Reactions on polymers with amine groups. III. Description of the addition reaction of pyridine and imidazole compounds with ?,?-unsaturated monocarboxylic acids

Bărboiu, Virgil; Holerca, Marian N.; Streba, Emilia; Luca, Cornelia

doi:10.1002/(sici)1099-0518(19960130)34:2<261::aid-pola12>3.0.co;2-o

Cited by 7 publications

(1 citation statement)

References 5 publications

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“…The term polymers carrying betaine units (PB), or polyzwitterions, refers to polymers containing both negative (carboxylate group, sulfonate group or phosphonate/phosphate/phosphinate group) and positive ( onium group without hydrogen atoms) charges located in the same repeat unit and separated by an alkylene group [ 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

New Grafted Copolymers Carrying Betaine Units Based on Gellan and N-Vinylimidazole as Precursors for Design of Drug Delivery Systems

Racoviţă¹,

Baranov

Macsim³

et al. 2020

Molecules

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New grafted copolymers possessing structural units of 1-vinyl-3-(1-carboxymethyl) imidazolium betaine were obtained by graft copolymerization of N-vinylimidazole onto gellan gum followed by the polymer-analogous reactions on grafted polymer with the highest grafting percentage using sodium chloroacetate as the betainization agent. The grafted copolymers were prepared using ammonium persulfate/N,N,N′,N′ tetramethylethylenediamine in a nitrogen atmosphere. The grafting reaction conditions were optimized by changing one of the following reaction parameters: initiator concentration, monomer concentration, polymer concentration, reaction time or temperature, while the other parameters remained constant. The highest grafting yield was obtained under the following reaction conditions: ci = 0.08 mol/L, cm = 0.8 mol/L, cp = 8 g/L, tr = 4 h and T = 50 °C. The kinetics of the graft copolymerization of N-vinylimidazole onto gellan was discussed and a suitable reaction mechanism was proposed. The evidence of the grafting reaction was confirmed through FTIR spectroscopy, X-ray diffraction, 1H-NMR spectroscopy and scanning electron microscopy. The grafted copolymer with betaine structure was obtained by a nucleophilic substitution reaction where the betainization agent was sodium chloroacetate. Preliminary results prove the ability of the grafted copolymers to bind amphoteric drugs (cefotaxime) and, therefore, the possibility of developing the new sustained drug release systems.

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Section: Introductionmentioning

confidence: 99%

New Grafted Copolymers Carrying Betaine Units Based on Gellan and N-Vinylimidazole as Precursors for Design of Drug Delivery Systems

Racoviţă¹,

Baranov

Macsim³

et al. 2020

Molecules

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Spectroscopic and thermal studies of poly[(N‐vinylimidazole)‐co‐(maleic acid)] hydrogel and its quaternized form

Pekel

Güven

2007

Polymer International

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BACKGROUND: In this study, poly[(N‐vinylimidazole)‐co‐(maleic acid)] (poly(VIm/MA)) hydrogels were prepared by γ‐irradiation of ternary mixtures of N‐vinylimidazole–maleic acid–water using a 60Co γ‐source. Spectroscopic and thermal analyses of these hydrogels as a function of protonation showed that the results are consistent with the existence of an H‐bridged complex when the imidazole rings are partially protonated. Finally, the efficiency and binding trends of Cu2+, Co2+, Cd2+ and Pb2+ ions with both protonated and unprotonated poly(VIm/MA) hydrogels were determined.RESULTS: Gelation of 90% was reached at around 180 kGy dose at the end of irradiation. The poly(VIm/MA) hydrogels synthesized were further protonated in HCl solutions with different concentrations. Hydrogels originally showed 450% volumetric swelling; this ratio reached 1900% after protonation at pH = 5.0. Fourier transform infrared spectral changes in the +NH stretching region (3200–3600 and 1173 cm−1) and the ring mode deformation at 915 cm−1 are consistent with the formation of an H‐bridged complex between the protonated and unprotonated imidazole rings upon partial protonation. Similar changes were obtained from NMR spectra of both the protonated and unprotonated forms of the hydrogels.CONCLUSION: Protonated and unprotonated hydrogels have been used in heavy metal ion adsorption studies for environmental purposes. Adsorption decreased with decreasing pH value due to the protonation of the VIm ring. The adsorption of Me2+ ions decreased in the order Cu2+ > Co2+ > Cd2+ > Pb2+, which is related to the complexation stability as well as the ionic radius of the metal ions. These results show that P(VIm/MA) hydrogels can be used efficiently to remove heavy metal ions from aqueous solutions. However, the protonated form is a bad choice for heavy metal ion adsorption due to electrostatic repulsion forces; it can nevertheless be assumed to be a good choice for anion adsorption from environmental waste water systems. Copyright © 2007 Society of Chemical Industry

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Polymeric Betaines: Synthesis, Characterization, and Application

Kudaibergenov

Jaeger

Laschewsky

2006

Advances in Polymer Science

324

305

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Reactions on polymers with amine groups. III. Description of the addition reaction of pyridine and imidazole compounds with ?,?-unsaturated monocarboxylic acids

Cited by 7 publications

References 5 publications

New Grafted Copolymers Carrying Betaine Units Based on Gellan and N-Vinylimidazole as Precursors for Design of Drug Delivery Systems

New Grafted Copolymers Carrying Betaine Units Based on Gellan and N-Vinylimidazole as Precursors for Design of Drug Delivery Systems

Spectroscopic and thermal studies of poly[(N‐vinylimidazole)‐co‐(maleic acid)] hydrogel and its quaternized form

Polymeric Betaines: Synthesis, Characterization, and Application

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