A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines

Abstract

Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82–99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents.

Synthesis and Study of Physical and Mechanical Properties of Urethane-Containing Elastomers Based on Epoxyurethane Oligomers with Controlled Crystallinity

“…Such oligomers can be prepared from oligoglycols by a variety of synthetic routes. The most common synthetic route is a three-step procedure that includes mesylation, azidation, and reduction [ 32 ]. In addition, in [ 33 ], another preparation method for oligoether diamines is described.…”

Block Copolymers With Urethane Hydroxy Hard Segments Based on Oligoethertetraurethanediepoxide and a Binary Hardener

“…Функционализация олигогликолей может проходить несколькими методами. Один из них включает в себя последовательность реакций мезилирования, азидирования и восстановления [23]. Олигоэфирдиамины могут быть получены из соответствующих олигогликолей в результате каталитического аминирования в условиях высокого давления и температур [24].…”