Tyramine-Derived 5-Membered Cyclic Carbonate Resins:Synthesis, Curing, and Properties of the Cured Resins

Abstract

Tyramine triepoxide resin (TTE) was synthesized from tyramine and epichlorohydrin. Tyramine tricarbonate resin (TTC) was synthesized by reacting TTE with carbon dioxide in the presence of a lithium bromide catalyst. TTC resin was cured with stoichiometric amount of 4,7,10-trioxa-1,13-tridecanediamine (TODA) or m-xylene diamine (mXDA) by heating at 100°C for 24 hours. Thermogravimetric analysis showed that the 5% weight loss temperature was 215°C for the cured TTC/TODA resin and 208°C for the cured TTC/mXDA resin, indicating that both products were easy to be thermally decomposed. Differential scanning calorimetry and film tensile test showed that the cured TTC/TODA resin was a rubber-like flexible material at room temperature, with a glass transition temperature of －22°C, an elastic modulus of 0.76 GPa, and a maximum strength of 14.2 MPa, while the cured TTC/mXDA resin was a glass-like hard material at room temperature, with a glass transition temperature of 62°C, an elastic modulus of 6.8 GPa, and a maximum strength of 152 MPa. Shear adhesive strength to a stainless-steel substrate to a stainless substrate was-19.3 MPa for the cured TTC/TODA rein and 2.4 MPa for the cured TTC/mXDA resin. As a result of enzymatic degradation experiments using lipase and protease solutions, increases in water uptake were observed in the cured TTC/TODA resins, indicating the collapse of the molecular network structure, while almost no changes were observed in the cured TTC/mXDA resin.