Decyl butylcarbamate | 92411-95-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Decyl butylcarbamate
• 英文别名: decyl N-butylcarbamate
• CAS: 92411-95-5
• 化学式: C₁₅H₃₁NO₂
• 分子量: 257.417
• InChiKey: VOBKRDGNOKHRIF-UHFFFAOYSA-N

物化性质

• 沸点：
  305.4±10.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)
• 保留指数：
  2026

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  癸醇 、 异氰酸正丁酯 在 stannous octoate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以67%的产率得到Decyl butylcarbamate
  参考文献：
  名称：

  Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers

  摘要：

  Vitrimers are polymer networks whose cross-links undergo associative exchange processes at elevated temperature, usually in the presence of an embedded catalyst. This design feature enables the reshaping of materials with mechanical properties similar to thermoset resins. Here we report a new class of vitrimers consisting of polyhydroxyurethanes (PHUs) derived from six-membered cyclic carbonates and amines. PHU networks relax stress and may be reprocessed at elevated temperature and pressure in the absence of an external catalyst. The as-synthesized networks exhibit tensile properties comparable to those of leading thermosets and recover ca. 75% of their as-synthesized values following reprocessing. Stress relaxation occurs through an associative process involving nudeophilic addition of free hydroxyl groups to the carbamate linkages and exhibits an Arrhenius activation energy of 111 +/- 10 kJ/mol, which is lower than that observed for molecular model compounds (148 +/- 7 kJ/mol). These findings suggest that transcarbamoylation is activated by mechanical stress, which we attribute, on the basis of DFT calculations, to the twisting of N lone pairs out of conjugation with the carbonyl pi orbitals. PHU vitrimers are a promising new class of repairable networks because of their outstanding mechanical properties, avoidance of toxic isocyanate monomers, and catalyst-free repair processes.

  DOI：

  10.1021/jacs.5b08084

文献信息

• Thermoset Shape-Memory Polyurethane with Intrinsic Plasticity Enabled by Transcarbamoylation
  作者：Ning Zheng、Zizheng Fang、Weike Zou、Qian Zhao、Tao Xie

  DOI：10.1002/anie.201602847

  日期：2016.9.12

  classical thermoset shape‐memory polyurethane is readily capable of permanent reshaping (plasticity) after a topological network rearrangement that is induced by transcarbamoylation. By employing the Jianzhi technique (also known as kirigami), unexpected shape‐shifting versatility was observed for this otherwise classical material. As the essential carbamate moiety in polyurethanes is one of the most common

  热固性聚合物以其优异的热机械性能而闻名，但化学交联通常会导致难处理性。这反映在热固性和热塑性形状记忆聚合物之间的巨大差异。前者具有强大的形状记忆能力，但无法重新定义永久形状。与目前的知识相反，我们在这里揭示了经典的热固性形状记忆聚氨酯在通过转氨甲酰化反应引起的拓扑网络重排后，很容易永久变形（可塑性）。通过使用Jianzhi技术（也称为kirigami），对于这种原本经典的材料，观察到了意想不到的形状转换多功能性。由于聚氨酯中必需的氨基甲酸酯部分是最常见的聚合物构建单元之一，
• US4464390A
  申请人：——

  公开号：US4464390A

  公开（公告）日：1984-08-07
• Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers
  作者：David J. Fortman、Jacob P. Brutman、Christopher J. Cramer、Marc A. Hillmyer、William R. Dichtel

  DOI：10.1021/jacs.5b08084

  日期：2015.11.11

  Vitrimers are polymer networks whose cross-links undergo associative exchange processes at elevated temperature, usually in the presence of an embedded catalyst. This design feature enables the reshaping of materials with mechanical properties similar to thermoset resins. Here we report a new class of vitrimers consisting of polyhydroxyurethanes (PHUs) derived from six-membered cyclic carbonates and amines. PHU networks relax stress and may be reprocessed at elevated temperature and pressure in the absence of an external catalyst. The as-synthesized networks exhibit tensile properties comparable to those of leading thermosets and recover ca. 75% of their as-synthesized values following reprocessing. Stress relaxation occurs through an associative process involving nudeophilic addition of free hydroxyl groups to the carbamate linkages and exhibits an Arrhenius activation energy of 111 +/- 10 kJ/mol, which is lower than that observed for molecular model compounds (148 +/- 7 kJ/mol). These findings suggest that transcarbamoylation is activated by mechanical stress, which we attribute, on the basis of DFT calculations, to the twisting of N lone pairs out of conjugation with the carbonyl pi orbitals. PHU vitrimers are a promising new class of repairable networks because of their outstanding mechanical properties, avoidance of toxic isocyanate monomers, and catalyst-free repair processes.