(3-丙烯酰氧基)丙基(3-脱氢枞酰胺)丙基二甲基溴化铵的制备及性能

以脱氢枞酸、3-二甲氨基丙胺为原料通过酰胺化反应制备了N-(3-二甲氨基)丙基-脱氢枞酸酰胺(DHA-DA),然后再和3-溴丙醇丙烯酸酯经过季铵化反应合成了水溶性松香可聚合单体(3-丙烯酰氧基)丙基(3-脱氢枞酰胺)丙基二甲基溴化铵(DHA-DA-Br)。使用核磁共振(NMR)、红外光谱(FT-IR)、质谱(MS)等对其进行结构表征,利用差示扫描量热仪(DSC)对其聚合行为进行研究,采用表面张力仪对其表面张力(γCMC)、临界胶束浓度(CMC)进行测定。结果表明:试验成功合成了水溶性松香可聚合松香基单体DHA-DA-Br; DHA-DA-Br单体可发生自聚反应(DSC最大放热峰为131℃),在引发剂偶氮二异丁腈作用下,反应温度明显降低(DSC最大放热峰为112℃); DHA-DA-Br水溶液在25℃时CMC为0.003 2 mol/L,此时单体水溶液的γCMC值为35 mN/m。DHA-DA-Br在制备或改性水溶性聚合物领域具有较好应用前景。
Rosin, which consists primarily of 90% rosin acids and 10% neutral compounds, is one of the most important forest products in China. Rosin-based derivatives can be used as additives to lower the glass transition temperature and improve the mechanical properties of polymers such as epoxy resin, coating and polyamide. However, the synthesis of water-soluble rosin-based derivatives is rarely reported. In this study, a water-soluble rosin-based monomer was prepared and characterized. First, the N-(3-dimethylamino)propyl-dehydroabietic acid(DHA-DA)was prepared from dehydroabietic acid and 3-dimethylaminopropylamine by amidation reaction; and then the water-soluble rosin-based monomer 3-(acryloyloxy)-N-(3-(dehydroabietyl-1-carboxamido)-N,N-dimethylpropan-1-aminium bromide(DHA-DA-Br)was synthesized by 3-bromopropyl acrylate and DHA-DA via quaternization reaction. The structure of DHA-DA-Br was characterized by nuclear magnetic resonance(NMR), mass spectrometry(MS)and Fourier transform infrared spectoscopy(FT-IR). The polymerization behavior was investigated by differential scanning calorimeter(DSC). Surface tension(γCMC)and critical micelle concentration(CMC)were measured by surface tension meter. The results indicated that the water-soluble rosin-based monomer DHA-DA-Br was successfully synthesized; when used 2,2'-azobis(2-methylpropionitrile)(AIBN)as the initiator, the obtained rosin-based monomer exhibited a lower polymerization temperature(DSC exothermic peak was 112℃)than the polymerization temperature of pure water-soluble rosin-based monomer(DSC exothermic peak was 131℃)did; and the CMC values of rosin-based monomer solution was 0.003 2 mol/L at 25℃, and the γCMC was 35 mN/m. The synthesized rosin-based monomer DHA-DA-Br has a great potential for preparation or modification of water-soluble polymer