Preparation and Properties of Self-Healing Polyurethane Elastomer Derived from Tung-Oil-Based Polyphenol

Abstract

A tung-oil-based polyphenol (ATOM), containing the phenolic hydroxyl group, was synthesized from tung oil and 4-maleimidophenol by the Diels–Alder addition reaction. Then self-healing thermosetting polyurethanes were prepared from ATOM and the polyurethane prepolymer. The chemical structure and cross-link network were confirmed by Fourier transform infrared spectroscopy (FTIR) and swelling tests. The products partially dissolved in trichlorobenzene when the temperature rose to 110 °C. Temperature-variable FTIR confirmed that the phenolic urethane starts to partially dissolve at 100 °C, which can be explained by the experimental phenomenon in swelling tests. Tensile property analysis showed that the broken and healed thermosets maintained about 46–64% of their original tensile strengths and 81–88% of their original elongations at break, respectively.

Hydrophobic Shape-Memory Biocomposites from Tung-Oil-Based Bioresin and Onion-Skin-Derived Nanocellulose Networks

“…A sharp decrease in the storage modulus was observed in the range −10 • C to 20 • C for T1F3 and −10 • C to 40 • C for T1F6 and T1F9, due to the increase in segmental mobility of the long flexible hydrocarbon chains from the acrylated TO moiety. The rubbery plateau observed at >20 • C for T1F3, and at >40 • C for T1F6 and T1F9 indicates the presence of a stable crosslinked network in all the cured resins [11,12,54]. During curing of the resins, styrene molecules react with the acrylated TO molecule via free radical polymerization, leading to a crosslinked polymer network.…”

“…During curing of the resins, styrene molecules react with the acrylated TO molecule via free radical polymerization, leading to a crosslinked polymer network. The crosslinking densities of the cured resins and composites can be calculated (Table 2) by rubber elasticity theory using the expression: E = 3nRT, where E is the storage modulus in the rubbery region, n is the crosslinking density, R is the universal gas constant and T is the absolute temperature in K (T = T g + 398 K) [12,54]. Low crosslinking densities in the cured resins caused the films to tear at temperatures above 80 • C due to the low strength of the materials [55].…”

Dynamic Covalent Polyurethane Network Materials: Synthesis and Self‐Healability

“…The damaged and healed thermosets maintained 46–64% of their original tensile strengths and 81–88% of their original elongations at break. [ 46 ]…”

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

“…(i) its direct polymerization with bismaleimides for the synthesis of networks, and (ii) its bulk reaction with an excess of furfurylamine, leading to the formation of an AB monomer containing a furan ring and the three conjugated double bonds of α-eleostearic acid, to be further polymerized with bismaleimides [ 134 ] ( Figure 12 ). More recently, the Diels–Alder reaction of tung oil with 4-maleimidophenol was conducted for the synthesis of polyols and, in a further step, of polyurethane elastomers [ 135 ]. Eleostearic diethanolamide was synthesized from tung oil and diethanolamine and then reacted with hydroxymethylmaleimide to give a triol, which was mixed with castor oil and isophorone diisocyanate for the synthesis of polyurethanes [ 136 ].…”