Thiol-ene-based degradable 3D printed network from bio resource derived monomers ethyl-lactate and isosorbide

被引:9
作者
Pal, Shibam [1 ,2 ]
Asha, S. K. [1 ,2 ]
机构
[1] CSIR Natl Chem Lab, Polymer Sci & Engn Div, Dr Homi Bhabha Rd, Pune 411008, India
[2] Acad Sci & Innovat Res, Sect 19, Ghaziabad 201002, Uttar Pradesh, India
关键词
Poly (acrylate ethyl lactate); Degradation; Thiol-ene; 3D printing; Digital light processing; STATISTICAL KINETIC-MODEL; BULK DEGRADATION; PERFORMANCE; CHEMISTRY; POLYMERS;
D O I
10.1016/j.eurpolymj.2024.112761
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A polymeric ene-based thiol-ene network is reported that was demonstrated for light-based 3D printing. Allyl poly (acrylate ethyl lactate) (PAEL) was synthesized starting from ethyl lactate in an efficient and scalable manner. Ethyl lactate is a biobased material obtained naturally or chemically in high yields in the form of ethyl ester of lactic acid. Isosorbide, which is also a bio based resource was converted into thiol derivative and was used along with Pentaerythritol tetrakis(3-mercaptopropionate) (PETMP) as multifunctional thiol. The polymeric nature of the ene (i.e. PAEL) imparted exceptionally high mechanical properties like Young's modulus of 1.75 GPa as well as high thermal stability with a decomposition temperature (Td,10%) exceeding 350 C for all the networks studied. The properties could also be customized by fine tuning the type and stoichiometric ratio of the thiol crosslinked employed. For instance, the Young's modulus range from 1.75 GPa to 1.03 GPa and glass transition temperature range from 44 C to 54 C could be achieved. DLP 3D printing was used to demonstrate the printability of the resins with high resolution and structural fidelity. The study also highlights the basemediated rapid hydrolytic degradation efficiency of the 3D printed parts, demonstrating the applicability of these novel polymeric ene based thiol-ene for sustainable and eco-friendly 3D printable formulations.
引用
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页数:10
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[1]   An effective method to prepare sucrose polymers by Thiol-Ene photopolymerization [J].
Acosta Ortiz, Ricardo ;
Garcia Valdez, Aida E. ;
Martinez Aguilar, Marty Georgina ;
Berlanga Duarte, Maria Lydia .
CARBOHYDRATE POLYMERS, 2009, 78 (02) :282-286
[2]  
[Anonymous], 2020, J. Polym. Sci., V58, P1105
[3]   Introduction: 3D Printing for Biomaterials [J].
Atala, Anthony G. .
CHEMICAL REVIEWS, 2020, 120 (19) :10545-10546
[4]   Polyacrylates Derived from Biobased Ethyl Lactate Solvent via SET-LRP [J].
Bensabeh, Nabil ;
Moreno, Adrian ;
Roig, Adria ;
Monaghan, Olivia R. ;
Ronda, Juan C. ;
Cadiz, Virginia ;
Galia, Marina ;
Howdle, Steven M. ;
Lligadas, Gerard ;
Percec, Virgil .
BIOMACROMOLECULES, 2019, 20 (05) :2135-2147
[5]   Thiol-Ene Clickable Gelatin: A Platform Bioink for Multiple 3D Biofabrication Technologies [J].
Bertlein, Sarah ;
Brown, Gabriella ;
Lim, Khoon S. ;
Jungst, Tomasz ;
Boeck, Thomas ;
Blunk, Torsten ;
Tessmar, Joerg ;
Hooper, Gary J. ;
Woodfield, Tim B. F. ;
Groll, Juergen .
ADVANCED MATERIALS, 2017, 29 (44)
[6]   In vitro compatibility testing of thiol-ene/acrylate-based shape memory polymers for use in implantable neural interfaces [J].
Black, Bryan J. ;
Ecker, Melanie ;
Stiller, Allison ;
Rihani, Rashed ;
Danda, Vindhya Reddy ;
Reed, Isabella ;
Voit, Walter E. ;
Pancrazio, Joseph J. .
JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A, 2018, 106 (11) :2891-2898
[7]   Nano- to macro-scale control of 3D printed materials via polymerization induced microphase separation [J].
Bobrin, Valentin A. ;
Yao, Yin ;
Shi, Xiaobing ;
Xiu, Yuan ;
Zhang, Jin ;
Corrigan, Nathaniel ;
Boyer, Cyrille .
NATURE COMMUNICATIONS, 2022, 13 (01)
[8]   State-of-the-art UV-assisted 3D printing via a rapid syringe-extrusion approach for photoactive vegetable oil acrylates produced in one-step synthesis [J].
Briede, Sabine ;
Jurinovs, Maksims ;
Nechausov, Sergey ;
Platnieks, Oskars ;
Gaidukovs, Sergejs .
MOLECULAR SYSTEMS DESIGN & ENGINEERING, 2022, 7 (11) :1434-1448
[9]   Highly stable thiol-ene systems: from their structure-property relationship to DLP 3D printing [J].
Chen, Li ;
Wu, Qingyang ;
Wei, Guo ;
Liu, Ren ;
Li, Zhiquan .
JOURNAL OF MATERIALS CHEMISTRY C, 2018, 6 (43) :11561-11568
[10]   Bioderived 4D Printable Terpene Photopolymers from Limonene and β-Myrcene [J].
Constant, Eric ;
King, Olivia ;
Weems, Andrew C. .
BIOMACROMOLECULES, 2022, 23 (06) :2342-2352