Thermoreversible Poly(alkyl acrylates) Consisting of Self-Complementary Multiple Hydrogen Bonding

The synthesis and characterization of novel self-complementary multiple hydrogen-bonded (SCMHB) polymers containing pendant 2-ureido-4[1H]-pyrimidone (UPy) units are described. SCMHB pendant polymers, poly(butyl acrylate-co-SCMHB methacrylate), were prepared via free radical copolymerization of butyl acrylate (BA) and a novel SCMHB methacrylate (SCMHB MA) monomer, which was synthesized via a quantitative coupling reaction between 2-isocyanatoethyl methacrylate (ICEMA) and methyl isocytosine (MIS) in DMSO. The glass transition temperatures of poly(BA-co-SCMHB MA) increased in a linear fashion as the SCMHB MA content increased. Thermogravimetric analysis of the copolymers exhibited an onset of weight loss at 217 °C. Solution viscosity analysis indicated that SCMHB pendant polymers strongly aggregated in nonpolar solvents, such as toluene and CHCl3, and dissociated in polar solvents, such as THF. Based on melt rheological characterization, the melt viscosity of soluble SCMHB pendant polymers was an order of ...