Oxazoline-functional polymer particles graft with azo-dye

Jerca, Valentin Victor; Nicolescu, Florica Adriana; Trușcă, Roxana; Vasile, Eugeniu; Băran, Adriana; Anghel, Dan F.; Vasilescu, Dan Sorin; Vuluga, Dumitru Mircea

doi:10.1016/j.reactfunctpolym.2010.12.004

Cited by 29 publications

(25 citation statements)

References 41 publications

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“…This orthogonal dual functionality of IPOx has recently attracted considerable interest as it provides an avenue for postpolymerization modification through the latent groups not involved in IPOx polymerization. Typically, the double bond is substituted through thiol–ene click reactions, , while the 2-oxazoline moiety is usually modified through reactions with thiols , and carboxylic acids − or serves as an initiation site for CROP of another 2-oxazoline monomer. − The unique functionality of IPOx has been exploited in numerous applications, including the preparation of block , and graft copolymers, polymeric brushes, − ,− thermoresponsive polymers, , biocompatible hydrogels, − polymeric coatings, − glycopolymers, photoresponsive polymers, , blend compatibilizers, fluorescent particles, humidity sensors, or kinetic hydrate inhibitors . In addition, biocompatibility and immunomodulative properties of poly(2-isopropenyl-2-oxazoline) (PIPOx) have been recently highlighted by Kroneková et al…”

Section: Introductionmentioning

confidence: 99%

Well-Defined Linear and Grafted Poly(2-isopropenyl-2-oxazoline)s Prepared via Copper-Mediated Reversible-Deactivation Radical Polymerization Methods

et al. 2020

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2-Isopropenyl-2-oxazoline (IPOx) is an important double functional monomer with multiple potential applications. However, until now, the attempts at reversible-deactivation radical polymerization (RDRP) of IPOx via its double bond have met with little success, leading to low conversions and high-dispersity products. Here, we demonstrate that IPOx can be polymerized through aqueous Cu(0)-mediated RDRP in a controlled way using the 2-chloropropionitrile/CuCl(CuCl2)/TPMA initiation and catalytic system and 0.67 M NaCl as a solvent. It is shown that the polymerization is highly sensitive to the initiator concentration and the CuCl/CuCl2 ratio; however, with careful optimization of the polymerization parameters, low-dispersity products can be obtained at quantitative conversions. The synthesized poly(IPOx) polymers were subsequently transformed into different ATRP macroinitiators by the reaction of the pendant 2-oxazoline units with 2-bromoisobutyric or 2-chloropropionic acid under optimized reaction conditions. Styrene and methyl methacrylate were then grafted as model monomers from these macroinitiators under ATRP conditions, confirming that defined poly(IPOx)-based graft copolymers with controlled grafting density and molecular weights of the poly(IPOx) backbone and of the grafts are accessible by the presented method. This provides a straightforward route to a new class of 2-oxazoline-based materials.

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Section: Introductionmentioning

confidence: 99%

Well-Defined Linear and Grafted Poly(2-isopropenyl-2-oxazoline)s Prepared via Copper-Mediated Reversible-Deactivation Radical Polymerization Methods

et al. 2020

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“…2-Isopropenyl-2-oxazoline (iPOx) is a versatile monomer with dual functionality that can be polymerized into poly(2-isopropenyl-2-oxazoline) (PiPOx) by radical, anionic, group transfer polymerization, and more recently controlled radical polymerization [ 35 , 36 , 37 , 38 , 39 , 40 ]. PiPOx is a versatile polymer possessing 2-oxazoline rings as reactive side chains that can be used for a variety of post-functionalization reactions to introduce various functional groups or to yield molecular brushes via cationic ring opening polymerization [ 41 , 42 , 43 , 44 , 45 ]. PiPOx possesses many advantages such as high hydrophilicity and biocompatibility, it is inert to moisture and oxygen, and the 2-oxazoline ring modification with (di)carboxylic acids requires simple, mild reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Reduction-Responsive Molecularly Imprinted Poly(2-isopropenyl-2-oxazoline) for Controlled Release of Anticancer Agents

Cegłowski

Jerca

et al. 2020

Pharmaceutics

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Trigger-responsive materials are capable of controlled drug release in the presence of a specific trigger. Reduction induced drug release is especially interesting as the reductive stress is higher inside cells than in the bloodstream, providing a conceptual controlled release mechanism after cellular uptake. In this work, we report the synthesis of 5-fluorouracil (5-FU) molecularly imprinted polymers (MIPs) based on poly(2-isopropenyl-2-oxazoline) (PiPOx) using 3,3′-dithiodipropionic acid (DTDPA) as a reduction-responsive functional cross-linker. The disulfide bond of DTDPA can be cleaved by the addition of tris(2-carboxyethyl)phosphine (TCEP), leading to a reduction-induced 5-FU release. Adsorption isotherms and kinetics for 5-FU indicate that the adsorption kinetics process for imprinted and non-imprinted adsorbents follows two different kinetic models, thus suggesting that different mechanisms are responsible for adsorption. The release kinetics revealed that the addition of TCEP significantly influenced the release of 5-FU from PiPOx-MIP, whereas for non-imprinted PiPOx, no statistically relevant differences were observed. This work provides a conceptual basis for reduction-induced 5-FU release from molecularly imprinted PiPOx, which in future work may be further developed into MIP nanoparticles for the controlled release of therapeutic agents.

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“…Several different methods have been developed for producing microspheres such as emulsion, suspension and dispersion polymerization . Among them dispersion polymerization has been the preferred method to obtain micron‐sized particles due to its simplicity and easy control of the particle diameter and size distribution in a single batch process …”

Section: Introductionmentioning

confidence: 99%

Factorial design optimization of polystyrene microspheres obtained by aqueous dispersion polymerization in the presence of poly(2‐ethyl‐2‐oxazoline) reactive stabilizer

Iordache

Banu

Giol

et al. 2020

Polymer International

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The present study highlights the use of statistical design to establish an effective model for the synthesis of polystyrene microspheres by aqueous dispersion polymerization using poly(2-ethyl-2-oxazoline) reactive stabilizer. The significant parameters (e.g. solvent polarity, stabilizer and initiator concentration) influencing the characteristic responses of the process such as yield, particle size and size distribution, as well as the interactions between the variables, were identified. The macromonomer concentration and solvent polarity influence both particle size and size distribution, whereas initiator concentration influences the yield. Analysis of the variance of process variables indicates that the models can be successfully used to describe the dispersion polymerization process. Moreover, the factorial design allows the development of microspheres with optimal properties with respect to size and size distribution. The experimental data regarding yield, particle size and size distribution of the optimized dispersion polymerization shows less than 7% difference compared with the predicted responses. In view of these results, the implementation of statistical design models represents an efficient solution for optimizing microparticle synthesis while aiming for industrial applications.

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Oxazoline-functional polymer particles graft with azo-dye

Cited by 29 publications

References 41 publications

Well-Defined Linear and Grafted Poly(2-isopropenyl-2-oxazoline)s Prepared via Copper-Mediated Reversible-Deactivation Radical Polymerization Methods

Well-Defined Linear and Grafted Poly(2-isopropenyl-2-oxazoline)s Prepared via Copper-Mediated Reversible-Deactivation Radical Polymerization Methods

Reduction-Responsive Molecularly Imprinted Poly(2-isopropenyl-2-oxazoline) for Controlled Release of Anticancer Agents

Factorial design optimization of polystyrene microspheres obtained by aqueous dispersion polymerization in the presence of poly(2‐ethyl‐2‐oxazoline) reactive stabilizer

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