Reactive & Functional Polymers, Vol.70, No.10, 827-835, 2010
Synthesis and characterization of side-chain oxazoline-methyl methacrylate copolymers bearing azo-dye
We synthesized new polymeric structures by attaching a side-chain azo-moiety on poly(oxazoline) and poly(oxazoline-co-methyl methacrylate)s. For the polymer analogous transformation, we took advantage of the highly effective ring-opening addition of carboxyl group to the oxazoline cycle. The comonomers feed ratio allowed us to control the composition of the products while the kinetic treatment, employing an integral method, revealed a statistical copolymerization tendency of 2-isopropenyl-2-oxazoline with methyl methacrylate in acetonitrile at 70 degrees C. The elemental analysis and (1)H NMR spectroscopy provided almost identical composition data for both the substrates and the side-chain copolymers. The UV spectroscopy sustained the quantitative addition of 4-(4-hydroxy-3,5-dimethylphenylazo)benzoic acid to the oxazoline rings. Both the unmodified copolymers and the coloured ones exhibited good thermal stabilities, up to 371 degrees C and 302 degrees C, respectively. The glass transition temperatures ranged from 141.5 to 177.5 degrees C and from 153.8 to 200.9 degrees C for the substrates and for the modified copolymers, respectively. Preliminary investigations showed fluorescence activity for all copolymers bearing azo-moieties. (C) 2010 Elsevier Ltd. All rights reserved.
Keywords:2-Isopropenyl-2-oxazoline;Azobenzene;Methyl methacrylate;Polymer analogous reaction;Ester-amide