Synthesis and properties of polyurethane cationomers with urethane-cholesteryl and dodecylmethylammonium moieties

Abstract

A new diol-type monomer, N-(carbonyloxycholesteryl)diethanolamine, was prepared to be used in the synthesis of segmented polyurethane cationomers incorporating cholesteryl units and dodecylmethylammonium groups. The flexible segments used in this study were polycaprolactone diol alone or together with poly(ethylene oxide) diol of average molecular weight 2000, and the hard segments were derived from aliphatic diisocyanates and the above-mentioned diols. The characterization tests for all polymers included IR spectral data, viscosity measurements, GPC, optical activity, thermal and elemental analysis. The opposite rotation of the polycation ([α D ] = +9.1) compared to that observed for the starting monomer ([α D ] = −31.8) suggests a chiral perturbation of the ordered conformations in solution. Preliminary results concerning biodegradation of some ionomers in a phosphate buffer solution containing Pseudomonas lipase showed that in appropriate conditions the enzymatic degradation process in polymeric film occurred.

Ionic polymers with tunable liquid‐crystalline properties

“…Polymers based on diethanolamine (DEA) or dipropanolamine have found potential applications in a wide diversity of fields. For example, diethanolamine polyethers have been used as biodegradable demulsifiers for the treatment of pollution in refinery wastewater;1 DEA‐fatty amides are useful for the preparation of poly(urethane amide)s for anticorrosive coatings;2–5 and poly(ether amide)s have been applied for anticorrosive coatings in combination with melamine resins 6. In addition, many dendrimers and hyperbranched polymers based on dialkanolamines have been the subject of extensive research over the past 10 years since they provide a large number of different functional groups 7.…”