2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
• 英文别名: 2-(2-hydroxyethyl)-7-(hydroxymethyl)-4,7a-dihydro-3aH-4,7-epoxyisoindole-1,3-dione
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: JSNRNGPFCHLLJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 生成 N-(2-羟乙基)马来酰亚胺
  参考文献：
  名称：

  Self-Healing Polyurethanes with Shape Recovery

  摘要：

  Two new thermoresponsive self‐healing polyurethanes (1DA1T and 1.5DA1T) based on the Diels–Alder (DA) reaction between furan and maleimide moieties are developed that use the shape‐memory effect to bring crack faces into intimate contact such that healing can take place. Unlike other self‐healing polymers, these polymers do not require external forces to close cracks but rather they use the shape‐memory effect to autonomously close the crack. Both polyurethanes have a stable polymer structure and comparable mechanical properties to commercial epoxies. A differential scanning calorimeter is employed to check the glass transition temperature of the polymers as well as the DA and retro‐DA (rDA) reaction temperatures. These DA and rDA reactions are confirmed with variable‐temperature proton nuclear magnetic resonance. Healing efficiency is calculated using a measurement of the failure load from compact tension testing. The results show that the shape‐memory effect can replace external forces to close two crack surfaces and the DA reaction can be repeatedly employed to heal the cracks.

  DOI：

  10.1002/adfm.201400299
• 作为产物：
  描述：

  4-(2-羟基乙基)-10-噁-4-氮杂三环[5.2.1.02,6]-8-癸烯-3,5-二酮 以 甲苯 、 苯 为溶剂， 反应 44.0h， 生成 2-(2-hydroxyethyl)-4-(hydroxymethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
  参考文献：
  名称：

  玻璃化转变温度决定着Diels–Alder交联聚甲基丙烯酸酯网络的热解交联行为

  摘要：

  准备了一系列涵盖广泛玻璃化转变温度（T g）的Diels–Alder（DA）交联聚甲基丙烯酸酯网络，以建立T g与这些网络的热解交联行为之间的关系。还准备了一系列永久交联和未交联的类似物，以更好地理解在高温下DA网络中发生的热固性向热塑性转变。使用动态力学分析研究了网络序列，建立了T g与T g之间的反比关系。和去交联能力。差示扫描量热法证实了所有配方中DA键的可行性，并且用9-蒽甲醇进行的捕集实验表明，即使是反应最差的网络，只要进行适当的热处理，也能够进行去交联。尽管长期以来人们一直将聚合物链的移动性视为可修复材料的关键因素，但这项工作验证了该参数在DA网络脱交联中的重要性。©2019 Wiley Periodicals，Inc.J.Polym。科学 2020，58，193-203

  DOI：

  10.1002/pola.29524

文献信息

• 二官能度丙烯酸酯类交联剂及其在3D打印中 的应用
  申请人：杭州龙勤新材料科技有限公司

  公开号：CN105294936B

  公开（公告）日：2017-07-18

  本发明涉及光固化3D打印快速成型制备高分子材料领域，旨在提供一种二官能度丙烯酸酯类交联剂及其在3D打印中的应用。其制备步骤包括：在氮气保护下，将糠醇、N‑羟烷基马来酰亚胺和溶剂反应后，抽滤、洗涤、真空干燥，得到双端羟基Diels‑Alder加成物；将加成物溶于溶剂中，加入吡啶类催化剂和酸酐反应后，加入甲醇继续反应，二氯甲烷溶解产物后洗涤、收集有机相得到最终产物。本发明初始原料来源广泛，制备过程以及纯化简单，适合工业化生产过程；产物具有通用性，制备的乙烯基聚合物在常温下具有热固性材料的优异机械力学性能和耐溶剂性能，在高温下又具有热塑性塑料的可再回收加工特性；满足了制品的使用性能，是3D打印材料制备技术的重要突破。
• Thermodynamic and Kinetic Study of Diels–Alder Reaction between Furfuryl Alcohol and N-Hydroxymaleimides—An Assessment for Materials Application
  作者：Jamerson Carneiro de Oliveira、Marie-Pierre Laborie、Vincent Roucoules

  DOI：10.3390/molecules25020243

  日期：——

  The study of Diels-Alder reactions in materials science is of increasing interest. The main reason for that is the potential thermoreversibility of the reaction. Aiming to predict the behavior of a material modified with maleimido and furyl moieties, 1H NMR and UV-Vis solution studies of the Diels-Alder reaction between furfuryl alcohol and two N-hydroxymaleimides are explored in the present study. Rate

  在材料科学中对Diels-Alder反应的研究越来越受到关注。其主要原因是反应的潜在热可逆性。为了预测用马来酰亚胺基和呋喃基部分改性的材料的行为，在本研究中探索了糠醇与两种N-羟基马来酰亚胺之间的Diels-Alder反应的1H NMR和UV-Vis溶液研究。速率常数，活化能，熵和形成焓由两种反应体系的每种技术确定。内消旋异构体和外消旋异构体在1H NMR中有所区别，并且在研究的温度范围内可以观察到从动力学的受控Diels-Alder反应到热力学的转变。讨论了其对材料中应用的影响。选择的方法将Diels-Alder反应的简化平衡视为动力学模型，从而使材料科学家能够评估使用反应分子创建热响应性材料的适用性。所提出的方法确定了动力学常数，而没有平衡常数值的直接影响，从而允许进行更客观的数据分析。讨论了动力学模型选择，分析方法和数据处理的影响。从而可以进行更客观的数据分析。讨论了动力学模型选择，
• Highly stretchable, tough, healable and mechanoresponsive polyurethane elastomers for flexible capacitor applications
  作者：Amir Khan、Chuan-Fu Wang、Ravinder Reddy Kisannagar、Wei-Tsung Chuang、Pham Quoc Nhien、Sadiq Mahmood、Monica Katiyar、Dipti Gupta、Kung-Hwa Wei、Hong-Cheu Lin

  DOI：10.1039/d2ta06541j

  日期：——

  Mechanochromic, tough and healable polyurethane films are synthesized and their properties are thoroughly characterized. The optimum films are utilized to explore the potential applications of shape memory and flexible capacitor devices.

  我们合成了机械变色、坚韧和可愈合的聚氨酯薄膜，并对其特性进行了深入研究。最佳薄膜可用于探索形状记忆和柔性电容器设备的潜在应用。
• Shape-memory-self-healing polymers (SMSHPS)
  申请人：University of Florida Research Foundation, Inc.

  公开号：US10202484B2

  公开（公告）日：2019-02-12

  A shape-memory self-healing polymeric network (SMSHP) is useful as a molded part, a coating, or as a matrix for a composite that can be repaired by heating to a controlled temperature. The SMSHP has thermally reversible repeating units where a thermally reversible adduct is situated between two common linking units formed during a polymerization process between thermally reversible monomers and cross-linking monomers. Optionally, other repeating units can be present from other monomers. Shape-memory results when the SMSHP is warmed to a temperature in excess of its glass transition temperature and self-healing then proceeds when a higher temperature is achieved where thermally reversible adducts dissociates to complementary groups that subsequently reform the adduct without distortion of the memorized shape. The thermally reversible adducts can be Diels-Alder (DA) adducts in a polyurethane, poly urea, or amine epoxy SMSHP network.

  形状记忆自修复聚合物网络（SMSHP）可用作模制件、涂层或复合材料的基体，通过加热至可控温度进行修复。SMSHP 具有热可逆重复单元，其中热可逆加合物位于热可逆单体和交联单体聚合过程中形成的两个共同连接单元之间。此外，其他单体也可能含有其他重复单元。当 SMSHP 升温至超过其玻璃化转变温度时，会产生形状记忆；当温度升高时，热可逆加成物会解离成互补基团，随后对加成物进行重整，而不会扭曲已记忆的形状。热可逆加合物可以是聚氨酯、聚脲或胺环氧 SMSHP 网络中的 Diels-Alder (DA) 加合物。
• Lubricant and Functional Fluid Compositions Containing Viscosity Index Improver
  申请人：Price David

  公开号：US20140031269A1

  公开（公告）日：2014-01-30

  The disclosed invention relates to lubricant or functional fluid compositions containing viscosity index improvers in the form of self-healing polymers. The polymers may comprise one or more cleavable linkages, such as one or more disulfide bonds and/or one or more diene/dienophile linkages, to permit the polymer to reform if cleaved during use.