1,1'-hexamethylenebis(2-oxo-3-azepanylurea) | 503549-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 1,1'-hexamethylenebis(2-oxo-3-azepanylurea)
• 英文别名: 1-(2-Oxoazepan-3-yl)-3-[6-[(2-oxoazepan-3-yl)carbamoylamino]hexyl]urea；1-(2-oxoazepan-3-yl)-3-[6-[(2-oxoazepan-3-yl)carbamoylamino]hexyl]urea
• CAS: 503549-86-8
• 化学式: C₂₀H₃₆N₆O₄
• 分子量: 424.544
• InChiKey: SCQFGGUXLMMWOB-UHFFFAOYSA-N

物化性质

• 沸点：
  851.8±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  141
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  DL-氨基己内酰胺 、 1,6-己二异氰酸酯 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 1,1'-hexamethylenebis(2-oxo-3-azepanylurea)
  参考文献：
  名称：

  Hydrogen-bonded supramolecular polymers from derivatives of α-amino-ε-caprolactam: A bio-based material

  摘要：

  AbstractHydrogen‐bonded supramolecular polymers were prepared from the derivatives of α‐amino‐ε‐caprolactam (ACL), obtained from a renewable resource. Several self‐complimentary bis‐ or tetra‐caprolactam monomers were synthesized by varying the number of carbons of the spacer between the hydrogen‐bonding end groups. Physical properties of these hydrogen‐bonded polymers were clearly demonstrated by differential scanning colorimetry, solid‐state NMR, and X‐ray powder diffraction analyses. The supramolecular behavior was also supported by fiber formation from the melt for several of these compounds, and stable glassy materials were prepared from the physical mixtures of two different biscaprolactams. The self‐association ability of ACL was also used by incorporating ACL at the chain ends of low‐molecular weight Jeffamine (Mn = 900 g/mol) using urea and amide linkages. The transformation of this liquid oligomer at room temperature into a self‐standing, transparent film clearly showed the improvement in mechanical properties obtained by the introduction of terminal hydrogen‐bonding groups. Finally, the use of monomers with a functionality of four gave rise to network formation either alone or combination with bifunctional monomers. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

  DOI：

  10.1002/pola.24676

文献信息

• Hydrogen-bonded supramolecular polymers from derivatives of α-amino-ε-caprolactam: A bio-based material
  作者：Eylem Tarkin-Tas、Christopher A. Lange、Lon J. Mathias

  DOI：10.1002/pola.24676

  日期：2011.6.1

  AbstractHydrogen‐bonded supramolecular polymers were prepared from the derivatives of α‐amino‐ε‐caprolactam (ACL), obtained from a renewable resource. Several self‐complimentary bis‐ or tetra‐caprolactam monomers were synthesized by varying the number of carbons of the spacer between the hydrogen‐bonding end groups. Physical properties of these hydrogen‐bonded polymers were clearly demonstrated by differential scanning colorimetry, solid‐state NMR, and X‐ray powder diffraction analyses. The supramolecular behavior was also supported by fiber formation from the melt for several of these compounds, and stable glassy materials were prepared from the physical mixtures of two different biscaprolactams. The self‐association ability of ACL was also used by incorporating ACL at the chain ends of low‐molecular weight Jeffamine (Mn = 900 g/mol) using urea and amide linkages. The transformation of this liquid oligomer at room temperature into a self‐standing, transparent film clearly showed the improvement in mechanical properties obtained by the introduction of terminal hydrogen‐bonding groups. Finally, the use of monomers with a functionality of four gave rise to network formation either alone or combination with bifunctional monomers. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
• Controlled synthesis of crosslinked polyamide 6 using a bis-monomer derived from cyclized lysine
  作者：Hassen Bouchékif、Deniz Tunc、Cédric Le Coz、Alain Deffieux、Philippe Desbois、Stéphane Carlotti

  DOI：10.1016/j.polymer.2014.09.050

  日期：2014.11

  The controlled synthesis of polyamide 6 chemical networks by anionic ring-opening copolymerization of epsilon-caprolactam (CL) with synthesized bis-epsilon-caprolactam derived from alpha-amino-epsilon-caprolactam, i.e. N-functionalized alpha-amino-epsilon-caprolactam bis-monomers, using sodium epsilon-caprolactamate as an initiator and hexamethylene-1,6-dicarbamoylcaprolactam as di-functional fast activator was examined in bulk at 140 degrees C. An urea-based bis-monomer and CL were first shown to copolymerize with a decreasing polymerization rate due to side reactions. On the contrary, quantitative copolymerization of CL with various amounts of bis-N(2-oxo-3-azepanyl)-1,6-tetramethylenediamide, an amide-based bis-monomer, leads to fast kinetics similar to the homopolymerization of CL Crosslinked PA6 with network exhibiting elastic or viscoelastic behaviors, depending on the amount of crosslinker, were observed and characterized by swelling in hexafluoroisopropanol, dynamic mechanical analysis and rheology measurements. Crystallinity and swelling were shown to decrease with the increasing content of the crosslinking agent. (C) 2014 Elsevier Ltd. All rights reserved.