Author :
Mallakpour, shadpour E.,Mohammdi, farhad
Descriptors :
Trans-3,3-dichoro-1-phenyl-1-propene,Double Diels-Alder and Diels-Alder-Ene polymerization,Triazolinediones,Trans-cinammaldehyde,E-stilbenedioldiacetate,Intrinsic viscosity.
Abstract :
The reaction of 4-phenyl-1,2,4-triazoline-3,5-dione (PhTD) (2) with trans-3,3-dichloro-1-phenyl-1-propene (4) was investigated at room and reflux temperatures in methylene chloride solution. Although the reaction is slow, it givs quantitative yield. This reaction leads to the formation of two 2:1 adducts via double Diels-Alder-Ene reactions in a ratio of about 1:7. The major product was isolated by means of fractional crystallization as a pure compound and was characterized by infra-red (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectra and elemental analysis. The structure of the minor product was determined by IR and H NMR. These compounds were used as models for the polymerization reactions. The reaction of bistriazolinediones (1,6-bis-3,5-dioxo-1,2,4-triazoline-4-yl) hexane and bis-(p-3,5-dioxo-1,2,4-triazoline-4-ylphenyl) methane) with (4) was carried out in dimethylformamide (DMF). The reactions gave novel polymers via repetitive double Diels-Alder and Diels-Alder-Ene polyaddition reactions. with the major componet being a Diels-Alder-Ene structute. These polymers have intrinsic viscostites in a range from 0-08 to 0.18 dlg**-1 in DMF. The physical properties and structrual characterization of these polymers have been studied and are reported.
