Jun Zhu, Shi‐hu Zhu, Ai‐ling Sun, Chun Chang, Liu‐he Wei, Yu‐han Li
{"title":"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","authors":"Jun Zhu, Shi‐hu Zhu, Ai‐ling Sun, Chun Chang, Liu‐he Wei, Yu‐han Li","doi":"10.1002/pen.26872","DOIUrl":null,"url":null,"abstract":"<jats:label/>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 <jats:sup>1</jats:sup>H 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<jats:list list-type=\"bullet\"> <jats:list-item>High elasticity, softness, and high tensile polyamide elastomer.</jats:list-item> <jats:list-item>Thiol‐Michael addition click reaction conforms to atomic economy.</jats:list-item> <jats:list-item>Long molecular chain contains extraordinary evolution of hydrogen bonding.</jats:list-item> </jats:list>","PeriodicalId":20281,"journal":{"name":"Polymer Engineering and Science","volume":"93 1","pages":""},"PeriodicalIF":3.2000,"publicationDate":"2024-07-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An atom economy polyamide elastomer derived from polyether amine‐based bis‐acrylamide and dithiol monomer and synthesized by thiol‐Michael addition click reaction\",\"authors\":\"Jun Zhu, Shi‐hu Zhu, Ai‐ling Sun, Chun Chang, Liu‐he Wei, Yu‐han Li\",\"doi\":\"10.1002/pen.26872\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<jats:label/>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 <jats:sup>1</jats:sup>H 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<jats:list list-type=\\\"bullet\\\"> <jats:list-item>High elasticity, softness, and high tensile polyamide elastomer.</jats:list-item> <jats:list-item>Thiol‐Michael addition click reaction conforms to atomic economy.</jats:list-item> <jats:list-item>Long molecular chain contains extraordinary evolution of hydrogen bonding.</jats:list-item> </jats:list>\",\"PeriodicalId\":20281,\"journal\":{\"name\":\"Polymer Engineering and Science\",\"volume\":\"93 1\",\"pages\":\"\"},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-07-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Polymer Engineering and Science\",\"FirstCategoryId\":\"5\",\"ListUrlMain\":\"https://doi.org/10.1002/pen.26872\",\"RegionNum\":4,\"RegionCategory\":\"工程技术\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"ENGINEERING, CHEMICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Polymer Engineering and Science","FirstCategoryId":"5","ListUrlMain":"https://doi.org/10.1002/pen.26872","RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"ENGINEERING, CHEMICAL","Score":null,"Total":0}
An atom economy polyamide elastomer derived from polyether amine‐based bis‐acrylamide and dithiol monomer and synthesized by thiol‐Michael addition click reaction
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.HighlightsHigh 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.
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.