Glycidyl Methacrylate-ethylene Glycol Dimethacrylate Research Articles

Magnetic field-induced self-assembly of urchin-like polymeric particles: mechanism, dispersity, and application in wastewater treatment

Pollutant treatment is critical in modern society and existing purification methods often cannot address this problem quickly and economically. Recently, hierarchically organized particles have attracted much academic attention in wastewater treatment because of their unusual geometry associated with the favorable properties of nanoscale units and three-dimensional assemblies synchronously. Here, we synthesized hierarchically organized Fe3O4/poly(glycidyl methacrylate-ethylene glycol dimethacrylate) (poly(GMA-EDMA)) meso-particles (UPPs) by a magnetic field-induced self-assembly strategy. Under the orientation of the external magnetic field, poly(GMA-EDMA) nanoparticles polymerized by GMA and EDMA organically self-assembled around Fe3O4 nanoparticles into mesoscale UPPs. The obtained UPPs showed high dispersity in both aqueous and organic solutions due to that the spikes on the surface of UPPs weaken attractive van der Waals forces between particles. The high dispersity in solutions guarantees the high mass transfer efficiency between UPPs and solutions. Moreover, the incorporation of Fe3O4 nanoparticles endows UPPs with a fast reversible macroscopic assembly & disassembly ability by controlling the external magnetic field, which is beneficial to the collection and regeneration of UPPs. Taking advantage of the features, we grafted iminodiacetic acid (IDA) on the surface of UPPs to obtain a heavy metal ion adsorbent. The IDA-modified UPPs showed high adsorption capacities, fast adsorption rates, and good recyclability for Cu2+ and Pb2+. Besides, the IDA-modified UPPs can allow to be loaded by β-FeOOH nanocatalyst, showing a good photocatalytic performance toward methylene blue, promising a great potential in wastewater treatment.

Schiff base network-1 incorporated monolithic column for in-tube solid phase microextraction of antiepileptic drugs in human plasma

A novel monolithic column incorporated with Schiff base network-1 (SNW-1) was prepared for in-tube solid phase microextraction (SPME) of antiepileptic drugs. The SNW-1 nanoparticles was synthesized by a solvent thermal method and embedded in the poly(glycidyl methacrylate-ethylene glycol dimethacrylate) (GMA-EGDMA) monolithic column by in situ polymerization. The amount of SNW-1 in polymerization solution for preparation of monolithic column was optimized. Fourier transform infrared spectrometry and scanning electron microscope were used to characterize the obtained monolithic column. The SNW-1-monolithic column was connected to the high-performance liquid chromatography (HPLC) system and applied for online extraction and analysis of antiepileptic drugs. The extraction conditions including sample solution flow rate, desorption time, acetonitrile content, pH of sample solution and sample volume were investigated. Under optimal conditions, the proposed SPME-HPLC method showed high extraction efficiency, good linearity, low limits of detection (0.2 ng/mL) and good repeatability (relative standard deviations < 2.41%). This method was also applied to the analysis of antiepileptic drugs in human plasma samples and the recoveries were in the range of 88.6–106.1% with RSDs less than 3.51%.

Glycidyl Methacrylate-ethylene Glycol Dimethacrylate Copolymers with Varied Pore Structures Prepared with Different Reaction Parameters

Abstract Copolymers based on glycidyl methacrylate (GMA) are considered attractive as sorbents because the epoxy groups can be easily converted into other groups. Studies involving the influence of the synthesis parameters on the morphological characteristics of these copolymers are scarce. This work investigates the synthesis of copolymers of poly(GMA-co-EGDMA) with different porosity degrees obtained by varying the synthesis parameters. GMA-EGDMA copolymers were synthesized by suspension polymerization employing varied conditions and characterized by measuring apparent density, surface area and pore volume distribution, optical and scanning electron microcopies, FT-IR, thermogravimetry and titration of epoxide rings. The copolymer with highest surface area and pore volume (260.4 m2/g and 0.5 cm3/g) was prepared employing cyclohexane as diluent, 80% EGDMA in monomeric composition and 100% of dilution degree. There was a relation between the epoxide content of the copolymers determined by titration and the residue content formed in the first decomposition stage.

Preparation of Monodisperse Enrofloxacin Molecularly Imprinted Polymer Microspheres and Their Recognition Characteristics.

This study presents a new strategy for the detection of enrofloxacin (ENR) in food samples by the use of monodisperse ENR molecularly imprinted polymers (MIPs). Using enrofloxacin as template molecule, methacrylic acid as functional monomer, and ethylene diglycidyl ether as cross-linker, surface molecularly imprinted polymers (MIPs) were prepared on the surface of polymeric glycidyl methacrylate-ethylene glycol dimethacrylate (PGMA-EDMA) microspheres. The surface morphology and imprinting behavior of PGMA-EDMA@MIPs were investigated and optimized. Synthesized PGMA-EDMA@MIPs showed good physical and chemical stability and specific recognition toward fluoroquinolones. The introduction of PGMA-EDMA microspheres greatly increased the adsorption area of PGMA-EDMA@MIPs and increased the adsorption capacity of target molecules. The core shell structure increased the adsorption rate, and adsorption equilibrium was achieved within 6 min, much higher than that of MIPs synthesized by traditional methods. Enrofloxacin in milk samples was detected by molecular imprinting solid phase extraction (MISPE) combined with high performance liquid chromatography (HPLC). Implementing this method resulted in a recovery rate of 94.6~109.6% with a relative standard deviation (RSD) of less than 3.2%. The limit of detection (LOD) of this method was identified as three times the signal-to-noise ratio (10 μg/L). In summary, this work proposed a sensitive, rapid, and convenient method for the determination of trace ENR in food samples.

Cobalt Phthalocyanine Tetracarboxylic Acid Functionalized Polymer Monolith for Selective Enrichment of Glycopeptides and Glycans.

In this study, poly(glycidyl methacrylate-ethyleneglycol dimethacrylate) monolith functionalized with cobalt phthalocyanine tetracarboxylic acid is prepared. The polymer monolithic material is used for glycopeptides enrichment coupled with MALDI-TOF MS. By taking advantage of cobalt phthalocyanine including hydrogen bonds between isoindole subunits of phthalocyanine and glycans, coordination interaction between cobalt and glycopeptides, the monolithic material is successfully applied to the enrichment of glycopeptides efficiently and selectively. With IgG and horse radish peroxidase as the model glycoproteins, 28 and 17 glycopeptides could be identified respectively after enrichment with the monolith, only four and three glycopeptides could be obtained for direct analysis. The monolith is also employed to the digests mixture of BSA and IgG (50:1, m/m), indicating the high enrichment selectivity of glycopeptides even in the presence of a large interference ratio. The detection limit is determined to be 6.7fmol, implying that the present method had great potential for trace sample analysis. In addition, the monolith was successfully applied to the enrichment of N-linked glycans in human serum samples, demonstrating its great potential for the analysis of glycoproteins.

Preparation of copper tetra(N-carbonylacrylic) aminephthalocyanine functionalized zwitterionic-polymer monolith for highly specific capture of glycopeptides.

In this work, poly(glycidyl methacrylate-ethyleneglycol dimethacrylate) monolith functionalized with copper tetra(N-carbonylacrylic) aminephthalocyanine and iminodiacetic acid was successfully synthesized. Owing to hydrogen bonding and hydrophilic interactions, the monolith exhibited good performance for glycopeptide enrichment. When the tryptic digests of horseradish peroxidase were enriched by the developed monolith, a total of 20 glycopeptides could be captured and identified by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analysis with a detection limit as low as 0.5fmolμL-1. With the mixture of bovine serum albumin and horseradish peroxidase digests (200:1, m/m) as the sample, 14 glycopeptides were identified after enrichment, showing the high selectivity of the monolith. Moreover, the functionalized monolith exhibited good stability and reproducibility. It was successfully applied to enrich glycopeptides from human serum, demonstrating its potential applications in selective and efficient capture of glycopeptides in complex biological samples. Graphical abstract ᅟ.

Preparation of cobalt phthalocyanine functionalized polymer monolith and application to enrichment of transferrin glycopeptides

Poly(glycidyl methacrylate-ethyleneglycol dimethacrylate) (Poly(GMA-EDMA)) monolith functionalized with cobalt phthalocyanine tetracarboxylic acid (CoPcTc) was prepared. The monolith was used for transferrin (Tf) glycopeptide enrichment. By taking advantage of hydrogen bonds between isoindole subunits of phthalocyanine and glycans and coordination interaction between cobalt and glycopeptides, the monolithic material was efficient and selective. After enrichment of transferrin through the functionalized monolith, 17 glycopeptides were identified by electrospray ionization quadrupole time-of-flight mass spectrometry. When the concentration of transferrin was reduced to 8.8×10-10mol/L, three glycopeptides could still be obtained. The present method has great potential for trace sample analysis.

Polyethylenimine and tris(2-aminoethyl)amine modified p(GA–EGMA) microbeads for sorption of uranium ions: equilibrium, kinetic and thermodynamic studies

Poly(glycidyl methacrylate-ethyleneglycol dimethacrylate), p(GA–EGMA), microbeads were prepared through suspension polymerization. It was decorated with polyethylene imine (PEIM) and tris(2-aminoethyl)amine (TAEA) ligands to decorate with polyamine groups. These microbeads were used for sorption of uranium ions from aqueous solution. The maximum sorption of uranium ions on the PEIM and TAEA modified microbeads was observed at pH 6.0. The maximum sorption capacity of acid hydrolyzed p(GA–EGMA)–OH, p(GA–EGMA)–PEIM and p(GA–EGMA)–TAEA microbeads was found to be 7.21, 87.8 and 64.3 mg g−1. The sorption process conforms to the pseudo-second order kinetic model and the Langmuir and Temkin isotherm models well.

Enhanced adsorption capacity of cryogel bed by incorporating polymeric resin particles

Novel composite cryogel monoliths were fabricated by incorporating polymeric resin particles and grafting anion-exchange groups on the pore wall surfaces. The embedded resin particles in different size distributions were prepared by grinding poly(glycidyl methacrylate–ethylene glycol dimethacrylate) monoliths. Observations by scanning electron microscopy clearly indicated that the composite cryogel had interconnected large pores (10–100μm in width), similar to normal (pure) cryogel. However, the composite material had very rough pore walls, which provided larger surface area for protein adsorption. As a result, the dynamic binding capacity of bovine serum albumin (BSA) on the composite cryogel bed reached 6mg/mL bed (flow velocity, 5cm/min), which was 2.8 times higher than a cryogel bed without embedding the ground resin particles. The capacity value was also much higher than the BSA capacities of cryogel beds reported in literature (1–4mg/mL). Though the capacity decreased by about 1mg/mL with the increase of flow rate from 0.5 to 5cm/min, it then kept almost unchanged till a flow rate up to 15cm/min. The height equivalent to a theoretical plate of the composite bed was in the range of 1.1–1.4mm, and kept nearly constant in a flow rate range of 5–20cm/min. The results indicated that the composite cryogel bed offered a large improvement in protein adsorption capacity and was suitable for high-speed protein chromatography.

Methacrylate-based monolithic layers for planar chromatography of polymers

A series of macroporous monolithic methacrylate-based materials was synthesized by in situ free radical UV-initiated copolymerization of functional monomers, such as glycidyl methacrylate (GMA), butyl methacrylate (BuMA), 2-aminoethyl methacrylate (AEMA), 2-hydroxyethyl methacrylate (HEMA) and 2-cyanoethyl methacrylate (CEMA), with crosslinking agent, namely, ethylene glycol dimethacrylate (EDMA). The materials obtained were applied as the stationary phases in simple and robust technique – planar chromatography (PLC). The method of separation layer fabrication representing macroporous polymer monolith bound to the specially prepared glass surface was developed and optimized. The GMA–EDMA and BuMA–EDMA matrixes were successfully applied for the separation of low molecular weight compounds (the mixture of several dies), as well as poly(vinylpyrrolidone) and polystyrene homopolymers of different molecular weights using reversed-phase mechanism. The materials based on copolymers AEMA–HEMA–EDMA and CEMA–HEMA–EDMA were used for normal-phase PLC separation of 2,4-dinitrophenyl amino acids and polystyrene standards.

The use of monolithic polymeric sorbents to simulate virus-cell interactions

A simple virus-cell complementary model system can be obtained using polymer-analogous reactions of the epoxy groups of glycidyl methacrylate-ethylene glycol dimethacrylate monolithic macroporous polymeric support and of the carboxy groups of styrene-methyl methacrylate polymeric nanospheres. The effect of thus designed microenvironment on the affinity binding parameters of virus-mimicking nanoparticles with the functionalized sorbent surface is studied by high-performance monolithic disk affinity chromatography.

Fabrication of high-permeability and high-capacity monolith for protein chromatography

A novel approach for the fabrication of macroporous poly(glycidyl methacrylate-ethylene glycol dimethacrylate) monolith is presented. The method involved the use of sodium sulfate granules and organic solvents as co-porogens. Compared with the conventional monoliths [ML-(1-3)] using organic solvents only as a porogen, the improved monoliths [MLS-(1-3)] showed not only higher column efficiency and dynamic binding capacity (DBC) for protein (bovine serum albumin, BSA), but also higher column permeability and lower back pressure. It is considered that the superpores introduced by the solid granules played an important role for the improvement of the monolith performance. Moreover, poly(glycidyl methacrylate-diethylamine) tentacles were grafted onto the pore surface of MLS-3 monolith. This has further increased the DBC of BSA to 74.7 mg/ml, about three times higher than that of the monoliths without the grafted tentacles. This grafting does not obviously decrease the column permeability, so a new monolith of high column permeability and binding capacity has been produced for high-performance preparative protein chromatography.

Synthesis of strongly basic anion exchange resins based on glycidyl methacrylate-ethylene glycol dimethacrylate copolymer. Effect of amount and nature of diluent, and the degree of crosslinkage on the resins properties

A number of hydrophilic copolymers based on glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDM) were synthesized using the technique of suspension polymerization. A number of diluents such as dimethylpthalate (DMT), diethylpthalate (DET), dibutylpthalate (DBT) and bis-2-ethylhexylpthalate (diocylphthalate, DOT) were used. The resulting polymers were modified into strongly basic anion exchange resins using 50% aqueous trimethylamin hydrochloride solution. In this study, the effects of amount and nature of diluents on resin properties, i. e. porosity, density, mechanical properties and capacities, were investigated. The effect of amount of crosslinking agent, i.e. the amount of EGDM, was also studied. It was found that resin become porous as the number of methylene groups in diluents increases. The pore volume changes from 0.05 to 1.35 ml/g as the diluent change from DMT to DOT. The mechanical strength of the resin decreases on increasing the number of methylene groups in the diluent. However, the chloride capacity shows no significant change. By varying the amount of crosslinking agent (from 10 to 50%) the chloride capacity changes from 3.46 to 1.2 meq/g, respectively. The effect of crosslinking on porosity was also investigated. It was found that porosity of the resin increases on increasing the amount of EGDM. This is the first time that strongly basic anion exchange resin based on GMA-co-EGDM using different and varying amounts of diluents, as well as various degrees of crosslinkage, were synthesized and characterized. The important aspect of this study is that it provides a guideline for the synthesis of a resin with specific properties by selection of a diluent and varying its ratio with respect to the monomer.

Synthesis of strongly basic anion exchange resins based on glycidyl methacrylate-ethylene glycol dimethacrylate copolymer. Effect of amount and nature of diluent, and the degree of crosslinkage on the resins properties

A number of hydrophilic copolymers based on glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDM) were synthesized using the technique of suspension polymerization. A number of diluents such as dimethylpthalate (DMT), diethylpthalate (DET), dibutylpthalate (DBT) and bis-2-ethylhexylpthalate (diocylphthalate, DOT) were used. The resulting polymers were modified into strongly basic anion exchange resins using 50% aqueous trimethylamin hydrochloride solution. In this study, the effects of amount and nature of diluents on resin properties, i. e. porosity, density, mechanical properties and capacities, were investigated. The effect of amount of crosslinking agent, i.e. the amount of EGDM, was also studied. It was found that resin become porous as the number of methylene groups in diluents increases. The pore volume changes from 0.05 to 1.35 ml/g as the diluent change from DMT to DOT. The mechanical strength of the resin decreases on increasing the number of methylene groups in the diluent. However, the chloride capacity shows no significant change. By varying the amount of crosslinking agent (from 10 to 50%) the chloride capacity changes from 3.46 to 1.2 meq/g, respectively. The effect of crosslinking on porosity was also investigated. It was found that porosity of the resin increases on increasing the amount of EGDM. This is the first time that strongly basic anion exchange resin based on GMA-co-EGDM using different and varying amounts of diluents, as well as various degrees of crosslinkage, were synthesized and characterized. The important aspect of this study is that it provides a guideline for the synthesis of a resin with specific properties by selection of a diluent and varying its ratio with respect to the monomer.

Oligoamine-functionalised poly(glycidyl methacrylate-ethyleneglycol dimethacrylate) resins as moderate base extractants for gold from cyanide solutions

A series of oligoamines have been attached to poly(glycidyl methacrylate) resins to yield a corresponding group of moderate base resins. Species carrying ethylenediamine, diethylenetriamine, triethylenetetramine, N,N′-bis(3-aminopropyl)ethylenediamine, and 3,3′-aminobispropylamine and phenyl-2-imidazoline are described. These have been examined as extractants for gold from alkaline cyanide solutions, along with a commercially available polystyrene-based resin carrying a 2,5,7-triazabicyclo[4,4,0]dec-5-ene functionality. Feed solutions containing only gold cyanide and also gold in the presence of the base metals Cu, Co and Ni, have been examined. The stripping of metal loaded resins using various concentrations of NaOH has also been investigated. The results of loading and stripping experiments are discussed in the light of the basicity of the various oligoamines, and also in the context of relevant data already available in the literature. Overall, though very effective gold extraction has been demonstrated with high selectivity relative to base metals, efficient stripping is problematical and has been demonstrated in only a few cases. This suggests that gold extraction and stripping does not involve only protonation/deprotonation of the moderate base functions, but extraction probably involves a contribution from gold reduction as well.

Porous thiiranyl polymers: Newer supports for immobilization of penicillin G acylase

Spherical and macroreticular epithiopropyl methacrylate-ethylene glycol dimethacrylate (thiiranyl) and glycidyl methacrylate-ethylene glycol dimethacrylate (glycidyl) copolymer beads of two differing copolymer compositions were synthesized. Particle size was estimated to be in the range 250–420 μm for both sets of copolymers. The anomalous increase in both surface area and pore volume with crosslinking density reflects a bimodal distribution of the internal porous structure in both these copolymers. These reactive copolymer beads were investigated for the binding and expression of a biocatalyst, penicillin G acylase. The activity of immobilized penicillin G acylase obtained, 191 IU/g, compares well with established industrial immobilized enzymes.

Redox polymerization of acrylamide by polymer supported vanadium (V) ion

Macroreticular glycidyl methacrylate-ethylene glycol dimethacrylate (GMA-EGDM) copolymers of controlled particle size were synthesized by suspension polymerization. The copolymer beads were derivatized to incorporate di- and tetracarboxylic acid functionalities. Vanadium (V) ion was chelated on the modified copolymers. The vanadium chelated copolymers were used in combination with cyclohexanone as redox reagent for the free radical polymerization of acrylamide at 30°C. The molecular weights of the polyacrylamide were significantly higher than that prepared by a soluble vanadium (V) ion — cyclohexanone homogeneous redox initiator pair.