Synthesis And Application Of Rosin Multiisocyanate

Triacylisocyanate of fumaropimaric acid was synthesized from abietic acid through triacid amide of fumaropimaric acid by non-phosgene route. The new-style isocyanate was applied to prepare polyurethane foam. Triacylisocyanate of fumaropimaric acid reacted with benzylamine and fluoro benzylamine, obtained four acyl urea compounds, their biological activities were preliminary studied.1. Triacylisocyanate of fumaropimaric acid was synthesized from abietic acid, through Diels-Alder reaction, hydrolysis reaction, acylation reaction and ammonolysis reaction, etc. The structure was characterized indirectly by the compound(2a) which it reacted with methanol, through FT-IR,1H-NMR,13C-NMR and MS(ESI). The yield of triacylisocyanate of fumaropimaric acid was 77.50%. Triacylisocyanate of fumaropimaric acid and 2a were synthesized for the first time. In addition, the single crystal of triacid amide of fumaropimaric acid was obtained for the first time and was characterized by single crystal X-ray diffraction.2. The NCO percent of triacylisocyanate of fumaropimaric acid is 23.79%, the acidity is 0.77%, the density is 1.52 g/cm~3 at 25℃and the viscosity is 230 mPa?s at 25℃. Triacylisocyanate of fumaropimaric acid was mixed with PAPI, used to prepare a series of polyurethane foams with different amount of triacylisocyanate of fumaropimaric acid.The physical properties of triacylisocyanate of fumaropimaric acid showed that it has lower reactivity than PAPI, which caused larger pore radius. Density and compressive strength were affected by larger pore radius and the rigid structure of rosin rings. Density measurement indicated that when the mass fraction of triacylisocyanate of fumaropimaric acid was 10%, the polyurethane foam density was the same as that without triacylisocyanate of fumaropimaric acid, afterwards, polyurethane foam density increased as the amount of triacylisocyanate of fumaropimaric acid increased. Compressive strength measurement demonstrated that when the mass fraction of triacylisocyanate of fumaropimaric acid was 20%, the polyurethane foam compressive strength was higher than that without triacylisocyanate of fumaropimaric acid, afterwards, polyurethane foam compressive strength increased as the amount of triacylisocyanate of fumaropimaric acid increased. TGA analysis manifested that the addition of triacylisocyanate of fumaropimaric acid enhanced heat resistance of polyurethane foams, which rose as the mass fraction of triacylisocyanate of fumaropimaric acid rose.3. Triacylisocyanate of fumaropimaric acid reacted with benzylamine and fluoro benzylamine at 40℃for 24 h, obtained four acyl urea compounds(4a,4b,4c and 4d) for the first time. Their structures were characterized through FT-IR,1~H-NMR,(13)~C-NMR and MS(ESI).The antitumor activity of 4a,4b,4c and 4d were determined. The study results show that 4a,4b,4c,4d have inhibitory activity on hepatoma carcinoma cell HepG2 under high concentration. 4c and 4d have well inhibitory activity on gastric cancer cell SGC7901, the inhibitory rate are 45.57% and 47.36% respectively, when the concentration is 80μg/mL. However, 4a and 4b have no inhibitory activity on gastric cancer cell SGC7901. These results will provide some useful information for the synthesis of powerful antitumor drugs.