Synthesis and Properties of New Poly(urethane-acrylates) With Pendant Triazene Moieties

Abstract

New triazene urethane methacrylates, 1-(phenyl)-3-(2-methacryloyloxyethyl)-3-methyl triazene-1 (UMA-T1) and 1-(p-methoxyphenyl)-3-(2-methacryloyloxyethyl)-3-methyl triazene-1 (UMA-T2), were synthesized and characterized to be used as co-partners in the radical co-polymerization with methyl methacrylate for achieving triazene-co-polymethacrylates. The synthesized photo-polymers were spectrally and thermally characterized, the results being satisfactory for this class of materials. The most important feature of the co-polyacrylates is their photosensitivity, evaluated by the UV irradiation in DMF solution or thin films, following the disappearance of the π-π * absorption band, corresponding to the triazene chromophore, in the UV spectra. Such photolabile polymers with good film-forming properties could offer new possibilities in printing techniques and nanostructuring on surfaces. In addition, the triazene functions introduced as side-groups may be exploited for the tailoring of novel functional polymeric architectures.

Preparation of amphiphilic block copolymer containing triazene moieties and fluorescence study

“…[5][6][7] In this regard, our contribution in the synthesis of novel triazene polyurethanes and copolyacrylates that combine the sensitivity of the triazene structure with an almost unlimited structural variability offered by the macromolecular chemistry of these polymers should be mentioned. [8][9][10][11] Moreover, in recent publications, the important attribute of the triazene copolymers to emit a strong fluorescence with a maximum around 400 nm was confirmed, feature of interest in chemosensor applications for the detection of some metal ions. 12,13 Meanwhile, the modern developments in reversible addition-fragmentation chain transfer (RAFT) polymerization have proved that this is one of the most versatile methods of controlled radical polymerization, successfully employed in preparing complex macromolecular architectures such as linear block copolymers, star and brush polymers, dendrimers.…”

“…Dodecylacrylamide monomer (DA), triazene urethane methacrylate (UMA-T) and benzyl dithiobenzoate (BDTB) were obtained as previously reported. 11,37,38 The macroPAA was prepared through the RAFT polymerization of acrylic acid (9 g, 125 mmol) in dioxane, in the presence of benzyl dithiobenzoate (0.244 g, 1 mmol) and 1,1 -azobis (cyclohexanecarbonitrile) (0.124 g, 0.5 mmol) used as chain transfer agent and initiator, respectively. The mixture was reacted under microwave irradiation at 100 • C for 90 min, under purified nitrogen.…”