Direct synthesis of poly(N-alkyl acrylamide) (co)polymers with pendant reactive amino groups by organocatalyzed amidation of polymethylacrylate

Bernhard, Yann; Guyse, Joachim F. R. Van; Purino, Martín; Hoogenboom, Richard

doi:10.1016/j.eurpolymj.2023.112077

“…Finally, the reactivity of PMA towards a series of N ‐substituted diamines has also been explored, with the intention of eliminating polymer chain coupling reactions typically observed for modifications performed with ethylenediamine. We have shown that N ‐ethyl ethylenediamine was able to provide selective amidation with the primary amine in the presence of a N ‐ethyl substituted secondary amine [148] . Further investigation has shown that the combination primary and N ‐ethyl substituted secondary amine is crucial to impart selectivity as chain coupling reactions were observed for a diamine with a N ‐methyl substituted secondary amine, which highlights the role of steric hindrance.…”

Section: Transformations Of Poly(< Meth >Acrylate)smentioning

confidence: 80%

Non‐activated Esters as Reactive Handles in Direct Post‐Polymerization Modification

Guyse

¹

,

Bernhard

²

,

Podevyn

³

et al. 2023

Self Cite

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Non‐activated esters are prominently featured functional groups in polymer science, as ester functional monomers display great structural diversity and excellent compatibility with a wide range of polymerization mechanisms. Yet, their direct use as a reactive handle in post‐polymerization modification has been typically avoided due to their low reactivity, which impairs the quantitative conversion typically desired in post‐polymerization modification reactions. While activated ester approaches are a well‐established alternative, the modification of non‐activated esters remains a synthetic and economically valuable opportunity. In this review, we discuss past and recent efforts in the utilization of non‐activated ester groups as a reactive handle to facilitate transesterification and aminolysis/amidation reactions, and the potential of the developed methodologies in the context of macromolecular engineering.

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“…Therefore, the peak (sample 5) was slightly strengthened. In this study, the reactive anhydride group reacted with the amino group at the end of the PA molecule to form an amide bond first and then an imide bond through a closed loop to generate a PE-g-PA graft copolymer [20][21][22].…”

Section: Resultsmentioning

confidence: 99%

Effect of Polyethylene-Grafted Maleic Anhydride on the Properties of Flue-Gas Desulfurized Gypsum/Epoxy Resin Composites

Li,

Die

et al. 2023

Coatings

1

0

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Waste resource utilization can save energy, reduce costs, and is one of the important means to protect the environment. Flue-gas desulphurized (FGD) gypsum is a common industrial by-product. These by-products are not only difficult to use, but also have serious impacts on the ecological environment. The conventional process of the industrial utilization of the calcium sulfate whisker pretreatment process leads to a low utilization rate of FGD gypsum, further increasing the consumption of resources and leading to secondary pollution. This study presents a method of preparing composites by adding FGD gypsum directly into epoxy resin with polyethylene-grafted maleic (PGM) anhydride as a compatibilizer of FGD gypsum/epoxy resin composites. Results showed weak tensile properties and impact properties of the composites when only FGD gypsum was added. When the amount of PGM added was 6 wt%, the tensile properties and impact properties of FGD gypsum/epoxy resin composites improved by 75% and 63%, and compared with the neat epoxy resin, the tensile properties and impact properties of FGD gypsum/epoxy resin composites, respectively, improved by 30% and 57%. Additionally, laser particle size analysis, X-ray diffraction (XRD) analysis, Fourier transform infrared spectroscopy (FT-IR), Scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), a thermogravimetric analyzer (TGA), and a Differential scanning calorimeter (DSC) were used to examine the effects of PGM on the mechanical properties of FGD gypsum/epoxy resin composites and its mechanism of action. The recycling of FGD gypsum in resin materials has been extended in this study.

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“…We have shown that N-ethyl ethylenediamine was able to provide selective amidation with the primary amine in the presence of a N-ethyl substituted secondary amine. [148] Further investigation has shown that the combination primary and N-ethyl substituted secondary amine is crucial to impart selectivity as chain coupling reactions were observed for a diamine with a N-methyl substituted secondary amine, which highlights the role of steric hindrance. Important to note, is that the presence of the secondary amine was still able to catalyze the amidation reaction via intramolecular H-bonding.…”

Section: Amidation Of Poly(acrylate)smentioning

confidence: 99%

Non‐activated Esters as Reactive Handles in Direct Post‐Polymerization Modification

Guyse

¹

,

Bernhard

²

,

Podevyn

³

et al. 2023

Self Cite

View full text Add to dashboard Cite

Non‐activated esters are prominently featured functional groups in polymer science, as ester functional monomers display great structural diversity and excellent compatibility with a wide range of polymerization mechanisms. Yet, their direct use as a reactive handle in post‐polymerization modification has been typically avoided due to their low reactivity, which impairs the quantitative conversion typically desired in post‐polymerization modification reactions. While activated ester approaches are a well‐established alternative, the modification of non‐activated esters remains a synthetic and economically valuable opportunity. In this review, we discuss past and recent efforts in the utilization of non‐activated ester groups as a reactive handle to facilitate transesterification and aminolysis/amidation reactions, and the potential of the developed methodologies in the context of macromolecular engineering.

show abstract

Direct synthesis of poly(N-alkyl acrylamide) (co)polymers with pendant reactive amino groups by organocatalyzed amidation of polymethylacrylate

Cited by 6 publications

References 65 publications

Non‐activated Esters as Reactive Handles in Direct Post‐Polymerization Modification

Non‐activated Esters as Reactive Handles in Direct Post‐Polymerization Modification

Effect of Polyethylene-Grafted Maleic Anhydride on the Properties of Flue-Gas Desulfurized Gypsum/Epoxy Resin Composites

Non‐activated Esters as Reactive Handles in Direct Post‐Polymerization Modification

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