Stearyl Methacrylate Research Articles

Synthesis and properties of superhydrophobic monomer stearyl methacrylate-modified polyacrylate latex pressure sensitive adhesives

Hybrid surfactants of long carbon chain hydrophobic nonionic emulsifier N-390 and conventional anionic emulsifier CO-436 were utilized in this study to enable successful emulsion polymerization of super-hydrophobic monomer stearyl methacrylate (SMA) together with butyl acrylate (BA), acrylic acid (AA), and 2-hydroxyethyl acrylate (HEA). The influences of SMA on the resulting latex and film properties were thoroughly investigated. Both FTIR and 1H NMR were used to confirm the successful participation of SMA in the emulsion polymerization. The results indicated that with introduction of SMA, the roughness of the latex film increases, while the light transmission decreases. It was also found that with the addition of SMA, contact angle of the latex PSA film increased from 115.1° to 127.2°, while water absorption decreased from 5.76 to 2.89 wt%. DSC curves demonstrated that SMA has participated more in the homopolymerization reaction than in the copolymerization reaction. TGA results showed that the initial decomposition temperature (T5%) of the latex film was increased from 302.8 to 332.7 °C with the increase of SMA dosage from 0 to 20 wt%. Finally, adhesion properties results indicated that loop tack and 180° peel force of the PSA films were decreased from 11.51 to 1.88 N/25 mm and 6.36 to 3.44 N/25 mm, respectively, while shear strength was increased from 732 to 2865 min.

Effect of Stearyl Methacrylate Comonomer on the Mechanical and Physical Properties of Dimethacrylate-Based Dental Resins.

This study evaluated the effect of stearyl methacrylate addition on the physical and mechanical properties of bisphenol A glycidyl methacrylate- and triethylene glycol dimethacrylate-based polymers, which are traditionally used in dental applications. Methacrylate-based monomer compositions are polymerized under the visible blue light spectrum. An analysis of double bond conversion, surface microhardness test, three-point bending test and water sorption and water solubility were tested to determine the physical and mechanical properties of the dental polymers. The results indicated that stearyl methacrylate addition up to 25 wt% reduced the water sorption of the polymers. At amounts of stearyl methacrylate higher than 25 wt%, the solubility of the polymer in water increases due to the monofunctional structure. Mechanical properties are negatively affected by the increasing stearyl methacrylate ratio. Further, the addition of stearyl methacrylate slightly increased thermal stability. As such, the amount of stearyl methacrylate in a polymer composition is critical for the optimization of its mechanical and physical properties. According to the results, the amount of stearyl methacrylate has to be between 12.5-25 wt%.

Imparting semi-permanent demoldability to stainless steel mold using surface-initiated solution polymerization of stearyl methacrylate

The growing market demand for compact and precisely-designed polymeric products has raised challenges during the demolding stage of manufacturing. An increased contact area between the product and the mold increases adhesion, which reduces dimensional stability and aesthetics. Conventional solutions like surface roughness improvement or release agent coatings suffer from reduced productivity and impurity-related issues affecting mechanical properties. To address these challenges, we imparted the semi-permanent demoldability to a stainless steel (SUS) mold by polymerizing stearyl methacrylate monomer on its surface using a surface-initiated solution polymerization technique. The polymerization state was confirmed through Fourier transform infrared spectroscopy and field emission scanning electron microscopy. The demoldablity was investigated using the appropriately-designed lap shear tests to simulate the demolding stage of epoxy resin-filled SUS mold to ensure sufficient performance compared with the neat and commercial release agent (RA) treated molds, and durability of the demoldability was confirmed via repetitive single-lap shear tests simulating the molding and demolding processes. The surfaced polymerized mold exhibited excellent demoldability with 96.5 % improvement over the neat one, and showed excellent durability over 5 repeated molding cycles, while the commercial RA showed significant degradation of demoldability. Furthermore, the mechanism of demoldability enhancement using the proposed surface polymerization was investigated by characterization of the surface dewetting pattern and contact angle measurements of the epoxy resin on the modified mold surface.

Fabrication of highly stretchable composite organohydrogel for strain sensors with high sensitivity and broad temperature tolerance

Elastically stretchable conductive hydrogels have garnered significant scholarly interest for their potential applications in wearable sensing technologies. Yet, these highly elastic hydrogels often display diminished sensory capacities, particularly under conditions of severe thermal variation. This investigation unveils a highly stretchable composite organohydrogel distinguished by its superior sensory proficiency and resilience to harsh thermal environments. Encapsulating carbonized crepe paper (CCP) within a hydrophobic association-driven organohydrogel-crafted through the micellar copolymerization of hydrophobic stearyl methacrylate with hydrophilic acrylamide, and incorporation of polyvinyl alcohol (PVA) and Al3+ in a binary solvent of glycerol and water-we attained a high stretchability of 3865 %, in conjunction with augmented tensile strength and sensory acuity. Moreover, this composite demonstrates a gauge factor of 263.1 for strains ranging from 400 to 550 %, a detection threshold of 0.1 %, swift response/recovery times (161/152 ms), and sustained durability over 1000 cycles at a 100 % strain. Such attributes facilitate its deployment in the realms of health monitoring, activity sensing, gesture recognition, and wireless motion control, even under extreme thermal conditions, heralding a pioneering strategy for the creation of cost-efficient, high-efficacy electronic conductive hydrogels.

Amphiphilic block and random copolymers: aggregation and hydrophobic modification on metal-free tanned collagen fibers

Hydrophobicity enhancement of metal-free leather, which is crucial for improving its comprehensive performance, can be achieved by using amphiphilic copolymer retanning agents. However, the relationship between the sequential structure and the hydrophobic modification effect of amphiphilic copolymers remains unclear. Herein, an amphiphilic block copolymer was synthesized using stearyl methacrylate and 2-(dimethylamino)ethyl methacrylate via atom transfer radical polymerization, and the corresponding random copolymer with similar monomer compositions and molecular weights was prepared for comparison. The aggregation behavior of block and random copolymers was investigated. DLS and TEM results indicate that the block copolymer exhibits a larger aggregate size than the corresponding random copolymer. Molecular dynamics simulations suggest that the block copolymer aggregate exhibit a thicker hydrophilic shell and more concentrated distribution of cationic DMA block than the random copolymer aggregate. Subsequently, the block and random copolymers were used for the hydrophobic modification of metal-free tanned collagen fibers (CFs). The block copolymer shows superior binding capacity to CFs than the random one because of its larger size and more concentrated charge distribution. Hence, the block copolymer can form a dense and uniform hydrophobic film on the surface of collagen fibrils and endow CFs with higher hydrophobicity than the random one. This work provides theoretical guidance for modulating the hydrophobicity of CFs by tailoring the sequential structure of amphiphilic copolymers, which is expected to inspire the manufacturing of high-performance metal-free leather.Graphical

Synthesis and application of polyer additive system for reducing the pour point depressant of crude oil in exploitation, transportation

Problems encountered when exploiting and transporting crude oil containing solid paraffins is that it easily crystallizes under normal temperature, causing many challenges such as paraffin wax deposition, reduced flow rate, gel formation, loss of pipe pressure... When the crude oil temperature is below the wax appearance temperature (WAT), paraffin will precipitate and separate from the oil. Many solutions that have been and are being used such as insulation, mechanical, thermal, chemical methods, using wax inhibitors - pour point depressants (PPD) and dispersants... The method of using additives to increase solidification temperature or inhibit wax, improve the rheology of crude oil and reduce paraffin deposition is considered one of the most effective method. In this study, polymers made from a combination of three monomers, behenyl acrylate, stearyl methacrylate and vinyl acetate, were studied to find the most optimal combination for the purpose of manufacturing pour point lowering additives for oils.

Impact of Ionic Liquid Functionalized ZrO2 Nanoparticles on Poly (stearyl methacrylate) Grafted Poly (vinylidene fluoride‐co‐hexafluoropropylene) Based Highly Conductive Gel Polymer Electrolytes for Lithium‐Metal Batteries

AbstractIn this study, an organic‐inorganic hybrid polymer membrane is successfully designed and developed by grafting stearyl methacrylate (SMA) side chains onto the backbone of the P(VDF‐HFP) copolymer followed by blending with varying amounts of imidazolium ionic liquids functionalized ZrO2 nanoparticles. Different microporous gel polymer electrolytes (MGPEs) are prepared by immersing the membranes into a LiTFSI salt‐dissolved ionic liquid electrolyte. The membranes′ crystallinity, surface morphology, porosity, and thermal stability are investigated using various characterization techniques. The copolymer membrane blended with 60 wt % functionalized nanoparticles exhibits the highest porosity of 64.5 %, which allows it to achieve a maximum electrolyte uptake of 387 wt %. That enables the corresponding MGPE to achieve the highest room temperature lithium ion conductivity of ~5.34×10−3 S cm−1 with a wide electrochemical stability window and good electrochemical stability against Li metal. Leveraging these advantageous characteristics, the lab‐scale truly solid‐state Li|MGPE|LiFePO4 and Li|MGPE|LiNi0.8Mn0.1Co0.1O2 cells demonstrate excellent rate capability and reversible cycling stability while maintaining high specific capacities (up to 154 and 172 mAh g−1, respectively, at 0.5 C) with >99.0 % coulombic efficiency over 100 cycles. Such exceptional interfacial compatibility with both low‐ and high‐voltage cathodes establishes the applicability of these newly developed MGPEs in next‐generation all‐solid‐state lithium‐metal batteries.

Preparation of Block Copolymer Self-Assemblies via Pisa in a Non-Polar Medium Based on RCMP.

Polymerization-induced self-assembly (PISA) is conducted in a non-polar medium (n-dodecane) via reversible complexation-mediated polymerization (RCMP). Stearyl methacrylate (SMA) is used to synthesize a macroinitiator, and subsequent block polymerization of benzyl methacrylate (BzMA) from the macroinitiator in n-dodecane afforded a PSMA-PBzMA block copolymer, where PSMA is poly(stearyl methacrylate) and PBzMA is poly(benzyl methacrylate). Because PSMA is soluble but PBzMA is insoluble in n-dodecane, the block copolymer formed a self-assembly during the block polymerization (PISA). Spherical micelles, worms, and vesicles are obtained, depending on the degrees of polymerization of PSMA and PBzMA. "One-pot" PISA is also attained; namely, BzMA is directly added to the reaction mixture of the macroinitiator synthesis, and PISA is conducted in the same pot without purification of the macroinitiator. The spherical micelle and vesicle structures are also fixed using a crosslinkable monomer during PISA. RCMP-PISA is highly attractive as it is odorless and metal-free. The "one-pot" synthesis does not require the purification of the macroinitiator. RCMP-PISA can provide a practical approach to synthesize self-assemblies in non-polar media.

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.

SYNTHESIS OF COPOLYMERS OF STEARYLMETHACRYLATE AND STEARYLACRYLATE WITH N-SUBSTITUTED ACRYLAMIDES IN THE PRESENCE OF REVERSIBLE CHAIN TRANSFER AGENTS AND STUDY OF THEIR EFFECT ON THE LOW-TEMPERATURE PROPERTIES OF DIESEL FUEL

The features of copolymerization of stearylacrylate (SA) and stearylmethacrylate with N-isopropylacrylamide and N,N-dimethylacrylamide in the presence of dibenzyltrithiocarbonate and 2-cyanoisopropyldodecyltrithiocarbonate as agents of reversible chain transfer have been studied. The choice of agents of reversible chain transfer (RAFT-agents) is due to the fact that sulfur-containing compounds with cyanoisopropyl radicals are most effective in the polymerization of methacrylic monomers, while benzyltrithiocarbonates are more active in the polymerization of acrylic monomers, as well as styrene and acrylonitrile. It has been established that polymerization of stearyl methacrylate (SMA) in the presence of RAFT-agents proceeds without a gel effect up to a high conversion. At the same time, although polystеarylmethacrylate samples are characterized by relatively high values of polydispersity coefficients (Mn/Mw) for controlled radical polymerization processes, they are nevertheless somewhat lower than for polymers of similar conversion synthesized in the absence of chain transfer agents. It has been shown that the process of copolymerization of stearyl acrylate and stearylmethacrylate with N-isopropylacrylamide and N,N-dimethylacrylamide in the presence of dibenzyltrithiocarbonate and 2-cyanoisopropyldodecyltrithiocarbonate proceeds without gelation to high conversions. The synthesized copolymers are characterized by a relatively narrow molecular weight distribution: the polydispersity coefficients of polymer samples vary from 1.18 to 1.57 in the case of using N-isopropylacrylamide and from 1.21 to 1.47 when using N,N-dimethylacrylamide as a comonomer to higher alkyl acrylates, which is typical for processes of radical polymerization proceeding in a controlled manner. At the same time, the synthesized copolymers exhibit a significant depressant effect when they are introduced into diesel fuel at a concentration of 1600 ppm. It has been established that copolymers of stearylmethacrylate and stearylacrylate with polar nitrogen-containing monomers have a more effective effect on the low-temperature properties of diesel fuel than homopolymers of stearylmethacrylate and stearylacrylate. At the same time, additives based on copolymers of stearylmethacrylate with N-isopropylacrylamide with a composition of 70/30 mol.% and stearylacrylate with N-isopropylacrylamide with a composition of 20/80 mol.% had the most significant effect on the low-temperature characteristics of the fuel.

Photocurable 3D printing high-strength gels for flexible wearable devices and surgical models

Hydrogels are considered to be ideal materials for the preparation of preoperative models and flexible wearable devices due to their softness and plasticity. However, there are still some problems in their application, such as how to achieve the construction of complex spatial structures through 3D printing and poor mechanical properties of the gel, especially poor tear resistance will greatly shorten the service life of hydrogels. In this study, with acrylamide (AM), stearyl methacrylate (SMA) and Multi-arm Crosslinking Agent (AGE-M) as the main raw materials, we provided a tear-resistance gel that can be photocurable for 3D printing. Through digital light processing (DLP)-based 3D printing, various gel-based preoperative models and devices with complex structures can be prepared. More importantly, the printed gel is endowed with excellent tear resistance by introducing the AGE-M as a nanoscale high-functionality crosslinker. In addition, the conductive substance sodium chloride is introduced to make the gel have a certain conductivity, and the organic solvent glycerol is introduced to replace part of the water to form a binary phase organic solvent, which endows the gel with excellent anti-drying and anti-freezing properties, to be suitable for more environments. Therefore, this work proposes a tear-resistance gel processed by DLP-based 3D printing technology, which can be used for the personalized manufacturing of organ models and flexible wearable devices, and is expected to be used in surgical training and artificial intelligence.

Self-healing elastomers from supramolecular random copolymers of 4-vinyl pyridine

For the first time hydrogen bonding complexes between poly(4-vinyl pyridine) (P4VP) and its copolymers were employed as a healing concept for building supramolecular materials with self-healability. P4VP and its random copolymers with stearyl acrylate and stearyl methacrylate were first synthesized via UV light-mediated metal-free polymerization using 4-(10H-phenothiazin-10-yl)-N,N-diphenylaniline as organic photocatalyst. Three complexes between the P4VP homopolymer and the obtained copolymers bearing “hairy” side groups with 3,3′-dithiodipropionic acid (DTDP) as a proton donor crosslinker were studied. Owing to the “solvent”-like mantle formed by lowly ordered stearyl side groups, the complex of poly(4-vinyl pyridine-random-stearyl methacrylate) and DTDP exhibited efficient self-healability of complete cuts at room temperature after 30 min, with tensile strength recovery of above 80%. The results of this work suggested that this dynamic supramolecular concept based on P4VP is promising for developing self-healing materials for various applications.

An oil-absorbing resin with a simple polymerization system with benzyl methacrylate as a functional monomer.

To solve the problem of the low absorbency of oil-absorbing resins, oil-absorbing resins (PAMs) were fabricated in this study by introducing commercially available benzyl methacrylate (BZMA) as a functional monomer copolymerized with stearyl methacrylate (SMA) and butyl acrylate (BA). The internal network structure of the PAMs expanded more easily when absorbing oils or organic solvents after introducing rigid groups of the benzene ring by an uncomplex polymerization process, which provided the oil-absorbing resin with good absorbency. The reagents were all commercially available, and there was no other pretreatment or posttreatment process. Then, the optimum parameters for the monomer feed ratio, water/oil mass ratio, and concentrations of initiator, stabilizer and crosslinker were studied. Simultaneously, the reusability, oil retention and thermal stability of PAMs were investigated in this article. The PAMs swelled in various oils and organic solvents (the values of oil absorbency were 44.52, 56.13, 25.54, 28.21, 32.85, 24.56, 14.17, 15.02 and 29.07 g g-1 for CCl4, CHCl3, CH2Cl2, benzene, toluene, xylene, n-hexane, 0# diesel oil and 93# gasoline, respectively) and displayed good oil absorbency, which met the absorption requirements for common oils or organic solvents.

Development of Effective Depressor Additives to Diesel Fuel, Based on Copolymers of Stearyl Methacrylate with Monomers of Various Structures

Development of Effective Depressor Additives to Diesel Fuel, Based on Copolymers of Stearyl Methacrylate with Monomers of Various Structures

Screening of Oligomeric (Meth)acrylate Vaccine Adjuvants Synthesized via Catalytic Chain Transfer Polymerization.

This report details the first systematic screening of free-radical-produced methacrylate oligomer reaction mixtures as alternative vaccine adjuvant components to replace the current benchmark compound squalene, which is unsustainably sourced from shark livers. Homo-/co-oligomer mixtures of methyl, butyl, lauryl, and stearyl methacrylate were successfully synthesized using catalytic chain transfer control, where the use of microwave heating was shown to promote propagation over chain transfer. Controlling the mixture material properties allowed the correct viscosity to be achieved, enabling the mixtures to be effectively used in vaccine formulations. Emulsions of selected oligomers stimulated comparable cytokine levels to squalene emulsion when incubated with human whole blood and elicited an antigen-specific cellular immune response when administered with an inactivated influenza vaccine, indicating the potential utility of the compounds as vaccine adjuvant components. Furthermore, the oligomers' molecular sizes were demonstrated to be large enough to enable greater emulsion stability than squalene, especially at high temperatures, but are predicted to be small enough to allow for rapid clearance from the body.

Evaluation of block copolymer and homopolymer of stearyl methacrylate as multifunctional additives for lubricating oil

Evaluation of block copolymer and homopolymer of stearyl methacrylate as multifunctional additives for lubricating oil

Enhanced ASO-Mediated Gene Silencing with Lipophilic pH-Responsive Micelles.

Herein, we examine the ASO-mediated gene silencing efficiency of pH-responsive micelles, by incorporating 2-(diisopropylamino)ethyl methacrylate (DIP) into the micelle core and comparing physical and biological properties with non-pH-responsive micelles. Additionally, the lipophilic effect of the micelle cores was examined in both types of micelles. Varying lipophilicity was achieved by varying alkyl monomer chain lengths─butyl (4), lauryl (12), and stearyl (18) methacrylate. Each of the micelles formed within our family offered the added benefit of well-defined and uniform templates for loading antisense oligonucleotide (ASO) payloads. Overall, the micelles followed previously established trends of outperforming their linear polymer (nonmicelle) analogs and ASO only control. More specifically, the highest performing micelles were the pH-responsive micelles with longer alkyl chains or higher lipophilicity─D-DIP+LMA and D-DIP+SMA (∼90% silencing). These two micelles demonstrated silencing efficiencies similar to Jet-PEI and Lipofectamine 2000 and caused lower toxicity than Lipofectamine 2000. The shortest alkyl chain pH-responsive micelle, D-DIP+BMA (64%), displayed strong gene silencing similar to that about that of its non-pH-responsive micelle, D-BMA (68%), and the pH-responsive micelle without an alkyl chain incorporated, D-DIP (59%). This work illuminates a minimum alkyl chain length dependence to allow gene silencing within our micelle family. However, including only longer alkyl chains into the micelle core without the pH-responsive unit DIP had a hindering effect, thus demonstrating the requirement of the DIP unit when including longer alkyl chain lengths. This work demonstrates the exemplary gene silencing efficiencies of polymeric micelles and uncovers the relationship between pH responsiveness and performance with lipophilic polymer micelles for enhancing ASO-mediated gene silencing.

Switchable Stiffness of Composite Hydrogels Triggered by Thermoresponsive Phase-Change Particles

Abstract Thermoresponsive hydrogel with switchable mechanical properties was developed by incorporating poly(stearyl methacrylate) (PSMA) as a responsive domain into bacterial cellulose (BC) as a supporting hydrogel. The PSMA particles in BC exhibited a reinforcing effect below their melting temperature (Tm) and a reduced effect above Tm, leading to significant responsive behavior.

Synthesis and properties of deformable porous polymeric particle for oil‐based drilling fluids

AbstractThe conventional filtration loss reducers, which help reduce the invasion into the formation, often make the rheology of the oil‐based drilling fluid difficult to control. In this paper, the new type of porous deformable polymeric particle was synthesized as filtration loss reducer (FLR), through dispersion polymerization using acrylamide and stearyl methacrylate. Fourier transform infrared spectroscopy, differential scanning calorimeter, thermogravimetric analysis, contact angle apparatus, nitrogen adsorption/desorption techniques and scanning electron microscope have been carried out to confirm the chemical structure of the FLR. The results illustrated that FLR is a hydrophobic porous solid particle with deformability. The oil‐based drilling fluid loaded with FLR retains high temperature resistance up to 180°C and the density of 2.2 g/cm3. The FLR help reduced the filtration loss to 3.2 mL, smaller than their counterparts, and synthesized FLR has small impact on the rheology of drilling fluids.

Shape-Stabilized Monolithic Composite for Switchable Stiffness Based on Cellulose and Poly(stearyl methacrylate)

Stiffness-changing materials (SCMs) have recently attracted attention because their mechanical strength can be changed in response to external stimuli. Although the stiffness of SCMs can be adjusted considerably, these materials do not necessarily possess sufficient mechanical robustness in their soft state, thereby limiting their practical applicability. In this study, a stimuli-responsive polymer was incorporated into a porous supporting material to fabricate SCMs with high structural stability. Poly(stearyl methacrylate) (PSMA) was utilized as the responsive domain owing to the phase-changing behavior of its long alkyl side chain. A cellulose monolith (CM) was selected as the support owing to its outstanding chemical and physical stability despite its high porosity. The PSMA-modified CM (PSMA-CM) exhibited clearly detectable stiffness changes in response to temperature as a result of melting and crystallization of the PSMA domain. The Young’s modulus of PSMA-CM at 60 °C was half as large as that at 20 °C. Furthermore, during cyclic compressive loading–unloading tests, PSMA-CM displayed good shape recoverability, and the changes in its thermoresponsive stiffness were highly repeatable owing to both the stability of CM and the reversible responsive properties of PSMA. In addition, as opposed to CM, the stiffness of PSMA-CM decreased as the polarity of the surrounding solvent decreased. This result indicates that PSMA was composited not only onto the surface but also into the interior of the CM skeletal backbone. PSMA clearly reflects the variable stiffness of the monolith derived from the PSMA domain without impeding the dimensional stability of the material.