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Novel poly(azomethine-urethane)s and their polyphenol derivatives derived from aliphatic diisocyanate compound: Synthesis and thermal characterization

机译:脂肪族二异氰酸酯化合物衍生的新型聚(甲亚胺-氨基甲酸酯)及其多酚衍生物:合成与热表征

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Until now, only a few kinds of poly(azomethine-urethane)s (PAMUs) including aromatic hydroxy benzaldehyde and aminophenol compounds were obtained and studied with thermal degradation steps. However, oligo/polyphenol-based PAMUs have not been synthesized yet. In this study, some kinds of this class of PAMUs were synthesized in three steps. At the first step polyurethane (PU) was synthesized by the copolymerization reaction of 2,4-dihydroxybenzaldehyde with hexamethylene diisocyanate (HDI) under argon atmosphere. At the second step, the poly(azomethine-urethane)s (PAMUs) were obtained by graft copolymerization of the preformed PU with aminophenols (2-aminophenol, 3-aminophenol, and 4-aminophenol). At the last step the obtained PAMUs were converted to the polyphenol derivatives via oxidative polycondensation reaction (OP). The structures of the obtained compounds were confirmed by FTIR, UV-vis, ~1H-NMR, and ~(13)C-NMR techniques. The number-average molecular weight (M _n), weight average molecular weight (M _w) and polydispersity index (PDI) values of the synthesized compounds were determined by the size exclusion chromatography (SEC). The synthesized compounds were also characterized by solubility tests, TG-DTA, and DSC. Fluorescence measurements were carried out in various concentrated DMF solutions to determine the optimum concentrations to obtain the maximal PL intensities.
机译:迄今为止,仅获得了几种包括芳族羟基苯甲醛和氨基酚化合物在内的聚(偶氮甲碱-氨基甲酸酯)(PAMU),并进行了热降解步骤的研究。然而,尚未合成基于寡聚/多酚的PAMU。在这项研究中,通过三个步骤合成了这类PAMU。第一步,在氩气气氛下,通过2,4-二羟基苯甲醛与六亚甲基二异氰酸酯(HDI)的共聚反应合成聚氨酯(PU)。在第二步骤中,通过将预先形成的PU与氨基酚(2-氨基酚,3-氨基酚和4-氨基酚)进行接枝共聚,获得聚(甲亚胺基氨基甲酸酯)(PAMU)。在最后一步,通过氧化缩聚反应(OP)将获得的PAMUs转化为多酚衍生物。所得化合物的结构通过FTIR,UV-vis,〜1H-NMR和〜(13)C-NMR技术确认。通过尺寸排阻色谱法(SEC)确定合成化合物的数均分子量(M_n),重均分子量(M_w)和多分散指数(PDI)值。还通过溶解度测试,TG-DTA和DSC对合成的化合物进行了表征。在各种浓缩的DMF溶液中进行荧光测量,以确定获得最大PL强度的最佳浓度。

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