由完全生物基双吡咯烷酮单体制成的高结晶性、耐热性和可生物降解的共聚聚酯

IF 5.4 1区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY GIANT Pub Date : 2024-04-29 DOI:10.1016/j.giant.2024.100276
Hanxu Zhu , Han Hu , Qingyang Luan , Chen Lin , Juanfang Xu , Jinggang Wang , Wu Bin Ying , Jin Zhu
{"title":"由完全生物基双吡咯烷酮单体制成的高结晶性、耐热性和可生物降解的共聚聚酯","authors":"Hanxu Zhu ,&nbsp;Han Hu ,&nbsp;Qingyang Luan ,&nbsp;Chen Lin ,&nbsp;Juanfang Xu ,&nbsp;Jinggang Wang ,&nbsp;Wu Bin Ying ,&nbsp;Jin Zhu","doi":"10.1016/j.giant.2024.100276","DOIUrl":null,"url":null,"abstract":"<div><p>Improving the heat resistance of bio-based and biodegradable polyesters is of great significance to extend their applications. Herein, N,N’-trans-1,4-cyclohexane-bis(pyrrolidone-4-methyl carboxylate) (T-CBPMC) was prepared through efficient Michael-addition reaction between dimethyl itaconate and trans-1,4-cyclohexanediamine. The obtained T-CBPMC was copolymerized into aliphatic poly(butylene succinate) (PBS), and a series of PBSPs copolymers with T-CBPMC (BP) molar percentages between 41−80 mol % and weight average molecular weight (<em>M<sub>w</sub></em>) values ranging between 5.77*10<sup>4</sup> and 6.67*10<sup>4</sup> g/mol were prepared. BP units efficiently facilitated the melting temperature (203-251 °C) and isothermal-crystallization rate (t<sub>1/2</sub> &lt; 20 s) of PBSPs, endowing the highest heat resistance among commercial biodegradable polyesters, which helps maintain stable in pasteurization, high-temperature disinfection, and microwave environments. Moreover, these copolymers displayed remarkable mechanical, gas barrier properties and degradability. PBSP40-PBSP60 obtained high elastic modulus (335–872 MPa) and tensile strength (24.7–31.5 MPa), and good toughness simultaneously. Multiple-ring structures and large steric hindrance of BP units resulted in superior O<sub>2</sub> barrier performance than that of non-degradable PET films. Importantly, the PBSP copolyesters showed obvious degradation in water environments and relatively better enzymatic degradation. It was interesting to find that even with 70 % of the BP units, the PBSP copolyesters still retained hydrolysis ability. The resulting PBSP copolyesters open the way for alternative candidates of biodegradable packaging materials with rapid crystallization, high heat-resistance and gas barrier.</p></div>","PeriodicalId":34151,"journal":{"name":"GIANT","volume":null,"pages":null},"PeriodicalIF":5.4000,"publicationDate":"2024-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666542524000419/pdfft?md5=d9808b7b5ce1ac0abad9a74a0e77ee7c&pid=1-s2.0-S2666542524000419-main.pdf","citationCount":"0","resultStr":"{\"title\":\"Highly crystalline, heat resistant and biodegradable copolyesters from fully bio-based bis(pyrrolidone) monomer\",\"authors\":\"Hanxu Zhu ,&nbsp;Han Hu ,&nbsp;Qingyang Luan ,&nbsp;Chen Lin ,&nbsp;Juanfang Xu ,&nbsp;Jinggang Wang ,&nbsp;Wu Bin Ying ,&nbsp;Jin Zhu\",\"doi\":\"10.1016/j.giant.2024.100276\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Improving the heat resistance of bio-based and biodegradable polyesters is of great significance to extend their applications. Herein, N,N’-trans-1,4-cyclohexane-bis(pyrrolidone-4-methyl carboxylate) (T-CBPMC) was prepared through efficient Michael-addition reaction between dimethyl itaconate and trans-1,4-cyclohexanediamine. The obtained T-CBPMC was copolymerized into aliphatic poly(butylene succinate) (PBS), and a series of PBSPs copolymers with T-CBPMC (BP) molar percentages between 41−80 mol % and weight average molecular weight (<em>M<sub>w</sub></em>) values ranging between 5.77*10<sup>4</sup> and 6.67*10<sup>4</sup> g/mol were prepared. BP units efficiently facilitated the melting temperature (203-251 °C) and isothermal-crystallization rate (t<sub>1/2</sub> &lt; 20 s) of PBSPs, endowing the highest heat resistance among commercial biodegradable polyesters, which helps maintain stable in pasteurization, high-temperature disinfection, and microwave environments. Moreover, these copolymers displayed remarkable mechanical, gas barrier properties and degradability. PBSP40-PBSP60 obtained high elastic modulus (335–872 MPa) and tensile strength (24.7–31.5 MPa), and good toughness simultaneously. Multiple-ring structures and large steric hindrance of BP units resulted in superior O<sub>2</sub> barrier performance than that of non-degradable PET films. Importantly, the PBSP copolyesters showed obvious degradation in water environments and relatively better enzymatic degradation. It was interesting to find that even with 70 % of the BP units, the PBSP copolyesters still retained hydrolysis ability. The resulting PBSP copolyesters open the way for alternative candidates of biodegradable packaging materials with rapid crystallization, high heat-resistance and gas barrier.</p></div>\",\"PeriodicalId\":34151,\"journal\":{\"name\":\"GIANT\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":5.4000,\"publicationDate\":\"2024-04-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S2666542524000419/pdfft?md5=d9808b7b5ce1ac0abad9a74a0e77ee7c&pid=1-s2.0-S2666542524000419-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"GIANT\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666542524000419\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"GIANT","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666542524000419","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

提高生物基和生物可降解聚酯的耐热性对扩大其应用范围具有重要意义。本文通过伊塔康酸二甲酯和反式-1,4-环己烷二胺之间的高效迈克尔加成反应,制备了N,N'-反式-1,4-环己烷-双(吡咯烷酮-4-甲基羧酸酯)(T-CBPMC)。将得到的 T-CBPMC 与脂肪族聚丁二酸丁二醇酯(PBS)共聚,制备出一系列 T-CBPMC 摩尔百分比(BP)介于 41-80 mol % 之间、重量平均分子量(Mw)介于 5.77*104 和 6.67*104 g/mol 之间的 PBSPs 共聚物。BP 单元有效地提高了 PBSP 的熔融温度(203-251 °C)和等温结晶速率(t1/2 < 20 s),在商用生物降解聚酯中具有最高的耐热性,有助于在巴氏杀菌、高温消毒和微波环境中保持稳定。此外,这些共聚物还具有显著的机械、气体阻隔性能和降解性。PBSP40-PBSP60 同时获得了较高的弹性模量(335-872 兆帕)和拉伸强度(24.7-31.5 兆帕)以及良好的韧性。与不可降解的 PET 薄膜相比,BP 单元的多环结构和较大的立体阻碍使其具有更优越的氧气阻隔性能。重要的是,PBSP 共聚多酯在水环境中降解明显,酶降解效果相对较好。有趣的是,即使添加了 70% 的 BP 单元,PBSP 共聚多酯仍能保持水解能力。由此产生的 PBSP 共聚多酯为替代具有快速结晶、高耐热性和气体阻隔性的可生物降解包装材料开辟了道路。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Highly crystalline, heat resistant and biodegradable copolyesters from fully bio-based bis(pyrrolidone) monomer

Improving the heat resistance of bio-based and biodegradable polyesters is of great significance to extend their applications. Herein, N,N’-trans-1,4-cyclohexane-bis(pyrrolidone-4-methyl carboxylate) (T-CBPMC) was prepared through efficient Michael-addition reaction between dimethyl itaconate and trans-1,4-cyclohexanediamine. The obtained T-CBPMC was copolymerized into aliphatic poly(butylene succinate) (PBS), and a series of PBSPs copolymers with T-CBPMC (BP) molar percentages between 41−80 mol % and weight average molecular weight (Mw) values ranging between 5.77*104 and 6.67*104 g/mol were prepared. BP units efficiently facilitated the melting temperature (203-251 °C) and isothermal-crystallization rate (t1/2 < 20 s) of PBSPs, endowing the highest heat resistance among commercial biodegradable polyesters, which helps maintain stable in pasteurization, high-temperature disinfection, and microwave environments. Moreover, these copolymers displayed remarkable mechanical, gas barrier properties and degradability. PBSP40-PBSP60 obtained high elastic modulus (335–872 MPa) and tensile strength (24.7–31.5 MPa), and good toughness simultaneously. Multiple-ring structures and large steric hindrance of BP units resulted in superior O2 barrier performance than that of non-degradable PET films. Importantly, the PBSP copolyesters showed obvious degradation in water environments and relatively better enzymatic degradation. It was interesting to find that even with 70 % of the BP units, the PBSP copolyesters still retained hydrolysis ability. The resulting PBSP copolyesters open the way for alternative candidates of biodegradable packaging materials with rapid crystallization, high heat-resistance and gas barrier.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
GIANT
GIANT Multiple-
CiteScore
8.50
自引率
8.60%
发文量
46
审稿时长
42 days
期刊介绍: Giant is an interdisciplinary title focusing on fundamental and applied macromolecular science spanning all chemistry, physics, biology, and materials aspects of the field in the broadest sense. Key areas covered include macromolecular chemistry, supramolecular assembly, multiscale and multifunctional materials, organic-inorganic hybrid materials, biophysics, biomimetics and surface science. Core topics range from developments in synthesis, characterisation and assembly towards creating uniformly sized precision macromolecules with tailored properties, to the design and assembly of nanostructured materials in multiple dimensions, and further to the study of smart or living designer materials with tuneable multiscale properties.
期刊最新文献
Small dop of comonomer, giant shift of dynamics: α-methyl-regulated viscoelasticity of poly(methacrylamide) hydrogels The effect of dynamic cross-links and mesogenic groups on the swelling and collapse of polymer gels Binary blends of poly(lactic acid) and poly(methyl methacrylate) for high energy density and charge/discharge efficiency capacitors Systematic anode engineering enabling universal efficiency improvements in organic solar cells Thermal response color-tunable electroluminescent device for real-time visual temperature monitoring
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1