Mechanically strong non-isocyanate polyurethane thermosets from cyclic carbonate linseed oil

Wang, Tongyao; Deng, Henghui; Li, Neng; Xie, Fei; Shi, Hebo; Wu, Mengting; Zhang, Chaoqun

doi:10.1039/d2gc02910c

Cited by 24 publications

(42 citation statements)

References 39 publications

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“…To evaluate the performance of the MHE films, their tensile strength and elongation at break were compared with those of some biomass-based films in literature. ,− According to our survey on literature shown in Figure g, so far, the oil-based films with the highest tensile strength were developed very recently by Zhang’s team . In the study of Zhang’s team, the epoxidized linseed oil was first reacted with CO 2 to produce cyclic carbonate which was then crosslinked by different diamines, resulting in non-isocyanate polyurethanes (NIPUs) films with tensile strength of 19–69 MPa and elongation at break of 15–179% . As it can be seen, the MHE films cured at different temperatures can provide either high strength with relatively low elongation at break or high elongation at break with low strength by adjusting curing temperatures.…”

Section: Resultsmentioning

confidence: 99%

“…11,33−46 According to our survey on literature shown in Figure 8g, so far, the oilbased films with the highest tensile strength were developed very recently by Zhang's team. 11 In the study of Zhang's team, the epoxidized linseed oil was first reacted with CO 2 to produce cyclic carbonate which was then crosslinked by different diamines, resulting in non-isocyanate polyurethanes (NIPUs) films with tensile strength of 19−69 MPa and elongation at break of 15−179%. 11 As it can be seen, the MHE films cured at different temperatures can provide either high strength with relatively low elongation at break or high elongation at break with low strength by adjusting curing temperatures.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…11 In the study of Zhang's team, the epoxidized linseed oil was first reacted with CO 2 to produce cyclic carbonate which was then crosslinked by different diamines, resulting in non-isocyanate polyurethanes (NIPUs) films with tensile strength of 19−69 MPa and elongation at break of 15−179%. 11 As it can be seen, the MHE films cured at different temperatures can provide either high strength with relatively low elongation at break or high elongation at break with low strength by adjusting curing temperatures. Particularly, the film cured at 160 °C presented tensile strength above 40 MPa which is superior to all the starch and soy protein-based biomass-based films reported in literature and only inferior to a few NIPU films.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Epoxidation of POs (EPOs) is currently one of the most successful modifications and can provide reactive monomers for sustainable polymer synthesis . Upon the presence of epoxy groups and long aliphatic carbon chain, EPO-based materials with fantastic properties have been widely investigated in the areas of films, , elastomers, , vitrimers, − typical thermosetting resins (including adhesives), − coatings, and so forth. To achieve significant properties for polymeric materials, crosslinking of EPOs is a valid strategy.…”

Section: Introductionmentioning

confidence: 99%

“…In parallel efforts, modifications before crosslinking can be done to generate highly reactive intermediate products for preparing final polymeric materials. Examples are conversion of EPOs into cyclic carbonates ,, and acrylated derivatives which were then crosslinked by other agents. Undoubtedly, direct crosslinking without modifications should be better choice since it is a more efficient and cost-effective strategy for utilization of EPOs.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Versatile Epoxidized Soybean Oil-Based Resin with Excellent Adhesion and Film-Forming Property

Zhang

Liu

et al. 2023

ACS Sustainable Chem. Eng.

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Deriving environmentally friendly and renewable polymers from epoxidized plant oils (EPOs) is one of the promising strategies for realizing the sustainable development of materials industry. Direct crosslinking EPOs without premodifications is a straightforward, efficient, and cost-effective way for the utilization of EPOs. Herein, a facile and green strategy that crosslinks epoxidized soybean oil with highly branched and flexible polyamine via ring-opening and amidation polymerizations successfully produced a novel resin with exceptional properties and versatile potential applications. After completely cured, the resin appeared to be super strong structural adhesive as it provided a room-temperature bonding strength of 12−24 MPa for metal and non-metal substrates, as well as a steel bonding strength of 11.6 MPa at cryogenic temperature (−196 °C), which is far superior to the previously reported oil-based adhesives. Meanwhile, the resin exhibited excellent film-forming ability. Particularly, by controlling the curing temperature, the films with tunable mechanical properties were obtained with a tensile strength of 3−40 MPa and an elongation at break of 17−230%. The features of uncured resin, including liquid viscoelasticity, good wettability, and high molecular weight, make it a qualified pressure-sensitive adhesive which demonstrated satisfied peel strength for various substrates.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Versatile Epoxidized Soybean Oil-Based Resin with Excellent Adhesion and Film-Forming Property

Zhang

Liu

et al. 2023

ACS Sustainable Chem. Eng.

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Design of crosslinked networks with hydroxyurethane linkages via bio‐based alkyl methacrylates and diamines

Farkhondehnia

Marić

2023

J of Applied Polymer Sci

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A hybrid methodology is used to combine the favorable properties of non‐isocyanate polyurethanes (NIPUs) in the side chains with poly(methacrylates) as the backbone into thermoset hybrid resins with hydroxyurethane linkages (HNIPU)s. Using NIPUs linkages avoids the use of toxic isocyanates in the poly(urethane) segments. The backbone is synthesized from cyclic carbonated copolymer templates derived from atom transfer radical polymerization (ATRP) of an alkyl methacrylate (C13MA with average side‐chain length of 13)/glycidyl methacrylate (GMA) mixtures (initial GMA mol fraction = 0.1–0.4). The resulting flexible resins with pendent epoxy functional groups were subsequently carbonated and then reacted with 1,10‐diaminodecane (90°C, 24 h) to form rigid side chains via hydroxyurethane linkages. Manipulating template functionality (2–11 urethane linkages out of 35 backbone units) yielded crosslinked networks with Young's moduli from 0.1 to 71.9 MPa while decreasing tensile elongation at break from 105% to 10%. Swelling ratios (SR) of the networks in tetrahydrofuran (THF) decrease as urethane linkage concentration increases, indicating tighter networks, consistent with the rheologically obtained molecular weight between crosslinks. Gel content indicated less than 15% of the networks are soluble in THF. The HNIPU networks derived show their ready tunability by simply changing the precursor functionality.

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Synthesis of non‐isocyanate polyurethanes with high‐performance and self‐healing properties

Zhang,

Shuai,

et al. 2023

J of Applied Polymer Sci

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Due to the utilization of the potentially hazardous monomer, isocyanate compound, polyurethanes (PUs) with good properties are restricted in several fields, such as bio‐engineering. Non‐isocyanate polyurethanes (NIPUs) with high overall performance and self‐healing properties were synthesized by dicarbamate, bio‐based isosorbide (IS) and polycarbonate diols (PCDLs) through a solvent‐free and ecologically friendly melt polycondensation route. Previously, few bio‐based monomers have been introduced into polycondensation reactions of PUs. Chemical structures of NIPUs were analyzed by Fourier transform‐infrared spectroscopy (FT‐IR), proton nuclear magnetic resonance (1H NMR) and gel permeation chromatography (GPC). With changing the IS content and the molecular weight of PCDL, the obtained NIPUs had linear structures and high molecular weights ranging from 3.3 × 104 to 5.9 × 104 g/mol. Results of tensile testing, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) suggested NIPUs had well thermal and mechanical properties, with Td,5% above 286.2°C and tensile strength between 8.0 and 16.7 MPa due to the crystallization and the hydrogen bonding interactions. Furthermore, the NIPUs exhibited self‐healing ability and recyclability, having great potential for industrialization.

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Mechanically strong non-isocyanate polyurethane thermosets from cyclic carbonate linseed oil

Abstract: Non-isocyanate polyurethanes (NIPU) from renewable resource have attracted much attention for significant benefit for sustainable development and green production. However, the low molar mass and poor mechanical properties of NIPU...

Cited by 24 publications

References 39 publications

Versatile Epoxidized Soybean Oil-Based Resin with Excellent Adhesion and Film-Forming Property

Versatile Epoxidized Soybean Oil-Based Resin with Excellent Adhesion and Film-Forming Property

Design of crosslinked networks with hydroxyurethane linkages via bio‐based alkyl methacrylates and diamines

Synthesis of non‐isocyanate polyurethanes with high‐performance and self‐healing properties

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