Dimethylaminopropyl Acrylamide Research Articles

Preparation and properties of a double quaternary ammonium copolymer used in acid fracturing

Triethylamine (TEA), 1, 4-dibromobutane (C 4 H 8 Br 2 ) and N, N -dimethylaminopropyl acrylamide (DMAPAA) were selected to synthesize a double quaternary ammonium cationic monomer (TDD). TDD, acrylamide (AM), 2-acrylamido-2-methylpropane sulfonic acid (AMPS) and acrylic acid (AA) were used to create a quadripolymer (PAAT) that was characterized by FT-IR and 1 H NMR. Following that, the basic performance of thickened acid was assessed. The results revealed that PAAT outperformed PAA (copolymerized by AM, AMPS and AA) in terms of acid solubility, thickening performance, temperature resistance and shear resistance. Furthermore, this crosslinked acid containing PAAT was subjected to a series of performance evaluations. The viscosity of the crosslinked acid could be kept at 67 mPa·s at 160°C after 90 min and the weight loss rate of crosslinked acid in acid-rock reaction at 60 min was 23%, indicating the temperature resistance and retarder performance of the crosslinked acid solution was significantly better than that of the thickening acid and the blank acid. A scanning electron microscopy experiment revealed that crosslinked acid has good corrosion ability and low damage to the reservoir. The above experimental results indicated that the thickener PAAT has a promising future application in acid fracturing of high-temperature and high-mineralization carbonate reservoirs.

Thermoresponsive Cationic Polymers: PFAS Binding Performance under Variable pH, Temperature and Comonomer Composition.

The versatility and unique qualities of thermoresponsive polymeric systems have led to the application of these materials in a multitude of fields. One such field that can significantly benefit from the use of innovative, smart materials is environmental remediation. Of particular significance, multifunctional poly(N-isopropylacrylamide) (PNIPAAm) systems based on PNIPAAm copolymerized with various cationic comonomers have the opportunity to target and attract negatively charged pollutants such as perfluorooctanoic acid (PFOA). The thermoresponsive cationic PNIPAAm systems developed in this work were functionalized with cationic monomers N-[3-(dimethylamino)propyl]acrylamide (DMAPA) and (3-acrylamidopropyl)trimethylammonium chloride (DMAPAQ). The polymers were examined for swelling capacity behavior and PFOA binding potential when exposed to aqueous environments with varying pH and temperature. Comonomer loading percentages had the most significant effect on polymer swelling behavior and temperature responsiveness as compared to aqueous pH. PFOA removal efficiency was greatly improved with the addition of DMAPA and DMAPAQ monomers. Aqueous pH and buffer selection were important factors when examining binding potential of the polymers, as buffered aqueous environments altered polymer PFOA removal quite drastically. The role of temperature on binding potential was not as expected and had no discernible effect on the ability of DMAPAQ polymers to remove PFOA. Overall, the cationic systems show interesting swelling behavior and significant PFOA removal results that can be explored further for potential environmental remediation applications.

Simultaneous Removal of Arsenic and Manganese from Synthetic Aqueous Solutions Using Polymer Gel Composites.

The groundwater in approximately 50% of the Bangladesh landmass contains Mn concentrations greater than the limit prescribed by the WHO drinking water guidelines. Although studies have suggested that γ-FeOOH can effectively remove Mn from water, its practicability has not been investigated, considering that the additional processes required to separate the adsorbents and precipitates are not environment-friendly. To improve the efficiency of adsorptive Mn-removal under natural conditions, we employed a cationic polymer gel composite, N,N’-Dimethylaminopropyl acrylamide, methyl chloride quaternary (DMAPAAQ) loaded with iron hydroxide (DMAPAAQ + FeOOH), and a non-ionic polymer gel composite, N,N’-Dimethylacrylamide (DMAA) loaded with iron hydroxide (DMAA + FeOOH). DMAPAAQ + FeOOH exhibited a higher As removal efficiency under natural conditions while being environment-friendly. Our results suggest that the higher efficiency of the cationic gel composite is owed to the higher γ-FeOOH content in its gel structure. The maximum adsorption of Mn by DMAPAAQ + FeOOH was 39.02 mg/g. Furthermore, the presence of As did not influence the adsorption of Mn on the DMAPAAQ + FeOOH gel composite and vice versa. DMAPAAQ adsorbed As and the γ-FeOOH particles simultaneously adsorbed Mn. Our findings can serve as a basis for the simultaneous removal of contaminants such as As, Mn, Cr, and Cd.

Purification and recycling of selenium in wastewater using polyacrylamide capsule containing selenate‐reducing bacterium

AbstractBACKGROUNDRare metals are often used in high‐technology industries and, as a result, their demand has increased in present years. The shortage of some kinds the metals is concerning for the industries in question. The development of technologies to recover metals from wastewater and wastes is necessary for securing a stable supply of these metals. The present physicochemical treatments cannot easily recover metals from wastewater and wastes when they are present in low concentrations. In contrast, biochemical treatments, such as biomineralization, are expected to recover these metals efficiently. Selenium (Se) is one of the indispensable metals used in various products, such as electronics, glass manufacturing, pigments, metallurgical additives, and so on. A selenium reducing bacterium, Pseudomonas stutzeri NT‐I, was isolated previously. This bacterium reduces soluble seleno‐oxyanions to solid elemental selenium efficiently via a bioprocess called biomineralization.RESULTSA polyacrylamide capsule (PAC) containing selenate‐reducing bacterium, Pseudomonas stutzeri NT‐I, was prepared by double‐capsulation to recover selenium from wastewater simply and efficiently. The double‐capsulation is inclusion of alginate beads (AB) containing NT‐I by polyacrylamide composed of N‐isopropylacrylamide (NIPAM), N‐(2‐hydroxyethyl)acrylamide (HEAA), N‐[3‐(dimethylamino)propyl]acrylamide (DMAPAA), or (3‐acrylamidopropyl)trimethylammonium chloride (APTAC) cross linked by N,N′‐methylenebisacrylamide (MBAA).CONCLUSIONThe PACs had good stability in NaCl aq. and basic water in comparison with non‐capsulated AB. HEAA‐PAC and APTAC‐PAC showed relatively high water‐retaining capacity under the wet conditions. Selenate reduction tests were conducted in selenate, Se(VI) aq. at 37 °C in the presence of PACs, and APTAC‐PAC was effective in reducing and capturing Se. © 2021 Society of Chemical Industry (SCI).

Molecular and thermal studies of carbon fiber precursor polymers with low thermal‐oxidative stabilization characteristics

ABSTRACTIn this investigation, terpolymers, copolymers, and homopolymer of acrylonitrile with dimethylaminopropyl acrylamide (DMAPA), itaconic acid (IA) viz., poly(acrylonitrile‐ran‐3‐dimethylaminopropyl acrylamide‐ran‐itaconic acid) [P(AN‐DMAPP‐IA)], poly(acrylonitrile‐co‐3, dimethylaminopropyl acrylamide) [P(AN‐DMAPP)] were synthesized with varying amounts of comonomers using solution polymerization process. The chemical structure, composition, bonding network were determined employing infrared, 1H and, 13‐carbon nuclear magnetic resonance spectroscopic techniques. Molecular characteristics of as‐synthesized polymers such as different kinds of average molecular weights, molecular weight distribution were estimated applying solution viscometry and size exclusion chromatography. The influence of comonomers (DMPAA, IA) on the thermal stabilization characteristics of acrylonitrile terpolymers in comparison with copolymers and homopolymers of acrylonitrile were studied using differential scanning calorimetry (DSC), hyphenated thermal techniques (thermal gravimetry coupled with differential thermal analyzer).The DSC curves of P(AN‐DMAPP‐IA) exhibit a distinct broader bimodal peaks with thermal exotherm initiating at as low as 165 °C, and followed by two peaks with temperature difference of 42 °C, releasing the evolved heat at a release rate of 0.7–0.11 J g−1s−1over 10 min as compared to 1.2, 7.5 J g−1s−1 in 4.5, 2 min as observed in P(AN‐DMAPP), polyacrylonitrile, respectively. The thermal stability of P(AN‐DMAPP‐IA) and P(AN‐DMAPP), as evidenced by TGA‐DTA was found to be higher than PAN homopolymers. Specific heat capacity measurements confirmed the DSC results. Bulk densities of P(AN‐DMAPP‐IA) were in the range 0.31–0.35 g/cc. These results confirm the low‐temperature stabilization characteristics and suitability of P(AN‐DMAPP‐IA) as low cost carbon fiber precursor polymers. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46381.

Novel Metal Ion Removal Method Using Protonated Hydrogel

SummaryHydrogels based on copolymers of N‐[3‐(dimethylamino)propyl] acrylamide (DMAPAA), N,N‐dimethylacrylamide (DMAA) and N,N’‐methylenebis(acrylamide) (MBAA) were prepared as selective metal ion removal media. MBAA was used as a crosslinking agent for the DMAPAA and DMAA monomers. Polymerization mixtures were polymerized to create cylindrical shapes. The hydrogels were protonated when they were swelled in water and exhibited higher pH value inside than surrounding water because of Donnan effect. The pH value of the hydrogel could be changed by the concentration of DMAPAA monomers at the preparation. Metal ion removal experiments were carried out by swelling the hydrogels in metal ion aqueous solutions. The metal ions diffused in to the hydrogels to produce metal hydroxide in the hydrogel. The hydrogel with metal hydroxide in them were easily separated from the solution. The removal ratio of the metal increased with increasing the swelling time. The removal amount of the metal in the hydrogel was increased with the concentration of the metal ions in the solution. The selective removal of a certain metal ion from the mixed metal ion solutions was attained by controlling the pH value of the hydrogel. The results obtained here suggest the possibilities of the novel metal ion removal method replacing the coagulation and/or adsorption methods.

Influences of monomer self‐association on the radical solution homopolymerization of N‐[3‐(dimethylamino)propyl](meth)acrylamide

ABSTRACTThe specific dependencies of the initial reduced polymerization rate on the initial monomer concentration were introduced for the radical homopolymerization of N‐[3‐(dimethylamino)propyl]acrylamide (DMAPA) and N‐[3‐(dimethylamino)propyl]methacrylamide (DMAPMA) in toluene, DMF, and water at 60 °С. The degree of the monomer self‐association and the ratio of the amides constituting various types of associates were evaluated using FT‐IR spectroscopy and computer simulation for the solutions of DMAPA and DMAPMA in toluene with different monomer concentrations. The hypothesis linking the type of predominant pre‐reaction monomer assemblies and the revealed concentration effects was proposed for the homopolymerization of aminoamide monomers and explaining unconventional experimental data. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44412.

A pH-Responsive Soluble-Polymer-Based Homogeneous Ruthenium Catalyst for Highly Efficient Asymmetric Transfer Hydrogenation (ATH).

A pH-responsive polymer has been synthesized successfully by means of copolymerization of dimethyl aminopropyl acrylamide (DMAPA) and N-p-styrenesulfonyl-1,2-diphenylethylenediamine (V-TsDPEN). The pH-responsive polymer coordination ruthenium complex was thus prepared and employed as an efficient catalyst for the asymmetric transfer hydrogenation (ATH) of various ketones. The polymer catalyst exhibited an attractive pH-induced phase-separable behavior in water: it could be dissolved in water when the pH of the solution was lower than 6.5 at the beginning of the reaction, but was precipitated completely from water when the pH of the solution was above 8.5 after reaction. Additionally, the catalysts were highly efficient for the ATH of a wide range of substrates that bore different functional groups and could be recycled easily from the aqueous solution by means of self-separation. They could be recycled eight times without significant changes in catalytic activity and enantioselectivity.

Membrane-based purification of proteins from nanoparticle dispersions: Influences of membrane type and ultrafiltration conditions

Abstract The combination of nanoparticles with proteins to form functional hybrid systems is receiving undiminished attention because of its many biotechnological and medical applications. The separation of these hybrid materials from unbound free biomolecules has posed difficult challenges to fractionation and purification. Here, a model study has been carried out by removing proteins (bovine serum albumin (BSA) or lysozyme (LYS)) from the dispersion mixtures with silica nanoparticles (nominal size 20 nm) using ultrafiltration (UF) membranes. Regenerated cellulose (RC) and polyethersulfone (PES) membranes with nominal molecular weight cut-off (NMWCO) of 100 kDa, and a PES UF membrane (NMWCO 300 kDa) functionalized with UV-grafted amphoteric polymer hydrogel layer consisting of N -[3-(dimethylamino)propyl]-acrylamide (DMAPAA) and 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) and having an experimentally determined cut-off of 180 kDa (identical with the experimental data for PES 100 kDa) were studied. Membrane properties and filtration conditions, in particular pH value and flux, were selected or adapted based on data for single component feeds to achieve maximum protein transmission, complete silica retention and, hence, maximum silica/protein selectivity. Batch dead-end and continuous diafiltration processes were used for fractionation and purification. Overall, the performance of PES UF membranes was inferior compared to the other membranes because of too strong fouling. With membrane RC 100, the transmission data of LYS and BSA from the mixture with silica were 80% and 30%, respectively. With the hydrogel-functionalized PES membrane, the respective transmissions from the mixture were ∼35% and ∼15% for LYS and BSA, respectively. In both cases, quantitative rejection of silica could be achieved. Using continuous diafiltration, membrane RC 100 had better purification efficiency, removing a total of 91% of LYS using 6 diavolumes (DV) in 2.4 h and 84% of BSA using 10 DV in 5.5 h. With the hydrogel-functionalized PES membrane, 82% of LYS and 74% of BSA were removed using 6 and 10 DV within larger time, i.e. 4.0 and 6.8 h, respectively. Importantly, the retained silica nanoparticles remained stable in the dispersion, without any indication of aggregation. Overall, this study will add valuable knowledge to the most efficient use of ultrafiltration sieving properties for the removal or purification of proteins from systems comprising other colloidal particles having a size which is larger by a factor of only 3–10.

A Novel Thermosensitive Gel Adsorbent for Phosphate Ions

AbstractSummary: A novel thermosensitive gel adsorbent for phosphate ions was developed and its adsorption/desorption properties were investigated. The gel adsorbent was made by the copolymerization of N‐isopropylacrylamide (NIPA) and N‐[3‐(dimethylamino)propyl]acrylamide (DMAPAA). The adsorbent has a volume phase transition temperature (VPTT), below which it becomes hydrophilic. The tertiary amino groups of DMAPAA were ionized and showed a cationic state when the gel swelled. Phosphate ions were adsorbed onto the ionized tertiary amino groups in the gel network below the VPTT and were desorbed above the VPTT because of the suppression of the ionization of the tertiary amino groups of gel and the shrinkage of the gel.

Poly(N‐hydroxyethylacrylamide) Prepared by Atom Transfer Radical Polymerization as a Nonionic, Water‐Soluble, and Hydrolysis‐Resistant Polymer and/or Segment of Block Copolymer with a Well‐Defined Molecular Weight

AbstractN‐Hydroxyethylacrylamide (HEAA) was polymerized using the atom transfer radical polymerization (ATRP) with ethyl 2‐chloropropionate (ECP), copper(I) chloride (CuCl), and tris[2‐(dimethylamino)ethyl]amine (Me6TREN) in ethanol/water, producing poly(N‐hydroxyethylacrylamide) (PHEAA) with well‐defined molecular weights. The thermogravimetric analysis (TGA) indicated that the obtained PHEAA broadly decomposed with a two‐stage weight loss. The first loss was due to the decomposition of the hydroxyethyl groups, which started at temperatures ranging from 249.2 to 277.1 °C. The remaining polyacrylamide backbones started to decompose at temperatures ranging from 352.5 to 383.4 °C. The differential scanning calorimetry (DSC) indicated that PHEAA had a glass transition temperature (Tg) ranging from 70.6 to 117.8 °C. The ability of the obtained PHEAA as a prepolymer to initiate other acrylamide derivatives is described. N,N‐Dimethylacrylamide (DMAA), N‐acyloylmorpholine (NAM), and N‐[3‐(dimethylamino)propyl]acrylamide (DMAPAA) were subsequently added to the solutions after the polymerization of HEAA with ECP/CuCl/Me6TREN, producing the corresponding block copolymers.magnified image

Glucose sensors based on a responsive gel incorporated as a Fabry-Perot cavity on a fiber-optic readout platform

An optical sensor for detection of glucose is implemented by incorporating a carbohydrate sensitive hydrogel as a Fabry-Perot cavity at the end of optical fiber for high sensitivity readout of the gel length. The glucose sensing functionality was achieved by incorporating boronic acid moieties into an acrylamide-based hydrogel. The interaction between glucose and boronic acid changes the driving forces for gel swelling thus inducing a glucose sensitive hydrogel swelling. The effects on the carbohydrate swelling response, with respect to sensitivity and selectivity, by incorporation of a cationic monomer, dimethyl-aminopropyl acrylamide, into the boronic acid functionalized responsive gels were determined. The linear gel swelling response in aqueous solutions at aqueous 2.5mM carbohydrates were determined to −1760nm/mM for glucose whereas mannose, sucrose, fructose and galactose displayed a response of about 10% of the glucose response for the hydrogels containing 10mol% dimethylaminopropyl acrylamide. This gel composition with 10mol% dimethylaminopropyl acrylamide is the most promising for detection of glucose at physiological pH and ionic strength. A mechanism where carbohydrate specific stabilisation of the boronic acid group and possible carbohydrate mediated additional crosslinking of the elastically active polymer chains is suggested.

Characterization of Insulin Adsorption Behavior on Amphoteric Charged Membranes

With view to develop an amphoteric charged membrane for drug delivery, we have studied the adsorption of insulin on it. In the present study, the amphoteric charged membranes were prepared by pore-surface modification of porous poly(acrylonitrile) (PAN) membranes by grafting with acrylic acid (AAc) and/or N,N-(dimethylamino)propyl acrylamide (DMAPAA). Their surface charge properties and the insulin adsorption behaviors were investigated by zeta potential measurement and UV spectrophotoscopy, respectively, at different pHs. The equilibrium adsorbed amount of insulin correlates well with the charge properties of the membranes and insulin, which indicates that electrostatic interaction played an important role in the insulin adsorption. In addition, adsorption kinetics changed from a Fickian mode to a non-Fickian one when adsorbed amount increased to very high values.

Ionic-bonded negative photosensitive polyimides having pendant aminoalkyl (meth)acrylamide groups

Soluble polyimides having pendant carboxyl groups were prepared by a direct one-pot polycondensation of various acid dianhydrides with 3,5-diaminobenzoic acid and bis[4-(3-aminophenoxy)phenyl]sulfone in the presence of γ-valerolactone/pyridine catalyst in 1-methyl-2-pyrrolidone (NMP)/toluene mixture at 180 °C. The pendant carboxyl groups were blocked with photopolymerizable (meth)acrylamides, N-[3-(dimethylamino)propyl]acrylamide (DMAPAA), N-[3-(dimethylamino)propyl]methacrylamide (DMAPMA), or N-[3-(diethylamino)propyl]methacrylamide (DEAPMA), through ionic bonding at room temperature. The ionic-bonded photosensitive polyimide films containing photosensitizer Michler’s ketone (MK) and ethylene glycol dimethacrylate (EGDMA) as an external multifunctional cross-linker gave negative-tone behavior by near-UV irradiation followed by development with 10% aqueous NaOH at 25 °C. The SEM photograph of the resultant images showed fine patterns (line/space 20/20 μm) with ∼15 μm in film thickness. The sensitivity of photosensitive polyimides with DMAPAA or DMAPMA was higher than that of photosensitive polyimides with (meth)acrylate esters such as 2-(dimethylamino)ethyl acrylate (DMAEA), 3-(dimethylamino)propyl acrylate (DMAPA), 2-(dimethylamino)ethyl methacrylate (DMAMA), and 2-(diethylamino)ethyl methacrylate (DEAMA).

Characterization of Self-Association in Water of Polycations Hydrophobically Modified with Hydrocarbon and Siloxane Chains

Terpolymers of quaternized N-(N‘,N‘-dimethylaminopropyl)acrylamide (DMAPAA), N-dodecylmethacrylamide (C12MAm), and a methacrylate substituted with a poly(dimethylsiloxane) chain of a degree of polymerization of 29 (Si29MA), Q/C12(x)/Si29(y), were synthesized by free radical terpolymerization. The self-association properties of these terpolymers were investigated in 0.1 M NaCl aqueous solutions in comparison with those of copolymers of quaternized DMAPAA with C12MAm (Q/C12(x)) or with Si29MA (Q/Si29(y)). In the terpolymers, the C12MAm contents (fC12 (i.e., x)) and Si29MA contents (fSi29 (i.e., y)) range from 3.6 to 26 and from 2.8 to 3.3 mol %, respectively, while in the Q/C12(x) and Q/Si29(y) reference copolymers, fC12 and fSi29 range from 7.4 to 31 and from 0.47 to 2.4 mol %, respectively. The following conclusions were drawn from experimental data by quasi-elastic light scattering, fluorescence, and 1H NMR (two-dimensional nuclear Overhauser enhancement spectroscopy and spin−lattice relaxation times) st...

Photocrosslinking of dimethylaminopropylacrylamide copolymer

UV irradiation of methylmetacryiate (MMA) and styrene (St) copolymers with dimethylaminopropylacrylamide (DMAPAM) in solide state resulted in yellow crosslinked films. Poly(DMAPAM-co-MMA) are more sensitive to crosslink than the poly(DMAPAM-co-St). The sensitivity to crosslink is a function of: a) the mole fraction of DMAPAM in the copolymer, b) the irradiation time, and c) the nature of the comonomers.

Swelling behaviors of amphoteric gels and the dissociation mechanisms

Various types of amphoteric gels were made with the combinations of anionic monomers (sodium acrylate and sodium styrenesulfonic acid and cationic monomers (dimethylaminopropyl acrylamide and trimethyl-n-acryloly-3-aminopropane ammonium chloride) and the pH-dependent volume behaviors of these amphoteric gels were examined. As a consequence, the specific binding formed in each amphoteric gel could be dissociated into ions in a unique fashion with changes in pH. Four types of dissociation mechanisms could be presumed as follows; 1) ionization of the constituent groups (weak anion and cation groups) in both acidic and alkali solutions, 2) ionization of the constituent group (strong anion groups) in alkali solution, 3) ionization of the constituent group (strong cation groups) in acidic solution, and 4) ionization of the constituent groups (strong anion and cation groups) in both acidic and alkali solutions.

The synthesis of microgels composed of polyelectrolytes

AbstractMicrogels composed of dimethylaminopropylacryl amide (MAPA) or sodium salt of vinylbenzenesulfonic acid (VBS) were prepared by the crosslinking of primary polymers Poly(MAPA‐co‐acrylamide) or poly(VBS‐co‐acrylamide) with glutaraldehyde in aqueous solutions. Almost mono disperse spheric microgels with the diameter of 120 nm were obtained in the very wide concentration range (up to 5 w/v% for the former and 12 w/v% for the latter). In the copolymerization of MAPA and N‐methyloylacrylamide, microgel with the diameter of 120–140 nm was formed during polymerization.

Oxygen permeability in polymers, III. Dependence of the oxygen permeability on the chemical structure of styrene‐maleic acid‐copolymers

AbstractThe paper gives a report on the oxygen permeability in films of poly(styrene‐comaleic acid) halfesters and halfamides as well as other polymers containing carboxylic groups in comparison with commercially available glass forming polymers at room temperature. The presence of oxygen in the polymer layers was proved by the quenching of the delayed fluorescence of pyronin B. The permeability of the halfesters/halfamides (Pox = 2…7.10‐14 cm2/Pa .s) corresponds to that of common polymers like poly(methyl methacrylate) (PMMA) or poly(vinyl acetate) (PVAc), and is nearly one order of magnitude higher than that of poly(acrylic acid) (PAAc), poly(styrene‐comaleic acid) (SMAc) and carboxymethylcellulose (CMC). Presumably, intramolecular hydrogen bonds in the halfester/halfamides compete successfully with the intermolecular interactions and hence cause an increase in permeability as also do bulky substituents. Addition of bases like dimethyl aminopropanol (DMAP) and dimethyl aminopropyl acrylamide (DMAPAA) decreases the permeability to about 1/40 of the initial value. The permeability is then similar to the low permeability of polymers with predominant ionic interaction sodium polyacrylate (NaPAAC), sodium carboxymethylcellulose (NaCMC)).