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Macro-azo-initiators (MAIs) having poly(ethylene glycol) (PEG) units were obtained by various multistep synthetic approaches. In the first stage, macro-azo-initiators of PEG type with azo groups inserted in the main chain were prepared. MAIs were then characterized by chemical analyses, spectral methods, 1 H-NMR, GPC, and DSC techniques. They were used in the free-radical bulk polymerization of dicyclohexylitaconate to synthesize AB block copolymers of poly(ethylene glycol-b-dicyclohexylitaconate) (PEG-b-PDCHI).