Recyclable non-isocyanate polyurethanes containing a dynamic covalent network derived from epoxy soybean oil and CO<sub>2</sub>

Yang, Xinxin; Ren, Cheng; Liu, Xiuxiu; Sun, Penghao; Xu, Xu; Li, He; Shen, Minggui; Shang, Shibin; Song, Zhanqian

doi:10.1039/d1qm00765c

Cited by 39 publications

(40 citation statements)

References 53 publications

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“…Under catalyst free conditions, they reported an E a of 89.2 kJ mol –1 . [ 137 ] Liu and coworkers replaced the DDM by another fossil‐based diamine featuring a disulfide moiety, i.e., 4,4’‐diaminodiphenyldisulfide (DDS) to adjust the temperature and energy required for the bond exchange reaction. [ 138 ] Such dual dynamic networks benefited from a synergetic effect between the two dynamic covalent chemistries, as the relaxation times at a specific temperature and E a were lower than the ones of single disulfide and PHU‐networks.…”

Section: Transcarbamoylation Reactionsmentioning

confidence: 99%

Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers

Vidil

Llevot

2022

Macro Chemistry & Physics

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Improving the sustainability of polymer networks is a crucial challenge in polymer science due to their important role in industry. Their traditional syntheses conflict with several principles of green chemistry as the employed monomers are petroleum-based, their production involves the use of toxic reagents, and their permanently cross-linked structures impede their chemical recycling and reshaping. The development of vitrimers represents a unique solution to address the issue of polymer network end-of-life by enabling reprocessability while maintaining good thermomechanical properties and solvent resistance. Although over the last decades biomass has proved to be an excellent feedstock for the production of permanently cross-linked polymers, the field of biobased vitrimers is still in its infancy. In this review, a comprehensive overview of vitrimers synthesized from biobased monomers is presented. The emphasis is set on the compatibility of the biomass structure with the nature of the dynamic covalent chemistry, as well as the sustainability of the synthetic approaches. Implementing renewable feedstocks and recyclability in the production of polymer networks paves the way for the development of the next generation of sustainable materials.

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Section: Transcarbamoylation Reactionsmentioning

confidence: 99%

Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers

Vidil

Llevot

2022

Macro Chemistry & Physics

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“…54 Yang's team developed bio-based NIPU with a dual dynamic network using cyclic carbonates derived from epoxy soybean oil and CO 2 ; the sample exhibited reprocessing and shape memory performance. 55,56 Anitha et al synthesized a self-blowing poly(hydroxyurethane) (PHU) foam from cyclic carbonate with amine-terminated oligomeric phenylhydroxyamine (AOPHA) in the presence of a catalyst. The cyclic carbonate group reacts with the OH group of the AHOPA and leads to evolution of CO 2 gas, which then plays the role of a blowing agent for generating PHU foam.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characteristics of nonisocyanate polyurethane composed of bio‐based dimer diamine for supercritical CO₂ foaming applications

Mao

Chen

Yan

et al. 2022

J of Applied Polymer Sci

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Nonisocyanate polyurethane (NIPU) was synthesized using different concentrations of C36‐alkylenediamine (C36DDA), hexamethylene diamine, and a cyclic carbonate monomer synthesized from bisphenol A epoxy resin and carbon dioxide. The structures, molecular weights, thermal behaviors, and stabilities of the NIPU copolymers were evaluated using 1H nuclear magnetic resonance, Fourier transform infrared spectroscopy, gel permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry measurements. All synthesized NIPUs were amorphous and exhibited good Td−5% thermal stabilities above 250°C; Tg decreased from 73 to 51°C as C36DDA content increased from 0% to 10% based on dynamic mechanical analysis tests. Furthermore, ethylenediamine (EDA) as a chain extender incorporating a small amount of crosslinker 1,2,4,5‐benzenetetracarboxylic acid (PMA) can enhance the melt strength of a partially three‐dimensional network, and the attained NIPU showed elastic properties. Thus, the NIPU synthesized with 7.5% and 10% C36DDA containing small amounts of EDA and PMA were suitable choices for supercritical CO2 foaming; their morphologies and mechanical behaviors were examined by scanning electron microscopy and DMA, and the densities of foamed NIPU with 7.5% and 10% C36DDA were calculated as 432 and 215 kg m−3 with pore sizes of 10–20 μm, respectively. The maximum stresses were attained at 149.5 and 123.4 kPa, and the foamed NIPU displayed rigid foam behaviors owing to the compression behaviors of the stress–strain curves.

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“…During the past decades, efforts have been made to lower their costs and improve their bonding performances. Plant oils are also bio-based products from which sustainable polymers can be derived. − Among all of the plant oils, soybean oil has been intensively studied and widely used in the industry owing to its abundant availability and low cost. − Particularly, producing polymers based on conversion of the double bonds in the long carbon chains into reactive epoxy groups, resulting in epoxidized soybean oil (ESO), has attracted considerable attention. − High-performance ESO-based resin materials have been reported in the recent literature. − It is natural to relate ESO to commercial epoxy resins since both of them have reactive epoxy groups. As adhesives, epoxy resins exhibit excellent bonding performance for different substrates, metal or nonmetal.…”

Section: Introductionmentioning

confidence: 99%

Cocuring of Epoxidized Soybean Oil-Based Wood Adhesives and the Enhanced Bonding Performance by Plasma Treatment of Wood Surfaces

Duan

Jiang

et al. 2022

ACS Sustainable Chem. Eng.

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Application of epoxidized soybean oil (ESO) in the wood industry as an adhesive has been limited due to the difficulty in fast curing ESO. Due to the advantages of the ureaformaldehyde (UF) resin, like low cost, high molecular weight, rich functional groups, as well as fast self-curing property, fast cocuring ESO-UF adhesives were prepared by mixing UF with ESO in different ratios (15−50%). Bonding performance tests indicated that the ESO-UF adhesives well balanced bonding strengths and the formaldehyde emission level; especially, the adhesives provided satisfactory water resistance. Structural characterization of cured ESO-UF adhesives showed that a copolymerization reaction occurred between epoxy groups of ESO and the hydroxyl groups of UF. Combined with gliding arc discharge (GAD) plasma treatment of the veneer surface, better bonding performances were achieved. X-ray photoelectron spectroscopy (XPS) analysis on the wood surfaces showed that the GAD treatment significantly increased the content of oxygencontaining groups like −OH and −COOH through oxidation and degradation of the chemical components on the wood surface. The generated reactive groups on the wood surface participated in the curing reaction of ESO-UF adhesives and led to improved bonding performances. Thus, the ESO-UF-activated wood surface (ESO-UF-AWS) system was developed in this study. The results of this study have demonstrated that the combination of seeking an efficient cocuring agent along with activating the wood surface is a valid strategy for realizing applications of ESO in the wood product industry.

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Recyclable non-isocyanate polyurethanes containing a dynamic covalent network derived from epoxy soybean oil and CO₂

Abstract: As one of the important reasons for the greenhouse effect, CO2 can be effectively fixed by reacting with epoxides to synthesize the raw material cyclic carbonate of non-isocyanate polyurethanes (NIPUs)....

Cited by 39 publications

References 53 publications

Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers

Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers

Synthesis and characteristics of nonisocyanate polyurethane composed of bio‐based dimer diamine for supercritical CO₂ foaming applications

Cocuring of Epoxidized Soybean Oil-Based Wood Adhesives and the Enhanced Bonding Performance by Plasma Treatment of Wood Surfaces

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Recyclable non-isocyanate polyurethanes containing a dynamic covalent network derived from epoxy soybean oil and CO2

Abstract: As one of the important reasons for the greenhouse effect, CO2 can be effectively fixed by reacting with epoxides to synthesize the raw material cyclic carbonate of non-isocyanate polyurethanes (NIPUs)....

Cited by 39 publications

References 53 publications

Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers

Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers

Synthesis and characteristics of nonisocyanate polyurethane composed of bio‐based dimer diamine for supercritical CO2 foaming applications

Cocuring of Epoxidized Soybean Oil-Based Wood Adhesives and the Enhanced Bonding Performance by Plasma Treatment of Wood Surfaces

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Product

Resources

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Recyclable non-isocyanate polyurethanes containing a dynamic covalent network derived from epoxy soybean oil and CO₂

Synthesis and characteristics of nonisocyanate polyurethane composed of bio‐based dimer diamine for supercritical CO₂ foaming applications