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Vanillin‐based polymers: IV. Hydrovanilloin epoxy resins
Author(s) -
Amarasekara Ananda S.,
GarciaObergon Rocio,
Thompson Audie K.
Publication year - 2019
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.47000
Subject(s) - epichlorohydrin , epoxy , diglycidyl ether , oligomer , bisphenol a , diamine , polymer chemistry , ether , vanillin , isophorone , isophorone diisocyanate , materials science , chemistry , nuclear chemistry , organic chemistry , polyurethane
In this study, hydrovanilloin synthesized by electrochemical dimerization of vanillin has been used as a renewable substitute for bisphenol A for the preparation of epoxy resins. The reaction of the disodium salt of hydrovanilloin:epichlorohydrin 1:2 mol ratio at 80°C for 30 min in water gave a hydrovanilloin – diglycidyl ether phenoxy resin. This hard thermoplastic resin showed T g of 135°C and stable up to 255°C in air. On the other hand, the disodium salt of hydrovanilloin:epichlorohydrin 1:4 mol ratio at 80°C for 30 min in water gives a curable oligomer of hydrovanilloin – diglycidyl ether with 2.1 repeating units. This oligomer could be cured with aliphatic diamines: 1,2‐diaminoethane, 1,4‐diaminobutane, 1,6‐diaminohexane, and isophorone diamine to give hard epoxy resins with T g values of 116, 118, 149 and 146°C, respectively. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 47000.