Sustainable Series of New Epoxidized Vegetable Oil-Based Thermosets with Chemical Recycling Properties

Mauro, Chiara Di; Malburet, Samuel; Genua, Aratz; Graillot, Alain; Mija, Alice

doi:10.1021/acs.biomac.0c01059

Cited by 118 publications

(104 citation statements)

References 53 publications

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“…The hypothesis of the authors is corrected if we consider that it is well known from the literature that the presence of S−S bonds thermally destabilizes thermosets because their lower dissociation energy compared with that of C−C bonds [36]. In addition, the French researchers correctly considered the effect of the oxirane ring content, that lead to the formation of more ester and hydroxyl groups during the curing, thus contributing to the thermal scissions of the networks [37]. Since they found a strictly link among EVO functionality, reactivity, cross-linking density, and final performances, they continued their studies by proposing the synthesis and thermal characterization of a reprocessable thermosets, whose recyclability was designed through a dual mechanism (i.e., disulfide metathesis; transesterifications), obtaining similar performance compared to the control ones.…”

Section: Thermal Techniques In Polymers' Recycling and Preparation Of Recyclable Polymersmentioning

confidence: 99%

The Use of Thermal Techniques in the Characterization of Bio-Sourced Polymers

Blanco

Siracusa

2021

Materials

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The public pressure about the problems derived from the environmental issues increasingly pushes the research areas, of both industrial and academic sectors, to design material architectures with more and more foundations and reinforcements derived from renewable sources. In these efforts, researchers make extensive and profound use of thermal analysis. Among the different techniques available, thermal analysis offers, in addition to high accuracy in the measurement, smartness of execution, allowing to obtain with a very limited quantity of material precious information regarding the property–structure correlation, essential not only in the production process, but overall, in the design one. Thus, techniques such as differential scanning calorimetry (DSC), differential thermal analysis (DTA), dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA) were, are, and will be used in this transition from fossil feedstock to renewable ones, and in the development on new manufacturing processes such as those of additive manufacturing (AM). In this review, we report the state of the art of the last two years, as regards the use of thermal techniques in biopolymer design, polymer recycling, and the preparation of recyclable polymers as well as potential tools for biopolymer design in AM. For each study, we highlight how the most known thermal parameters, namely glass transition temperature (Tg), melting temperature (Tf), crystallization temperature (Tc) and percentage (%c), initial decomposition temperature (Ti), temperature at maximum mass loss rate (Tm), and tan δ, helped the researchers in understanding the characteristics of the investigated materials and the right way to the best design and preparation.

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Section: Thermal Techniques In Polymers' Recycling and Preparation Of Recyclable Polymersmentioning

confidence: 99%

The Use of Thermal Techniques in the Characterization of Bio-Sourced Polymers

Blanco

Siracusa

2021

Materials

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“…The development of vitrimers containing dynamic covalent bonds (DCBs) makes it possible to recycle thermosets under mild conditions [8,9,[15][16][17][18][19][20][21][22][23][24][25]. Over the past few decades, researchers have developed an array of vitrimers through incorporating various DCBs (e.g., disulfide [25,26], imine-amine exchange [27], and hindered urea bond [28]), among which epoxy vitrimer prepared from the curing reactions of epoxy-anhydride [29][30][31] or epoxycarboxylic [32][33][34] is the most investigated vitrimer system.…”

Section: Introductionmentioning

confidence: 99%

Recyclable High-Performance Epoxy-Anhydride Resins with DMP-30 as the Catalyst of Transesterification Reactions

Zhao

Wang

2021

Polymers

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Epoxy-anhydride resins are widely used in engineering fields due to their excellent performance. However, the insolubility and infusibility make the recycling of epoxy resins challenging. The development of degradable epoxy resins with stable covalent networks provides an efficient solution to the recycling of thermosets. In this paper, 2,4,6-tris(dimethylaminomethyl)phenol (DMP-30) is incorporated into the epoxy-glutaric anhydride (GA) system to prepare high-performance epoxy resins that can be recycled below 200 °C at ordinary pressure via ethylene glycol (EG) participated transesterification. The tertiary amine groups in DMP-30 can catalyze the curing reaction of epoxy and anhydride, as well as the transesterification between ester bonds and alcoholic hydroxyl groups. Compared with early recyclable anhydride-cured epoxy resins, the preparation and recycling of diglycidyl ether of bisphenol A (DGEBA)/GA/DMP-30 systems do not need any special catalysts such as TBD, Zn(Ac)2, etc., which are usually expensive, toxic, and have poor compatibility with other compounds. The resulting resins have glass transition temperatures and strengths similar to those of conventional epoxy resins. The influences of GA content, DMP-30 content, and temperature on the dissolution rate were studied. The decomposed epoxy oligomer (DEO) is further used as a reaction ingredient to prepare new resins. It is found that the DEO can improve the toughness of epoxy resins significantly. This work provides a simple method to prepare readily recyclable epoxy resins, which is of low-cost and easy to implement.

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“…The epoxy resins based on disulfide bonds can be recycled in DMF solution of dithiothreitol [ 14 , 28 , 30 ]. Figure 8 A and Figure S8A present the full degradation and chemical recycling ability after 24 h at 50 °C of the thermosets based on ECMO/DTBA x DTDA y and ECMO/DTBA x 4-AFD y .…”

Section: Resultsmentioning

confidence: 99%

“…Rekondo et al [ 8 ] synthesized a polyurethane elastomer using an aromatic diamine disulfide crosslinker, 4-aminophenyl disulfide (4-AFD), and showed that self-healing occurred at room temperature with a repairing efficiency of more than 95%. Zeng et al [ 9 ] obtained a reprocessable castor oil-based polyurethane by incorporating 4-AFD and reported [ 10 , 11 , 12 , 13 , 14 ] that the mechanical properties were completely recovered after reprocessing. For the first time, our team produced reprocessable, repairable and recyclable epoxidized vegetable oil (EVO) thermosets by using 2,2′-dithiodibenzoic acid (DTBA) as a crosslinker.…”

Section: Introductionmentioning

confidence: 99%

Kinetical Study, Thermo-Mechanical Characteristics and Recyclability of Epoxidized Camelina Oil Cured with Antagonist Structure (Aliphatic/Aromatic) or Functionality (Acid/Amine) Hardeners

2021

Self Cite

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In an attempt to prepare sustainable epoxy thermosets, this study introduces for the first time the idea to use antagonist structures (aromatic/aliphatic) or functionalities (acid/amine) as hardeners to produce reprocessable resins based on epoxidized camelina oil (ECMO). Two kinds of mixtures were tested: one combines aromatic/aliphatic dicarboxylic acids: 2,2′-dithiodibenzoic acid (DTBA) and 3,3′-dithiodipropionic acid (DTDA); another is the combination of two aromatic structures with acid/amine functionality: DTBA and 4-aminophenyl disulfide (4-AFD). DSC and FT-IR analyses were used as methods to analyze the curing reaction of ECMO with the hardeners. It was found that the thermosets obtained with the dual crosslinked mechanism needed reduced curing temperatures and reprocessing protocols compared to the individual crosslinked thermosets. Thanks to the contribution of disulfide bonds in the network topology, the obtained thermosets showed recycling ability. The final thermomechanical properties of the virgin and mechanical reprocessed materials were analyzed by DMA and TGA. The obtained thermosets range from elastomeric to rigid materials. As an example, the ECMO/DTBA704-AFD30 virgin or reprocessed thermosets have tan δ values reaching 82–83 °C. The study also investigates the chemical recycling and the solvent resistance of these vitrimer-like materials.

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Sustainable Series of New Epoxidized Vegetable Oil-Based Thermosets with Chemical Recycling Properties

Cited by 118 publications

References 53 publications

The Use of Thermal Techniques in the Characterization of Bio-Sourced Polymers

The Use of Thermal Techniques in the Characterization of Bio-Sourced Polymers

Recyclable High-Performance Epoxy-Anhydride Resins with DMP-30 as the Catalyst of Transesterification Reactions

Kinetical Study, Thermo-Mechanical Characteristics and Recyclability of Epoxidized Camelina Oil Cured with Antagonist Structure (Aliphatic/Aromatic) or Functionality (Acid/Amine) Hardeners

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