INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
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2017
·
IF 2.843
Xiaobin Shen,Xiaoqing Liu,Jinggang Wang,Jinyue Dai,Jin Zhu
A bio-based epoxy 2,5-bis[(2-oxiranylmethoxy)methyl]-furan (BOF) has been synthesized from 2,5-furandimethanol and toughened by its Diels–Alder (DA) reaction adduct DA-BOF, which contained a flexible pendant chain. The chemical structures of the synthesized monomers were identified by nuclear magnetic resonance (1H NMR and 13C NMR). The thermal reversibility of DA-BOF was investigated by differential scanning calorimetry and ultraviolet–visible (UV–vis) spectroscopy. On the basis of the UV–vis results, the degree of retro Diels–Alder reaction was determined to be 25–27% in different cured systems. The study of the mechanical properties indicated that when the content of DA-BOF reached 50%, an 85% increase in impact strength could be obtained without seriously sacrificing its tensile strength or modulus. The strategy described in this work could help us to achieve a bio-based epoxy resin with increased impact strength and nearly unaffected tensile properties.
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RSC Advances
·
2016
·Vol. 6
·期 99
·96721-96728
·
IF 3.289
Xiaodong Zhang,Yuehua Cong,Baoyan Zhang
A effective way for covalent modification of reduced graphene oxide (RGO) by a chiral side-chain liquid crystalline oligomer (CSLCO) is firstly established. CSLCO consists chiral mesogenic units, non-mesogenic units with carboxyl groups and nematic mesogenic units with conjugated diene structure, the properties of materials should be determined by their structures. The conjugated diene structure can be grafted onto the RGO surface via Diels–Alder (DA) reaction, the chiral mesogenic units would enable CSLCO to have optical rotation and the carboxyl groups are expected to constitute coordination bonds with nano titanium oxide (TiO2) to fabricate composites. Spectroscopic tools (Raman and XRD) are used to confirm the completion of the DA reaction. Fourier transform infrared imaging system is utilized to analyze the dispersibility of RGO in the RGO–CSLCO composites. Due to the excellent thermal property of RGO and the interactions between RGO and CSLCO, the dispersed RGO can increase the glass transition and the decomposition activation energy of CSLCO. RGO can enhance the photocatalytic degradation of TiO2 due to its high electron mobility and large specific surface area. By preventing the aggregation of TiO2 and RGO, the CSLCO covalently modified RGO is better than pure RGO to enhance the photocatalytic degradation efficiency of TiO2.
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POLYMER COMPOSITES
·
2024
·
IF 4.8
Fenglei Zhang,Dongdong Han,Ning Xu,Xing Cui,Lei Zhang
Epoxy asphalt, a thermosetting polymer, is characterized by stable, irreversible internal chemical bonds that prevent recovery and spontaneous micro-crack healing, unlike conventional asphalt. This study introduces a renewable nano-modifier synthesized via esterification of carboxyl-functionalized carbon nanotubes (CNTs-COOH) and furfuryl alcohol (FA), termed CNTs-FA. The successful synthesis of CNTs-FA was confirmed through various microscopic techniques. Integrating CNTs-FA into epoxy asphalt materials, the optimal dosage was identified as 0.05% of the total epoxy asphalt mass using tensile tests and fluorescence microscopy. Thermal reversible effects and mechanisms were further analyzed through multiple regeneration cycles using tensile properties, fluorescence microscopy, and infrared spectroscopy. The study elucidates that the thermal reversibility in epoxy asphalt is facilitated by the Diels-Alder (DA) reaction between the conjugated diene structure in FA and the curing agent oleylamine. This research provides an effective solution to the non-recoverability and unrepairable micro-cracks of traditional epoxy asphalt mixtures. Highlights CNTs-FA was successfully prepared by esterification reaction. Using nano modification methods, introduce DA reaction into curing system. Renewable function of epoxy asphalt by DA reversible reaction.
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CARBOHYDRATE POLYMERS
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2020
·
IF 7.182
Chuanwei Lu,Xiaoliang Guo,Chunpeng Wang,Jifu Wang,Fuxiang Chu
Well-defined sustainable and recyclable thermoset elastomers derived from cellulose, fatty acid and furfural were successfully prepared via photoinduced metal-free ATRP and Diels-Alder (DA) reaction. Firstly, metal free ATRP was applied to prepare a range of thermoplastic cellulose graft copolymers with furfural groups. Then, a modified epoxidized soybean oil bearing 6-maleimidohexanoic group (ESOM) as a crosslinker was employed to perform DA reaction with furfural groups in these cellulose graft copolymers, by which the copolymer formed the dynamic crosslinked network and achieved the thermoset elastomers. The dynamic crosslinked network formed by DA reaction not only could increase the chain entanglement that was associated with the improved flexibility and could contribute to enhancing the mechanical strength up to 166 %, but also endowed these thermoset elastomers with recyclability, excellent shape memory and self-healing property. These thermoset elastomers can be used as self-healing strain sensor and wearable sensing devices after compounding them with carbon nanotubes.
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PubMed
高影响因子
JOURNAL OF POLYMER RESEARCH
·
2025
·Vol. 32
·期 12
·475
·
IF 2.8
Huang Min,Ge Huan,Lin Changhong,Zhang Zhengwei,Lin Mu,Mo Minhua,Yu Laiming,Levchenko Vladimir
Epoxy resin is a class of thermosetting polymer widely used in high performance protective coating due to its excellent physical and chemical properties. However, its inherent brittleness, along with difficulties in self-healing and recycling, limits its application. In this study, an epoxy resin coating was modified by the combination of Diels-Alder (DA) dynamic reversible bond and soft polyurethane segment. The DA bonds endowed the coating with the ability to repair damage and to be reprocessed, while the polyurethane chain segments, introduced through the DA reaction, can effectively enhance the toughness of the epoxy resin. The chemical structure and properties of the materials were characterized by FTIR, DSC, TGA and universal testing machine. The results showed that due to the presence of soft polyurethane segment, improve the corrosion resistance and wear resistance of coating. Additionally, the Diels-Alder bond endowed the material with excellent thermal self-healing and recycling properties. Therefore, this modified epoxy coating shows great potential in extending service life of metal materials and bringing considerable economic and social benefit.
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Polymer Chemistry
·
2020
·Vol. 11
·期 36
·5851-5860
·
IF 5.342
Shuhui Liu,Xiaoyan Liu,Zongke He,Liying Liu,Hui Niu
Designing reversibly cross-linked polymer materials is of great importance for repeated processing. In this work, a Diels–Alder (DA) reaction between furan and maleimide was utilized to achieve thermoreversible cross-linking of ethylene/propylene rubber (EPR) by first constructing EPR with furyl pendent groups and then adding bismaleimide molecules as a cross-linking agent. The kinetics of the cross-linking reaction was detected using the rheological test, and the apparent kinetic rate coefficient (kCL) and Arrhenius activation energy (Ea, CL) of the cross-linking reaction were determined. By adjusting the furyl content of EPR and the molecular structure of the bismaleimide, the influence of the furan/maleimide ratio as well as the bismaleimide structure on the Ea, CL value was investigated, which might provide support for the efficient realization of reversible cross-linking in polymers and the repeated processing of materials via DA chemistry.
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POLYMER SCIENCE SERIES B
·
2023
·
IF 1.2
Zhonglin Cao,Xiaoling Zuo
Abstract To increase the range of applications of bio-based polymer materials by attributing them self-healing ability is an efficacious way. It is an effective method to use Diels-Alder reaction for self-healing. However, self-healing materials synthesized by multifunctional monomers with Diels-Alder groups possess a low use temperature due to reversibility of DA bonds. In this study, the branched poly(furfuryl methacrylate) was synthesized from furfuryl alcohol, which is a biobased raw material prepared from crops. Using poly(furfuryl methacrylate) and bismaleimide, biobased self-healing polymeric materials were synthesized successfully based on the Diels-Alder reversible reaction. The Diels-Alder direct and reverse reactions occurred upon heating, resulting in self-healing of cracks on the polymer coatings. The thermal stability and use temperature of materials were also improved. All results demonstrated that synthesized materials possessed the characteristics of thermo-reversibility and self-healing and held great potential for self-healing coating applications.
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ACS Sustainable Chemistry & Engineering
·
2025
·
IF 7.3
Hongliang Ding,Lu Liu,Xiaohua Liu,Hongfei He,Lini Wu,Na Sun,Keqing Zhou,Wei Wang,Chao Ding,Bin Yu
Designing multifunctional polyurethane or polyurea elastomers that are simultaneously strong, recyclable, flame-retardant, and sustainable remains a major challenge in advanced elastomer research. Herein, a phosphorus-containing biobased diol (HMF–DOPO) was synthesized by the reaction between 5-hydroxymethylfurfural (HMF) and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO). Then, the tough, repairable, recyclable, and flame-retardant poly(urethane–urea) (PUA) elastomers cross-linked via reversible Diels–Alder (DA) bonds were developed. The synthesized elastomers exhibited excellent mechanical properties, while PUA–HMF-20% showed the best performance with a high tensile strength of 51.9 MPa and notable toughness of 167.6 MJ m–3. The thermally reversible DA reaction endowed PUA materials with excellent repair and recycling properties. The cut pieces can be reformed into a complete film during hot pressing and solvent reprocessing. Due to the existence of the phosphorus-containing structure, PUA–HMF elastomers also exhibited excellent self-extinguishing capability, while PUA–HMF-40% showed the highest limiting oxygen index (LOI) value of 27% and reached a V-0 rating in the UL-94 vertical burning test. In the cone test, both the peak heat release rate (PHRR) and total heat release (THR) values of the PUA–HMF samples were significantly reduced. This work provides a promising strategy to expedite high-performance sustainable advanced elastomers and expand the industrial application.
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
·
2015
·Vol. 53
·期 18
·2094-2103
·
IF 3.113
Xiao Kuang,Guoming Liu,Xia Dong,Xianggui Liu,Jianjun Xu,Dujin Wang
A reversibly cross-linked epoxy resin with efficient reprocessing and intrinsic self-healing was prepared from a diamine Diels-Alder (DA) adduct cross-linker and a commercial epoxy oligomer. The newly synthesized diamine cross-linker, comprising a DA adduct of furan and maleimide moieties, can cure epoxy monomer/oligomer with thermal reversibility. The reversible transition between cross-linked state and linear architecture endows the cured epoxy with rapid recyclability and repeated healability. The reversibly cross-linked epoxy fundamentally behaves as typical thermosets at ambient conditions yet can be fast reprocessed at elevated temperature like thermoplastics. As a potential reversible adhesive, the epoxy polymer with adhesive strength values about 3 MPa showed full recovery after repeated fracture-thermal healing processes. The methodology explored in this contribution provides new insights in modification of conventional engineering plastics as functional materials. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53 , 2094–2103
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2026
·
IF 8.7
Xiaojing Su,Fawei Xie,Yiyang Huang,Jiaran Wang,Xiaoting Pan,Kaifeng Liang,Zeyuan Lu,Kunquan Li,Hongqiang Li,Wenjian Wu
A cellulose-based superhydrophobic composite coating is prepared. • The coating is covalently crosslinked via Diels-Alder reaction and dehydration condensation. • The coating shows robust water repellency to resist various damage. • The coating enables dual repairability in surface chemistry and microstructure. • Efficient and repeatable recovery relies on dynamic Diels-Alder chemistry. Superhydrophobic surfaces frequently exhibit performance degradation in practical applications owing to the simultaneous deterioration of low-surface-energy components and micro-nano structures under chemical and mechanical stresses. To address this issue, designing self-repairable structures has emerged as a pivotal strategy for enhancing the long-term durability of superhydrophobic materials. However, the development of superhydrophobic materials capable of concurrently repairing both chemical damage and microstructural defects remains a formidable challenge. Furthermore, the repair mechanisms employed in existing microstructurally repairable superhydrophobic materials often compromise their heat resistance and chemical durability, thereby limiting their applicability in harsh environments. Herein, we propose a bio-based durable superhydrophobic composite coating with dual repairability for surface chemistry and microstructure. Furan-functionalized heterogeneous cellulose nanocrystals (FHCC) and maleimide-functionalized polydimethylsiloxane (MPDMS) were synthesized and crosslinked to form the FHCC-MPDMS coating via Diels-Alder (DA) cycloaddition reaction. Subsequent 1 H ,1 H ,2 H ,2 H -perfluorodecyltrimethoxysilane (PFDTS) modification yielded the superhydrophobic F-FHCC-MPDMS coating with a WCA of 157 o . DA covalent network endowed the coating with exceptional chemical stability against temperature, solvents, and acid/base. Importantly, the plasma-etched F-FHCC-MPDMS coating (superhydrophilicity with a WCA of 0 o ) was fully restored through thermal-driven rotation and rearrangement of MPDMS and PFDTS. Moreover, the retro-DA reaction triggered by both solvent and heat enabled localized MPDMS dissolution, regenerating hierarchical micro/nanostructures after abrasion damage and thereby efficiently recovering superhydrophobicity upon tetrahydrofuran immersion. This work demonstrates a bio-derived superhydrophobic coating with dual self-repair capability, offering a promising solution for durable applications in harsh environments.
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PubMed
高影响因子
IRANIAN POLYMER JOURNAL
·
2023
·Vol. 32
·期 10
·1307-1319
·
IF 3.1
Li Qinsheng,Li Yupeng,Li Yaru,Huang Qinghua,Hu Zhongyu,Yang Yuping,Xiong Zhenhua,Cheng Chuanjie
It is urgent and important to design and prepare functional polymers utilizing biomass or bio-based platform chemicals due to fossil resource/energy crisis. We designed and synthesized two linear polymers LP 1 and LP 2 from bio-based platform chemical furfural as well as other biomass-derived feedstock adipic acid and 1,6-hexadiamine using efficient and 100% atom-economy Passerini three-component reaction. The number-average molecular weights of LP 1 and LP 2 are 2189 da and 5464 da, respectively. The products LP 1 and LP 2 were crosslinked with N,N ´-4,4´-diphenylmethyene bismaleimide (BMI) through Diels–Alder cycloaddition reactions to form the corresponding polymer networks CP 1 and CP 2 , respectively. Both CP 1 and CP 2 showed good chemical resistance to acid and ethyl acetate, but relatively poor resistance toward base and THF. Gel fraction values of CP 1 and CP 2 were 82% and 74%, respectively, indicating that most of the linear segments of LP 1 and/or LP 2 were crosslinked after Diels–Alder reactions. Thermal property analysis indicated that the two polymer networks were at rubbery state as their T g values were 14.78 and 7.00 °C, respectively. Td 10 values of CP 1 and CP 2 were 151 °C and 131 °C, respectively. The presence of dynamic D–A bonds caused both CP 1 and CP 2 to exhibit intrinsic self-healable performance at 60 °C or higher. Furthermore, CP 2 also showed rapid self-healing behavior (within 3 min) under UV (360 nm) irradiation due to the existence of dynamic disulfide bonds in the main chain. Graphical abstract
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RSC Advances
·
2022
·Vol. 12
·期 28
·17990-18003
·
IF 4.036
Wenguang Yu,Xuefeng Gao,Zhicheng Yuan,Haihui Liu,Xuechen Wang,Xingxiang Zhang
The widespread use of graphene as a next-generation material in various applications requires developing an environmentally friendly and efficient method for fabricating functionalized graphene. Chemically, graphene can be used as an electron donor or attractor. Here, graphite was successfully exfoliated, and an in situ Diels–Alder reaction (D–A) was carried out to fabricate functionalized graphene with sole functional groups via mechanochemical ball milling. The reactivities of graphene acting as a diene or a dienophile were investigated. Few-layer (≤2 layers) graphene specimens were obtained by wet ball milling, heating in a nitrogen atmosphere, and solvent ultrasonic treatment. The ball-milling method was more effective than heating in a nitrogen atmosphere, and the [2 + 4] D–A of graphene was more dominant than the [4 + 2] D–A in the ball-milling process. The surface tension of functionalized graphene decreased, which provided a theoretical basis for the dispersion and exfoliation of graphite in a suitable solvent. Functionalized graphene still had a high electrical conductivity, which has far-reaching significance for functionalized graphene to be applied in electronic semiconductors and related applications. Meanwhile, functionalized graphene was applied to polymer composite fibers, the tensile strength and the Young's modulus could reach 780 MPa and 19 GPa. The volume resistivity was two orders of magnitude lower than that of pure fiber. Thus, the use of ball milling to efficiently exfoliate and in situ functionalize graphite will help to develop a strategy that can be widely used to manufacture nanomaterials for various application fields.
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