Synthesis and characterization of novel methacrylate monomer and their polymers having pendant oxime esters and their copolymerization with styrene

In the first step of this study, benzophenone oxime and acetophenone oxime was prepared by reaction ofbenzophenone and acetophenone substances with hydroxylamine hydrochloride in the presence sodiumhydroxide at the 25 oC in ethyl alcohol. In the second step, diphenylmethanone o-(2-chloroacetyl) oxime and 1-phenylethanone o-(2-chloroacetyl) oxime was prepared by reaction of benzophenone oxime and acetophenoneoxime with chloroacetyl chlorid in the presence potassium carbonate at the 0 oC in dichloromethane. In the thirdstep, 2-{[(diphenylmethylene)amino]oxy}-2-oxoethyl methacrylate (DPOMA) and 2-{[(1-phenylethylidiene)amino]oxy}-2-oxoethyl methacrylate (MMOMA) monomers were prepared by the reaction ofdiphenylmethanone o-(2-chloroacetyl) oxime and 1-phenylethanone o-(2-chloroacetyl) oxime compounds withsodium methacrylate at 80 oC in acetonitrile. The homopolymerization of DPOMA and MMOMA were carriedout in glass ampoules under N2 atmosphere in 1,4-dioxan solution at 60 oC with AIBN as an initiator. The freeradical copolymerizations of DPOMA and MMOMA with styrene (ST) were carried out in 1,4-dioxan solvent by13using AIBN initiator. The monomers, homopolymers and copolymers were characterized by Infrared (IR), C-1NMR and H-NMR techniques. The copolymer compositions were determined by elemental analysis. Thermalproperties of the polymers were also studied by thermogravimetric analysis (TGA) and differantial scanningcalorimetry (DSC). The monomer reactivity ratios were calculated according to the general copolymerizationequation using Kelen-Tüdos (K-T) and Fineman-Ross (F-R) linearization methods. In addition, the biologicalactivity of the monomers and polymers were investigated on the various bacteria and fungis.KEY WORDS: Methacrylate, Oxime esters, Styrene, Monomer reactivity ratios, Thermogravimetri, biologicalactivity