Ethylene Glycol Vinyl Glycidyl Ether Research Articles

New smart thermosensitive biomaterials on the basis of collagen modified by ethylene glycol vinyl glycidyl ether for 4D bioprinting

In this study, collagen reactive under UV radiation was obtained for the first time via the functionalization of the side amino groups of lysine moieties with unsaturated ethylene glycol vinyl glycidyl ether (Vinylox) containing, similarly to glycidyl methacrylate, an epoxy group. The presence of this group having a moderate reactivity provides selective grafting of the side amino groups of collagen in a neutral or weakly alkaline medium and excludes the formation of by-products in the Michael reaction and hydrolysis characteristic of the analog—glycidyl methacrylate. Photometry data indicate that with modification in a weakly basic aqueous solution at room temperature and a significant excess of Vinylox, a grafting degree of 23.4% can be achieved. For the first time, film-forming composites capable of photocuring were obtained by adding polyethylene glycol diacrylate and poly(N-isopropylacrylamide) to a weakly acidic aqueous solution of collagen. The presence of vinyl oxide groups provided satisfactory mechanical characteristics of films as the result of UV-initiated collagen cross-linking, while the presence of poly(N-isopropylacrylamide) ensured hydrophilic-hydrophobic smart sensitivity. The films have a well-developed fibrillar structure, and the size of voids enables the free movement of nutrients and other compounds. According to MTT assay data, the films release no cytotoxic components and maintain the metabolic activity of stem cells, providing sufficient density of stem cells on their surface. All of the factors mentioned above determine the prospects of using the films both as an artificial extracellular matrix scaffold and as smart thermosensitive scaffolds used to grow stem cells on their surfaces for subsequent laser transfer bioprinting.

Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization.

The functional polyethers of N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole (in up to 61% yield, Mw = 8.7–11.7 kDa) and copolymers with ethylene glycol methylglycidyl ether (Mw = 5.6–14.2 kDa) and ethylene glycol vinylglycidyl ether (Mw = 6.4–12.3 kDa) have been synthesized via anionic ring-opening polymerization in the presence of KOH without solvent. The polymerization involves the opening of the epoxy ring to deliver the linear polyethers bearing free tetrahydroindole rings and oxyethylene or vinyloxy groups in the side chain. The polyethers are soluble in ethanol, benzene, chloroform, dioxane, DMF, and DMSO. The polyethers obtained exhibit the properties of high-resistance organic semiconductors: their electrical conductivity reaches 10−14 S/cm.

Sulfonated polymer-polyorganosiloxane proton exchange membrane for alternative energy applications and environmental problem solving

By the sol-gel synthesis involving copolymers of ethylene glycol vinyl glycidyl ether and vinyl chloride (VGE–VC) and carbofunctional organosilicon precursor 2-([triethoxysilylpropyl]amino)pyridine (TEAP), hybrid organic–inorganic membranes possessing proton conductivity after doping with orthophosphoric acid have been fabricated. The proton conductivity of the membranes VC/TEAP/H3PO4 in the temperature range of 30-80 °C is characterized by the values of 1.19-2.89 mS cm−1.

Proton-Exchange Hybrid Membranes: A Copolymer of Ethylene Glycol Vinyl Glycidyl Ether and Vinyl Chloride/Polyorganylsilsesquioxane

Copolymers of ethylene glycol vinyl glycidyl ether (VGE) and vinyl chloride (VC) have been obtained via radical copolymerization of VGE with VC at 70°C in the presence of the initiator azobisisobutyronitrile. By the sol–gel synthesis involving VGE–VC copolymers and carbofunctional organosilicon precursors, such as N,N'-bis(3-triethoxysilylpropyl)thiocarbamide (BTM) and 2-([triethoxysilylpropyl]amino)pyridine (TEAP), hybrid organic–inorganic membranes possessing proton conductivity after doping with orthophosphoric acid have been fabricated. The proton conductivity of the membranes in the temperature range of 30–80°C is characterized by the values of 3.52–4.88 × 10−3 S cm−1 for VGE–VC/ BTM/H3PO4 and 1.19–2.89 × 10−3 S cm−1 for VGE–VC/TEAP/H3PO4.

Composite proton-conducting membranes based on poly(ethylene glycol vinyl glycidyl ether)

Composite proton-conducting membranes in the form of interpolymer films are prepared in an aqueous medium from sulfo-acid-modified poly(ethylene glycol vinyl glycidyl ether) and poly(vinyl alcohol). The initial poly(hydroxysulfo acid) is synthesized through the radical polymerization of ethylene glycol vinyl glycidyl ether followed by modification with sodium sulfite via epoxy groups and treatment with a cationite in the H form. The proton-conducting membranes feature improved thermal stability (200–250°C), a breaking strength of 1.0–8.9 MPa, elasticity (a relative elongation at break of 1.0–8.2%), chemical resistance, and specific proton conductivity attaining 10−1 S/cm after doping with orthophosphoric acid.

Synthesis and Properties of Composite Membranes for Polymer Electrolyte Membrane Fuel Cells

The paper is devoted to the sol-gel synthesis of proton conductive organic-silicon composite membranes based on tetraethyl orthosilicate (TEOS) and copolymers of 2-methyl-5-vinylpyridine and vinyl chloride (MVP-VC), 2-methyl-5-vinylpyridine and vinyl acetate (MVP-VA), copolymers of ethylene glycol vinyl glycidyl ether and styrene (KS-1 and KS-2), and nitrogen-containing heteroaromatic derivatives of sulfonic acids: 2-phenyl-5-benzimidazolsulfonic acid (PBISA) and pyridine-3-sulfonic acid (PSA). Properties of synthesized membranes, such as proton conductivity, activation energy, ion exchange capacity, dimensional stability have been investigated.

Synthesis and Properties of Hybrid Materials for Ion-Exchange and Complexing Membranes

Hybrid materials are attractive for a large range of applications from medicine and biotechnology to telecommunication systems and fuel cells. In the present research we have studied sol-gel synthesis of hybrid composites based on carbofunctional organosilicon monomers N,N-bis-(3-triethoxysilylpropyl) thiocarbamide (I) or 2-{[3-(triethoxysilyl) propyamino} pyridine (II), and copolymers of ethylene glycol vinyl glycidyl ether with vinyl chloride.The polymeric materials were characterized by scanning electron microscope (SEM) and IR-spectroscopy. Gel products possess high thermal stability (decomposition temperatures reach 250 °С) and have developed specific surface (to 20 m2g-1).The synthesized composites comprise semi-interpenetrating polymer networks, consisting of three-dimensional and linear polymers that cannot be separated due to the mechanical interlacing of theirs chains. Hybrid composites have a value of sorption capacity for Pt (IV) ions of 70 (I) and 28 (II) mgg-1. Proton conductivity of membranes based on the synthesized composites is characterized by the values 3.52 10-2(I) and 1.19 10-2(II) Scm-1measured at temperature of 25 °C.

Catechol-Initiated Polyethers: Multifunctional Hydrophilic Ligands for PEGylation and Functionalization of Metal Oxide Nanoparticles

Bifunctional CA-PEG (catechol-poly(ethylene glycol)) and multifunctional CA-PEG-PGA/PEVGE (poly(glycidyl amine)/poly(ethylene glycol vinyl glycidyl ether)) ligands for the functionalization and solubilization of nanoparticles are introduced. Tunable polymers with polydispersities <1.25 and molecular weights in the range 500-7700 g mol(-1) containing a catechol moiety for conjugation to metal oxide nanoparticles were prepared. The functional PEG ligands were synthesized starting from the acetonide-protected catechol initiator 2,2-dimethyl-1,3-benzodioxole-5-propanol (CA-OH) for oxyanionic polymerization. CA-OH was used both for homopolymerization of ethylene oxide (EO) as well as copolymerization with functional epoxides N,N-diallyl glycidyl amine (DAGA), releasing primary amino groups and ethylene glycol vinyl glycidyl ether (EVGE), exhibiting a double bond for click-type reactions, to generate CA-PEG and CA-PEG-PGA/PEVGE. We demonstrate the potential of the functional ligands by binding to MnO nanoparticles, rendering the PEGylated nanoparticles highly stable in aqueous environment. Furthermore, addressability of the functional groups has been proven, for example, by coupling with fluoresceine isothiocyanate (FITC), to allow for optical monitoring of the nanoparticle fate in biological systems.

Reactivity ratios, and mechanistic insight for anionic ring-opening copolymerization of epoxides.

Reactivity ratios were evaluated for anionic ring-opening copolymerizations of ethylene oxide (EO) with either allyl glycidyl ether (AGE) or ethylene glycol vinyl glycidyl ether (EGVGE) using a benzyl alkoxide initiator. The chemical shift for the benzylic protons of the initiator, as measured by (1)H NMR spectroscopy, were observed to be sensitive to the sequence of the first two monomers added to the initiator during polymer growth. Using a simple kinetic model for initiation and the first propagation step, reactivity ratios for the copolymerization of AGE and EGVGE with EO could be determined by analysis of the (1)H NMR spectroscopy for the resulting copolymer. For the copolymerization between EO and AGE, the reactivity ratios were determined to be r(AGE) = 1.31 ± 0.26 and r(EO) = 0.54 ± 0.03, while for EO and EGVGE, the reactivity ratios were r(EGVGE) = 3.50 ± 0.90 and r(EO) = 0.32 ± 0.10. These ratios were consistent with the compositional drift observed in the copolymerization between EO and EGVGE, with EGVGE being consumed early in the copolymerization. These experimental results, combined with density functional calculations, allowed a mechanism for oxyanionic ring-opening polymerization that begins with coordination of the Lewis-basic epoxide to the cation to be proposed. The calculated transition-state energies agree qualitatively with the observed relative rates for polymerization.

Copolymerization of N-vinylpyrrole-2-carbaldehydes with styrene, N-vinylpyrrolidone, and ethylene glycol vinyl glycidyl ether

Polyfunctional reactive copolymers of N-vinylpyrrole-2-carbaldehydes with styrene, N-vinylpyrrolidone, and ethylene glycol vinyl glycidyl ether are synthesized in the presence of AIBN (2 wt %, 80°C, 50 h) with a yield of up to 98% and a molecular mass of up to 4800. The copolymers show paramagnetic behavior (N = 2.0 × 1015−2.0 × 1017 g−1) and possess the properties of organic semiconductors (σ = 0.9 × 10−11–2.8 × 10−7 S/cm after doping with I2).

Modified copolymers of bifunctional vinyl ethers with methyl vinyl sulfide as active matrices of solid superbases

Reactive linear and crosslinked copolymers of diethylene glycol divinyl ether and ethylene glycol vinyl glycidyl ether with methyl vinyl sulfide have been synthesized in the presence of 2,2′-azobis(isobutyronitrile) (2%, 60 °C, 45–55 h) in ∼53% yield. The hydrolyzed at the residual vinyloxy and epoxy groups and oxidized at the methylthio groups copolymers upon treatment with KOH afford alkoxide (complex) and crown-like superbases. They are capable of catalyzing the acetone ethynylation, as well as the prototropic isomerization of methyl propargyl ether to allenyl methyl ether and vinylation of ethylene and diethylene glycols with acetylene.

Cholesterol vinyl ether in free-radical homo-and copolymerization reactions

Vinyl ether of cholesterol has been polymerized through the free-radical mechanism with a yield of up to 30% to obtain optically active soluble oligomers. By the example of acrylonitrile, N-vinylpyrrolidone, ethylene glycol vinyl glycidyl ether, and N-vinyl-4,5,6,7-tetrahydroindole, it has been established that optically active copolymers of cholesterol may be synthesized.

Vinyl ethers with polysulfide and hydroxyl functions and polymers therefrom as binders for lithium–sulfur batteries

AbstractBis‐[3‐(vinyloxyethoxy)‐2‐hydroxypropyl‐]polysulfides (BVPS) have been prepared by reacting ethylene glycol vinyl glycidyl ether (EGVGE) with Na2S4 in the presence of NaHCO3 and a phase transfer catalyst, triethylbenzylammonium chloride. The polysulfides obtained are inactive in radical polymerization but polymerize readily upon thermal initiation (140°C, 1 h) or in the presence of cationic catalysts [BF3·OEt2, CF3COOH, H(AuCl4)·4H2O, LiBF4‐dimethoxyethane, 20–70°C]. Polymerization leads to the formation of crosslinked polymers. It has been shown that BVPS and their polymers can be used as active binders in cathode compositions of lithium–sulfur power sources. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 4051–4055, 2006

Polymerization of 1-allenylpyrroles

1-Allenylpyrroles are polymerized under the conditions of thermal (60 °C) and radical initiation at both 1,2- and 2,3-positions of the allenyl group to form soluble reactive polymers with various ethylenic, including polyvinylic, fragments. The possibility to prepare 1-allenylpyrrole copolymers has been demonstrated using 1-vinylpyrrolidone and ethylene glycol vinylglycidyl ether as an example. Doped layers based on poly-1-allenyl-4,5,6,7-tetrahydroindole are photosensitive.

Antisilicotic activity of fractions of the copolymer of ethylene glycol vinyl glycidyl ether and N-vinylpyrrolidone

Antisilicotic activity of fractions of the copolymer of ethylene glycol vinyl glycidyl ether and N-vinylpyrrolidone

Synthesis and antisilicotic activity of copolymers of N-vinylpyrrolidone with ethylene glycol vinyl glycidyl ether

Synthesis and antisilicotic activity of copolymers of N-vinylpyrrolidone with ethylene glycol vinyl glycidyl ether