Degradable and recyclable bio-based thermoset epoxy resins

Chen, Xianchao; Chen, Sufang; Xu, Zejun; Zhang, Junheng; Miao, Menghe; Zhang, Daohong

doi:10.1039/d0gc01250e

Cited by 92 publications

(49 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To check the degradation nature and recover 38,45–50 the starting material from the epoxy resin of A2B2, self‐cured and cured with DDM, the epoxy resins were treated with 25% NaOH solution. The self‐cured A2B2 epoxy resin was soluble in DMSO (Figure 8), whereas the epoxy resins obtained from A2B2 with DDM were only soluble at high temperatures (100°C), and the DGEBA/DDM epoxy resin was insoluble in DMSO even at 100°C.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

Sivanesan

Seo

Lim

et al. 2021

J of Applied Polymer Sci

View full text Add to dashboard Cite

The synthesis of bio‐based monomers and polymers from renewable feedstock, such as plant biomass, is desirable because of the depletion of fossil fuel resources and the reliance of thermosetting epoxy resin on non‐renewable petrochemical monomers. Despite the excellent polymeric properties of bisphenol‐based epoxy resins, these negatively impact human health. Herein, the synthesis of self‐curable epoxy polymers from the bio‐based material isoeugenol by forming α‐hydroxyl esters is reported. The epoxides are named AB (single epoxide and ester groups) and A2B2 (double epoxide and ester groups), based on the number of active ester and epoxide groups. The materials derived from the bio‐based material, AB and A2B2, were initiated with and without the catalyst N,N′‐dimethylaminopyridine (DMAP) and curing agent diaminodiphenylmethane. Without the catalyst, AB and A2B2 self‐polymerized at 247 and 210°C, respectively. Notably, the polymerization temperatures for AB and A2B2 decreased after the addition of DMAP. The self‐cured epoxy resin without the catalyst showed the highest thermal stability and glass transition temperature (Tg = 156°C). Degradation and recovery studies suggested forward that 51% of the material could be recovered and 94% of the polymer could be degraded from the self‐cured A2B2 in 25 wt% NaOH solution.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

Sivanesan

Seo

Lim

et al. 2021

J of Applied Polymer Sci

View full text Add to dashboard Cite

show abstract

“…When comparing the spectra of E_GUA and pure GUA, an increase in intensity of the peaks around 3000 cm −1 occurred, correlating to the characteristic vibrational peaks of the epoxy group. Moreover, after the reaction, two peaks appeared at 1139 cm −1 and 866 cm −1 , which represent the asymmetric and symmetric stretching C-O-C vibrations of epoxy molecules [20]. At 1259 cm −1 , an increase in the peak intensity could be seen in the case of E_GUA, representing the epoxy ring vibration, while an increase in the peak at 917 cm −1 represents the epoxy ring deformation [21].…”

Section: Resultsmentioning

confidence: 99%

Bio-Based Epoxy Adhesives with Lignin-Based Aromatic Monophenols Replacing Bisphenol A

Velde¹,

Javornik²,

Sever³

et al. 2021

Polymers

View full text Add to dashboard Cite

A bio-epoxy surface adhesive for adherence of the metal component species to glass substrate with desirable adhesion strength, converted controlled removal upon request, and bio-based resource inclusion was developed. For the development of resin, three different lignin-based aromatic monophenols, guaiacol, cresol, and vanillin, were used in the chemical epoxidation reaction with epichlorohydrin. The forming transformation process was studied by viscoelasticity, in situ FTIR monitoring, and Raman. Unlike other hydroxyl phenyls, guaiacol showed successful epoxide production, and stability at room temperature. Optimization of epoxide synthesis was conducted by varying NaOH concentration or reaction time. The obtained product was characterized by nuclear magnetic resonance and viscosity measurements. For the production of adhesive, environmentally problematic bisphenol A (BPA) epoxy was partially substituted with the environmentally acceptable, optimized guaiacol-based epoxy at 20, 50, and 80 wt.%. Mechanics, rheological properties, and the possibility of adhered phase de-application were assessed on the bio-substitutes and compared to commercially available polyepoxides or polyurethanes. Considering our aim, the sample composed of 80 wt.% bio-based epoxy/20 wt.% BPA thermoset was demonstrated to be the most suitable among those analyzed, as it was characterized by low BPA, desired boundary area and recoverability using a 10 wt.% acetic acid solution under ultrasound.

show abstract

“…DCTRs contain dynamic chemical bonds that can dissociate or be exchanged in response to external stimuli, which renders them malleable; therefore, DCTRs can be used to realize polymer recyclability and reprocessability. [17][18][19][20] Many dynamic chemical bonds have been exploited in studies aimed at synthesizing recyclable and reprocessable DCTRs. [10,21,22] Among the recognized dynamic chemical bonds, the dynamic imine bond (À C=NÀ ) is unique because it can dissociate in a solution containing amino groups and transition between imine and amine groups.…”

Section: Introductionmentioning

confidence: 99%

Fabricating a Repairable, Recyclable, Imine‐based Dynamic Covalent Thermosetting Resin with Excellent Water Resistance by Introducing Dynamic Covalent Oxime Bonds

Zhang

Yang

et al. 2021

ChemSusChem

View full text Add to dashboard Cite

The sustainable production of adaptive, recyclable and iminebased dynamic covalent thermosetting resins (DCTRs) presents an opportunity for polymer scientists to address the prevalent environmental and energy concerns associated with current petroleum-based plastics. However, the imine-based DCTRs easily decompose in the presence of water, which can weaken the mechanical properties in imine-based polymers. In this study, we designed oxime-imine DCTRs that are stable in the presence of water and exhibit good mechanical properties. In the presence of one kind of amino group catalyst, the oximeimine DCTRs could be completely recycled. Additionally, these well-designed oxime-imine DCTRs have good mechanical properties, high glass transition temperatures (166°C), and good thermal stabilities. Taken together, this work offers a sustainable solution for the design and manufacture of highvalue degradable materials intended for applications in which recyclability and reusability are indispensable.

show abstract

Degradable and recyclable bio-based thermoset epoxy resins

Abstract:
A degradable and recyclable thermoset hyperbranched epoxy resin was synthesized from bio-based 2,5-furandicarboxylic acid.

Cited by 92 publications

References 54 publications

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

Bio-Based Epoxy Adhesives with Lignin-Based Aromatic Monophenols Replacing Bisphenol A

Fabricating a Repairable, Recyclable, Imine‐based Dynamic Covalent Thermosetting Resin with Excellent Water Resistance by Introducing Dynamic Covalent Oxime Bonds

Contact Info

Product

Resources

About

Degradable and recyclable bio-based thermoset epoxy resins

Abstract: A degradable and recyclable thermoset hyperbranched epoxy resin was synthesized from bio-based 2,5-furandicarboxylic acid.

Cited by 92 publications

References 54 publications

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

Synthesis of isoeugenol biobased epoxy polymer by forming α‐hydroxyl ester and degradation studies

Bio-Based Epoxy Adhesives with Lignin-Based Aromatic Monophenols Replacing Bisphenol A

Fabricating a Repairable, Recyclable, Imine‐based Dynamic Covalent Thermosetting Resin with Excellent Water Resistance by Introducing Dynamic Covalent Oxime Bonds

Contact Info

Product

Resources

About

Abstract:
A degradable and recyclable thermoset hyperbranched epoxy resin was synthesized from bio-based 2,5-furandicarboxylic acid.