Synthesis of a novel polymer containing sulfur via polycondensation

3-Hydroxypropyl methoxycarbonylethyl sulfide (HPMES) and 3-hydroxypropyl carboxyethyl sulfide (HPCES) were synthesized by Michaelis addition of methyl 3-mercaptopropionate (MMP) and 3-mercaptopropionic acid (3-MPA) with allyl alcohol. Polycondensation of HPMES and HPCES was performed under various conditions to obtain corresponding polythioethers with a number average molecular weight of up To 5700. The polycondensation of HPMES was performed with several metal acetates as catalysts. For the polycondensation of HPCES, two types of carbodiimide derivatives and 4-dimethylaminopyridine (DMAP) were used as a condensation reagent and catalyst. All the polymers obtained in these reactions had the same structure, judging from H-1 NMR spectra. The degree of crystallinity, melting points, decomposition points, and glass transition points were 36 similar to 46%, 37 similar to 47 degrees C, 164 similar to 260 degrees C, and -61 similar to-70 degrees C, respectively.