Loghina Liudmila, Machotova Jana, Svoboda Roman, Houdek Jakub, Kohl Miroslav, Ruzickova Zdena, Jambor Roman, Vlcek Miroslav
Center of Materials and Nanotechnologies, Faculty of Chemical Technology, University of Pardubice 53002 Pardubice Czech Republic
Institute of Chemistry and Technology of Macromolecular Materials, Faculty of Chemical Technology, University of Pardubice 53210 Pardubice Czech Republic.
RSC Adv. 2025 Aug 13;15(35):28827-28840. doi: 10.1039/d5ra05109f. eCollection 2025 Aug 11.
Synthetic latexes are widely used as binders for outdoor barrier applications, where ultraviolet (UV) protection is of high practical importance. This study reports the synthesis of two novel, highly photoluminescent phenanthroimidazole (PPI) derivatives and their application as covalently linked UV-absorbing stabilizers in waterborne, photostable coatings based on all-acrylic latex polymers. Vinyl-functionalized phenanthroimidazole-based monomers, namely 1,2-bis(4'-vinyl-[1,1'-biphenyl]-4-yl)-1-phenanthro[9,10-]imidazole (DV-bPPI) and 1,2-bis(4-vinylphenyl)-1-phenanthro[9,10-]imidazole (DV-PPI), were synthesized Suzuki cross-coupling with high yield up to 85%. The synthesized monomers were characterized by multinuclear NMR, FTIR spectroscopy, and single-crystal X-ray diffraction analysis. PPI derivatives, in amounts ranging from 0.05 to 1 wt% (based on monomers), were copolymerized with methyl methacrylate, butyl acrylate, and methacrylic acid using a standard emulsion polymerization technique. The resulting coatings were fully transparent in the visible region and were characterized by UV-vis and photoluminescence measurements. Dynamic mechanical analysis demonstrated that DV-bPPI and DV-PPI, at concentrations of 0.5-1 wt% and 0.25-0.5 wt%, respectively, effectively prevented UV-induced degradation of the polymer films.
合成乳胶被广泛用作户外防护应用的粘合剂，其中紫外线（UV）防护具有很高的实际重要性。本研究报告了两种新型的、具有高光致发光性能的菲并咪唑（PPI）衍生物的合成及其作为共价连接的紫外线吸收稳定剂在基于全丙烯酸乳胶聚合物的水性光稳定涂料中的应用。通过铃木交叉偶联反应合成了乙烯基官能化的菲并咪唑基单体，即1,2-双（4'-乙烯基-[1,1'-联苯]-4-基）-1-菲并[9,10-]咪唑（DV-bPPI）和1,2-双（4-乙烯基苯基）-1-菲并[9,10-]咪唑（DV-PPI），产率高达85%。通过多核NMR、FTIR光谱和单晶X射线衍射分析对合成的单体进行了表征。使用标准乳液聚合技术，将0.05至1 wt%（基于单体）的PPI衍生物与甲基丙烯酸甲酯、丙烯酸丁酯和甲基丙烯酸共聚。所得涂层在可见光区域完全透明，并通过紫外可见光谱和光致发光测量进行了表征。动态力学分析表明，DV-bPPI和DV-PPI分别在浓度为0.5-1 wt%和0.25-0.5 wt%时，有效地防止了紫外线诱导的聚合物薄膜降解。
