Well‐Defined Thermoresponsive Polymethacrylamide Copolymers with Ester Pendent Groups through One‐Pot Statistical Postpolymerization Modification of Poly(2‐Isopropenyl‐2‐Oxazoline) with Multiple Carboxylic Acids

Jerca, Florica Adriana; Jerca, Valentin Victor; Hoogenboom, Richard

doi:10.1002/pola.29188

Cited by 14 publications

(10 citation statements)

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“…The N -octylmethacrylamide/ N -methylolmethacrylamide copolymers (1:3, 1:4, and 1:6) were made using a literature procedure . The esteramide derivative of poly(2-isopropyl-2-oxazoline) (PiPOx-AAc/APr, M n 5900 g/mole, cloud point 32.1 °C) was supplied by Professor Richard Hoogenboom, University of Gent, Belgium. , Hyperbranched polyethyleneimine ethyl/octyl amine oxide (HPEI-Et/Oct-AO) was made by the literature method using Epomin SP012 from Nippon Shokubai. , …”

Section: Experimental Methodskhi Testingmentioning

confidence: 99%

Does the Cloud Point Temperature of a Polymer Correlate with Its Kinetic Hydrate Inhibitor Performance?

Dirdal

Kelland

2019

Energy Fuels

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Most polymers used in commercial kinetic hydrate inhibitor (KHI) formulations show thermoresponsive behavior in aqueous solution. This means that they exhibit a cloud point (or lower critical solution temperature) which is often low and not far above the equilibrium temperature for gas hydrate formation. For example, poly(N-vinyl caprolactam) has a cloud point of about 30−40 °C and poly(N-isopropylmethacrylamide) has a cloud point of about 35−45 °C depending on the molecular weight and method of polymerization. This report is divided into two parts. First, we review previous KHI studies and show that low cloud point is a useful factor, but not the most critical factor, to be considered within a specific class of polymers in designing a high-performance KHI. This statement is supported in the second part of this report, which is an experimental KHI study. In this study, we present results of KHI tests for a natural gas/deionized water structure II gas hydrate-forming system using low cloud point polymers with a variety of different shapes, molecular weights, functional groups, and sizes of pendant hydrophobic groups. We conclude that the low cloud point, near the hydrate formation temperature, appears to be useful for high KHI efficacy of a polymer but only if certain criteria are met. These include low molecular weight, pendant hydrophobic groups of an optimal size close to the polymer backbone, and the correct hydrophilic functional groups. Possible theories as to why low cloud point for a KHI polymer can be beneficial are discussed, as well as some guidelines for the KHI polymer design.

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Section: Experimental Methodskhi Testingmentioning

confidence: 99%

Does the Cloud Point Temperature of a Polymer Correlate with Its Kinetic Hydrate Inhibitor Performance?

Dirdal

Kelland

2019

Energy Fuels

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“…In a recent study, we demonstrated that PiPOx can be chemically modified with monocarboxylic acids, yielding soluble thermoresponsive polymers. , Modulation of the cloud point temperature was achieved by controlling the modification degree and/or by changing the hydrophobic character of the acid. Consequently, it may be expected that PiPOx-based hydrogels containing longer hydrophobic ester amide chains exhibit a volume-phase transition temperature (VPTT).…”

Section: Results and Discussionmentioning

confidence: 99%

“…In a recent study, we demonstrated that PiPOx can be chemically modified with mono carboxylic acids yielding soluble thermoresponsive polymers. 53,63 Modulation of the cloud point temperature was achieved by controlling the modification degree and/or by changing the hydrophobic character of the acid.…”

Section: Thermoresponsive Properties Of the H4-h12 Hydrogelsmentioning

confidence: 99%

“…Then, we used the highly effective ring-opening addition reaction of the pendant iPOx rings with several nontoxic and bio-based dicarboxylic acids and prepared eight hydrogel series with different chemical compositions (see Scheme ). Using this PiPOx postpolymerization modification approach, which was well documented in our group for soluble polymers, ,,, we ensure reproducible synthesis at any stage of the hydrogel preparation. Another advantage of this approach is that we can control the quantity of ester–amide cross-links generated during the postmodification reactions, in order to preserve the balance between hydrophilic character vs structural integrity of the final hydrogels.…”

Section: Introductionmentioning

confidence: 99%

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Poly(2-isopropenyl-2-oxazoline) Hydrogels for Biomedical Applications

et al. 2018

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Synthetic polymers have had a major impact on the biomedical field. However, all polymers have their advantages and disadvantages, so that the selection of a certain polymeric material always is a compromise with regard to many properties, such as synthetic accessibility, solubility, thermal properties, biocompatibility and degradability. The development of novel polymers with superior properties for medical applications is the focus of many research groups. The present study highlights the use of poly(2-isopropenyl-2-oxazoline) (PiPOx), as biocompatible functional polymer to develop synthetic hydrogel materials using a simple straightforward synthesis protocol. A library of hydrogels was obtained by chemical cross-linking of PiPOx, using eight different non-toxic and bio-based dicarboxylic acids. The equilibrium swelling degree (ESD) of the final material can be modulated by simple modification of the composition of the reaction mixture, including the polymer concentration in the feed ratio between the 2-oxazoline pendent groups and the carboxylic acid groups as well as the cross-linker 2 length. The hydrogels with the highest water uptake were selected for further investigations regarding their potential use as biomaterials. We evaluated the thermoresponsiveness, the pH-degradability under physiological conditions and demonstrated proof-of-concept drug delivery experiments. The in vitro cellular studies demonstrated the noncytotoxic character of the PiPOx hydrogels, and its protein repellent properties, while mineralization studies revealed that such scaffolds do not promote mineralization/calcification phenomena. In view, of these results, these hydrogels show potential use as ophthalmologic materials or in drug delivery applications.

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“…tuned the T c of poly(2‐isopropenyl‐2‐oxazoline) (PiPOx)‐based thermoresponsive polymers. [ 100,101 ] The oxazoline unit is often used for postmodification. [ 102,103 ] Since the pendant 2‐oxazoline side chain in PiPOx reacts with carboxyl groups by partial ring‐opening in the absence of any catalysts and producing no byproducts, the authors chose various aliphatic carboxylic acids, such as acetic acid (AAc), propionic acid (APr), butyric acid (ABu), and isobutyric acid (AiBu), for postmodification ( Figure ).…”

Section: Tuning the Stimuli‐responsiveness By Postmodificationmentioning

confidence: 99%

Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli‐Responsive Polymers

Michinobu

2021

Macro Chemistry & Physics

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Stimuli‐responsive polymers are a type of functional polymers showing a change in their physicochemical properties in response to external stimuli, such as temperature, pH, and electrochemical potential application, and they can be used in biosensors, biomedicine, and separation technology. Postmodification of polymers plays an important role in designing stimuli‐responsive polymers in terms of their synthesis, tuning of their thermoresponsivity, and functionalization. A variety of topological polymer structures, such as a comb, sphere, and dendrimer, can be produced, and the resultant tuning of the transition temperatures and phase types (lower critical solution temperature‐ or upper critical solution temperature‐type) can be achieved. Furthermore, postmodification techniques are employed as a useful tool to functionalize precursor polymers or improve the responsive properties of the polymers, which expands the applicable fields of these polymers. In this review, click chemistry‐related reactions, the esterification reaction, and surface‐initiated polymerization are the focus as efficient postmodification reactions to produce high‐performance stimuli‐responsive polymers.

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Well‐Defined Thermoresponsive Polymethacrylamide Copolymers with Ester Pendent Groups through One‐Pot Statistical Postpolymerization Modification of Poly(2‐Isopropenyl‐2‐Oxazoline) with Multiple Carboxylic Acids

Cited by 14 publications

References 47 publications

Does the Cloud Point Temperature of a Polymer Correlate with Its Kinetic Hydrate Inhibitor Performance?

Does the Cloud Point Temperature of a Polymer Correlate with Its Kinetic Hydrate Inhibitor Performance?

Poly(2-isopropenyl-2-oxazoline) Hydrogels for Biomedical Applications

Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli‐Responsive Polymers

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