title: A deeper insight into the postpolymerization modification of polypenta fluorophenyl methacrylates to poly(n-(2-hydroxypropyl) methacrylamide).
abstract: This work provides a detailed insight into the synthesis of N-(2-hydroxypropyl)methacrylamide (HPMA) polymers employing the activated ester approach. In this approach, polypenta fluorophenyl methacrylate (PFPMA)-activated ester polymers are synthesized by the reversible addition-fragmentation chain transfer (RAFT) polymerization and transferred into HPMA-based systems by the use of 2-hydroxypropylamine. To prove quantitative conversion in the absence of side reactions, special attention is devoted to investigate different reaction conditions by different analytical methods ((1) H, (19) F, inverse-gated (13) C NMR, and zeta potential measurements). Furthermore the influence of common solvent impurities, such as water, is investigated. Besides differences in polymer tacticity, the poly(N-(2-hydroxypropyl) methacrylamide) (PHPMA) synthesized under water-free conditions display the same properties like the conventional synthesized control-PHPMA. However, 3% water content in the dimethylsulfoxide are already sufficient to yield PHPMA polymers with a negative zeta potential of -15.8 mV indication the presence of carboxylic groups due to partial hydrolysis of the activated ester.
authors: Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099, Mainz, Germany.
authors: Nicole
authors: N
authors: Mohr
authors: Matthias
authors: M
authors: Barz
authors: Romina
authors: R
authors: Forst
authors: Rudolf
authors: R
authors: Zentel
mesh_terms: D004952:Esters; D006868:Hydrolysis; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D058105:Polymerization; D011108:Polymers / Q000737:chemistry*; D011109:Polymethacrylic Acids / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D004952:Esters; D011108:Polymers; D011109:Polymethacrylic Acids; D014867:Water; C011533:Duxon
keywords: N-(2-hydroxypropyl) methacrylamide; PHPMA; RAFT; activated ester; postpolymerization modification