双亲羟烷胺基-1,3,5-三嗪的合成与表征Synthesis and Characterization of Amphiphilic Multi-hydroxyalkyl Amine-1,3,5-triazine
陈荣国;孟东伟;肖荔人;李丹;姜明;钱庆荣;陈庆华;
摘要(Abstract):
以三聚氯氰(CYC)、二乙醇胺(DEA)和伯胺为反应剂,分步考察碱催化剂、反应时间等对胺亲核取代嗪氯反应结果的影响,并在此基础上合成了一系列的多元羟烷胺基-1,3,5-三嗪(3a,3b,3c),其结构均经元素分析、FTIR、1H NMR和ESI-MS表征。结果表明,CYC第一、二、三氯的取代反应,宜分别选二乙醇胺、三乙胺和碳酸氢钠作碱催化剂,并依次在-15℃、455℃、4550℃和8550℃和8590℃下反应2 h、7 h和16 h;所得多元羟烷胺基-1,3,5-三嗪具有双亲性.
关键词(KeyWords): 双亲;羟烷胺基-1,3,5-三嗪;亲核取代;合成
基金项目(Foundation): 福建省教育厅科技计划项目(JA12236);; 福建省自然科学基金资助项目(2011J01287)
作者(Authors): 陈荣国;孟东伟;肖荔人;李丹;姜明;钱庆荣;陈庆华;
参考文献(References):
- [1]MENICAGLI R,SAMARITANI S,SIGNORE G,et al.In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines:new molecules in anticancer research[J].Journal of Medicinal Chemistry,2004,47(19):4649-4652.
- [2]BANSAL K K,KAKDE D,GUPTA U,et al.Development and characterization of triazine based dendrimers for delivery of antitumor agent[J].Journal of Nanoscience and Nanotechnology,2010,10(12):8395-8404.
- [3]ADELI M,ZARNEGAR Z,KABIRI R.Dendritic macromolecules containing several types of functional groups[J].Journal of Applied Polymer Science,2010,115(1):9-14.
- [4]NAMAZI H,ADELI M.Synthesis of barbell-like triblock copolymers,dendritic triazine-block-poly(ethylene glycol)–block-dendritic triazine and investigation of their solution behaviors[J].Polymer,2005,46(24):10788-10799.
- [5]LI B,XU M.Effect of a novel charring-foaming agent on flame retardancy and thermal degradation of intumescent flame retardant polypropylene[J].Polymer Degradation and Stability,2006,91(6):1380-1386.
- [6]YANG H,YANG C Q,HE Q L.The bonding of a hydroxy-functional organophosphorus oligomer to nylon fabric using the formaldehyde derivatives of urea and melamine as the bonding agents[J].Polymer Degradation and Stability,2009,94(6):1023-1031.
- [7]DULIBAN J.Amine Modifiers with an s-triazine ring for unsaturated polyester resins,1[J].Macromolecular Materials and Engineering,2006,291(2):137-147.
- [8]陈荣国,姜明,陈庆华,等.一种6-(N,N-二羟乙基)胺基-2,4-二氯–1,3,5-三嗪制备方法[P].中国,201210223760.X,2012.
- [9]SAMARITANI S,PELUSO P,MALANGA C,et al.Selective amination of cyanuric chloride in the presence of 18-crown-6[J].European Journal of Organic Chemistry,2002(9):1551-1555.
- [10]陈庆华,陈荣国,姜明,等.一种2,4,6-三(N,N-二羟乙基)胺基-1,3,5-三嗪制备方法[P].中国,201210226879.2,2012.
- [11]陈荣国,肖荔人,姜明,等.6-(N,N-二羟乙基)胺基-2,4-二氯–1,3,5-三嗪的合成[J].福建师范大学学报(自然科学版),2015,31(2):49-52.
- [12]SAITO K,NISHIMUR N,SASAKI S,et al.Synthesis of polyguanamines from 2-N,N-dibutylamino-4,6-dichloro-1,3,5-triazine with aromatic diamines[J].Reactive&Functional Polymers,2013,73(5):756-763.
- [13]LEI H T,SHEN Y D,SONG L J,et al.Hapten synthesis and antibody production for the development of a melamine immunoassay[J].Analytica Chimica Acta,2010,665(1):84-90.
- [14]GRZEGORZ B.Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis[J].Tetrahedron,2006,62(41):9507-9522.
- [15]YAN Z,XUE W L,ZENG Z X,et al.Kinetics of cyanuric chloride hydrolysis in aqueous solution[J].Industrial&Engineering Chemistry Research,2008,47(15):5318-5322.
- [16]HUANG Z,SHI W.Synthesis and properties of a novel hyperbranched polyphosphate acrylate applied to UV curable flame retardant coatings[J].European Polymer Journal,2007,43(4):1302-1312.
- [17]ZHANG P,SONG L,LU H,et al.Synergistic effect of nanoflaky manganese phosphate on thermal degradation and flame retardant properties of intumescent flame retardant polypropylene system[J].Polymer Degradation and Stability,2009,94(2):201-207.
- [18]梁晓天.核磁共振:高分辨氢谱的解析和应用[M].北京:科学出版社,1976:242-251.
- [19]GOTTLIEB H E,KOTLYAR V,NUDELMAN A.NMR chemical shifts of common laboratory solvents as trace impurities[J].Journal of Organic Chemistry,1997,62(21):7512-7515.