Synthesis and characterization of α,ω-dihydroxy-telechelic oligo(p-dioxanone)??

Journal of Materials Chemistry Pub Date: 2007-08-21 DOI: 10.1039/B707104C

Abstract

The homopolymer of 1,4-dioxane-2-one (pDO) is well known as an established biomaterial, especially for degradable surgical sutures. Well-defined α,ω-dihydroxy telechelics based on pDO are introduced in this paper. pDO was synthesized via a one step reaction modified to a literature procedure with a yield of 50–60%. The monomer was polymerized in bulk to oligomeric products via ring-opening polymerization. The polymerization was performed without or with dibutyltin oxide as catalyst using low molecular weight alcohols as initiators. The oligomeric products have number average molecular weights (Mn) between 1800 g mol–1 and 4200 g mol–1. They were soluble in 1,2-dichloroethane or chloroform as common solvents for further reaction in solution. The α,ω-dihydroxy-functionality of the obtained telechelics was investigated by MALDI-TOF MS and 1H NMR spectroscopy. Polymerization in the presence of the catalyst lead to macrocyclic byproducts which have been detected by MALDI-TOF MS. The telechelics were semicrystalline with melting points Tm between 86 °C and 95 °C, increasing with increasing molecular weight. The melting enthalpies ΔHm ranged from 67.7 to 82.3 J g–1. An example of the synthetic opportunities arising from the availability of well-defined telechelic oligomers as starting materials are multiblock copolymers, which were synthesized successfully from oligo(p-dioxane)diol, poly[(rac-lactide)-ran-glycolide]diol and trimethylhexane diisocyanate with weight average molecular weights Mw between 62?000 and 149?000 g mol–1.

Graphical abstract: Synthesis and characterization of α,ω-dihydroxy-telechelic oligo(p-dioxanone)
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