Methacrylamide with TMP Group as a Side Chain

Methacrylamide monomers are widely used as monomers for hydrophilic nanogel and hydrogel synthesis due to their high hydrophilicity. TMPMA (1) is a methacrylamide monomer having a tetramethylpiperidine (TMP) moiety in its side chain, which shows high solubility in both organic solvents and water. In addition, the TMP moiety of 1 is not only a base but also a functional group exhibiting antioxidant activity.¹⁾
An example of the use of 1 is the synthesis of carbon dioxide adsorbing nanogel particles (NPs) by Rieger et al.²⁾ NPs are obtained by copolymerization of 1, NIPAAm, and N,N'-methylenebisacrylamide. The resulting NPs show reversible contraction and expansion in water by temperature variation. By heating the NPs to 85 °C, the particle size is shrunk to 135 nm. After the contracted NPs are cooled to room temperature, the particle size expands to 340 nm. pH of the NP also significantly drops from 10.25 to 7.65 due to the shrinkage caused by heating. Taking advantage of this property, the NP adsorbs carbon dioxide at room temperature and releases it under heating. Carbon dioxide adsorption and desorption are also reversible. At most 35 mL of carbon dioxide was adsorbed and desorbed per 1 g of NP.

References

• 1) Antioxidant Properties of 2-Hydroxyethyl Methacrylate-Based Copolymers with Incorporated Sterically Hindered Amine
  • L. Poláková, V. Raus, L. Kostka, A. Braunová, J. Pilař, V. Lobaz, J. Pánek, Z. Sedláková, Biomacromolecules 2015, 16, 2726.
• 2) Thermo- and pH-Responsive Nanogel Particles Bearing Secondary Amine Functionalities for Reversible Carbon Dioxide Capture and Release
  • P. D. L. Werz, J. Kainz, B. Rieger, Macromolecules 2015, 48, 6433.

Related Compounds

I0401

N-Isopropylacrylamide (= NIPAAm) (stabilized with MEHQ)

M2877

N,N'-Methylenebisacrylamide

A2735

2,2'-Azobis(2-methylpropionamidine) Dihydrochloride (= AAPH)

H0081

Hexadecyltrimethylammonium Bromide (= CTAB)

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