Premium
Poly(ether urethane)s from aromatic diisocyanates based on lignin‐derived phenolic acids
Author(s) -
Kuhire Sachin S,
Nagane Samadhan S,
Wadgaonkar Prakash P
Publication year - 2017
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.5333
Subject(s) - ether , glass transition , syringic acid , methylene , lignin , vanillic acid , polymer chemistry , chemistry , organic chemistry , chemical structure , polymer , materials science , gallic acid , antioxidant
A series of new bio‐based aromatic diisocyanates, namely bis(4‐isocyanato‐2‐methoxyphenoxy)alkane and bis(4‐isocyanato‐2,6‐dimethoxyphenoxy)alkane, were synthesized starting from lignin‐derived phenolic acids, namely vanillic acid and syringic acid, via the Curtius rearrangement. The diisocyanates were employed to synthesize poly(ether urethane)s by reacting them with potentially bio‐based aliphatic diols, namely 1,10‐decanediol and 1,12‐dodecanediol. The chemical structures of diisocyanates and poly(ether urethane)s were confirmed using Fourier transform infrared, 1 H NMR and 13 C NMR spectroscopy. Inherent viscosities and number‐average molecular weights of the poly(ether urethane)s were in the ranges 0.58–0.68 dL g −1 and 32 100–58 500 g mol −1 , respectively, indicating the formation of reasonably high molecular weight polymers. The poly(ether urethane)s exhibited 10% weight loss in the temperature range 304–308 °C. The glass transition temperatures of the poly(ether urethane)s were in the range 49–74 °C and were dependent both on the number of methylene units in the diols and on the number of methoxy substituents on the aromatic rings of the diisocyanate component. © 2017 Society of Chemical Industry