A Biobased Epoxy Vitrimer with Dual Relaxation Mechanism: A Promising Material for Renewable, Reusable, and Recyclable Adhesives and Composites

被引:30
作者
Verdugo, Pere [1 ,2 ]
Santiago, David [1 ,3 ]
de la Flor, Silvia [3 ]
Serra, Angels [2 ]
机构
[1] Technol Ctr Catalonia, Chem Technol Unit, Tarragona 43007, Spain
[2] Univ Rovira & Virgili, Dept Analyt & Organ Chem, Tarragona 43007, Spain
[3] Univ Rovira & Virgili, Dept Mech Engn, Tarragona 43007, Spain
关键词
vanillin; epoxy; vitrimers; disulfide; imine; composite; adhesion; COVALENT ADAPTABLE NETWORKS; TRANSESTERIFICATION;
D O I
10.1021/acssuschemeng.4c00205
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This study presents the synthesis of a novel biobased epoxy monomer derived from vanillin and cystamine, incorporating imine and disulfide exchangeable groups within its structure. A series of epoxy-based vitrimers with two simultaneous exchange relaxation processes have been produced using this monomer. These exchange mechanisms operate without the need for any catalyst. Four different amine curing agents have been employed to achieve vitrimers with glass transition temperatures around100 degrees C and excellent thermal stability. Through dynamic-mechanical analyses, thermomechanical properties and vitrimeric characteristics have been investigated, revealing remarkably fast stress relaxation at relatively low temperatures without significant creep below the glass transition temperature. Leveraging the dual exchange mechanism, the chemical degradability of these vitrimers has been explored through two accessible methodologies, and the material's reformation after degradation has been demonstrated in both cases. Furthermore, the material has been mechanically recycled, maintaining almost the same properties. Finally, these materials have been used to fabricate and recycle carbon-fiber-reinforced composite material and reversible adhesives, showcasing their promising potential applications.
引用
收藏
页码:5965 / 5978
页数:14
相关论文
共 65 条
[1]   Epoxy vitrimers with a covalently bonded tertiary amine as catalyst of the transesterification reaction [J].
Altuna, Facundo I. ;
Hoppe, Cristina E. ;
Williams, Roberto J. J. .
EUROPEAN POLYMER JOURNAL, 2019, 113 :297-304
[2]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[3]  
[Anonymous], 1975, POLYM HDB
[4]   The effect of matrix on shape properties of aromatic disulfide based epoxy vitrimers [J].
Azcune, Itxaso ;
Huegun, Arrate ;
Ruiz de Luzuriaga, Alaitz ;
Saiz, Eduardo ;
Rekondo, Alaitz .
EUROPEAN POLYMER JOURNAL, 2021, 148
[5]  
Briggs J., 2011, Patent Application Publication Pub, Patent No. 0178315
[6]   Rapid Stress Relaxation and Moderate Temperature of Malleability Enabled by the Synergy of Disulfide Metathesis and Carboxylate Transesterification in Epoxy Vitrimers [J].
Chen, Mao ;
Zhou, Lin ;
Wu, Yeping ;
Zhao, Xiuli ;
Zhang, Yongjun .
ACS MACRO LETTERS, 2019, 8 (03) :255-260
[7]   Mechanisms of imine exchange reactions in organic solvents [J].
Ciaccia, Maria ;
Di Stefano, Stefano .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) :646-654
[8]   DITHIOTHREITOL NEW PROTECTIVE REAGENT FOR SH GROUPS [J].
CLELAND, WW .
BIOCHEMISTRY, 1964, 3 (04) :480-&
[9]   MECHANISM OF HYDROLYSIS OF SCHIFF BASES DERIVED FROM ALIPHATIC AMINES [J].
CORDES, EH ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (18) :2843-&
[10]   Chemical control of the aromatic disulfide exchange kinetics for tailor-made epoxy vitrimers [J].
de Rekondo, Alaitz Ruiz ;
Solera, Gema ;
Azcarate-Ascasua, Izaskun ;
Boucher, Virginie ;
Grande, Hans-Jurgen ;
Rekondo, Alaitz .
POLYMER, 2022, 239