Recyclable, malleable and intrinsically flame-retardant epoxy resin with catalytic transesterification

Chen, Jiahui; Lu, Jiong; Pu, Xiaolu; Chen, Li; Wang, Yu‐Zhong

doi:10.1016/j.chemosphere.2022.133778

Cited by 50 publications

(10 citation statements)

References 57 publications

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“…After three shape memory cycles, their R f values still exceed 93%. Note that among previously reported flame retarding SMPs, only some of them were provided specific shape memory data (R f = 58.0%-100%, R r = 43.4%-98.0%, Table S1), 5,6,11,[13][14][15][16][17]20 but only one belongs to halogenfree and phosphorus-free flame retarding shape memory thermosetting resin and it has low R r (43.4%). 5 Therefore, it is reasonable to state that the three MD-x resins reported herein have superior shape memory properties (R f = 93.7%-97.2%, R r = 94.1%-97.9%), this is attributed to their unique crosslinked network, that is, which contains not only aromatic structure formed through "Ene" reaction and "Diels-Alder" reaction as the stationary phase, but also flexible aliphatic chains and Si O Si structure as the reversible phase.…”

Section: Shape Memory Propertymentioning

confidence: 99%

“…Reviewing the literatures in the SCI database by June 6, 2022, there are 19 articles related on flame retardant SMPs including thermoplastics and thermosets (Table S1), [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] from which three problems are generally found. First, most SMPs get their flame retardancy from phosphorus-related flame retardants, however, phosphorusrelated flame retardants have been reported to cause eutrophication of the water bodies 24 ; moreover, they also tend to degrade thermal stability of thermally resistant resins.…”

Section: Introductionmentioning

confidence: 99%

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Thermally resistant and strong shape memory bismaleimide resin with intrinsic halogen‐free and phosphorus‐free flame retardancy

Zhou

Yuan

Liang

et al. 2022

J of Applied Polymer Sci

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Fabricating thermally resistant and strong shape memory bismaleimide resin with intrinsic halogen-free and phosphorus-free flame retardancy is still an interesting issue with significant challenge. Herein, a new bismaleimide (MSi) containing siloxane structure was synthesized, which was copolymerized with 2,2 0 -diallylbisphenol A to develop three new resins coded as MD-x, x represents the molar ratio of allyl to maleimide. The composition-structure-performance relationship and mechanism of MD-x resins are systematically studied. All MD-x resins not only show self-distinguish feature, but also have high glass transition temperatures (127.4-160.1 C), high impact strengths (12.09-18.77 kJ/m 2 ), high flexural strengths (91.3-97.5 MPa) and excellent shape memory properties, their shape fixation rates and shape recovery rates exceed 93% after three shape memory cycles. These attractive and competitive comprehensive performances demonstrate that the problems for halogen-free and phosphorus-free flame retardant shape memory polymers have been successfully solved, this is derived from the unique structure of MD-x resins.

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Section: Shape Memory Propertymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermally resistant and strong shape memory bismaleimide resin with intrinsic halogen‐free and phosphorus‐free flame retardancy

Zhou

Yuan

Liang

et al. 2022

J of Applied Polymer Sci

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“…[ 28 ] Many epoxy vitrimers have since been reported, featuring excellent properties. [ 29–77 ] Other reported vitrimers are based on polybutadienes, [ 78–82 ] polyurethanes, [ 83–99 ] polyhydroxyurethanes, [ 100,101 ] polyurethane urea, [ 102,103 ] polyesters, [ 104–115 ] polycarbonates, [ 116 ] and polyimides. [ 117,118 ] These materials have low‐to‐medium‐to‐high glass transition temperatures, with polyimide vitrimer achieving T g of 274 °C and a 5% weight loss temperature of 429 °C.…”

Section: Introductionmentioning

confidence: 99%

High‐Performance Vitrimeric Benzoxazines for Sustainable Advanced Materials: Design, Synthesis, and Applications

Anagwu

Thakur

Skordos

2022

Macro Materials & Eng

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Polybenzoxazines are high-performance materials capable of replacing conventional thermosets such as phenolics, epoxies, and bismaleimides in composites manufacturing due to their excellent thermomechanical and chemical behavior. Their versatility and compatibility with biobased precursors make them an attractive option as composite matrices. Like other thermosets, polybenzoxazines are not recyclable and cannot be reprocessed. Incorporating dynamic bonds in benzoxazine monomers can produce vitrimeric polybenzoxazines, which can potentially overcome this limitation and can be tuned to exhibit smart functionalities such as self-healing and shape memory. Dynamic bond exchange mechanisms for vitrimer development such as transesterification, imine bond, disulfide exchange, transamination, transcarbamoylation, transalkylation, olefin metathesis, transcarbonation, siloxane-silanol exchange, boronic ester, silyl ether exchange, and dioxaborolane metathesis are potentially applicable to benzoxazine chemistry, with disulfide bond and transesterification having successfully vitrimerized benzoxazines with topological transitions at −8.5 and 88 °C, respectively. Benzoxazine vitrimers featuring glass transitions of 193, 224, and 222-236 °C are now known. These place polybenzoxazines at the forefront of the development of reprocessable and recyclable thermosetting polymers and composite matrices.

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“…Meanwhile, the FTIR tests of EP and 2%HPDAl/EP residues maintained in the muffle furnace at different temperatures were performed, and the curves are shown in Figure 5 a,b. Some structural information of the char residues was revealed: -OH or -NH (3430 cm −1 and 1620 cm −1 ), -CH 3 (2960 cm −1 ), -CH 2 (2850 cm −1 ), C-O-C (1265-1010 cm −1 ), C=O (1740 cm −1 ), C-N (1320 cm −1 ), and benzene ring (1510-1450 cm −1 , 815 cm −1 , and 740 cm −1 ) [ 35 ]. The big difference was that P=O (1200 cm −1 ), P-O (1120 cm −1 ), and P-O-C (919 cm −1 ) appeared in 2%HPDAl/EP, and there were still intense absorption peaks up to 700 °C.…”

Section: Resultsmentioning

confidence: 99%

A Phosphorous-Based Bi-Functional Flame Retardant Based on Phosphaphenanthrene and Aluminum Hypophosphite for an Epoxy Thermoset

Liu

Wei

et al. 2022

IJMS

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A phosphorous-based bi-functional compound HPDAl was used as a reactive-type flame retardant (FR) in an epoxy thermoset (EP) aiming to improve the flame retardant efficiency of phosphorus-based compounds. HPDAl, consisting of two different P-groups of aluminum phosphinate (AHP) and phosphophenanthrene (DOPO) with different phosphorous chemical environments and thus exerting different FR actions, exhibited an intramolecular P-P groups synergy and possessed superior flame-retardant efficiency compared with DOPO or AHP alone or the physical combination of DOPO/AHP in EP. Adding 2 wt.% HPDAl made EP composites acquire a LOI value of 32.3%, pass a UL94 V-0 rating with a blowing-out effect, and exhibit a decrease in the heat/smoke release. The flame retardant modes of action of HPDAl were confirmed by the experiments of the scanning electron microscope (SEM), X-ray photoelectron spectroscopy (XPS), and thermogravimetry–Fourier transform infrared spectroscopy–gas chromatograph/mass spectrometer (TG-FTIR-GC/MS). The results indicate that the phosphorous-based FRs show different influences on the flame retardancy of composites, mainly depending on their chemical structures. HPDAl had a flame inhibition effect in the gas phase and a charring effect in the condensed phase, with a well-balanced distribution of P content in the gas/condensed phase. Furthermore, the addition of HPDAl hardly impaired the mechanical properties of the matrix due to the link by chemical bonds between them.

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Recyclable, malleable and intrinsically flame-retardant epoxy resin with catalytic transesterification

Cited by 50 publications

References 57 publications

Thermally resistant and strong shape memory bismaleimide resin with intrinsic halogen‐free and phosphorus‐free flame retardancy

Thermally resistant and strong shape memory bismaleimide resin with intrinsic halogen‐free and phosphorus‐free flame retardancy

High‐Performance Vitrimeric Benzoxazines for Sustainable Advanced Materials: Design, Synthesis, and Applications

A Phosphorous-Based Bi-Functional Flame Retardant Based on Phosphaphenanthrene and Aluminum Hypophosphite for an Epoxy Thermoset

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