Synthesis of rosin‐based imidoamine‐type curing agents and curing behavior with epoxy resin

Abstract

Rosin is an abundantly available natural product. The characteristic fused ring structure of rosin acids is analogous to that of some aromatic compounds in rigidity, and makes rosin and its derivatives potential substitutes for those aromatic compounds. In the study reported, the synthesis of biobased curing agents containing imide structure using rosin and the cure reaction were investigated. Rosin‐based imidoamine‐type curing agents were synthesized, and the chemical structure was confirmed using 1H NMR, Fourier transform infrared and electrospray ionization spectroscopy. The curing behavior with diglycidyl ether of bisphenol A epoxy was studied using differential scanning calorimetry. The thermal mechanical properties and thermal stability of the cured epoxy resins were evaluated using dynamic mechanical analysis and thermogravimetry, respectively. The results indicate that the curing behavior of the rosin‐based curing agents is similar to that of curing agents with analogous structures. Cured products have good thermal stability due to the presence of the imide group and the bulky hydrogenated phenanthrene ring structure. Rosin acids have a great potential in the synthesis of epoxy curing agents as replacements for some of the current commercial aromatic or cycloaliphatic analogues. Copyright © 2010 Society of Chemical Industry

Monomers and Resulting Polymers from Biomass

“…The Diels-Alder product of abietic-type acids, in particular levopimaric acid, with maleic anhydride has received much attention as a curing agent for epoxy resins. This Diels-Alder reaction is shown in Scheme 5.6 [118,[147][148][149][150][151]. The cure kinetics and thermal mechanical properties of these agents are comparable to their fossil-based counterparts, and they exhibit slightly better T g [147,150].…”

“…This Diels-Alder reaction is shown in Scheme 5.6 [118,[147][148][149][150][151]. The cure kinetics and thermal mechanical properties of these agents are comparable to their fossil-based counterparts, and they exhibit slightly better T g [147,150]. However, the degradation temperatures for these systems are slightly below those of their fossil-based counterparts [147,150].…”

“…The cure kinetics and thermal mechanical properties of these agents are comparable to their fossil-based counterparts, and they exhibit slightly better T g [147,150]. However, the degradation temperatures for these systems are slightly below those of their fossil-based counterparts [147,150]. A two-step process to produce epoxy curing agents from [118].…”

Synthesis of bio-based building blocks from vegetable oils: a platform chemicals approach

“…Besides amines, acid hardeners lead to interesting curing properties and some studies have proposed nontoxic or biobased acid hardeners for epoxy resins. Thus, a study reports the use of abietic acid and maleic acid to synthesize a diacid for epoxy curing (Wang et al, 2011). Acid functionalized lignin was also reported as epoxy hardener (Hiroko et al, 2009).…”

Study on the synthesis of bio-based epoxy curing agent derived from myrcene and castor oil and the properties of the cured products

“…10 The fully biobased epoxy resins prepared from terpene maleic anhydride and maleopimaric acid have comparable or even better mechanical properties and thermal stability than the bisphenol A type epoxies cured by petroleum-based curing agents. 5 Terpenes, which are natural monomers containing carbon skeletons of isoprene, can be extracted from many essential oils and used as a versatile chemical feedstock.…”