Ethylene Glycol Phenyl Ether Acrylate Research Articles

Reversibly Adhesive, Anti-Swelling, and Antibacterial Hydrogels for Tooth-Extraction Wound Healing.

Oral wound treatment faces challenges due to the complex oral environment, thus, sealing the wound quickly becomes necessary. Although some materials have achieved adhesion and sterilization, how to effectively solve the contradiction between strong adhesion and on-demand removal remains a challenge. Herein, a reversibly adhesive hydrogel is designed by free radical copolymerization of cationic monomer [2-(acryloyloxy) ethyl] trimethylammonium chloride (ATAC), hydrophobic monomer ethylene glycol phenyl ether acrylate (PEA) and N-isopropylacrylamide (NIPAAm). The cationic quaternary ammonium salts provide electrostatic interactions, the hydrophobic groups provide hydrophobic interactions, and the PNIPAAm chain segments provide hydrogen bonding, leading to strong adhesion. Therefore, the hydrogel obtains an adhesion strength of 18.67KPa to oral mucosa and can seal wounds fast within 10s. Furthermore, unlike pure PNIPAAm, the hydrogel has a lower critical solution temperature of 40.3°C due to the contribution of ATAC and PEA, enabling rapid removal with 40°C water after treatment. In addition, the hydrogel realizes excellent anti-swelling ratio (≈80%) and antibacterial efficiency (over 90%). Animal experiments prove that the hydrogel effectively reduces inflammation infiltration, promotes collagen deposition and vascular regeneration. Thus, hydrogel as a multi-functional dressing has great application prospects in oral wound management.

High-performance aluminum nitride made by Vat photopolymerization through optimization of resin refractive index and plasticizer content

In this study, we evaluated the effects of three resins with different refractive index on the viscosity and curing behavior of aluminum nitride (AlN) ceramic suspensions. Our findings indicate that the viscosity of the AlN suspensions increased with the concentration of polyethylene glycol o-phenylphenyl ether acrylate (OPPEA). Conversely, the viscosity decreased with increasing concentrations of cyclic trimethylolpropane formal acrylate (CTFA) and ethylene glycol phenyl ether acrylate (PHEA). Regarding the curing behavior, the AlN ceramic suspension prepared with OPPEA exhibited the largest cure depth and excess width, whereas the suspension prepared with CTFA had the lowest cure depth and excess width. Further analysis of the sensitivity and critical energy revealed that the suspension containing OPPEA demonstrated the highest sensitivity in the vertical direction and the lowest sensitivity in the horizontal direction. This implies that the smallest critical energy is in the vertical direction, and the largest critical energy is in the horizontal direction. Additionally, an increase in the content of the plasticizer dibutyl phthalate (DBP) was beneficial for reducing cracks in the AlN ceramic debinding bodies. Finally, high-performance AlN ceramics were produced, exhibiting a relative density exceeding 98 %, a bending strength of 470.39 ± 6.5 MPa, and a thermal conductivity of 163.45 W/m·K.

On-line extraction and determination of coumarins compounds from mouse plasma based on a homemade phenyl-hybrid monolithic adsorbent

A phenyl-hybrid monolithic adsorbent was prepared using an organic monomer of ethylene glycol phenyl ether acrylate and inorganic monomers of tetramethoxysilane and vinyltrimethoxysilane, via polycondensation and polymerization in a stainless-steel column, which shows porous structure and multiple functional groups, according to the measurements of scanning electron microscopy, nitrogen adsorption-desorption method and infrared spectroscopy. The resulting hybrid phenyl-based monolith was used as a solid-phase extraction column, combining with an analytical column in conjunction with high-performance liquid chromatography system for the on-line extraction and determination of coumarins (praeruptorin A and praeruptorin B) in Peucedani Radix from mouse plasma. The homemade hybrid monolithic solid-phase extraction column exhibits good removal ability for the sample matrices, as well as unique selectivity for the two praeruptorins. Methodology validation results indicate that the present method is applicable for the on-line extraction and quantitative analysis of praeruptorin A and praeruptorin B in Peucedani Radix from mouse plasma with a limit of quantitation 0.06 μg/mL and a linear range 0.06–5 μg/mL (r＞0.999), thus indicating the present method is a promising and alternative method for the quantitative determination of similar target components with micro or trace concentration from complex extract solution and plasma.

Extraction and Determination of Evodiamine from Euodia Fructus with SPE-HPLC Based on a Homemade Phenyl-Based Monolithic Cartridge.

A phenyl-based monolithic adsorbent was prepared in a 50-mm-long stainless steel tube, which was initiated by the redox system, using ethylene glycol phenyl ether acrylate as the monomer and ethylene glycol dimethacrylate as the crosslinker. The effects of monomer/crosslinker ratio and the porogens on the permeability and morphology of the resulting adsorbents were investigated, and the optimal adsorbent shows relatively uniform pore structure according to the characterizations of scanning electron microscopy and nitrogen adsorption-desorption method. The column that filled with the adsorbent was used as the solid-phase extraction (SPE) cartridge, exhibiting unique selectivity for the extraction of evodiamine from Euodia fructus (the fruits of Euodia rutaecarpa (Juss.)Benth.), which attributes to the interactions of π-π and hydrogen bonding between the adsorbent and evodiamine. Combined with a C18 analytical column via high-performance liquid chromatography (HPLC) system, an online SPE-HPLC method was established for extraction, enrichment and determination of evodiamine from Euodia fructus. Method validation demonstrates that the relative standard deviation of the precision is less than 0.66%, and the spiked recovery is in the range of 93.11-98.06%. Furthermore, it is worth noting that the prepared SPE cartridge can be reused for no less than 100 times. These results show that the developed method is simple and efficient for online extraction and enrichment of evodiamine from Euodia fructus.

Tiny yet tough: Maximizing the toughness of fiber-reinforced soft composites in the absence of a fiber-fracture mechanism

Tiny yet tough: Maximizing the toughness of fiber-reinforced soft composites in the absence of a fiber-fracture mechanism

A Facile Fabrication Route of Poly(Ethylene Glycol Phenyl Ether Acrylate) Photopolymers with Efficient Optical Response for Holographic Storage

A series of photopolymers based on ethylene glycol phenyl ethyl arylate (EGPEA) monomers and poly(methyl methacrylate) (PMMA) matrix with varying initiator concentrations and sample thicknesses have been synthesized and their optical performance characterized in this study. The advantages of lowering the initiator concentration, including a rather short initiation time within a few seconds; a sharp rising optical response; and a stable saturated diffraction efficiency are demonstrated. The variation in the diffraction efficiency and response time with the exposure energy under various sample thickness and initiator concentrations is examined; a diffraction efficiency as high as 80% and a relatively short response time of 12–39 s are attainable. The dependence of the normalized optical parameter “sensitivity” on the exposure time is depicted, and the peak value of S ranges vastly from about 0.2 to 1.2 × 104 cm/J within a period of 15 s or so, with a maximum value of nearly 1.2 × 104. Favorable evidence of low initiator concentration can further be found when the dependence of the saturated diffraction efficiency with the exposure energy is examined. The data from this study using a low initiator concentration cover a range of exposure energy from 100 to 800 mJ/cm2 and a saturated diffraction efficiency from about 15% to 80%. The successful image reconstruction of 6-membered-ring metal nuts on a hologram based on this EGPEA/PMMA photopolymer system using a reflective holographic recording setup is demonstrated to verify its applicability to holographic storage.

Photocured conductive PANI/acrylate composites for digital light processing. Influence of HDODA crosslinker in rheological and physicochemical properties

The design of novel photocurable conductive acrylic composites demands thorough research to find appropriate balance between the relative concentrations of monofunctional/ multifunctional monomers, photoinitiators and conductive filler, besides adjusting polymerization conditions. Likewise, when an intrinsically conductive polymer such as polyaniline (PANI) is selected as conductive filler, the homogeneous distribution of its nanometric aggregates is essential to prevent heterogeneous curing due to its strong UV absorption. In this work, the influence of PANI-HCl on the physical properties of acrylic composites based on Ethyleneglycolphenylether acrylate (EGPEA) and Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO), photoinitiator, was examined in the frame-work of the percolation model. Rheological testing combined with Scanning Electron Microscopy (SEM) were used for efficient control of the filler dispersion in order to better understand the electrical conductivity-structure behaviour. Infrared Spectroscopy probed the degree of monomer conversion and the filler interaction with the polymer matrix, whereas the thermal properties were evaluated with the aim of establishing the maximum working temperatures. Above the percolation threshold, the formulation with 4.8 wt% PANI was selected as the most suitable composition achieving maximum conductivity (10-3 S cm−1) at the lowest PANI content. The problem of excessive aggregation of PANI clusters was tackled by the addition of a 15 wt% of the reactive diluent 1,6-hexanediol diacrylate (HDODA) to the previous formulation. The outcomes were improved dispersion and better integration of PANI nanorods within the acrylic matrix plus a smoother film surface, while retaining high electrical conductivity. The viscosity of the selected prepolymer formulations and penetration depth of UV photons gave encouraging results for the use of the developed compositions as anticorrosion coatings, digital light processing (DLP) or piezoelectric sensors. The high critical cure dosages obtained will be easily overcome by adjusting the type and/or amount of photoinitiator.

A rapid method for on-line solid-phase extraction and determination of dioscin in human plasma using a homemade monolithic sorbent combined with high-performance liquid chromatography.

A phenyl-based polymer monolithic column was prepared via free radical polymerization in a stainless steel column with the size of 4.6 mm i.d. × 50 mm, using ethylene glycol phenyl ether acrylate as the monomer. The resulting monolithic column shows high porosity of 73.42% and relative uniform pore structure, as characterized by mercury porosimetry and scanning electron microscopy, respectively. The optimized polymer monolith column was used for on-line solid-phase extraction prior to the reversed phase mode HPLC-UV analysis for the determination of dioscin in human plasma, using a COSMOSIL C18 column (4.6 mm × 150 mm, 4.5 μm). Water was used to wash non-retained components from the SPE sorbent, and methanol water (80:20, V/V) was used as the mobile phase for isocratic elution of dioscin. The maximum adsorbed quantity of dioscin to the SPE column is 6.79 mg/g, which is high enough for the quantitative analysis of dioscin in plasma, due to the low content of dioscin in plasma. The method was validated by assessing the linearity, lower limit of quantification, intra- and inter-day precision, accuracy, and repeatability. The developed method was applied for the analysis of dioscin in plasma from a volunteer who had orally administered an aqueous extract of dioscorea nipponica rhizome, showing the method capable of detecting dioscin in the plasma. These results show that the developed method is a rapid method for on-line solid-phase extraction and determination of dioscin from plasma, exhibiting good selectivity with hydrogen bond interaction and hydrophobic interaction, good clean-up ability, cost-saving, and time-saving. Graphical abstract.

Influence of co‐monomer‐type and amount on thermomechanical properties of ultrafast‐curing acrylic resins using a triacrylic crosslinker

ABSTRACTAn ultrafast ultraviolet‐light‐cured acrylic resin was developed. The monoacrylic monomers ethylene‐glycol‐phenyl‐ether acrylate (EGPEA), 2‐hydroxy‐3‐phenoxypropyl acrylate (HPPA), di(ethyleneglycol)‐ethyl‐ether acrylate (DEGEEA), or poly(ethyleneglycol)‐phenyl‐ether acrylate (PolyEGPEA) were each mixed with varying amounts of the triacrylic crosslinker tris[2‐(acryloyloxy)ethyl] isocyanurate (ICTA). The curing time was 1 s at room temperature (average degrees of curing between 55 and 85%). The specimens of ICTA‐EGPEA showed a maximum tensile strength of 76.0 ± 1.4 MPa, an E‐modulus of 4216 ± 188 MPa, an elongation at break of 2.3 ± 0.1%, and a glass transition temperature (T g) of 100 °C. The development of properties with increasing amount of crosslinker could be well described on the basis of percolation theory. Below the percolation threshold the behavior is dominated by the auxiliary co‐monomer. Above the percolation threshold the behavior is dominated by ICTA. On exchanging EGPEA by HPPA, the influence of hydrogen bonding on the thermomechanical properties was extracted. Exchanging EGPEA by DEGEEA or PolyEGPEA allowed for exploring the influence of beta‐relaxation of the monoacrylic monomers on the thermomechanical properties of the resin. Large ester side‐groups reduced the tensile strength, the E‐modulus, and the T g decisively. The impact strength in turn was decisively increased using PolyEGPEA as auxiliary co‐monomer. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47294.

3D printing a mechanically-tunable acrylate resin on a commercial DLP-SLA printer

Multi-material 3D printing with several mechanically distinct materials at once has expanded the potential applications for additive manufacturing technology. Fewer material options exist, however, for additive systems that employ vat photopolymerization (such as stereolithography, SLA, and digital light projection, DLP, 3D printers), which are more commonly used for advanced engineering prototypes and manufacturing. Those material selections that do exist are limited in their capacity for fusion due to disparate chemical and physical properties, limiting the potential mechanical range for multi-material printed composites. Here, we present an ethylene glycol phenyl ether acrylate (EGPEA)-based formulation for a polymer resin yielding a range of elastic moduli between 0.6 MPa and 31 MPa simply by altering the ratio of monomer and crosslinker feedstocks in the formulation. This simple chemistry is also well suited to form seamless adhesions between mechanically dissimilar formulations, making it a promising candidate for multi-material DLP 3D printing. Preliminary tests with these polymer formulations indicate that variability due to molecular differences between hard and soft formulations is less than 3% of the prescribed model dimensions, comparable to existing commercial DLP and SLA resins, with unique advantages of a wide range of elastomer stiffness and seamless fusion for 3D printing of structurally detailed and mechanically heterogeneous composites.

An effectively inhibiting lithium dendrite growth in-situ-polymerized gel polymer electrolyte

Polyacrylate polymer is a promising polymer matrix for gel polymer electrolyte (GPE) in lithium-ion batteries. Herein, in-situ polymerized poly(ethylene glycol phenyl etheracrylate) (PEGPEA) based GPE combined with 1 M LiPF6 in ethylene carbonate/dimethyl carbonate/ethyl methyl carbonate (EC/DMC/EMC, 1:1:1 in volume) solvents was introduced. The maximum recoverable strain of the in-situ polymerized PEGPEA-GPE was up to 99%. The outstanding interfacial compatibility between PEGPEA-GPE and the lithium electrode was also obtained. Surprisingly, lithium dendrite was effectively suppressed in charge-discharge cycling because of polymer-enhanced solid electrolyte interphase (SEI) and excellent contact interface. Furthermore, the PEGPEA-GPE exhibited wide electrochemical stability window up to 4.9 V versus Li+/Li, and achieved an ionic conductivity of 3.35 × 10−3 S cm−1 at 25 °C. When used as electrolyte, the Li[Ni0.5Co0.2Mn0.3]O2/PEGPEA-GPE/Li batteries showed high discharge capacity retention rate of 97.5% after 70 charge-discharge cycles and considerable discharge rate capability, i.e., 155 mAh g−1 0.2C, 142 mAh g−1 0.5C, 120 mAh g−1 1C, 60 mAh g−1 2C. These results demonstrate that this highly elastic in-situ polymerized PEGPEA-GPE is a potential electrolyte system for high-performance polymer electrolyte lithium-ion batteries and has excellent application prospects in wearable and flexible batteries.

The Effect of 3-Isocyanato-1-Propene on Adhesive Properties of UV-Curing Urethane/Siloxane Acrylate Resin.

We synthesized the urethane/siloxane acrylate oligomer from isophorone diisocyanate (IPDI), hydroxyl alkyl terminated polydimethylsiloxane and 2-hydroxyethyl acrylate (2-HEA). UV-curable resins were formulated from the synthesized oligomer, ethylene glycol phenyl ether acrylate (PHEA), 1,6-hexanediol diacrylate (HDDA), trimethylolpropane triacrylate (TMPTA) as a reactive diluent, 3-isocyanato-1-propene as an adhesion promoter and photoinitiators. The PET film was treated with plasma in order to introduce the functional group on the PET surface and the functional group was observed through X-ray photoelectron spectroscopy (XPS) and the Fourier transform infrared (FT-IR). The adhesion strength between the PET film and the UV-cured resin were increased by using the adhesion promoter. Also, the thermal stability, the modulus and surface hardness were increased, as the adhesion promoter was added.

Preparation and Characterization of UV Cured Optical Films Containing a Fluorene Compound

In this study, the high refractive coating films applicable for optical materials were produced. the conversion and the photo curing behaviors were examined through FTIR-ATR and photo-DSC, and thermal and mechanical properties of cured films were examined by using DMA and UTM, and pencil hardness, refractive index and optical transmittance of film were measured. Urethane metacrylate oligomer was synthesized by mixing bisphenoxyethanolfluorene (BPEF), polycaprolactone diol (PCL), and polytetramethylene ether glycol (PTMeG) in varying ratios. Also, as the results of mixing ethylene glycol phenyl ether acrylate (PHEA) and trimethylolpropanetriacrylate (TMPTA) in varying ratios, the more time UV irradiated, the higher conversion and the heat of enthalpy (ΔH) and the initial curing rate increased with increasing TMPTA content up to 70%. Also, as the trifunctional monomer increased, the storage modulus and Tg increased, and the stress increased while the strain decreased to reach its maximum value. Also, as the BPEF ratio increased, the maximum value of stress increased while the strain decreased, the refractive index and pencil hardness increased, and light transmittance was all over 80%.

Nanoconfinement and Chemical Structure Effects on Permeation Selectivity of Self-Assembling Graft Copolymers.

Permeation of small molecule solutes through thin films is typically described by the solution-diffusion model, but this model cannot predict the effects of nanostructure due to self-assembly or additives. Other models focusing on diffusion through isolated nanopores indicate that confining permeation to channels slightly larger than the size of the solute can lead to an increased influence of solute-pore wall interactions on permeation rate. In this study, we analyze how differences in polymer nanostructure affect the relative contributions of solute size and polymer-solute interactions on transport rate. We compared the diffusion rates of several small molecules through two polymer thin films: A cross-linked, homogeneous film of poly(ethylene glycol phenyl ether acrylate) (PEGPEA) and a graft copolymer with a poly(vinylidene fluoride-co-chlorotrifluoroethylene) (P(VDF-co-CTFE)) backbone and PEGPEA side chains that self-assemble into continuous ∼1-3 nm PEGPEA domains through which transport occurs. We correlated these rates with the size of each solute and its chemical affinity to PEGPEA, as measured by the difference between their solubility parameters. Diffusion rate through the homogeneous polymer film was controlled by solute size, whereas diffusion rate through the copolymer was strongly controlled by the difference between the solubility parameters. Furthermore, permeation selectivity between two selected molecules was 2.5× higher for the nanostructured copolymer, likely enhanced by the nanoconfinement effects. These initial results indicate that polymer self-assembly is a promising tool for designing polymeric membranes that can differentiate between solutes of similar size but differing chemical structures.

Synthesis of ethylene glycol phenyl ether acrylate by direct ethoxylation of phenyl acrylate

One-pot synthesis of ethylene glycol phenyl ether acrylate (EGPEA) was achieved by the reaction of phenyl acrylate and ethylene oxide catalyzed by Al/Mg composite oxide. The catalytic activity sensitively relied on the Al-Mg molar ratios. The assayed Lewis acids blended into the catalyst, such as BF3 and AlCl3, decreased the catalytic activity; while the assayed inorganic base and potassium halides could promote the direct ethoxylation reaction. EGPEA was obtained in a yield of 54.2% when KI was utilized as a co-catalyst.

Synthesis and characterization of novel polymers bearing fluorescein units: thermal and optical properties

In this work, we report the synthesis and characterization of four novel series of copolymers bearing fluorescein moieties. Two monomers: fluorescein methacrylate and dimethacrylate were prepared and were copolymerized in the presence of four different acrylic monomers bearing oligo(ethylene glycol) segments: ethylene glycol phenyl ether acrylate, ethylene glycol phenyl ether methacrylate, poly(ethylene glycol) methyl ether acrylate (Mn = 475 g/mol), and poly(ethylene glycol) methyl ether methacrylate (Mn = 480 g/mol). The obtained copolymers were fully characterized by Fourier Transform Infrared Spectroscopy (FTIR) and Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy. Their thermal properties were determined by thermogravimetric analysis and differential scanning calorimetry, and their optical properties were studied by absorption and fluorescence spectroscopy in solution and in solid state.

Holographic Recording on Photopolymers Containing Pyrene for Enhanced Fluorescence Intensity

Photopolymer films containing pyrene were studied for fluorescence intensity enhancement by holographic recording. Photopolymer films were prepared from a solution containing a monomer mixture of s-triazine dimethacrylic monomer (DT) and ethylene glycol phenyl ether acrylate (PA), polysulfone as a binder, pyrene as a fluorescent dopant, and a visible light sensitive photoinitiator. The films were exposed by means of holographic techniques, resulting in a spatial intensity distribution in the films. The diffraction efficiency of the film containing 1 wt % of pyrene reached a maximum of 93%. The fluorescence intensity of the film was enhanced in conjunction with diffraction efficiency growth, proving that the increase in the fluorescence intensity of the film originated from the increased pyrene monomer emission in response to the increased viscosity around the pyrene molecules. The enhancement of the fluorescence intensity of the recorded area was ∼2 in reference to the unrecorded area. The recorded area showed grating, which could be identified by transmittance as well as fluorescence scan. The grating spacing and fluorescence intensity of the recorded area were correlated to the pyrene content and incident angle of recording beam.

Fluorescent Grating Patterns of Photopolymer Film Containing Ethylene Glycol Phenyl Ether Acrylate

Photopolymer films containing photoreactive monomers in the presence of fluorescent polyanthracene were investigated for fluorescent grating pattern formation using a 3D holographic method. A monofunctional acrylate, ethylene glycol phenyl ether acrylate (PA), was used as the core monomer for the formation of the polymerization induced grating pattern. Photopolymer films were prepared from a mixture of PA and polyanthracene with a binder polymer and a photo radical initiator. The film's thickness was adjusted by the solution's composition to optimize grating pattern efficiency (>90%). The diffraction efficiency was increased in the presence of polyanthracene. Furthermore, the fluorescence intensity was more enhanced after grating formation. A vivid fluorescent gap electrode pattern with fine gratings was patterned, providing a new method for patterning organic thin films with distinct read-out processes.

3D Image Recording on Photopolymer Films Containing Molecular Composites of a New s-Triazine Monomer and Acrylate Monomer by Dual Photopolymerization

Three dimensional (3D) image recording on photopolymer film was explored using a mixture of s-triazine diepoxy (SEP) and ethylene glycol phenyl ether acrylate (PA) as a monomer to induce cationic and radical polymerization during the holographic recording. The photopolymer films were sensitive to a visible light source and polymerized upon excitation with a visible laser. 3D image was recorded on the photopolymer film by holographic recording using a 491 nm laser. The film containing a molecular composite of SEP and PA showed high diffraction efficiency via dual photo polymerization. Within 10 min of recording the image formation was vivid. In this way 3D screw and a letter image with large viewing angle were obtained onto the photopolymer film. The images were stable for longer than 3 month at RT and 5 hr at 85 degrees C, when read by a visible light.

Thermodynamic and Electro-Optic Characteristics of UV-Cured Monofunctional Acrylate/Nematic Liquid Crystal Mixtures

Polymer Dispersed Liquid Crystals (PDLC) were prepared via a Polymerization Induced Phase Separation (PIPS) mechanism using U.V. radiation. The samples were obtained from the liquid crystalline mixture E7 and a monofunctional monomer (Ethylene Glycol Phenyl Ether Acrylate). The thermodynamic properties of cured samples were studied by Differential Scanning Calorimetry (DSC). The LC solubility limit in the polymer matrix, A, and the fractional amount of LC contained in the droplets, α, were determined (A=20 wt-% α=0.76 for 50 wt-% LC). The electro-optic characteristics of the PDLC films were investigated as a function of the LC composition and of the amplitude of the applied voltage. For a series of PDLC films with different thicknesses, the droplet distributions and the droplets densities were found nearly identical.