Preparation of environmentally friendly bio-based vitrimers from vanillin derivatives by introducing two types of dynamic covalent C N and S–S bonds

Guo, Zijian; Liu, Bangjie; Li, Zhou; Wang, Lingna; Majeed, Kashif; Zhang, Baoliang; Zhou, Fengtao; Zhang, Qiuyu

doi:10.1016/j.polymer.2020.122483

Cited by 50 publications

(39 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, the possibility to reduce the stress relaxation time of self-healing, chemically degradable and recyclable vanillin-based CANs were demonstrated by the introduction of multiple reversible covalent bonds (i.e., imine and disulfide bonds). [46] In particular, the presence of the disulfide linkages in the network turned out to positively affect the stress relaxation time, which decreased with the temperature, in agreement with the Arrhenius equation, due to a synergistic effect of imine and disulfide bond exchange pathways.…”

Section: % Tough and Functional Compoite Thermoset Showing Uv Shieldi...supporting

confidence: 63%

Designed from Biobased Materials for Recycling: Imine‐Based Covalent Adaptable Networks

Liguori

Hakkarainen

2022

Macromol. Rapid Commun.

View full text Add to dashboard Cite

Turning thermosets into fully sustainable materials requires utilization of biobased raw materials and design for easy recyclability. Here, dynamic covalent chemistry for fabrication of covalent adaptable networks (CANs) could be an enabling tool. CAN thermosets ideally combine the positive material properties of thermosets with thermal recyclability of linear thermoplastics. Among the dynamic covalent bonds, imine bond, also called Schiff base, can participate in both dissociative and associative pathways. This induces potential for chemical recyclability, thermal reprocessability and self‐healing. This review presents an overview of the current research front of biobased thermosets fabricated by Schiff base chemistry. The discussed materials are categorized on the basis of the employed biobased components. The chemical approaches for the synthesis and curing of the resins, as well as the resulting properties and recyclability of the obtained thermosets are described and discussed. Finally, challenges and future perspectives are briefly summarized.

show abstract

Section: % Tough and Functional Compoite Thermoset Showing Uv Shieldi...supporting

confidence: 63%

Designed from Biobased Materials for Recycling: Imine‐Based Covalent Adaptable Networks

Liguori

Hakkarainen

2022

Macromol. Rapid Commun.

View full text Add to dashboard Cite

show abstract

“…The E a values of PV-1071 and PV-1074 were calculated to be 12.33 and 15.93 kJ/mol, respectively, based on the slope of the fitting lines. Because of the long aliphatic chain of the amine structure in polyimine vitrimers, the E a is lower compared to the values reported in the literature. , Biobased Priamine 1071 (C 36 H 74 N 2 and C 54 H 109 N 3 ) and 1074 (C 36 H 70 N 2 ) with long branched carbon chains participated in the preparation of polyimine vitrimers instead of a short carbon chain with a small molecule. ,,,,, The calculated results indicated that the dynamic covalent bond exchange of imine metathesis was carried out and could lead to the rearrangement of network topology, realizing the thermotropic reprocessing of vitrimers.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Vanillin-Based Polyimine Vitrimers with Excellent Reprocessability, Fast Chemical Degradability, and Adhesion

Zhou

Liu

et al. 2020

ACS Appl. Polym. Mater.

View full text Add to dashboard Cite

A series of biobased polyimine vitrimers was synthesized by condensation between a dialdehyde or trialdehyde derived from vanillin and a commercial biobased aliphatic amine. The structure, thermal stability, mechanical properties, and reprocessability of vitrimers with different crosslinking degrees were investigated. The results indicated that the glass transition temperature (T g ) of vitrimers increased with the increase of cross-linking density. In addition, the vitrimers showed good malleability and recyclability even with high cross-linking degree based on fast imine metathesis. The degradation test of polyimine vitrimers suggested that the decomposition rate increased with the rising temperature, and the vitrimer degraded rapidly in 0.1 M HCl aqueous solution. After acid degradation, the aldehyde monomer was precipitated, and it can be reused to prepare a vitrimer to realize the closed-loop cycle. Finally, the biobased polyimine vitrimers can be used as adhesives, and the shear tensile strength showed that the bond strength of the vitrimer was up to 6.79 MPa.

show abstract

“…These values of thermal degradation are in line with the reported results for isosorbide-derived epoxy cured with the diamine crosslinkers containing or not disulphide bonds [ 10 ]. Guo et al [ 34 ] also reported comparable data for the bis-disulphide dynamic epoxy resins obtained from the synthetized bis (4-glycidyloxyphenyl) disulphide crosslinked with 4-AFD.…”

Section: Resultsmentioning

confidence: 80%

Influence of the Presence of Disulphide Bonds in Aromatic or Aliphatic Dicarboxylic Acid Hardeners Used to Produce Reprocessable Epoxidized Thermosets

Mauro

Mija

2021

Polymers

View full text Add to dashboard Cite

The design of polymers from renewable resources with recycling potential comes from economic and environmental problems. This work focused on the impact of disulphide bonds in the dicarboxylic acids reactions with three epoxidized vegetable oils (EVOs). For the first time, the comparison between aromatic vs. aliphatic dicarboxylic acids, containing or not S–S bonds with EVOs was discussed and evaluated by dynamic scanning calorimetry. The obtained thermosets showed reprocessability, by the dual dynamic exchange mechanism. The virgin and reprocessed materials were characterized and the thermomechanical properties were compared. The thermosets derived from EVOs with high epoxy content combined with aromatic diacids containing disulphide bridges showed high glass transition values (~111 °C), high crosslink densities and good solvent stability.

show abstract

Preparation of environmentally friendly bio-based vitrimers from vanillin derivatives by introducing two types of dynamic covalent C N and S–S bonds

Cited by 50 publications

References 43 publications

Designed from Biobased Materials for Recycling: Imine‐Based Covalent Adaptable Networks

Designed from Biobased Materials for Recycling: Imine‐Based Covalent Adaptable Networks

Synthesis of Vanillin-Based Polyimine Vitrimers with Excellent Reprocessability, Fast Chemical Degradability, and Adhesion

Influence of the Presence of Disulphide Bonds in Aromatic or Aliphatic Dicarboxylic Acid Hardeners Used to Produce Reprocessable Epoxidized Thermosets

Contact Info

Product

Resources

About