An atom economy polyamide elastomer derived from polyether amine‐based bis‐acrylamide and dithiol monomer and synthesized by thiol‐Michael addition click reaction

IF 3.2 4区 工程技术 Q2 ENGINEERING, CHEMICAL
Jun Zhu, Shi‐hu Zhu, Ai‐ling Sun, Chun Chang, Liu‐he Wei, Yu‐han Li
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引用次数: 0

Abstract

Traditional polyamide elastomer synthesis via polycondensation of diamines and dicarboxylic acids involves high energy use and by‐product mass loss. Here, we present a novel method using thiol‐Michael addition click chemistry to produce these elastomers under mild conditions, marking the first use of this strategy. The polymerization involves coupling bis‐acrylamide (BAA) with 3,6‐dioxa‐1,8‐octanedithiol (DODT), catalyzed by 1,5‐diazabicyclo[4.3.0]non‐5‐ene (DBN). BAA is synthesized from polyetheramine and acryloyl chloride, creating a compound with amide groups and carbon double bonds at chain ends. These double bonds' electron‐withdrawing effect facilitates the click reaction efficiently, avoiding high energy and mass loss. The resulting polymers have a molecular weight of approximately 10,000 g/mol, verified by 1H NMR and FTIR spectroscopy, which show amide group presence. SAXS and AFM confirm nanophase separation of these groups. Tensile strength ranges from 0.235 to 0.542 MPa, decreasing with lower polyetheramine content but still showing notable elasticity. This method's low energy use, no mass loss, and good mechanical properties make it promising for developing high‐performance polyamide plastics and elastomers, appealing to researchers in both academia and industry.Highlights High elasticity, softness, and high tensile polyamide elastomer. Thiol‐Michael addition click reaction conforms to atomic economy. Long molecular chain contains extraordinary evolution of hydrogen bonding.
由聚醚胺基双丙烯酰胺和二硫醇单体通过硫醇-迈克尔加成点击反应合成的原子经济性聚酰胺弹性体
通过二胺和二羧酸缩聚合成聚酰胺弹性体的传统方法能耗高、副产品质量损失大。在这里,我们提出了一种利用硫醇-迈克尔加成点击化学在温和条件下生产此类弹性体的新方法,标志着这一策略的首次应用。聚合过程涉及双丙烯酰胺(BAA)与 3,6-二氧杂-1,8-辛二硫醇(DODT)的偶联,并由 1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)催化。BAA 由聚醚胺和丙烯酰氯合成,形成一种在链端具有酰胺基团和碳双键的化合物。这些双键的抽电子效应可有效促进点击反应,避免高能量和质量损失。经 1H NMR 和傅立叶变换红外光谱验证,所得聚合物的分子量约为 10,000 g/mol,显示出酰胺基团的存在。SAXS 和原子力显微镜证实了这些基团的纳米相分离。拉伸强度在 0.235 至 0.542 兆帕之间,随着聚醚胺含量的降低而降低,但仍显示出显著的弹性。这种方法能耗低、无质量损失、机械性能好,因此很有希望开发出高性能聚酰胺塑料和弹性体,对学术界和工业界的研究人员都很有吸引力。巯基-迈克尔加成点击反应符合原子经济性。长分子链包含非凡的氢键演化。
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来源期刊
Polymer Engineering and Science
Polymer Engineering and Science 工程技术-高分子科学
CiteScore
5.40
自引率
18.80%
发文量
329
审稿时长
3.7 months
期刊介绍: For more than 30 years, Polymer Engineering & Science has been one of the most highly regarded journals in the field, serving as a forum for authors of treatises on the cutting edge of polymer science and technology. The importance of PE&S is underscored by the frequent rate at which its articles are cited, especially by other publications - literally thousand of times a year. Engineers, researchers, technicians, and academicians worldwide are looking to PE&S for the valuable information they need. There are special issues compiled by distinguished guest editors. These contain proceedings of symposia on such diverse topics as polyblends, mechanics of plastics and polymer welding.
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