Sustainable Fatty Acid Modification of Cellulose in a CO2-Based Switchable Solvent and Subsequent Thiol-Ene Modification,Biomacromolecules

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Sustainable Fatty Acid Modification of Cellulose in a CO2-Based Switchable Solvent and Subsequent Thiol-Ene Modification
Biomacromolecules ( IF 5.5 ) Pub Date : 2020-12-08 , DOI: 10.1021/acs.biomac.0c01444
Eren Esen ₁ , Pauline Hädinger ₂ , Michael A R Meier _{1,

2}

Affiliation

Searching for more sustainable materials as an alternative to petroleum-based products is of increasing interest due to different environmental issues. Cellulose and fatty acids are two very promising candidates for biobased material design. Herein, we report a sustainable synthesis of fatty acid cellulose esters (FACEs) via transesterification of cellulose with methyl-10-undecenoate in a CO₂-based switchable solvent system. FACEs with a degree of substitution between 0.70 and 1.97 were synthesized by simple variation of reaction parameters and characterized in detail. Subsequently, a FACE with a degree of substitution (DS) of 0.70 was modified via thiol-ene reaction, demonstrating an efficient and versatile method to tune the structure and properties of the new cellulose derivatives. Films were produced from each sample via solvent casting, and their mechanical properties were examined using tensile tests. Elastic moduli (E) ranging from 90 to 635 MPa and elongations at break between 2 and 23% were observed, depending on the DS of the FACE and the type of thiol employed for the modification. Finally, contact angle measurements confirmed an increase in the surface hydrophobicity (75–91°) for the thiol-ene-modified samples.

中文翻译：

在基于CO ₂的可切换溶剂中对纤维素进行可持续脂肪酸修饰和随后的硫醇-烯修饰

由于不同的环境问题，寻找更多可持续性材料替代石油基产品的兴趣日益浓厚。纤维素和脂肪酸是生物基材料设计的两个非常有希望的候选物。本文中，我们报告了通过纤维素与10-十一碳烯酸甲酯在CO _2中的酯交换反应，可持续合成脂肪酸纤维素酯（FACE）的可切换溶剂系统。通过简单改变反应参数合成了取代度为0.70至1.97的FACE，并对其进行了详细的表征。随后，通过硫醇-烯反应对取代度（DS）为0.70的FACE进行了改性，证明了一种有效且通用的方法可调节新型纤维素衍生物的结构和性能。通过溶剂浇铸从每个样品生产薄膜，并使用拉伸试验检查其机械性能。弹性模量（ē）的范围从90到635 MPa，观察到的断裂伸长率在2％到23％之间，具体取决于FACE的DS和改性所用硫醇的类型。最后，接触角测量结果证实了硫醇-烯改性样品的表面疏水性增加（75-91°）。

更新日期：2021-02-08

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