Hydrogen-bonded supramolecular polymers as self-healing hydrogels: Effect of a bulky adamantyl substituent in the ureido-pyrimidinone monomer

Chirila, Traian V., Lee, Hui Hui, Oddon, Mathieu, Nieuwenhuizen, Marko M. L., Blakey, Idriss and Nicholson, Timothy M (2014) Hydrogen-bonded supramolecular polymers as self-healing hydrogels: Effect of a bulky adamantyl substituent in the ureido-pyrimidinone monomer. Journal of Applied Polymer Science, 131 4: . doi:10.1002/app.39932


Author Chirila, Traian V.
Lee, Hui Hui
Oddon, Mathieu
Nieuwenhuizen, Marko M. L.
Blakey, Idriss
Nicholson, Timothy M
Title Hydrogen-bonded supramolecular polymers as self-healing hydrogels: Effect of a bulky adamantyl substituent in the ureido-pyrimidinone monomer
Journal name Journal of Applied Polymer Science   Check publisher's open access policy
ISSN 0021-8995
1097-4628
Publication date 2014-02-15
Year available 2013
Sub-type Article (original research)
DOI 10.1002/app.39932
Volume 131
Issue 4
Total pages 12
Place of publication Hoboken, NJ United States
Publisher John Wiley and Sons Inc.
Collection year 2014
Language eng
Subject 2505 Materials Chemistry
2507 Polymers and Plastics
2508 Surfaces, Coatings and Films
1600 Chemistry
Abstract In an attempt to generate supramolecular assemblies able to function as self-healing hydrogels, a novel ureido-pyrimidinone (UPy) monomer, 2-(N ′-methacryloyloxyethylureido)-6-(1-adamantyl)-4[1H]-pyrimidinone, was synthesized and then copolymerized with N,N-dimethylacrylamide at four different feed compositions, using a solution of lithium chloride in N,N- dimethylacetamide as the polymerization medium. The assembling process in the resulting copolymers is based on crosslinking through the reversible quadruple hydrogen bonding between side-chain UPy modules. The adamantyl substituent was introduced in order to create a "hydrophobic pocket" that may protect the hydrogen bonds against the disruptive effect of water molecules. Upon hydration to equilibrium, all copolymers generated typical hydrogels when their concentration in the hydrated system was at least 15%. The small-deformation rheometry showed that all hydrated copolymers were hydrogels that maintained a solid-like behavior, and that their extrusion through a syringe needle did not affect significantly this behavior, suggesting a self-healing capacity in these materials. An application as injectable substitutes for the eye's vitreous humor was proposed.
Keyword Biomaterials
Copolymers
Gels
Rheology
Supramolecular structures
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

 
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