Synthesis of a New Polyanion Possessing Dense 1,2,3-Triazole Backbone.

Linlin Xu,Yuri Kamon,Akihito Hashidzume

doi:10.3390/polym13101614

Abstract

Polyanions are an important class of water-soluble polymers because polyanions are utilized in a wide range of industrial fields. It is thus a great challenge to develop polyanions with novel structures to make their applications broader. In this study, a new polyanion with a dense 1,2,3-triazole backbone, poly(4-azido-5-hexanoic acid) (poly(AH)), was synthesized by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerization of t-butyl 4-azido-5-hexanoate followed by hydrolysis of the t-butyl ester groups. Turbidimetric and potentiometric titration data indicated that poly(AH) was well soluble in water under basic conditions (pH < 7) and a weaker polyanion (apparent pKa = 5.4) than polyacrylic acid (apparent pKa = 4.5). Adsorption tests exhibited that sodium salt of poly(AH) (poly(AH)Na) adsorbed most preferably Fe3+ among the four metal ions examined, i.e., Cu2+, Pb2+, Li+, and Fe3+. 1H spin-lattice relaxation time measurements indicated that Fe3+ ions were adsorbed favorably onto the 1,2,3-triazole residues.

Highlights

Polyanions are an important class of water soluble polymers showing various effects, e.g., thickening, gelling, dispersing, cohesive, adhesive, moisturizing, and metal-ion scavenging effects
On the basis of the effects, polyanions are utilized in a wide range of industrial fields including detergents, cosmetics, pharmaceuticals, foods, paints, textiles, civil engineering, and construction [1,2,3,4,5,6]
According to the procedure reported previously [32], t-butyl 4-azido-5-hexanoate (tBuAH) was polymerized by CuAAC to yield poly(tBuAH) consisting of 1,4-disubstituted 1,2,3-triazole residues

Summary

Introduction

It is known that 1,4-disubstituted 1,2,3-triazoles are formed efficiently and selectively in the presence of copper(I) compounds [18,19,20]. This reaction is known as copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC). CuAAC has been used in a variety of fields as the most important reaction in click chemistry [21,22]. CuAAC has been utilized for synthesis of polymers possessing 1,2,3-triazole units [23,24,25,26]. We have been working on synthesis of polymers with the backbone composed of dense 1,2,3-triazole units by CuAAC polymerization of

Methods

Results

Conclusion