Polymeric phthalates: Potential nonmigratory macromolecular plasticizers



The synthesis of 4-vinyl-1,2-phthalate esters via Suzuki coupling is described, followed by nitroxide-mediated polymerization to prepare short homopolymers (degree of polymerization [DP] = 10–40, polydispersity index [PDI] = 1.1–1.3). Random copolymers with n-butyl acrylate (NBA) were prepared. Copolymers rich in phthalate ester residues of medium lengths (DP = 16–48, PDI = 1.2–1.8) and of shorter lengths (DP = 8–17, PDI = 1.2–1.3) were prepared. Copolymers rich in NBA residues were also prepared (DP = 13–19, PDI = 1.2–1.3). All polymers were oily liquids, with glass transitions temperatures undetected between 75 and −40 °C, indicating these polymeric phthalates hold promise as potential nonmigratory phthalate plasticizers. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013