Analysis of the Cross-Linking Reaction of Lignin with Triethyl Phosphate by MALDI-TOF and 13C NMR

Polymers (Basel). 2017 Jun 4;9(6):206. doi: 10.3390/polym9060206.

Abstract

The reaction of condensation and cross-linking of desulfurized kraft lignin with triethyl phosphate (TEP) was explored. Catechol, a simple model of the aromatic ring of lignin, and glycerol, a model compound of the aliphatic hydroyl groups of the side chain of lignin, were employed under similar reaction conditions. Solid state cross-polarisation/magic-angle spinning (CP-MAS) 13C NMR and matrix assisted laser desorption ionization time-of-flight (MALDI-TOF) spectroscopy studies showed that polycondensation occurs on phenolic hydroxyl groups of lignin, as well as on aliphatic hydroxyls groups of its side chain. The reactions appear to be favoured by higher temperatures and in the presence of ammonia. Preliminary adhesion tests on wood shown good hydrophobicity properties of the surface treated with lignin-TEP-based resin. Initial application tests carried out at high temperature demonstrated as good performance as metallic coating.

Keywords: 13C NMR; MALDI-TOF; catechol; glycerol; lignin; polymerization and cross-linking; triethyl phosphate.