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Bioinspired flame retardant polymers of tyrosol
Author(s) -
Bouldin Ryan M.,
Xia Zhiyu,
Klement Thomas J.,
Kiratitanavit Weeradech,
Nagarajan Ramaswamy
Publication year - 2017
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.45394
Subject(s) - polymer , thermogravimetric analysis , gel permeation chromatography , chemistry , phenol , monomer , polymer chemistry , fire retardant , organic chemistry , char , polymerization , chemical engineering , pyrolysis , engineering
The enzyme catalyzed polymerization of flame retardant (FR) polymers from the renewable resource 2‐(4‐hydroxyphenyl) ethanol (HPE), commonly known as tyrosol, is presented. The synthesis is environmentally friendly and requires only monomer, peroxidase catalyst, dilute hydrogen peroxide, and deionized water. Phenolic polymers are produced in short, one pot, high yield reactions that require minimal purification. Fourier transform infrared spectroscopy and 1 H‐NMR analysis suggest the polymers are coupled through the 1, 2, 4, and 5 positions of the phenol ring and through the phenoxy substituent. Thermogravimetric analysis and pyrolysis combustion flow calorimeter show HPE homopolymers exhibit very low heat release rate and total heat release, while copolymerization with phenol increases already high char yields. Gel permeation chromatography reveals the molecular weight of the polymer increases with ethanol cosolvent concentration. The alcohol cosolvent also increases the proportion of oxyphenylene linkages to the detriment of FR properties. Preliminary quantitative structure–activity relationship toxicity modeling predicts the polymers are negative for developmental toxicity and Ames mutagenicity. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134 , 45394.