Synthesis and polymerizations of new metal chelating monomers from alkyl α‐hydroxymethacrylates

Abstract

AbstractTwo new diethyl iminodiacetate‐containing monomers (EBMA‐ID and CMAC‐ID) were synthesized through the reaction of ethyl α‐bromomethacrylate (EBMA) and α‐chloromethacryloylchloride (CMAC) with diethyl iminodiacetate (ID). The hydrolysis of the ethyl ester groups with potassium hydroxide gave two chelating monomers with potassium salt of iminodiacetic acid (EBMA‐IDA‐K+ and CMAC‐IDA‐K+). The homopolymerization and copolymerization with 2‐hydroxyethyl methacrylate (HEMA) of EBMA‐ID and CMAC‐ID were investigated by photodifferential scanning calorimetry at 40°C using 2,2′‐dimethoxy‐2‐phenyl‐acetophenone (DMPA) as initiator. The monomers showed very low homopolymerization reactivity which may be attributed to the steric effect of N,N‐disubstituted methacrylamides, the presence of allyl amine group that can undergo degradative chain transfer and the bulky ID group close to the double bond. Also, addition of these monomers to HEMA decreased polymerization rate and conversion with fraction added. EBMA‐IDA‐K+ and CMAC‐IDA‐K+ were copolymerized with acrylamide in water using 2,2′‐azobis(N,N′‐amidinopropane) dihydrochloride (V‐50) initiator. Here also, it was observed that the incorporation of the synthesized monomers into acrylamide reduced both the rate of polymerization and conversion. The copolymers were characterized by 1H‐NMR spectroscopy, thermogravimetric analysis (TGA) and Fourier transform infrared (FTIR) spectroscopy. The UV‐visible and TGA spectra confirmed that the synthesized monomers showed chelating ability for Ni+2 and Cr+3. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008