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Journal articles on the topic 'Phosphonate polymers'

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Author: Grafiati

Published: 6 September 2023

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1

Amjad, Zahid, and Amannie Kweik. "HYDROXYAPATITE DISPERSION BY PHOSPHONATES, POLYMERS AND PHOSPHONATE/POLYMER BLENDS." Phosphorus Research Bulletin 30 (2015): 19–25. http://dx.doi.org/10.3363/prb.30.19.

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2

Dolan, Ciarán, Briar Naysmith, Simon F. R. Hinkley, Ian M. Sims, Margaret A. Brimble, David E. Williams, and Jianyong Jin. "Synthesis of Novel Triazole-Containing Phosphonate Polymers." Australian Journal of Chemistry 68, no. 4 (2015): 680. http://dx.doi.org/10.1071/ch14513.

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The objective of this research was to develop novel phosphonate-containing polymers as they remain a relatively under researched area of polymer chemistry. Herein, we report the synthesis and characterization of 2-(1-(2-(diethoxyphosphoryl)ethyl)-1H-1,2,3-triazol-4-yl)ethyl acrylate (M1) and diethyl (2-(4-(2-acrylamidoethyl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate (M2) monomers using the copper-catalyzed azide–alkyne cycloaddition (CuAAC) ‘click’ reaction, and their subsequent polymerization via both uncontrolled and reversible addition–fragmentation chain transfer (RAFT) polymerization techniques yielding phosphonate polymers (P1–P4).

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3

Squeo, Benedetta Maria, Francesco Carulli, Elisa Lassi, Francesco Galeotti, Umberto Giovanella, Silvia Luzzati, and Mariacecilia Pasini. "Benzothiadiazole-based conjugated polyelectrolytes for interfacial engineering in optoelectronic devices." Pure and Applied Chemistry 91, no. 3 (March 26, 2019): 477–88. http://dx.doi.org/10.1515/pac-2018-0925.

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Abstract Polar semiconducting polymers based on a conjugated polymer backbone endowed with chemically anchored polar groups on the side chains have proved to be particularly interesting as optimization layer at organic/cathode interface in optoelectronic devices. In particular, the pendant phosphonate groups impart water-alcohol solubility allowing easy solution processing, and improve electron injection thanks to both a favorable interfacial dipole of phosphonate groups and an intense coordination interaction between the phosphonate groups and Al cathode. In this work we synthesize alternating fluorene-benzothiadiazole copolymers by proposing a post-polymerization reaction to insert the phosphonate groups. Thanks to this approach it is possible to use standard Suzuki coupling conditions, simplifying the process of synthesis, purification and characterization. The polymer Poly[9,9-bis(6′-diethoxylphosphorylhexyl)-alt-benzothiadiazole] (P2), is tested in conventional organic solar cells as cathode interfacial layers showing, with respect to the control device, an increasing of all the photovoltaic parameters, with a final power conversion efficiency that reaches 5.35% starting from 4.6%. The same trend is observed for multilayered polymer light-emitting diodes with an external quantum efficiency of the P2-based PLED enhanced of 1.5 times with respect to the basic devices with bare Al cathode, and negligible roll-off efficiency. The synergic effects of energy gap modulation and of polar phosphonated pendant functionalities of P2 are compared with the corresponding fluorene-based polar homopolymer. Our results show that, not only a proper selection of side functionalities, but also the tailoring of the energy gap of cathode interfacial materials (CIMs) is a possible effective strategy to engineer cathode of different optoelectronic devices and enhance their performance.

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4

Meng, Bin, Yingying Fu, Zhiyuan Xie, Jun Liu, and Lixiang Wang. "Phosphonated conjugated polymers for polymer solar cells with a non-halogenated solvent process." Polymer Chemistry 6, no. 5 (2015): 805–12. http://dx.doi.org/10.1039/c4py01294a.

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5

Jordan, Myles M., and Michael Johnston. "Enhanced Carbonate Scale Inhibition in the North Sea via Synergistic Inhibitor Molecule Blends." Journal of Petroleum Technology 75, no. 01 (January 1, 2023): 44–49. http://dx.doi.org/10.2118/0123-0044-jpt.

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_ Controlling inorganic sulphate and carbonate scales with polymer, phosphonate, and phosphate ester scale inhibitors is commonplace in the oilfield services industry. It is well understood in what environments induvial inhibitor types work best; for example, sulphonates are very effective for sulphate scale control in low temperatures (SPE 80229) whereas phosphonates are much less effective under these same conditions but improve at higher temperatures (SPE 179889). Less well understood is the potential for scale inhibitors utilizing synergistic interactions with blends of polymers, phosphonates, and phosphate esters to reduce chemical cost, treatment rates, and transport logistics, resulting in a more effective scale management program with a reduced operational footprint. To evaluate performance of a selected range of blended inhibitors, ChampionX performed a trial on a North Sea produced water system, which was applying monoethanolamine (MEA) phosphonate-type scale inhibitor as well as novel cleaning programs to counter a high carbonate saturation ratio in the heater (SPE 204365). The objective was to find an improved scale inhibitor formulation that would outperform MEA phosphonate to control the high calcite saturation ratio brine. In this application, produced fluids pass through a heater with a skin temperature between 90°C and 105°C. Identifying the Scale Challenge Studies of synergistic properties of phosphonates and polymer scale inhibitors show there is potential to create blends of existing chemicals to make a formulation that shows a performance greater than either inhibitor component on its own. Four generic scale inhibitors that could effectively prevent scale at 105°C were considered. 1. A poly aspartate acid, generally found to be thermally stable to 120°C 2. The incumbent MEA phosphonate chemical, which is widely used for this type of scale inhibition at elevated temperature 3. A phosphate ester, found to be thermally stable at temperatures of 90°C 4. Phosphonate-functionalized biopolymer, which showed good carbonate inhibition properties and excellent environmental properties The goal was to develop a synergistic blend that would mitigate the legislative (cost of REACH registration) and economic (cost of new raw material product set up within the supply chain system) issues associated with the development of new classes of scale inhibitor for a relatively small market. There are two primary methods of scale inhibition in produced water. The first is crystal nucleation inhibition, which prevents the onset of scale formation itself by keeping the ions in solution. This mechanism of inhibition is best evaluated via dynamic scale loop (DSL) tests. The polymer-type scale inhibitors (such as carboxylic acid functionated homo and copolymers, for example VS-Co) work well within this test, as they prevent deposition at low treatment rate. The other principal inhibition mechanism is crystal-growth inhibition. This prevents the continued growth of microscale crystals as the inhibitor interacts with the scale crystal surface to prevent further addition of sulphate/barium ions. This is best evaluated via static bottle tests. Phosphonate-type scale inhibitors, for example, diethylenetriamine penta (methylene phosphonic acid), work well within this type of test.

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6

Venkatramaiah, Nutalapati, Ricardo F. Mendes, Artur M. S. Silva, João P. C. Tomé, and Filipe A. Almeida Paz. "A ladder coordination polymer based on Ca2+and (4,5-dicyano-1,2-phenylene)bis(phosphonic acid): crystal structure and solution-state NMR study." Acta Crystallographica Section C Structural Chemistry 72, no. 9 (August 25, 2016): 685–91. http://dx.doi.org/10.1107/s2053229616012328.

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The preparation of coordination polymers (CPs) based on either transition metal centres or rare-earth cations has grown considerably in recent decades. The different coordination chemistry of these metals allied to the use of a large variety of organic linkers has led to an amazing structural diversity. Most of these compounds are based on carboxylic acids or nitrogen-containing ligands. More recently, a wide range of molecules containing phosphonic acid groups have been reported. For the particular case of Ca2+-based CPs, some interesting functional materials have been reported. A novel one-dimensional Ca2+-based coordination polymer with a new organic linker, namely poly[[diaqua[μ4-(4,5-dicyano-1,2-phenylene)bis(phosphonato)][μ3-(4,5-dicyano-1,2-phenylene)bis(phosphonato)]dicalcium(II)] tetrahydrate], {[Ca2(C8H4N2O6P2)2(H2O)2]·4H2O}n, has been prepared at ambient temperature. The crystal structure features one-dimensional ladder-like∞1[Ca2(H2cpp)2(H2O)2] polymers [H2cpp is (4,5-dicyano-1,2-phenylene)bis(phosphonate)], which are created by two distinct coordination modes of the anionic H2cpp2−cyanophosphonate organic linkers: while one molecule is only bound to Ca2+cationsviathe phosphonate groups, the other establishes an extra single connectionviaa cyano group. Ladders close pack with water molecules through an extensive network of strong and highly directional O—H...O and O—H...N hydrogen bonds; the observed donor–acceptor distances range from 2.499 (5) to 3.004 (6) Å and the interaction angles were found in the range 135–178°. One water molecule was found to be disordered over three distinct crystallographic positions. A detailed solution-state NMR study of the organic linker is also provided.

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7

Gelfand, Benjamin S., Jared M. Taylor, and George K. H. Shimizu. "Extracting structural trends from systematic variation of phosphonate/phosphonate monoester coordination polymers." CrystEngComm 19, no. 27 (2017): 3727–36. http://dx.doi.org/10.1039/c7ce00579b.

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8

Papathanasiou, Konstantinos E., Maria Vassaki, Argyro Spinthaki, Fanouria-Eirini G. Alatzoglou, Eleftherios Tripodianos, Petri Turhanen, and Konstantinos D. Demadis. "Phosphorus chemistry: from small molecules, to polymers, to pharmaceutical and industrial applications." Pure and Applied Chemistry 91, no. 3 (March 26, 2019): 421–41. http://dx.doi.org/10.1515/pac-2018-1012.

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Abstract (Poly)phosphonic acids constitute an exciting family of phosphorus compounds. One of the attractive attributes of these molecules is the rich chemistry of the phosphonate moiety, and, in particular, its high affinity for metal ions and mineral surfaces. Whether the phosphonate group belongs to a “small” molecule or to a polymeric matrix, phosphonate-containing compounds have found a phalanx of real-life applications. Herein, we address a special category of phosphorus compounds called bisphosphonates (BPs, a.k.a. “-dronates”) and also phosphonate containing polymers. The success of BPs in mitigating osteoporosis notwithstanding, these “-dronate” drugs present a number of challenges. Nevertheless, the main drawback of BPs is their limited oral bioavailability. It is, therefore, imperative to design and fabricate “smart” systems that allow controlled delivery of the active BP agent. Here, easy-to-prepare drug delivery systems are presented based on silica gels. These have been synthesized, characterized, and studied as hosts in the control release of several BP drugs. They exhibit variable release rates and final % release, depending on the nature of bisphosphonate (side-chain length, hydro-philicity/-phobicity, water-solubility), cations present, pH and temperature. These gels are robust, injectable, re-loadable and re-usable. Furthermore, alternative drug delivery systems are presented that are based on metal-organic frameworks (MOFs). In these biologically acceptable inorganic metal ions have been incorporated, together with BPs as the organic portion. These materials have been synthesized, characterized, and studied for the self-sacrificial release (by pH-driven dissolution) of the BP active ingredient. Several such materials were prepared with a variety of bisphosphonate drugs. They exhibit variable release rates and final % release, depending on the actual structure of the metal-bisphosphonate material. Lastly, we will present the use of phosphonate-grafted polymers as scale inhibitors for water treatment applications.

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9

Parvulescu, Viorica, Adriana Popa, Gabriela Paun, Ramona Ene, Corneliu-Mircea Davidescu, and Gheorghe Ilia. "Effect of polymer support functionalization on enzyme immobilization and catalytic activity." Pure and Applied Chemistry 86, no. 11 (November 1, 2014): 1793–803. http://dx.doi.org/10.1515/pac-2014-0715.

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Abstract Two enzymes, laccase and peroxidase, were immobilized on chloromethylated styrene-divinylbenzene copolymers supports functionalized with phosphonates ((RO)2PO) or mixed ammonium and phosphonium groups (N+R3Cl–, P+Ph3Cl–). Phosphonates groups and quaternary ammonium salts were grafted on the “gel-type” copolymer by Michaelis–Becker polymer analogue reaction. Mixed polymer-supported ammonium and phosphonium salts were obtained by transquaternization of the ammonium groups to phosphonium group. The degrees of functionalization for obtained polymers were relatively high ensuring a sufficient concentration of active centers per unit mass of the copolymer. The obtained materials were characterized by thermal analysis, FTIR spectroscopy and SEM microscopy. The effects of OR1 and R2 radicals from phosphonate and respectively ammonium groups, as well as those of glutaraldehyde utilization on the immobilization yield and the catalytic properties of the supported enzymes were indicated. The activity of enzymes increased after immobilization and high immobilization yield was obtained for all the samples. The higher interaction of enzymes with support was indicated for mixed ammonium and phosphonium functions. A higher catalytic activity was obtained for peroxidase in oxidation of phenol and laccase in oxidation of anisole. The low effect of glutaraldehyde on enzyme activity reveals the strong interaction of enzyme with the polymer support, respectively with the functional groups.

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10

Brianna Barbu. "Phosphonate polymers for greener MRI color." C&EN Global Enterprise 101, no. 27 (August 21, 2023): 7. http://dx.doi.org/10.1021/cen-10127-scicon5.

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11

Ho, Hien The, Nam Hoai Nguyen, Marion Rollet, Trang N. T. Phan, and Didier Gigmes. "Phosphonate-Functionalized Polycarbonates Synthesis through Ring-Opening Polymerization and Alternative Approaches." Polymers 15, no. 4 (February 15, 2023): 955. http://dx.doi.org/10.3390/polym15040955.

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Well-defined phosphonate-functionalized polycarbonate with low dispersity (Ð = 1.22) was synthesized using organocatalyzed ring-opening polymerization (ROP) of novel phosphonate-based cyclic monomers. Copolymerization was also performed to access different structures of phosphonate-containing polycarbonates (PC). Furthermore, phosphonate-functionalized PC was successfully synthesized using a combination of ROP and post-modification reaction.

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12

Wilk-Kozubek, Magdalena, Katarzyna N. Jarzembska, Jan Janczak, and Veneta Videnova-Adrabinska. "Synthesis, structural characterization and computational studies of catena-poly[chlorido[μ3-(pyridin-1-ium-3-yl)phosphonato-κ3 O:O′:O′′]zinc(II)]." Acta Crystallographica Section C Structural Chemistry 73, no. 5 (April 5, 2017): 363–68. http://dx.doi.org/10.1107/s2053229617004478.

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Coordination polymers are constructed from two basic components, namely metal ions, or metal-ion clusters, and bridging organic ligands. Their structures may also contain other auxiliary components, such as blocking ligands, counter-ions and nonbonding guest or template molecules. The choice or design of a suitable linker is essential. The new title zinc(II) coordination polymer, [Zn(C5H5NO3P)Cl] n , has been hydrothermally synthesized and structurally characterized by single-crystal X-ray diffraction and vibrational spectroscopy (FT–IR and FT–Raman). Additionally, computational methods have been applied to derive quantitative information about interactions present in the solid state. The compound crystallizes in the monoclinic space group C2/c. The four-coordinated ZnII cation is in a distorted tetrahedral environment, formed by three phosphonate O atoms from three different (pyridin-1-ium-3-yl)phosphonate ligands and one chloride anion. The ZnII ions are extended by phosphonate ligands to generate a ladder chain along the [001] direction. Adjacent ladders are held together via N—H...O hydrogen bonds and offset face-to-face π–π stacking interactions, forming a three-dimensional supramolecular network with channels. As calculated, the interaction energy between the neighbouring ladders is −115.2 kJ mol−1. In turn, the cohesive energy evaluated per asymmetric unit-equivalent fragment of a polymeric chain in the crystal structure is −205.4 kJ mol−1. This latter value reflects the numerous hydrogen bonds stabilizing the three-dimensional packing of the coordination chains.

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13

The Ho, Hien, Justine Coupris, Sagrario Pascual, Laurent Fontaine, Thierry Lequeux, and Thi Nhàn Pham. "Synthesis and characterization of innovative well-defined difluorophosphonylated-(co)polymers by RAFT polymerization." Polymer Chemistry 6, no. 25 (2015): 4597–604. http://dx.doi.org/10.1039/c5py00690b.

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Well-defined polymers incorporating difluorophosphonylated moieties in the side-chain and at the chain-end were synthesized by RAFT polymerization. The dealkylation of phosphonate ester groups was achieved in order to target difluorophosphonic acid functionalized polymers.

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14

Shankar, Ravi, Archana Jain, Atul Pratap Singh, and Kieran C. Molloy. "Diorganotin Sulfonate and Phosphonate-Based Coordination Polymers." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 6 (June 1, 2011): 1375–78. http://dx.doi.org/10.1080/10426507.2010.543110.

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15

Meisel, Manfred, and Dirk Wulff-Molder. "New Vanadium Phosphonate Clusters and Coordination Polymers." Phosphorus, Sulfur, and Silicon and the Related Elements 144, no. 1 (January 1, 1999): 231–34. http://dx.doi.org/10.1080/10426509908546224.

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16

Nishita, Ryunosuke, Kosuke Kuroda, Shohei Ota, Takatsugu Endo, Shiori Suzuki, Kazuaki Ninomiya, and Kenji Takahashi. "Flame-retardant thermoplastics derived from plant cell wall polymers by single ionic liquid substitution." New Journal of Chemistry 43, no. 5 (2019): 2057–64. http://dx.doi.org/10.1039/c8nj04797a.

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17

Xu, Meiyun, Xiaoli Han, Tao Wang, Shenhua Li, and Daoben Hua. "Conjugated microporous polymers bearing phosphonate ligands as an efficient sorbent for potential uranium extraction from high-level liquid wastes." Journal of Materials Chemistry A 6, no. 28 (2018): 13894–900. http://dx.doi.org/10.1039/c8ta02875c.

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18

Guraieb, Paula, Ross Tomson, Victoria Brooks, Ji-young Lee, and Jay Weatherman. "A Game Changer in Scale-Squeeze Technology." Journal of Petroleum Technology 73, no. 02 (February 1, 2021): 40–43. http://dx.doi.org/10.2118/0221-0040-jpt.

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Background Field trials using a new scale-inhibitor technology that improves treatment lifetime of scale squeezes have been successfully performed in the Gulf of Mexico. Tomson Technologies, in partnership with Shell, developed proprietary nanoparticle carriers that enhance scale-inhibitor adsorption to the reservoir and control the return rate for extended periods of time. This technology results in less chemical bleed off in the initial flowback and increases the chemical retained in the reservoir, allowing for more effective squeeze treatments. Both nanoparticle-enabled phosphonate and polymer inhibitors have now been developed and successfully squeezed in the field. Phosphonate inhibitors are widely used for squeeze treatment due to their desirable adsorption and release properties in carbonate and sandstone reservoirs. Minor changes have been made to the chemistry, but overall, the fundamentals have remained unchanged for decades. Polymeric scale inhibitors have also been developed for cases in which phosphonates are not applicable. The nano-enhanced technology provides a large improvement of treatment lifetime of 2 to 4 times (200-400%) when compared to incumbents, making this technology advancement attractive even in cases where current squeezes are considered successful. The well selected for this case study is an offshore formation with a predominantly sandstone mineralogy (approximately 80% quartz) with 25-30% porosity and bottomhole temperature of 183°F (83°C). Technology From the Lab to Field A sandpack sample from the trial well was used in the laboratory to deter-mine the adsorption and desorption properties of the nano-enabled inhibitor in realistic rock conditions. Multiple conditioning steps were used before product was injected in a sequence that mimicked field squeeze treatments. Mass-balance results from the sandpack experiment show adsorption of approximately 8 mg of polymer retained per gram of crushed reservoir rock used in the experiment. A typical rule of thumb for phosphonate-scale inhibitors (only as a comparison since this is a polymeric scale inhibitor) is 1-2 mg of inhibitor retained per gram of rock. Therefore, this is considered a large improvement on adsorption. There are challenges associated with measuring polymers in brine as residuals; however, multiple methods, both in-house and external, were com-pared to ensure accuracy. The results using the nano-enhanced scale inhibitor show concentrations higher than 1 mg/L of active polymer for over 7,000 pore volume of return in the sandpack experiment. Complete intact core experiments were also conducted with reservoir fluids and showed no formation damage during the injection of the product with regained oil permeability of 96%. Oil permeability was in the 150-200 mD range for the intact core experiments. Third-party coreflood testing was performed with nitrified and foamed stages to ensure compatibility with the nano-enabled chemistry. No formation damage was observed with the nitrification of the stages containing the nano-enabled chemistry. Field Application Case Study After extensive lab validation of the product and supporting corefloods to de-risk the technology, Well A was selected by Shell to be the first well treated with the new nano-enabled extended-lifetime inhibitor.

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Husna, Ully Zakyatul, Khaled Abdalla Elraies, Juhairi Aris B. M. Shuhili, and Ahmed Abdulla Elryes. "A review: the utilization potency of biopolymer as an eco-friendly scale inhibitors." Journal of Petroleum Exploration and Production Technology 12, no. 4 (November 19, 2021): 1075–94. http://dx.doi.org/10.1007/s13202-021-01370-4.

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AbstractScale formation is one of the major issues in the petroleum industry. The development of these scale layers could result in production losses and equipment instability because of pipeline blockage, energy leakage, corrosion acceleration and severe accidents which will impact the safety of the production process. The utilization of chemical scale inhibitors (SIs) is considered an economical and successful route for the scale prevention. Two main components of the chemical SIs are phosphonate and polymer. Many of the phosphorous compounds are toxic and very expensive. Besides, portions of the phosphonate compounds are thermally less stable than polymeric scale inhibitors in a harsh environment of high temperature and high pressure (HTHP). This is considered as an issue as a good scale inhibitor should be able to be applied under wide range of temperature and pressure. Therefore, the continuous development in petroleum production imposes the need to develop a novel phosphorus-free scale inhibitor. Meanwhile, polymers have been broadly applied as a scale inhibitor in oil and gas fields because of their enhanced thermal stability and improved environmental compatibility. Polymeric scale inhibitors also show better dispersing efficiency. Today, the biopolymers have pulled in a tremendous consideration from the industry to replace the utilization of synthetic polymer due to their interesting qualities such as their lightness, strong mechanical properties, and appealing functionality. Biopolymers are insensitive toward brine salinity yet are vulnerable to biological degradation. Specifically, these polymers present enormous potential for environmental application because of their biodegradability, chemical adaptability and reactivity, biocompatibility, and nontoxicity. Recently, several new eco-friendly scale inhibitors have been reported in the literature. Hence, this paper provides a review of the utilization of biopolymer as scale inhibitor in the application of oil and gas industry under laboratory approach or field trial application. The types of scales, chemical scale inhibitors (SIs) and biopolymers are likewise reviewed here. The presented work in this paper is expected to enhance the fundamental understanding of scale formation, as well as contribute to the development process of biopolymer scale inhibitors.

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20

Shu, Wei-Jye, Li-Hsiang Perng, and Wei-Kuo Chin. "Synthesis and Characteristics of Phosphonate-Containing Maleimide Polymers." Polymer Journal 33, no. 9 (2001): 676. http://dx.doi.org/10.1295/polymj.33.676.

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21

Hu, N., A. Peralta, S. Roy Choudhury, R. Zhang, R. M. Davis, and J. S. Riffle. "Acrylamide monomers and polymers that contain phosphonate ions." Polymer 65 (May 2015): 124–33. http://dx.doi.org/10.1016/j.polymer.2015.03.065.

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22

Shankar, Ravi, Nisha Singla, Meenal Asija, and Pavletta Shestakova. "A recipe for the synthesis of diorganotin(iv) phosphonates in a colloidal regime by a solution based approach." RSC Advances 5, no. 35 (2015): 27326–29. http://dx.doi.org/10.1039/c4ra14853c.

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Tin(iv) based coordination polymers bearing silaalkyl substituted phosphonate ligands adopt rod, rosette and spherical-shaped morphologies. The particle size can be modulated into a nano/colloidal regime by a solution based approach.

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23

Yamakita, Yoshihiro, Issei Takeuchi, Kimiko Makino, Hiroshi Terada, Akihiko Kikuchi, and Kolio Troev. "Thermoresponsive Polyphosphoester via Polycondensation Reactions: Synthesis, Characterization, and Self-Assembly." Molecules 27, no. 18 (September 15, 2022): 6006. http://dx.doi.org/10.3390/molecules27186006.

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Using a novel strategy, amphiphilic polyphosphoesters based on poly(oxyethylene H-phosphonate)s (POEHP) with different poly(ethylene glycol) segment lengths and aliphatic alcohols with various alkyl chain lengths were synthesized using polycondensation reactions. They were characterized by 1H NMR, 13C {H} NMR 31P NMR, IR, and size exclusion chromatography (SEC). The effects of the polymer structure on micelle formation and stability, micelle size, and critical micelle temperature were studied via dynamic light scattering (DLS). The hydrophilic/hydrophobic balance of these polymers can be controlled by changing the chain lengths of hydrophilic PEG and hydrophobic alcohols. A solubilizing test, using Sudan III, revealed that hydrophobic substances can be incorporated inside the hydrophobic core of polymer associates. Loading capacity depends on the length of alkyl side chains. The results obtained indicate that these structurally flexible polymers have the potential as drug carriers.

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24

Beduini, Alessandro, Domenico Albanese, Federico Carosio, Amedea Manfredi, Elisabetta Ranucci, Paolo Ferruti, and Jenny Alongi. "On the Suitability of Phosphonate-Containing Polyamidoamines as Cotton Flame Retardants." Polymers 15, no. 8 (April 13, 2023): 1869. http://dx.doi.org/10.3390/polym15081869.

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A novel polyamidoamine (M-PCASS) bearing a disulfide group and two phosphonate groups per repeat unit was obtained by reacting N,N′-methylenebisacrylamide with a purposely designed bis-sec-amine monomer, namely, tetraethyl(((disulfanediylbis(ethane-2,1-diyl))bis(azanediyl))bis(ethane-2,1-diyl))bis(phosphonate) (PCASS). The aim was to ascertain whether the introduction of phosphonate groups, well-known for inducing cotton charring in the repeat unit of a disulfide-containing PAA, increased its already remarkable flame retardant efficacy for cotton. The performance of M-PCASS was evaluated by different combustion tests, choosing M-CYSS, a polyamidoamine containing a disulfide group but no phosphonate groups, as a benchmark. In horizontal flame spread tests (HFSTs), M-PCASS was a more effective flame retardant than M-CYSS at lower add-ons with no afterglow. In vertical flame spread tests, the only effect was afterglow suppression with no self-extinguishment even at add-ons higher than in HFSTs. In oxygen-consumption cone calorimetry tests, M-PCASS decreased the heat release rate peak of cotton by 16%, the CO2 emission by 50%, and the smoke release by 83%, leaving a 10% residue to be compared with a negligible residue for untreated cotton. Overall, the set of results obtained envisage that the newly synthesized phosphonate-containing PAA M-PCASS may be suitable for specific applications as flame retardant, where smoke suppression or reduction of total gas released is a key requirement.

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25

Sakuma, Tatsuya, Kimiko Makino, Hiroshi Terada, Issei Takeuchi, Violeta Mitova, and Kolio Troev. "Synthesis and Characterization of Amphiphilic Diblock Polyphosphoesters Containing Lactic Acid Units for Potential Drug Delivery Applications." Molecules 28, no. 13 (July 6, 2023): 5243. http://dx.doi.org/10.3390/molecules28135243.

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Multistep one-pot polycondensation reactions synthesized amphiphilic diblock polyphosphoesters containing lactic acid units in the polymer backbone. At the first step was synthesized poly[poly(ethylene glycol) H-phosphonate–b-poly(ethylene glycol)lactate H-phosphonate] was converted through one pot oxidation into poly[alkylpoly(ethylene glycol) phosphate-b-alkylpoly(ethylene glycol)lactate phosphate]s. They were characterized by 1H, 13C {H},31P NMR, and size exclusion chromatography (SEC). The effects of the polymer composition on micelle formation and stability, and micelle size were studied via dynamic light scattering (DLS). The hydrophilic/hydrophobic balance of these polymers can be controlled by changing the chain lengths of hydrophobic alcohols. Drug loading and encapsulation efficiency tests using Sudan III and doxorubicin revealed that hydrophobic substances can be incorporated inside the hydrophobic core of polymer micelles. The micelle size was 72–108 nm when encapsulating Sudan III and 89–116 nm when encapsulating doxorubicin. Loading capacity and encapsulation efficiency depend on the length of alkyl side chains. Changing the alkyl side chain from 8 to 16 carbon atoms increased micelle-encapsulated Sudan III and doxorubicin by 1.6- and 1.1-fold, respectively. The results obtained indicate that these diblock copolymers have the potential as drug carriers.

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26

Nifant’ev, Ilya, Andrey Shlyakhtin, Vladimir Bagrov, Evgeny Shaputkin, Alexander Tavtorkin, and Pavel Ivchenko. "Functionalized Biodegradable Polymers via Termination of Ring-Opening Polymerization by Acyl Chlorides." Polymers 13, no. 6 (March 11, 2021): 868. http://dx.doi.org/10.3390/polym13060868.

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Aliphatic polyesters are an important class of polymeric materials for biomedical applications due to their versatile and tunable chemistry, biocompatibility and biodegradability. A capability of direct bonding with biomedically significant molecules, provided by the presence of the reactive end functional groups (FGs), is highly desirable for prospective polymers. Among FGs, N-hydroxysuccinimidyl activated ester group (NHS) and maleimide fragment (MI) provide efficient covalent bonding with –NH– and –SH containing compounds. In our study, we found that NHS- and MI-derived acyl chlorides efficiently terminate living ring-opening polymerization of ε-caprolactone, L-lactide, ethyl ethylene phosphonate and ethyl ethylene phosphate, catalyzed by 2,6-di-tert-butyl-4-methylphenoxy magnesium complex, with a formation of NHS- and MI-functionalized polymers at a high yields. Reactivity of these polymers towards amine- and thiol-containing model substrates in organic and aqueous media was also studied.

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27

Mel’nik, O. A., A. S. Shaplov, E. I. Lozinskaya, N. A. Popova, M. V. Makarov, I. L. Odinets, K. A. Lysenko, G. I. Timofeeva, I. A. Malyshkina, and Ya S. Vygodskii. "Polymers based on ionic monomers with side phosphonate groups." Polymer Science Series B 52, no. 5-6 (June 2010): 316–26. http://dx.doi.org/10.1134/s1560090410050088.

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28

Southard, Glen E., Kelly A. Van Houten, and George M. Murray. "Soluble and Processable Phosphonate Sensing Star Molecularly Imprinted Polymers." Macromolecules 40, no. 5 (March 2007): 1395–400. http://dx.doi.org/10.1021/ma062443e.

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29

Ignatious, Francis, Arjen Sein, Israel Cabasso, and Johannes Smid. "Novel carbamoyl phosphonate monomers and polymers from unsaturated isocyanates." Journal of Polymer Science Part A: Polymer Chemistry 31, no. 1 (January 1993): 239–47. http://dx.doi.org/10.1002/pola.1993.080310128.

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30

Kusunoki, Takayuki, Fumi Hamasaki, Kyoko Uemura, and Takaomi Kobayashi. "Thermally decomposable phosphonate ester polymer gels." Polymer Bulletin 65, no. 9 (May 25, 2010): 941–49. http://dx.doi.org/10.1007/s00289-010-0297-7.

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31

Chen, Yuxin, Yujuan Chen, Dandan Lu, and Yunren Qiu. "Synthesis of a Novel Water-Soluble Polymer Complexant Phosphorylated Chitosan for Rare Earth Complexation." Polymers 14, no. 3 (January 21, 2022): 419. http://dx.doi.org/10.3390/polym14030419.

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Combining the characteristics of rare earth extractants and water-soluble polymer complexants, a novel complexant phosphorylated chitosan (PCS) was synthesized by Kabachnik–Fields reaction with alkalized chitosan, dimethyl phosphonate, and formaldehyde as raw materials and toluene-4-sulfonic acid monohydrate (TsOH) as catalyst. The complexation properties of PCS and poly (acrylic acid) sodium (PAAS) for lanthanum ions in the solution were compared at the same pH and room temperature. In addition, the frontier molecular orbital energies of polymer–La complexes were calculated by the density functional theory method, which confirmed the complexation properties of the polymers to rare earths. The results indicate that the PCS has better water solubility compared with chitosan and good complex ability to rare earths, which can be used for rare earth separation by the complexation–ultrafiltration process.

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32

Pehl, Thomas M., Moritz Kränzlein, Friederike Adams, Andreas Schaffer, and Bernhard Rieger. "C–H Bond Activation of Silyl-Substituted Pyridines with Bis(Phenolate)Yttrium Catalysts as a Facile Tool towards Hydroxyl-Terminated Michael-Type Polymers." Catalysts 10, no. 4 (April 22, 2020): 448. http://dx.doi.org/10.3390/catal10040448.

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Herein, silicon-protected, ortho-methylated hydroxy-pyridines were reported as initiators in 2-aminoalkoxy-bis(phenolate)yttrium complexes for rare earth metal-mediated group-transfer polymerization (REM-GTP) of Michael-type monomers. To introduce these initiators, C−H bond activation was performed by reacting [(ONOO)tBuY(X)(thf)] (X = CH2TMS, thf = tetrahydrofuran) with tert-butyl-dimethyl-silyl-functionalized α-methylpyridine to obtain the complex [(ONOOtBuY(X)(thf)] (X = 4-(4′-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-2,6-di-methylpyridine). These initiators served as functional end-groups in polymers produced via REM-GTP. In this contribution, homopolymers of 2-vinylpyridine (2VP) and diethyl vinyl phosphonate (DEVP) were produced. Activity studies and end-group analysis via mass spectrometry, size-exclusion chromatography (SEC) and NMR spectroscopy were performed to reveal the initiator efficiency, the catalyst activity towards both monomers as well as the initiation mechanism of this initiator in contrast to commonly used alkyl initiators. In addition, 2D NMR studies were used to further confirm the end-group integrity of the polymers. For all polymers, different deprotection routes were evaluated to obtain hydroxyl-terminated poly(2-vinylpyridine) (P2VP) and poly(diethyl vinyl phosphonate) (PDEVP). Such hydroxyl groups bear the potential to act as anchoring points for small bioactive molecules, for post-polymerization functionalization or as macroinitiators for further polymerizations.

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33

Shaikh, Nabil, Jiajie Qian, Sewoon Kim, Hoa Phan, Juan S. Lezama-Pacheco, Abdul-Mehdi S. Ali, David M. Cwiertny, Tori Z. Forbes, Amanda J. Haes, and José M. Cerrato. "U(VI) binding onto electrospun polymers functionalized with phosphonate surfactants." Journal of Environmental Chemical Engineering 10, no. 5 (October 2022): 108448. http://dx.doi.org/10.1016/j.jece.2022.108448.

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34

Failla, Salvatore, Giuseppe Consiglio, and Paolo Finocchiaro. "New Diamine Phosphonate Monomers as Flame-Retardant Additives for Polymers." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 4 (March 31, 2011): 983–88. http://dx.doi.org/10.1080/10426507.2010.514307.

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35

Steinbauer, Patrick, Andreas Rohatschek, Orestis Andriotis, Nikolaos Bouropoulos, Robert Liska, Philipp J. Thurner, and Stefan Baudis. "Biomimetic adhesion motifs based on RAFT polymers with phosphonate groups." European Polymer Journal 143 (January 2021): 110188. http://dx.doi.org/10.1016/j.eurpolymj.2020.110188.

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36

Shankar, Ravi, Archana Jain, Gabriele Kociok-Köhn, and Kieran C. Molloy. "Diorganotin-Based Coordination Polymers Derived from Sulfonate/Phosphonate/Phosphonocarboxylate Ligands." Inorganic Chemistry 50, no. 4 (February 21, 2011): 1339–50. http://dx.doi.org/10.1021/ic1018423.

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37

Cabasso, Israel, Johannes Smid, and Suresh K. Sahni. "Radiopaque polymers based on acrylated phosphonate esters derived from polyols." Journal of Applied Polymer Science 41, no. 1112 (1990): 3025–42. http://dx.doi.org/10.1002/app.1990.070411136.

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38

Marestin, Catherine, Saber Chatti, and Regis Mercier. "Synthesis of poly(aryl ether)s bearing phosphonated side-chains from phosphonate ester-containing bisphenols." Polymer 222 (April 2021): 123647. http://dx.doi.org/10.1016/j.polymer.2021.123647.

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39

Tretsiakova-McNally, Svetlana, Aloshy Baby, Paul Joseph, Doris Pospiech, Eileen Schierz, Albena Lederer, Malavika Arun, and Gaëlle Fontaine. "Gaseous- and Condensed-Phase Activities of Some Reactive P- and N-Containing Fire Retardants in Polystyrenes." Molecules 28, no. 1 (December 29, 2022): 278. http://dx.doi.org/10.3390/molecules28010278.

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Polystyrene (PS) was modified by covalently binding P-, P-N- and/or N- containing fire-retardant moieties through co- or ter-polymerization reactions of styrene with diethyl(acryloyloxymethyl)phosphonate (DEAMP), diethyl-p-vinylbenzyl phosphonate (DEpVBP), acrylic acid-2-[(diethoxyphosphoryl)methylamino]ethyl ester (ADEPMAE) and maleimide (MI). In the present study, the condensed-phase and the gaseous-phase activities of the abovementioned fire retardants within the prepared co- and ter-polymers were evaluated for the first time. Pyrolysis–Gas Chromatography/Mass Spectrometry was employed to identify the volatile products formed during the thermal decomposition of the modified polymers. Benzaldehyde, α-methylstyrene, acetophenone, triethyl phosphate and styrene (monomer, dimer and trimer) were detected in the gaseous phase following the thermal cracking of fire-retardant groups and through main chain scissions. In the case of PS modified with ADEPMAE, the evolution of pyrolysis gases was suppressed by possible inhibitory actions of triethyl phosphate in the gaseous phase. The reactive modification of PS by simultaneously incorporating P- (DEAMP or DEpVBP) and N- (MI) monomeric units, in the chains of ter-polymers, resulted in a predominantly condensed-phase mode of action owing to synergistic P and N interactions. The solid-state 31P NMR spectroscopy, Scanning Electron Microscopy/Energy Dispersive Spectroscopy, Inductively-Coupled Plasma/Optical Emission Spectroscopy and X-ray Photoelectron Spectroscopy of char residues, obtained from ter-polymers, confirmed the retention of the phosphorus species in their structures.

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40

Kakati, D. K., R. Gosain, and M. H. George. "New polyurethane ionomers containing phosphonate groups." Polymer 35, no. 2 (January 1994): 398–402. http://dx.doi.org/10.1016/0032-3861(94)90710-2.

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41

Howell, Bob A. "Thermal Degradation of Organophosphorus Flame Retardants." Polymers 14, no. 22 (November 15, 2022): 4929. http://dx.doi.org/10.3390/polym14224929.

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The development of new organophosphorus flame retardants for polymeric materials is spurred by relatively low toxicity, effectiveness, and demand for replacement of more traditional materials. To function, these compounds must decompose in a degrading polymer matrix to form species which promote modification of the solid phase or generate active radical moieties that escape to the gas phase and interrupt combustion propagating reactions. An understanding of the decomposition process for these compounds may provide insight into the nature of flame retardant action which they may offer and suggest parameters for the synthesis of effective new organophosphorus flame retardants. The thermal degradation of a series of organophosphorus esters varying in the level of oxygenation at phosphorus—alkyl phosphate, aryl phosphate, phosphonate, phosphinate—has been examined. Initial degradation in all cases corresponds to elimination of a phosphorus acid. However, the facility with which this occurs is strongly dependent on the level of oxygenation at phosphorus. For alkyl phosphates elimination occurs rapidly at relatively low temperature. The same process occurs at somewhat higher temperature for aryl phosphates. Elimination of a phosphorus acid from phosphonate or phosphinate occurs more slowly and at much higher temperature. Further, the acids formed from elimination rapidly degrade further to evolve volatile species.

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42

Zemła, Marcin, Aleksander Prociak, and Sławomir Michałowski. "Bio-Based Rigid Polyurethane Foams Modified with Phosphorus Flame Retardants." Polymers 14, no. 1 (December 28, 2021): 102. http://dx.doi.org/10.3390/polym14010102.

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Rigid polyurethane foams (RPURF) containing a bio-polyol from rapeseed oil and different phosphorus-based flame retardants were obtained. Triethyl phosphate (TEP), dimethyl propane phosphonate (DMPP) and cyclic phosphonates Addforce CT 901 (20 parts per hundred polyol by weight) were used in the synthesis of RPURF. The influence of used flame retardants on foaming process, cell structure, and physical–mechanical properties as well as flammability of RPURF were examined. The addition of flame retardants influenced the parameters of the cellular structure and decreased compressive strength. All obtained foam materials had a low thermal conductivity coefficient, which allows them to be used as thermal insulation. The research results of bio-based RPURF were compared with foams obtained without bio-polyol. All modified materials had an oxygen index above 21 vol%; therefore, they can be classified as self-extinguishing materials. The analysis of parameters obtained after the cone calorimeter test showed that the modified RPURF have a lower tendency to fire development compared to the reference foams, which was particularly noticeable for the materials with the addition of DMPP.

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43

Velencoso, María M., María J. Ramos, Angel Serrano, Antonio de Lucas, and Juan F. Rodríguez. "Fire retardant functionalized polyol by phosphonate monomer insertion." Polymer International 64, no. 12 (August 19, 2015): 1706–14. http://dx.doi.org/10.1002/pi.4970.

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44

Wöhlbrandt, Stephan, Ole Beyer, Helge Reinsch, A. Ken Inge, Erik Svensson Grape, Ulrich Lüning, and Norbert Stock. "Five New Coordination Polymers with a Bifunctional Phosphonate-Sulfonate Linker Molecule." Zeitschrift für anorganische und allgemeine Chemie 645, no. 10 (May 7, 2019): 732–39. http://dx.doi.org/10.1002/zaac.201900056.

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45

Wehbi, Mohammad, Damien Bourgeois, and Bruno Améduri. "Use of poly(vinylidene fluoride-co-vinyl dimethylphosphonate) copolymers for efficient extraction of valuable metals." Polymer Chemistry 10, no. 30 (2019): 4173–84. http://dx.doi.org/10.1039/c9py00624a.

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46

Didier, Benoit, Mark F. Mohamed, Elizabeth Csaszar, Kate G. Colizza, Alexei A. Neverov, and R. Stan Brown. "Methanolysis of organophosphorus esters promoted by an M2+ catalyst supported on polystyrene-based copolymers." Canadian Journal of Chemistry 86, no. 2 (February 1, 2008): 91–100. http://dx.doi.org/10.1139/v07-099.

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The methanolysis of three neutral organophosphorus esters (a phosphonate, a phosphonothioate, and a phosphorothionate) promoted by several polymer-supported Zn(II) or Cu(II) containing catalysts was studied. The catalysts consist of a Zn(II) or Cu(II) complex with 1,5,9-triazacyclododecane or phenanthroline attached to a porous polystyrene resin. In each case, the polymer supported catalyst showed activity at near neutral sspH in methanol (8.38) and ambient temperature and provided accelerations of up to a factor of 2.9 × 106 relative to the background reaction at sspH 9.05. The solid materials could be reused several times and could be reactivated when the activity diminished. Various polymers of different porosity and extent of cross-linking were studied, with the net result being that larger porosities offer the best reactivity for catalyzed methanolysis of these OP species in methanol. This is explained by different parameters including the accessibility to reactive sites, the increase of concentration of catalytic sites on the surface of the polymer, and some cooperative effects between neighboring catalytic groups.Key words: functionalized polymer, metal containing, methanolysis, organophosphorus pesticides and CW agents, catalyst.

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47

Guazzelli, Elisa, Niccolò Lusiani, Gianfranca Monni, Matteo Oliva, Chiara Pelosi, Frederik R. Wurm, Carlo Pretti, and Elisa Martinelli. "Amphiphilic Polyphosphonate Copolymers as New Additives for PDMS-Based Antifouling Coatings." Polymers 13, no. 19 (October 5, 2021): 3414. http://dx.doi.org/10.3390/polym13193414.

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Poly(ethyl ethylene phosphonate)-based methacrylic copolymers containing polysiloxane methacrylate (SiMA) co-units are proposed as surface-active additives as alternative solutions to the more investigated polyzwitterionic and polyethylene glycol counterparts for the fabrication of novel PDMS-based coatings for marine antifouling applications. In particular, the same hydrophobic SiMA macromonomer was copolymerized with a methacrylate carrying a poly(ethyl ethylene phosphonate) (PEtEPMA), a phosphorylcholine (MPC), and a poly(ethylene glycol) (PEGMA) side chain to obtain non-water soluble copolymers with similar mole content of the different hydrophilic units. The hydrolysis of poly(ethyl ethylene phosphonate)-based polymers was also studied in conditions similar to those of the marine environment to investigate their potential as erodible films. Copolymers of the three classes were blended into a condensation cure PDMS matrix in two different loadings (10 and 20 wt%) to prepare the top-coat of three-layer films to be subjected to wettability analysis and bioassays with marine model organisms. Water contact angle measurements showed that all of the films underwent surface reconstruction upon prolonged immersion in water, becoming much more hydrophilic. Interestingly, the extent of surface modification appeared to be affected by the type of hydrophilic units, showing a tendency to increase according to the order PEGMA < MPC < PEtEPMA. Biological tests showed that Ficopomatus enigmaticus release was maximized on the most hydrophilic film containing 10 wt% of the PEtEP-based copolymer. Moreover, coatings with a 10 wt% loading of the copolymer performed better than those containing 20 wt% for the removal of both Ficopomatus and Navicula, independent from the copolymer nature.

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48

Ma, Jianfeng, Yazhuo Shang, Changjun Peng, Honglai Liu, Shuzhen Zheng, Han Yan, and Qianping Ran. "Foam and rheological behavior of polydentate phosphonate-modified polymers under cement system." Construction and Building Materials 290 (July 2021): 123205. http://dx.doi.org/10.1016/j.conbuildmat.2021.123205.

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49

Perry, Houston P., Kevin J. Gagnon, Justin Law, Simon Teat, and Abraham Clearfield. "Divalent metal phosphonate coordination polymers constructed from a dipiperidine-based bisphosphonate ligand." Dalton Transactions 41, no. 14 (2012): 3985. http://dx.doi.org/10.1039/c2dt11986b.

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50

Hartmann-Thompson, Claire, Douglas L. Keeley, and Skip Gallagher. "Hydrogen-bond basic siloxane phosphonate polymers for surface acoustic wave (SAW) sensors." Sensors and Actuators B: Chemical 115, no. 2 (June 2006): 697–99. http://dx.doi.org/10.1016/j.snb.2005.10.037.

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