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Maleic Anhydride
Catalysis Science & Technology · 2024 · IF 4.4

One-pot synthesis of 1,4-butanediol via the deep hydrogenation of maleic anhydride over Cu–xMo/SiO2 catalysts

Kai Cui,Jiaming Yang,Yuli Jing,Junwen Chen,Chen Zhao,Peng Wu,Xiaohong Li

Sustainability issues have led to a gradual market expansion for the 1,4-butanediol (BDO) monomer of the biodegradable plastics to replace conventional plastics. Maleic anhydride (MA) can be derived from the oxidation of bio-based furfural or fructose. Although the hydrogenation of MA can produce a series of products, including succinic anhydride (SA), γ-butyrolactone (GBL), BDO and tetrahydrofuran (THF), the one-pot deep hydrogenation of MA to BDO or THF under mild conditions has been rarely reported in the literature until now. Herein, we report the production of BDO from the one-pot deep hydrogenation of MA over a Cu–0.03Mo/SiO2 catalyst, achieving 100% MA conversion and 88.3% BDO yield. The Cu–0.03Mo/SiO2 catalyst also showed good long-term stability without obvious loss in activity or BDO selectivity during a 160 h time-on-stream test. Doping Mo to Cu/SiO2 catalysts in an optimal amount adjusted the distribution of Cu0/Cu+ species and modulated the interaction of Cu–SiO2 and surface acidity, so that the activation of hydrogen, MA and relevant intermediates can become balanced, in addition to the restriction of side-reactions. This study provides potential for the green synthesis of BDO with non-precious Cu-based catalysts.

CAS / MDL: 12125-02-9 12054-85-2
研究领域: 化学工程 · 可持续发展 · 催化科学
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LANGMUIR · 2025 · IF 3.9

Mussel-Inspired Universal Anti-Fogging Coating Based on Maleic Anhydride Copolymers with Customizable Structural Design for Functional Properties

Kaihui Pan,Zexin Zhang,Yang Liu,Yihao Wang,Li Wang,Wantai Yang

In this study, poly(ethylene-alt-maleic anhydride) (PEMA) was selected as the backbone, and PEMA-g-DA/DMAPA was synthesized through an amidation reaction with dopamine (DA) and N,N-dimethylaminopropylamine (DMAPA). The antifogging performance, stability, universality, and antibacterial property after quaternization of the PEMA-DA-DMAPA coating were tested and analyzed. Experimental results showed that the PEMA-DA-DMAPA coating exhibited great antifogging performance, with the water contact angle (WCA) as low as 10.7°. The coefficient of friction of the PEMA-DA-DMAPA coating decreased significantly compared with that of the substrate. Even after 5 days of immersion or 60 cycling tests, the coating still maintained excellent antifogging properties. This coating can be widely applied to the surfaces of transparent substrates, such as poly(methyl methacrylate)(PMMA), polyethylene terephthalate (PET), and polycarbonate (PC). Specifically, the WCA on the PC surface dropped significantly from 89.5° to 11.9°. After quaternization, the coating exhibited notable antibacterial activity against Staphylococcus aureus (S. aureus), with a maximum antibacterial rate of 97.23%.

CAS / MDL: 62-31-7
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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Preparation of Peanut-Shaped PS Nanoparticles Through Emulsion Polymerization by Using Styrene-Maleic Anhydride Copolymer as the Cosurfactant

Min Deng,Chuxiang Zhou,Gang Wu,Yinan Xu,Shenwen Fang,Ming Duan

Anisotropic particles have garnered significant attention due to their unique structural characteristics, and emulsion polymerization is one of the synthesis strategies. In this study, for the first time, poly(styrene-maleic anhydride) (SMAA) and small-molecule surfactant were employed as the composite emulsifiers during the emulsion polymerization of styrene (St) for synthesizing peanut-shaped polystyrene (PS) nanoparticles. The results of NMR, FTIR, and SEM confirmed this method was reliable. Furthermore, the polymerization conditions were optimized by using particle morphology as the primary optimization parameter. The optimized polymerization conditions are as follows: St concentration of 11 wt%, emulsifier concentration of 0.6 wt% in water, the emulsifier being a composite system of sodium dodecylbenzenesulfonate (SDBS) and SMAA in a mass ratio of 1:2, initiator concentration of 0.5 wt% (relative to St mass), crosslinker dosage 0.6 wt% (relative to St mass), reaction temperature of 70°C, and the reaction duration of 6 h. The resulting polymer products exhibited a distinct peanut-like morphology, with an average particle diameter of 54.1 nm and an aspect ratio of 2.44. These findings provide some novel insights into the preparation of anisotropic particles.

研究领域: 材料科学 · 高分子化学 · 纳米技术 · 化学工程
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ANALYTICA CHIMICA ACTA · 2026 · IF 6.1

Preparation of styrene-maleic anhydride copolymer nanobrush chromatographic stationary phase and its application in phospholipid analysis of exosomes

Ping Wang,Meijuan Xue,Xinhui Guan,Xiaofei Gu,Xiaoqiang Qiao

Background Phospholipids in serum exosomes are promising biomarkers for breast cancer diagnosis. However, the separation of phospholipids by liquid chromatography presents several challenges due to their inherent structural heterogeneity and the presence of isomeric forms. Traditional columns often struggle with the overlapping retention times of phospholipid species, which can result in poor resolution and difficulty in accurate quantification. Furthermore, the varying polarities and hydrophobicities of different phospholipid classes necessitate specialized stationary phases to achieve optimal separation. This study aimed to develop a novel chromatographic material for the comprehensive analysis of phospholipids in complex biological matrices. Results In this study, a novel silica-based Sil-SMA-GMS copolymer brush stationary phase was fabricated for the first time via reversible addition-fragmentation chain transfer (RAFT) polymerization, using styrene-maleic anhydride (SMA) copolymer as the functional matrix and glycerol monostearate (GMS) as the derivatization reagent. Benefiting from the synergistic effects of hydrophobic moieties (benzene rings and long alkyl chains) and hydrophilic groups (carboxyl and hydroxyl groups) in the SMA copolymer, the prepared stationary phase exhibited a unique mixed hydrophilic interaction chromatography/reversed-phase liquid chromatography (HILIC/RPLC) retention mechanism. It demonstrated excellent separation selectivity and stability for both hydrophilic and hydrophobic small molecules, achieving a maximum column efficiency of 81,029 N/m. Notably, this stationary phase overcame the limitations of traditional single-mode chromatographic columns, enabling the simultaneous separation and analysis of phospholipids that vary in class, acyl chain length, and degree of unsaturation. Furthermore, by coupling the Sil-SMA-GMS column with mass spectrometry (MS), a non-targeted analytical method for serum exosomal phospholipids was developed. Applying this method to serum exosomes from breast cancer patients and healthy controls led to the identification of 9 major classes encompassing 200 phospholipid molecular subtypes, as well as the screening of phospholipid markers closely associated with breast cancer pathogenesis. Significance This work presents a novel chromatographic material for the efficient separation of phospholipids in complex biological samples and establishes a technical foundation for the construction of multidimensional lipidomics platform. This advancement provides crucial support for the screening of cancer-related biomarkers, elucidating tumor metabolic mechanisms, and exploring targeted therapeutic targets.

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JOURNAL OF POLYMER RESEARCH · 2015 ·Vol. 22 ·期 3 ·1-12 · IF 1.92

Compatibilization of polypropylene/recycled polyethylene terephthalate blends with maleic anhydride grafted polypropylene in the presence of diallyl phthalate

Zhu Yeling,Liang Changsheng,Bo Yang,Xu Shiai

Bi-functional co-agent, diallyl phthalate (DAP), −assisted melting free-radical grafting of maleic anhydride (MAH) on polypropylene (PP) is carried out by reactive extrusion. The PP/recycled polyethylene terephthalate (rPET) blends with and without PP-g-MAH/DAP (PP grafted with both MAH and DAP) are conducted on a twin-screw extruder. It reveals that the introduction of DAP can significantly enhance the grafting degree of MAH and decrease the chain scission of PP. The maximum extent of MAH grafting (1.5 wt.%) is obtained when DCP and MAH contents are 0.5 and 6.0 wt.%, respectively, and the DAP/MAH molar ratio is 0.3. Besides, differential scanning calorimetry (DSC) analysis shows that the crystallization temperature of grafted PP is higher than that of pure PP due to the nucleation of grafted groups. Fourier transform infrared spectroscopy (FTIR) analysis proves that chemical reactions take place between PP-g-MAH/DAP and rPET. In particular, scanning electron microscopy (SEM) observations demonstrate that, the PP/rPET blends compatibilized with PP-g-MAH/DAP show enhanced adhesion at the interface comparing with the binary PP/rPET blend, which is also proved by DSC measurements, dynamic mechanical analysis (DMA) and mechanical properties.

研究领域: 高分子科学 · 材料工程 · 塑料回收 · 反应性相容化
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2019 · IF 4.784

Super-tough poly (l-lactide) materials: Reactive blending with maleic anhydride grafted starch and poly (ethylene glycol) diacrylate

Chengdong Yang,Mi Zhou,Yi Lin,Chong Cheng,Fei Cheng,Wenlong Liu,Puxin Zhu

Super-tough poly ( l -lactide) (PLLA) without compromising its biodegradability and biocompatibility was fabricated by reactive blending with PLLA and maleic anhydride grafted starch (MS)/poly (ethylene glycol) diacrylate (PEGDA). PEGDA as reactive compatibilizer exhibits higher compatibilization efficiency and significant plasticization effect in PLLA matrix. Fourier transform infrared spectroscopy (FT-IR) confirmed that PEGDA monomer successfully located at the molecules of MS and some interesterification reactions occurred between PEGDA and PLLA. The ductility of PLLA materials were significantly improved, for example, the elongation of break increased to 298% at the optimum PLLA/MS/PEGDA content. Dynamic mechanical thermal analysis (DMTA) demonstrated the glass transition temperature of blends decreased with the contents of MS/PEGDA increasing. The differential scanning calorimeter (DSC) results revealed that cold crystallization temperature and melting temperature of blends were decreased with the augment of the contents of MS/PEGDA. Wide angle X-ray diffraction (WARD) and DSC certified that a high crystalline article was obtained through practical extrusion process, which could propagate shear yielding deformation to dissipate energy during tensile fracture. Scanning electron microscope (SEM) demonstrated that the blends with PEGDA did not exhibit a visible phase-separated morphology from cryogenic fractured surfaces compared with the blend without PEGDA.

CAS / MDL: 26570-48-9
研究领域: 材料科学 · 生物医学工程
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Science China-Chemistry · 2016 ·Vol. 59 ·期 4 ·459-465 · IF 2.429

Effects of poly-(p-phenylene terephthamide) powder coated with polydopamine on ethylene-propylene-diene-terpolymer grafted maleic anhydride

Yuan Ye,Deng Sufen,Song Shaokun,Hu Weibo,Dong Lijie

In this paper, we reported a technique for the surface modification of poly-( p -phenylene terephthamide) (PPTA) powder coated with polydopamine (PDOPA). We used air oxidation to self-polymerize dopamine (DOPA) to ensure that the PPTA powder was coated. Our results indicate that the modified surface of PPTA powder enhances compatibility with the polymer matrix without damaging its structure. Additionally, it is possible to control the coating thickness of PDOPA by regulating the reaction time. The modified PPTA powder improved the comprehensive property of ethylene-propylene-diene-terpolymer grafted maleic anhydride (EPDM- g -MAH), and it proved that this method can enhance the strength and electric insulativity of EPDM- g -MAH.

CAS / MDL: 62-31-7
研究领域: 材料科学 · 高分子化学
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MOLECULAR PHARMACEUTICS · 2017 · IF 4.44

Poly(vinyl methyl ether/maleic anhydride)-Doped PEG–PLA Nanoparticles for Oral Paclitaxel Delivery To Improve Bioadhesive Efficiency

Qian Wang,Chan Li,Tianyang Ren,Shizhu Chen,Xiaoxia Ye,Hongbo Guo,Haibing He,Yu Zhang,Tian Yin,Xing-Jie Liang,Xing Tang

Bioadhesive nanoparticles based on poly(vinyl methyl ether/maleic anhydride) (PVMMA) and poly(ethylene glycol) methyl ether-b-poly(d,l-lactic acid) (mPEG-b-PLA) were produced by the emulsification solvent evaporation method. Paclitaxel was utilized as the model drug, with an encapsulation efficiency of up to 90.2 ± 4.0%. The nanoparticles were uniform and spherical in shape and exhibited a sustained drug release compared with Taxol. m-NPs also exhibited favorable bioadhesive efficiency at the same time. Coumarin 6 or DiR-loaded nanoparticles with/without PVMMA (C6-m-NPs/DiR-m-NPs or C6-p-NPs/DiR-p-NPs) were used for cellular uptake and intestinal adhesion experiments, respectively. C6-m-NPs were shown to enhance cellular uptake, and caveolae/lipid raft mediated endocytosis was the primary route for the uptake of the nanoparticles. Favorable bioadhesive efficiency led to prolonged retention in the intestine reflected by the fluorescence in isolated intestines ex vivo. In a ligated intestinal loops model, C6-m-NPs showed a clear advantage for transporting NPs across the mucus layer over C6-p-NPs and free C6. The apparent permeability coefficient (Papp) of PTX-m-NPs through Caco-2/HT29 monolayers was 1.3- and 1.6-fold higher than PTX-p-NPs and Taxol, respectively, which was consistent with the AUC0–t of different PTX formulations after oral administration in rats. PTX-m-NPs also exhibited a more effective anticancer efficacy, with an IC50 of 0.2 ± 1.4 μg/mL for A549 cell lines, further demonstrating the advantage of bioadhesive nanoparticles. The bioadhesive nanoparticles m-NPs demonstrated both mucus permeation and epithelial absorption, and thus, this bioadhesive drug delivery system has the potential to improve the bioavailability of drugs that are insoluble in the gastrointestinal environment.

研究领域: 药学 · 纳米技术 · 药物递送系统 · 癌症研究
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INTERNATIONAL JOURNAL OF POLYMER ANALYSIS AND CHARACTERIZATION · 2017 · IF 0

Synthesis, characterization, and degradation behaviors of poly(D,L-lactide-co-glycolide) modified by maleic anhydride and ethanediamine

Jiale Cui,Zhihua Zhou,Yun Yang,Wenjuan Liu,Yunfei Zhao,Cheng Peng,Tianlong Huang,Hu Zhou,Lihua Liu,Qiao Zhang

In order to improve hydrophilicity and settle the acidity in hydrolysis, a novel ethanediamine (EDA) and maleic anhydride (MAH) modified poly(D,L-lactide-co-glycolide) (PLGA) polymer (EMPLGA) was synthesized. Fourier Transform Infrared Spectrometer (FTIR), Gel Permeation Chromatography (GPC), Nuclear Magnetic Resonance (1HNMR), titration and the water contact angles were employed to characterize the synthesized polymer. The effects of various polymerization conditions on weight average molecular mass (Mw), polydispersity index (PDI) and anhydride content of MPLGA were investigated. The degradation behaviors of PLGA, MPLA and EMPLGA were also studied by observation of the changes of the pH value of incubation medium, molecular weight and weight loss ratio for a time interval of 25 days in-vitro, respectively. The results showed that MPLGA with high anhydride content was successfully obtained by directly ring-opening polymerization and ethanediamine was further grafted onto MPLGA, and there is almost unchanged in Mw between MPLGA and EMPLGA polymers. The introduction of anhydride and amino groups improved the hydrophilicity of PLGA. A uniform degradation of EMPLGA was observed in comparison with an acidity-induced auto-accelerating degradation featured by PLGA and MPLGA. The results revealed that the introduction of ethanediamine into PLGA has weakened or neutralized the acidity of PLGA degradation products.

CAS / MDL: 301-10-0
研究领域: 材料科学 · 生物医学工程
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POLYMER COMPOSITES · 2022 ·Vol. 43 ·期 4 ·2175-2183 · IF 3.531

Enhanced breakdown strength and restrained dielectric loss of polypropylene/maleic anhydride grafted polypropylene/core-shell ZrO2@SiO2 nanocomposites

Lu Cheng,Wenfeng Liu,Ziqi Zhang,Yongcun Zhou,Shengtao Li

To simoutinusly achieve improved breakdown strength (BDS) and suppressed dielectric loss, a modified ternary nanocomposite composed of polypropylene (PP), maleic anhydride-grafted PP and core-shell structure SiO 2 @ZrO 2 nanoparticles is proposed. By tailoring the thickness of SiO 2 shell from 3 to 11 nm and the nanofillers content from 0.5 to 5 wt%, the particles disparsion is improved and meanwhile both the deep trap density and the interaction force between molecules are enhanced. In consequence, the restricted transportation of electrons along molecule chains as well as between chains together raise the DC BDS, that the BDS of optimum sample film reaches 430.8 kV/mm, 23% higher than neat PP. Besides, the ternary nanocomposites with SiO 2 @ZrO 2 less than 3 wt% maintain the tanδ below 0.3% at a broad frequency ranging from 0.1 Hz to 100 kHz, which is an extremely low level same as neat PP.

研究领域: 材料科学 · 电气工程
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APPLIED CLAY SCIENCE · 2020 · IF 4.605

Selective location of kaolin and effects of maleic anhydride in kaolin/poly(ε-caprolactone)/poly(lactic acid) composites

Xin Ge,Mingming Chang,Wei Jiang,Bangwen Zhang,Ruiguang Xing,Chaoke Bulin

In the present work, maleic anhydride (MA) and biphenyl peroxide (BPO) were used in the preparation of kaolin (K)/poly(ε-caprolactone) (PCL)/poly(lactic acid) (PLA) composites with melt compounding method. Composition and structure of the composites were characterized by Fourier transformed infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and field emission-scanning electron microscopy (FE-SEM). Mechanical properties and thermal behaviors of the composites were further investigated. Kaolin selectively located in poly(ε-caprolactone) domains and at the phase boundaries, which improved the mechanical properties of the composites due to their rigid structure and high modulus. Influences of maleic anhydride on dispersion state of kaolin and two-phase structure of the composites were explored and discussed. Maleic anhydride enhanced the interactions among kaolin, poly(lactic acid) and poly(ε-caprolactone). Meanwhile, it improved the dispersion state of kaolin in the composites. In the presence of both kaolin and maleic anhydride, tensile strength at room temperature and storage modulus at 40 °C were enhanced to 41.2 MPa and 3.9 GPa, respectively.

CAS / MDL: 94-36-0 1332-58-7
研究领域: 材料科学 · 化学工程
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Polymer Chemistry · 2022 ·Vol. 13 ·期 27 ·4054-4063 · IF 5.364

A facile approach for the preparation of poly(benzothiophene-alt-maleic anhydride) microspheres by self-stabilized precipitation polymerization

Tianxiao Chang,Hongyi Qi,Chenxi Liang,Yanbin Huang,Wantai Yang

Benzothiophene is an under-explored monomer for free radical polymerization. Here we report the preparation of poly(benzothiophene-alt-maleic anhydride) (PBTMA) microspheres with high yield by self-stabilized precipitation polymerization. The chemical structure of the PBTMA copolymer was characterized by 1H-NMR, 13C-NMR, FT-IR and MALDI-TOF MS analyses. The effects of various reaction parameters, including the reaction medium, the monomer concentration, the initiator concentration and the reaction time, on the morphology, particle size and molecular weight (Mn) of the resultant PBTMA microspheres were investigated systematically. The experimental results demonstrated that the PBTMA copolymer was an alternating copolymer, whose composition was independent of the monomer composition. Uniform PBTMA microspheres with the diameter in the range of 400 nm to 3000 nm and Mn up to 12 000 g mol−1 were easily prepared. PBTMA had good solubility in common polar organic solvents and possessed much higher thermal stability than other maleic anhydride copolymers. PBTMA also showed interesting fluorescence properties both in the solid state and in solution. This research has laid the foundation for the further development of PBTMA copolymers as a new material.

CAS / MDL: 108-67-8
研究领域: 高分子科学 · 材料科学 · 化学工程
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