Eco-friendly Development of New Biodegradable and Renewable Polymers Based on Di(meth)Acrylated and Acrylamidated Monomers Derived from Limonene Dioxide

IF 4.7 3区 工程技术 Q2 ENGINEERING, ENVIRONMENTAL Journal of Polymers and the Environment Pub Date : 2024-09-19 DOI:10.1007/s10924-024-03406-2
Thainá Araruna, Jéssica F. Sousa, Ricardo H. Kruger, Angelo H. L. Machado, Fabricio Machado
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Abstract

In this work, new biobased polymeric materials were synthesized using interesting limonene-based multifunctional monomers as building blocks: the tetrafunctional 2,8-dihydroxy-1,9-diacrylate and 2,8-dihydroxy-1,9-dimethacrylate, and the trifunctional 2-hydroxy-1-acrylamide. These monomers were prepared by the addition reaction between the diepoxidized limonene and (meth)acrylic acid or N-hydroxyethyl acrylamide. The complete conversion of unsaturations of limonene into epoxides, as well as the formation of monomers, were confirmed by Nuclear Magnetic Resonance analysis of proton and carbon (1H and 13C NMR), Fourier Transform Infrared Spectroscopy (FTIR) and Mass Spectrometry (ESI-MS). The monomeric products were polymerized via miniemulsion polymerization with different initiators and co-stabilizers, resulting in new poly(meth)acrylates and polyamide polymers, which is a hydrogel. The polymers showed a high degree of crosslinking, porosity and good thermal properties characterized by Scanning Electron Microscopy (SEM), FTIR, Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TGA). In addition, the polymeric materials were tested to evaluate the formation of biofilm by the action of Comomanoas sp, whose results indicated that the synthesized new biobased polymers are susceptible to biodegradation.

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基于二(甲基)丙烯化和丙烯酰胺化柠檬二烯单体的新型可生物降解和可再生聚合物的生态友好型开发
本研究以有趣的柠檬烯基多功能单体为构建模块,合成了新型生物基聚合物材料:四官能团 2,8- 二羟基-1,9-二丙烯酸酯和 2,8- 二羟基-1,9-二甲基丙烯酸酯,以及三官能团 2- 羟基-1-丙烯酰胺。这些单体是通过二氧化柠檬烯和(甲基)丙烯酸或 N-羟乙基丙烯酰胺之间的加成反应制备的。质子和碳的核磁共振分析(1H 和 13C NMR)、傅立叶变换红外光谱分析(FTIR)和质谱分析(ESI-MS)证实了柠檬烯的不饱和物完全转化为环氧化物以及单体的形成。使用不同的引发剂和助稳定剂,通过小型乳液聚合法聚合单体产物,得到了新型聚(甲基)丙烯酸酯和聚酰胺聚合物,这是一种水凝胶。通过扫描电子显微镜(SEM)、傅里叶变换红外光谱(FTIR)、差示扫描量热仪(DSC)和热重分析(TGA),这些聚合物显示出高度的交联性、多孔性和良好的热性能。此外,还测试了聚合物材料在 Comomanoas sp 作用下形成生物膜的情况,结果表明合成的新型生物基聚合物易于生物降解。
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来源期刊
Journal of Polymers and the Environment
Journal of Polymers and the Environment 工程技术-高分子科学
CiteScore
9.50
自引率
7.50%
发文量
297
审稿时长
9 months
期刊介绍: The Journal of Polymers and the Environment fills the need for an international forum in this diverse and rapidly expanding field. The journal serves a crucial role for the publication of information from a wide range of disciplines and is a central outlet for the publication of high-quality peer-reviewed original papers, review articles and short communications. The journal is intentionally interdisciplinary in regard to contributions and covers the following subjects - polymers, environmentally degradable polymers, and degradation pathways: biological, photochemical, oxidative and hydrolytic; new environmental materials: derived by chemical and biosynthetic routes; environmental blends and composites; developments in processing and reactive processing of environmental polymers; characterization of environmental materials: mechanical, physical, thermal, rheological, morphological, and others; recyclable polymers and plastics recycling environmental testing: in-laboratory simulations, outdoor exposures, and standardization of methodologies; environmental fate: end products and intermediates of biodegradation; microbiology and enzymology of polymer biodegradation; solid-waste management and public legislation specific to environmental polymers; and other related topics.
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