N,N,N',N'-tetrapropargyl-2,2'-(ethylenedioxy)bis(ethylamine) | 1382353-49-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N,N',N'-tetrapropargyl-2,2'-(ethylenedioxy)bis(ethylamine)
• 英文别名: N-[2-[2-[2-[bis(prop-2-ynyl)amino]ethoxy]ethoxy]ethyl]-N-prop-2-ynylprop-2-yn-1-amine
• CAS: 1382353-49-2
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: QUWROMWZUZVROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 、 3-溴丙炔 在 四丁基溴化铵 、 水 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 以67%的产率得到N,N,N',N'-tetrapropargyl-2,2'-(ethylenedioxy)bis(ethylamine)
  参考文献：
  名称：

  Development of a triazole-cure resin system for composites: Evaluation of alkyne curatives

  摘要：

  We are developing a resin system that cures via triazole ring formation (cycloaddition reaction of azides with terminal alkynes) instead of the traditional oxirane/amine reaction. The high exothermicity of the azido/alkyne reaction is expected to yield higher extents of reaction under ambient-cure conditions, making the resin system potentially suitable for "out-of-autoclave" curing processes. The difunctional azide-terminated resin, di(3-azido-2-hydroxypropyl) ether of bisphenol-A, was selected as the baseline diazide. A number of alkyne crosslinkers were synthesized and characterized, including propiolate esters of di- and trifunctional alcohols, propargyl esters of di- and trifunctional carboxylic acids, propargyl ethers of di- and trifunctional alcohols, and N,N,N',N'-tetrapropargyl derivatives of primary diamines. Commercially available tripropargyl amine was also studied. Those systems employing a propiolate-based alkyne were found to be much more reactive toward the Huisgen 1,3-dipolar cycloaddition than the propargyl species. Curing energetics as a function of alkyne type, investigated through a dynamic differential scanning calorimetry approach, showed a distinct divide between the averaged activation energies of the propiolate and propargyl-type crosslinkers, 69.2-73.6 kJ/mol versus 82.3-86.4 kJ/mol, respectively. Cured network properties were readily manipulated through the incorporation of varying amounts of diversus tri- and tetra-functional alkynes or through incorporation of soft alkylene and alkyleneoxy versus rigid aromatic polyalkynes. As expected, mechanical properties, e.g., the temperature of the tan delta peak in dynamic mechanical analysis, were found to increase with increasing crosslink density. These results have allowed us to select the most promising systems for scale-up and fabrication of samples of both pure resin and composites for traditional mechanical property testing, which will be reported in a subsequent paper. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.04.002