114267-39-9Relevant academic research and scientific papers
Efficient Cu(I) acetate-catalyzed cycloaddition of multifunctional alkynes and azides: From solution to bulk polymerization
Sandmann, Benedict,Happ, Bobby,Hager, Martin D.,Vitz, Juergen,Rettler, Erik,Burtscher, Peter,Moszner, Norbert,Schubert, Ulrich S.
, p. 239 - 247 (2014)
"Click" chemistry is an effective and commonly used technique in polymer chemistry for the synthesis and modification of polymers. In this study, the bulk polymerization of multifunctional alkynes and azides was achieved by the copper(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition. The influence of different catalyst systems on the polymerization kinetics of the "click"reaction were evaluated by differential scanning calorimetry. Surprisingly, Cu(I) acetate showed the most efficient catalytic behavior among the applied Cu(I) salts. The polymerization kinetics in solution were investigated by 1H NMR spectroscopy and size exclusion chromatography. According to the 1H NMR investigation the copper(I)-catalyzed cycloaddition follows a second-order kinetics with external catalysis. Additionally, the mechanical properties of the resulting polymers were investigated by depth sensing indentation. Thereby the polymerizations of the alkyne tripropargylamine with the azides 1,3-bis(azidomethyl)benzene and 1,4-bis(azidomethyl)benzene resulted in mechanical hard materials. Furthermore, the combination of the alkynes tripropargylamine and di(prop-2-yn-1-yl) isophorone dicarbamate and polymerization with 1,2-bis(2-azidoethoxy)ethane resulted in high indentation moduli. Copyright
Catalyst free-click polymerization: A versatile method for the preparation of soybean oil based poly1,2,3-triazoles as coatings with efficient biocidal activity and excellent cytocompatibility
Gholami, Hoshyar,Yeganeh, Hamid,Gharibi, Reza,Jalilian, Mehrdad,Sorayya, Marziyeh
, p. 94 - 108 (2015)
Click polymerization was applied for the preparation of soybean oil-based poly1,2,3-triazoles (PTAs). Azidated soybean oil (ASBO) was prepared and reacted with two different propyn-functional urethane monomers. Azidated derivatives of a quaternary pyridinium salt (APS) and Cloisite 30B (MMT-N3) were also synthesized and tethered into the PTAs to control the physico-mechanical properties as well as biological activities. PTAs showed very good hardness (169-270 s-1) and adhesion strength (0.65-1.65 MPa) to Aluminum plate as model substrate. Qualitative and quantitative assessments confirmed promising cytocompatibility of PTAs against fibroblast cells (86-98% viability). Meanwhile, introduction of either APS or MMT-N3 in PTAs induced bactericidal and fungicidal activities against S. aureus, P. aeruginosa and C. albicans. Higher biocidal activity (up to 99% reduction) was detected when these modifiers were used mutually in coatings materials. This work provides a new insight for utilizing a biorenewable material for the preparation of high-performance coatings suitable for biomedical applications.
