www.scopus.com/inward/record.url?scp=85113240695&partnerID=8YFLogxK
U2 - 10.1039/d1py00818h
DO - 10.1039/d1py00818h
M3 - Article
AN - SCOPUS:85113240695
SN - 1759-9954
VL - 12
SP - 4661
EP - 4667
JO - Polymer chemistry
JF - Polymer chemistry
IS - 32
ER -