Synthesis of N-(2-hydroxyethyl) derivatives of β-alanine

Dokichev, T. V.; Latypova, D. R.; Biglova, R. Z.; Талипов, Р. Ф.

doi:10.1134/s0012500810020047

Cited by 1 publication

(1 citation statement)

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“…[16] Nevertheless, investigations have demonstrated that a direct addition is possible as in the case of the addition of acrylic acid to monoethanolamine performed in the presence of a heteroge neous catalyst such as alumina or bentonite, to selectively form a monoadduct (MA). [17] The reaction of primary and secondary aryl amines has been also investigated with acrylic acid in eth anol at room temperature. After 24 h, expected adducts were obtained and the temperature increased up to 65 °C without evidence of acrylic acid polymerization.…”

Section: Introductionmentioning

confidence: 99%

Zwitterionic Silicone Materials Derived from Aza‐Michael Reaction of Amino‐Functional PDMS with Acrylic Acid

Genest

Portinha

Pouget

et al. 2020

Macromol. Rapid Commun.

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Supramolecular zwitterionic silicones are synthesized by aza‐Michael reaction between acrylic acid and amine‐functional polydimethylsiloxanes. The in‐depth characterization of this chemistry, applied for the first time to silicones, is investigated first with model alkylamines (hexylamine, 2‐ethylhexylamine and N‐propylethylenediamine), a model oligosiloxane (3‐aminopropylmethyl bis(trimethylsiloxy)silane), and finally various amino‐polysiloxanes. It is shown that after a first acid–base reaction resulting in ionic pairing, aza‐Michael addition proceeds smoothly in mild conditions (50 °C, 1‐week reaction). Both monoadducts and di‐adducts, together with residual amine, are observed by NMR. The supramolecular assembly of the thus‐created zwitterionic moieties is highlighted by a concomitant increase in viscosity and phase separation, as observed by transmission electron microscopy, bringing an additional glass transition at –40 °C assigned to highly polar ionic clusters. Below the stoichiometry in acrylic acid, all zwitterionic silicones follow the same classical behavior of nonentangled polymers according to the Rouse model, whereas upon introducing an excess of acrylic acid to amino groups, an enhancement of the elasticity is observed. Finally, silicone elastomers with solid‐like behavior and elastomeric mechanical properties are obtained using a high molar mass polymer bearing bifunctional N‐(2‐aminoethyl)‐3‐aminopropyl units that favor a high degree of physical crosslinking.

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Section: Introductionmentioning

confidence: 99%