Maleic Anhydride Copolymer Research Articles

Polymeric conjugates of cefotaxime and its release kinetics

The present study examines reaction products in the solution of antibiotic cefotaxime with succinic anhydride, maleic anhydride copolymer, and dialdehyde wheat starch. The reaction of cefotaxime with succinic anhydride is shown to produce succinamide; to maleic anhydride copolymer, cefotaxime is likely to bind via noncovalent intermolecular interactions. An azomethine derivative of oxidized polysaccharide with cefotaxime was found to form; the molar ratio of initial glucosidic units in starch, unreacted dialdehyde units, and those bonded to cefotaxime through the azomethine linkage is 0.204:0.606:0.19. Drug release from the obtained matrix form was studied in different biorelevant media (saline, phosphate buffer, and Tris-HCl buffer). The amount of cefotaxime released in ten hours was found to approach 100%. Its release proceeds in two phases. In the first phase (1–2 h), 35 (pH 7.14) to 70% (pH 7.4–8.0) of the drug substance is released into the solution, followed by a significant decrease in the release rate. The processing of kinetic data using the first-order and Higuchi equations revealed consistency with both models. The obtained rate constants increase in proportion to the solution pH. It is assumed that first, the azomethine bond hydrolysis occurs with the release of cefotaxime molecules from the polymer matrix; then, the macromolecules of oxidized starch residing on the surface are dissolved; due to an increase in the viscosity of the solution layer surrounding the conjugate particle, the hydrolysis rate decreases. In general, cefotaxime release from the conjugate proceeds as a pseudo-first-order reaction accompanied by diffusion processes.

A novel recyclable hydrolyzed nanomagnetic copolymer catalyst for green, and one-pot synthesis of tetrahydrobenzo[b]pyrans

Polymer-based catalysts have garnered significant interest for their efficiency, reusability, and compatibility with various synthesis processes. In catalytic applications, polymers offer the advantage of structural versatility, enabling functional groups to be tailored for specific catalytic activities. In this study, we developed a novel magnetic copolymer of methyl methacrylate and maleic anhydride (PMMAn), synthesized via in situ chemical polymerization of methyl methacrylate onto maleic anhydride, using benzoyl peroxide as a free-radical initiator. This polymerization process results in a robust copolymer matrix, which was subsequently hydrolyzed in an alkaline aqueous solution to introduce additional functional groups, yielding hydrolyzed PMMAn. These functional groups enhance the copolymer’s ability to support the deposition of magnetic nanoparticles and participate in catalytic reactions. Following hydrolysis, we fabricated a unique magnetic composite, Fe3O4@Hydrol-PMMAn, by in situ coprecipitating Fe3O4 nanoparticles onto the hydrolyzed copolymer, creating a stable nanocatalyst. The structural and magnetic properties of Fe3O4@Hydrol-PMMAn were thoroughly analyzed using FTIR, XRD, SEM, EDX, VSM, and TGA. The Fe3O4@Hydrol-PMMAn nanocatalyst demonstrated remarkable catalytic performance in synthesizing tetrahydrobenzo[b]pyran derivatives through a three-component reaction, conducted without solvents to support green chemistry principles. A series of reaction parameters were optimized, including solvent choice, catalyst loading, and recyclability. The catalyst performed efficiently across a broad range of aldehydes, delivering high product yields (81–96%) with rapid reaction times (5–30 min) at a low catalyst loading of 0.015 g. A hot filtration test confirmed the heterogeneous nature of the nanocatalyst, which could be recycled up to four cycles with minimal loss in activity. The high yield, short reaction time, solvent-free conditions, and excellent reusability make Fe3O4@Hydrol-PMMAn a promising catalyst. These findings underscore its potential for converting waste products into valuable compounds, highlighting its utility in organic transformations and sustainable synthesis practices. Collectively, this work demonstrates that Fe3O4@Hydrol-PMMAn is highly effective for organic compound synthesis, advancing the development of versatile, sustainable nanocatalysts.

Kinetics and scale inhibition application studies towards bulk and RAFT copolymerization of maleic anhydride and acrylic acid

Poly(maleic anhydride) (PMA) is commonly reckoned as a better water scale inhibitor than poly(acrylic acid) (PAA) since each maleic anhydride unit can supply two carboxylic acid groups. However, pure PMA is difficult to achieve because the steric effect of its monomer MA. Herein, we synthesize copoly(MA-AA) copolymer by bulk polymerization method (bulk-copoly(MA-AA)), which avoids the use of any solvents which have to be removed afterwards. In addition, we also synthesize copoly(MA-AA) by reversible addition-fragmentation chain transfer (RAFT) polymerization method to afford RAFT-copoly(MA-AA) with low polydispersity index (PDI) less than 1.2, and the performance of RAFT-copoly(MA-AA) in water scale inhibition is more excellent relative to bulk-copoly(MA-AA). We also synthesize other copoly(MA-AA) copolymers by varying the molar ratio of MA to AA to study the polymerization mechanism. Through the static scale inhibition experiment, it is concluded that when the concentration of copoly(MA-AA) is 80 mg/L, the scale inhibition performance of RAFT-copoly(MA-AA) can reach 96.50 % which is the best among the control samples. It is also found that only 1:1 alternating copolymerization of MA and AA could be achieved as demonstrated by 1H nuclear magnetic resonance spectra of the copolymers, evidencing the strong steric hindrance of MA for its homo-polymerization.

Fabrication of PVC-based electromagnetic interference shielding composite film by positively charged SMA enhancing the dispersibility of carbon nanomaterial

To address the weak binding force and poor dispersion stability of carbon (C) nanoparticles in current non-covalent modification methods, we employed organic amine-grafted styrene maleic anhydride copolymers (SMA-N) to modify C nanoparticles (C@SMA-N) through π–π conjugation and positive charge interactions. The obtained C@SMA-N has excellent dispersion in N, N-dimethylacetamide (DMAc), which is attributed to the enhanced steric hindrance and electrostatic repulsion from the grafted organic amine chains. To study the impact of surface modification on the electromagnetic interference shielding effectiveness (EMI SE), C@SMA-N was used as a conductive filler in polyvinyl chloride (PVC) composite films, which exhibits a higher EMI SE performance than pristine C nanoparticles. Particularly, the obtained C@SMA-N using polyether amine (PEA) (C@SMA-PEA) exhibits a better EMI SE performance. By optimizing the SMA-PEA grafting parameters, the PVC/C@SMA-PEA composite films transition from insulators to conductors at a C@SMA-PEA content of 0.3 wt%. To achieve a higher EMI SE performance, the filler content, mixed filler composition, and film thickness were optimized. The results indicate that with a total filler content of 20 wt% and a mixed filler comprising fibrous form carbon nanotubes (CNT) and particles form carbon black (CB) in a 10:1 mass ratio (CB@SMA-PEA to CNT@SMA-PEA), the composite film has a thickness of 0.08 mm and an EMI SE value of 20.2 dB. Increasing the thickness to 0.2 mm enhances the EMI SE value to 31.5 dB. These findings indicate that thinner films have a higher EMI SE performance and promising application prospects in the field of electromagnetic shielding.

Vinyl Ether Maleic Acid Polymers: Tunable Polymers for Self-Assembled Lipid Nanodiscs and Environments for Membrane Proteins.

Native lipid bilayer mimetics, including those that use amphiphilic polymers, are important for the effective study of membrane-bound peptides and proteins. Copolymers of vinyl ether monomers and maleic anhydride were developed with controlled molecular weights and hydrophobicity through reversible addition-fragmentation chain-transfer polymerization. After polymerization, the maleic anhydride units can be hydrolyzed, giving dicarboxylates. The vinyl ether and maleic anhydride copolymerized in a close to alternating manner, giving essentially alternating hydrophilic maleic acid units and hydrophobic vinyl ether units along the backbone after hydrolysis. The vinyl ether monomers and maleic acid polymers self-assembled with lipids, giving vinyl ether maleic acid lipid particles (VEMALPs) with tunable sizes controlled by either the vinyl ether hydrophobicity or the polymer molecular weight. These VEMALPs were able to support membrane-bound proteins and peptides, creating a new class of lipid bilayer mimetics.

Detection of Sulfonamide Antibiotics Using an Elastic Hydrogel Microparticles-Based Optical Biosensor.

Sulfonamide antibiotics were the first synthetic antibiotics on the market and still have a broad field of application. Their extensive usage, wrong disposal, and limited degradation technologies in wastewater treatment plants lead to high concentrations in the environment, resulting in a negative impact on ecosystems and an acceleration of antibiotic resistance. Although lab-based analytical methods allow for sulfonamide detection, comprehensive monitoring is hampered by the nonavailability of on-site, inexpensive sensing technologies. In this work, we exploit functionalized elastic hydrogel microparticles and their ability to easily deform upon specific binding with enzyme-coated surfaces to establish the groundwork of a biosensing assay for the fast and straightforward detection of sulfonamide antibiotics. The detection assay is based on sulfamethoxazole-functionalized hydrogel microparticles as sensor probes and the biomimetic interaction of sulfonamide analytes with their natural target enzyme, dihydropteroate synthase (DHPS). DHPS from S. pneumoniae was recombinantly produced by E. coli and covalently coupled on a glass biochip using a reactive maleic anhydride copolymer coating. Monodisperse poly(ethylene glycol) hydrogel microparticles of 50 μm in diameter were synthesized within a microfluidic setup, followed by the oriented coupling of a sulfamethoxazole derivative to the microparticle surface. In proof-of-concept experiments, sulfamethoxazole, as the most used sulfonamide antibiotic in medical applications, was demonstrated to be specifically detectable above a concentration of 10 μM. With its straightforward detection principle, this assay has the potential to be used for point-of-use monitoring of sulfonamide antibiotic contaminants in the environment.

Low-Dose Hydrate Formation Inhibitors Derived from Copolymers of Maleic Anhydride and Isopropylacrylamide Amidated by Dibutylaminopropylamine

Low-Dose Hydrate Formation Inhibitors Derived from Copolymers of Maleic Anhydride and Isopropylacrylamide Amidated by Dibutylaminopropylamine

Experimental and theoretical insight into the use of maleic anhydride copolymer and modified sulfamic acid for removing oilfield blockage

In the process of oil production, the problem of oilfield production decline due to blockage is becoming more and more serious. To improve the exploitation efficiency of traditional fuel, it is very important to remove the blockage and inhibit the formation of the blockage. In this study, the primary constituents of the blockages in this oilfield were identified as asphaltene (organic blockage) and calcium carbonate (CaCO3, inorganic blockage). To address these blockages, maleic anhydride copolymer (MAC-1, MAC-2, and MAC-3) with different chain lengths were polymerized by maleic anhydride and allyl polyoxyethylene ether, which were used to disperse organic blockages. Additionally, modified sulfamic acid (MSA-1, MSA-2, and MSA-3) with different chain lengths were synthesized by sulfamic acid, polyethylene glycol, and lauroyl chloride, which were used to dissolve inorganic blockages. The efficacy of these agents in terms of blockage removal, scale inhibition capability, corrosion rate, and compatibility with formation water were comprehensively evaluated. Results showed that MAC-2, which possesses a moderate chain length, and MSA-1, which has a shorter chain length, demonstrated an optimal synergistic effect on blockage dissolution at concentrations of 4 wt% for MAC-2 and 5 wt% for MSA-1. The dissolution rate of this combination was 81.18 %, with a scale inhibition rate of 95.7 %. The corrosion rate increased with temperature, and the agents maintained good compatibility with the formation water. To elucidate the mechanism underlying the effectiveness of MAC, the interaction between MAC and asphaltene was simulated by molecular dynamics (MD). These simulations indicated that MAC-2 and asphaltene exhibit the highest interaction energy (-64.2618 kcal/mol). Furthermore, we investigated the dissolution kinetics of CaCO3 in MSA solutions and determined that the reaction between MSA and CaCO3 was first-order, with a reaction rate constant of 1.6 × 10−2 min−1. The insights gained from this study offer a valuable experimental and theoretical foundation for enhancing productivity in similar oilfields.

Ionic Liquid‐Supported Single‐Sodium‐Ion‐Conducting Styrene‐Maleic Anhydride Copolymer for Energy Storage Devices

Wide‐ranging research has been done on ionic liquid (IL)‐incorporated conducting polymers in energy storage devices. Herein, by taking the reaction advantage of styrene maleic anhydride (SMA) copolymer with sodium hydroxide, a sodium ion having polymeric material as an electrolyte is synthesized. 1,8‐Diazabicyclo[5.4.0]undec‐7‐enium acetate (DBU acetate) is prepared as an IL and added to the prepared polymer electrolyte to increase the matrix flexibility, semisolid nature, and ionic mobility inside the matrix. This semisolid sodium ion‐based electrolyte shows conductivity in the order of 10−5 S cm−1 and an electrochemical stability window of 2.52 volts with >97% of ionic transference. It also shows the diffusivity constant in the order of 10−4 m2 s−1 and ionic mobility in the order of 10−3 m2 v−1 s−1 at 30 °C. The hydrogel matrix shows a correlated type of hopping with a power exponent <1 at 30 °C with low‐energy requirement of ionic transport, that is, 0.709 eV. A high amount of capacitance is associated with electrolyte that has an insignificant electrode contribution. On behalf of these findings, SMA‐IL‐based semisolid polymer electrolyte confirms its potential for application in sodium ion‐based energy storage systems.

Enzyme‐Like Catalysis of Vinyl Copolymer Carrying Boron Directly Connected to Backbone: Catalytic Esterification through Cooperation of Boron with Neighboring Carboxylic Anhydride

AbstractAlternating‐rich copolymer of vinylboronic acid pinacol ester (VBpin) and maleic anhydride (MAH) was found to catalyze direct dehydrative esterification of carboxylic acid and alcohol. The key to the catalytic function is the activation of the MAH unit by the neighboring Lewis acidic boron directly connected to the backbone through the formation of five‐membered ring. The effects of the side‐chain cooperation were clarified through comparisons with the polymers having similar structures and a conventional titanium catalyst as well as the analyses of reactions with carboxylic acid or alcohol. The catalytic activity was enhanced as the molecular weight was higher, which is owing to the structural feature that boron is directly attached to the backbone. The cooperative catalysis is of interest because of its conceptual similarity with enzyme.

Maleic Anhydride-Derived Copolymers Conjugated with Beta-Lactam Antibiotics: Synthesis, Characterization, In Vitro Activity/Stability Tests with Antibacterial Studies

The synthesis and characterization of biocompatible three different maleic anhydride co-polymer conjugated with two different beta-lactam antibiotics at in vitro conditions were conducted. The polymer–drug conjugates were synthesized by coupling β-lactam antibiotics via amide bonds to the copolymer. In this work, six different drug-functionalized maleic anhydride copolymers (DFMACs) were synthesized by the chemical conjugation method. This method is based on the ring-opening reaction of the anhydride ring of the copolymer to form an amide bond linking the drug. The synthesized DFMACs were characterized by 1H NMR and FTIR/ATR spectroscopies and analyses were carried out by UV/VIS spectroscopy and Zeta-sizer instrument in detail with consecutive antibacterial tests. The existence of a newly formed amide covalent bond between the drug and the copolymer chains was confirmed by 1H NMR and FTIR/ATR studies. This is the first report on the application of the selected branched biodegradable polymeric matrices for the covalent conjugation of ampicillin and cefalexin. Optimum stability and activity conditions for the synthesized DFMACs were determined. Analyses were conducted under in vitro conditions including varying pH values and simulated body fluids as a function of time to obtain new drug delivery system candidates for the two different antibiotics.

Enzyme-Like Catalysis of Vinyl Copolymer Carrying Boron Directly Connected to Backbone: Catalytic Esterification through Cooperation of Boron with Neighboring Carboxylic Anhydride.

Alternating-rich copolymer of vinylboronic acid pinacol ester (VBpin) and maleic anhydride (MAH) was found to catalyze direct dehydrative esterification of carboxylic acid and alcohol. The key to the catalytic function is the activation of the MAH unit by the neighboring Lewis acidic boron directly connected to the backbone through the formation of five-membered ring. The effects of the side-chain cooperation were clarified through comparisons with the polymers having similar structures and a conventional titanium catalyst as well as the analyses of reactions with carboxylic acid or alcohol. The catalytic activity was enhanced as the molecular weight was higher, which is owing to the structural feature that boron is directly attached to the backbone. The cooperative catalysis is of interest because of its conceptual similarity with enzyme.

Recognition and detection of histamine in foods using aptamer modified fluorescence polymer dots sensors

Histamine has been known as a momentous cause of biogenic amine poisoning. Therefore, the content of histamine in foods is strictly required to be controlled within a certain range. Here, an aptamer fluorescent sensor was developed for detection of histamine. Poly [(9, 9-di-n-octylfluorenyl-2, 7-diyl)-alt-(benzo [2,1,3] thiadia-zol-4, 8-diyl)] (PF8BT) and the styrene maleic anhydride copolymer (PSMA) were used for the preparation of PF8BT-Polymer dots (PF8BT-Pdots). PF8BT-Pdots and the cyanine3-phosphoramidite (Cy3) were linked through aptamer to achieve the ratiometric detection for histamine. PF8BT-Pdots were partly quenched by Cy3 due to the fluorescence resonance energy transfer (FRET), when the histamine molecule was recognized by aptamer on the surface of PF8BT-Pdots. A linear range (3–21 μmol/L) was obtained for histamine detection with a low limit of detection (LOD = 0.38 μmol/L). PF8BT aptamer Pdots (PF8BT-A) were used to detect histamine in simply treated aquaculture water and tuna. The cell imaging of HeLa cells presented a good biosecurity and outstanding fluorescent imaging capability of PF8BT-A. The aptamer fluorescent sensors provided a new platform for rapid and accurate detection of histamine in aquatic products and had great potential for the application in food safety and quality control.

Amphiphilic molecules affording efficient aqueous degradation of unsaturated polyester resin

Enormous challenges have been encountered in the degradation and recycling of unsaturated polyester resin (UPR) in water, primarily due to its water resistance. Herein, a novel, efficient and green catalytic system of methanesulfonic acid (MSA)/sodium laurylsulfonate (SLS) was proposed to aqueously degrade UPR under mild conditions (200°C). This method is considerably milder compared to other reported works based on aqueous hydrolysis (230°C-380°C). What's more, amphiphilic SLS as a phase transfer reagent enhanced the concentration of catalyst at the H2O-UPR interface, which facilitated the mass transfer between organic motifs with inorganic reagents and thus accelerated the reaction. The NMR and FT-IR characterizations indicated the ester bonds were cleaved via hydrolysis with H2O catalyzed by MSA, and high value-added products, i.e., copolymer of styrene and maleic anhydride (SMA) and phthalic acid (PA), were reclaimed by a simple separation process, with the yield of 86.77% and 84.37%, respectively. Furthermore, a viable mechanism for degradation was proposed through the degradation performance of the model compounds. This study provides a practical approach for the chemical degradation and conversion of other resins containing ester bonds.

Preparation of transparent AlON ceramics with controlled shapes by a novel spontaneous coagulation casting and pressureless sintering method

Aluminum oxynitride (AlON) exhibits excellent mechanical properties and good optical transparency in the ultraviolet to near-infrared range and can be used in military and civilian fields. However, the troublesome molding of AlON, especially for complex shapes, limits its promotion and application. Therefore, transparent AlON ceramics with complex morphologies were prepared for the first time by a novel spontaneous coagulation casting (SCC) and pressureless sintering method. In this study, we report a simple carbothermal reduction and nitridation (CRN) method for synthesizing high-purity AlON powder, which is especially suitable for wet casting without anti-hydration treatment. The dispersion and gelation behavior of AlON slurries by isobutene maleic anhydride copolymer (Isobam104) and tetramethylammonium hydroxide (TMAH) were extensively investigated. With the addition of 0.9 wt% Isobam104 and 15 mL/L TMAH, the AlON slurries can achieve a solids loading of up to 45 vol% with the lowest viscosity (460.4 mPa·s-10 r/min) and the AlON green body is free of cracks and deformation during drying and demolding processes. Finally, the AlON green bodies with square and polygonal irregular morphologies were fabricated via a simple SCC method. High transparent AlON ceramics of a maximum transmittance up to 77.3% at 2000 nm and 72.2% at 632 nm were obtained by pressureless sintered at 2000 °C for 6 h. The SCC method has great potential in preparing ceramics with controllable shapes.

Synthesis and modification of copolymers of stearyl methacrylate and maleic anhydride and study of their effect on low-temperature characteristics of diesel fuel

Polymer-analogous transformations have been used to modify copolymers of stearyl methacrylate with maleic anhydride synthesized under radical polymerization conditions using reversible chain transfer agents of various structures. It has been established that copolymer of stearyl methacrylate with maleic anhydride modified by 25% with octanol-1 has a high depressant effect for a pour point of minus 19°С and at the same time significantly reduces both the cloud point values and the maximum filterability temperature of diesel fuel. In this regard, the obtained modified copolymers may be of interest in terms of their practical use as fuel additives.

Constructing flame retardant silica nanoparticles through styrene maleic anhydride copolymer grafting for PC/ABS composites

Organic-inorganic hybrid particles have been prepared by grafting styrene maleic anhydride copolymer (SMA) onto reactive amino-modified silica nanoparticles. The SMA modified SiO2 (SMA-SiO2) was incorporated into polycarbonate (PC)/acrylonitrile-butadiene-styrene (ABS) composites (4:1, wt%/wt%) with bisphenol A bis (diphenyl phosphate) (BDP) to simultaneously improve the mechanical properties and flame retardancy. The mechanical properties of the sample containing SMA-SiO2 are apparently improved compared with that of samples containing unmodified SiO2. It is found that SMA-SiO2 tends to distribute at the phase interface of PC/ABS, and therefore improves the compatibility between PC and ABS. Besides, the peak of heat release rate (PHRR) and the total smoke production (TSP) of the PC/ABS composites are decreased by the presence of SMA-SiO2. It is suggested that SMA-SiO2 can form a flame retarding shell at the phase interface to protect ABS. In summary, both the mechanical properties and flame retardancy of PC/ABS composites are significantly improved due to the selective distribution of SMA-SiO2.

Sodium alginate hydrogel-encapsulated trans-anethole based polymer: Synthesis and applications as an eradicator of metals and dyes from wastewater

Clean and safe water resources are essential for environmental safety and human health. Hydrogels and biomass polymers have attracted considerable attention in recent years, considering their nontoxicity, controllable performance, and high adsorption capacity. The interpenetrating network described here is a combination of a biomass polymer and a hydrogel adsorbent was established, the biomass polymer microspheres were first prepared with the combination of biomass monomer trans-anethole and maleic anhydride copolymer. A simple, environmentally friendly, and facile method of incorporating biomass polymer into sodium alginate biopolymer was developed by introducing the cross-linking agents calcium chloride and glutaraldehyde into the biomass polymer. Furthermore, the biomass polymer sodium alginate hydrogel (BP@SA/H) was characterized by FTIR, XPS, SEM, and XRD. In order to test materials' performance, the removal of pollutants and the adsorption study were also investigated after and before adsorption toward metals and dyes in water. We examined the factors influencing the materials, adsorption capability, such as initial concentration, time, absorbent amount, and pH. Moreover, the maximum adsorption values for Pb+2 and Cd+2 were 734.9 and 722 mg/g. While the adsorption toward RhB dye are 745 mg/g. In addition, the adsorption results were investigated using kinetic and isothermal models, demonstrating that biomass polymer hydrogel adsorption is chemisorption. Therefore, the as-developed biomass polymer sodium alginate hydrogel (BP@SA/H) is an exceptional multifunctional material that can be used to remove hazardous pollutants from wastewater.

Grafting α-aminoketone to SMA via highly efficient amide bond and their performances as macrophotoinitiators

Water-soluble macrophotoinitiators that can realize a high photoactivity together with low migration in waterborne photopolymerization systems are very necessary. However, the precise, highly efficient preparation of macrophotoinitiators remains a substantial challenge, such as grafting side chains according to stoichiometric ratios. Herein, based on styrene maleic anhydride copolymer (SMA) prepared by photopolymerization, water soluble macrophotoinitiators SMA5k-Ns and SMA13k-Ns series with controllable structure were successfully prepared through the amino bond of α-aminoketone small-molecule photoinitiator with maleic anhydride moieties. All of them exhibited excellent water dispersion properties, and solution photopolymerizations investigation showed they can be used as photoinitiators for radical polymerization with high conversion (up to 95%) in waterborne systems under LED@365–405 nm. Furthermore, the migration stabilities of these photoinitiators in photocured hydrogels were better than those of commercial photoinitiators. High efficiency and low migration make them have great potential applications in food packaging and biological materials.

Imidization of styrene–maleic anhydride copolymer for dispersing nano-SiO2 in water

Imidization of styrene–maleic anhydride copolymer for dispersing nano-SiO2 in water