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Title: Investigation and synthesis of alkyl cyanoacrylates and modification of X-ray contrast agents for incorporation into alkyl cyanoacrylate for use in medical devices
Author: Halliwell, Lauren
ISNI:       0000 0004 2749 4549
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 2013
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The work in this thesis involves the development of a protected transesterification route for the production of novel cyanoacrylate monomers. As well as the modification of iodinated contrast agents to increase their solubility in cyanoacrylate, to enable monitoring of the adhesive within the body for possible use in the treatment of brain aneurysms. Chapter 1 provides an introduction to biological adhesives, in particular alky 2-cyanoacrylates and how they degrade to release formaldehyde. Details into iodinated X-ray contrast agents, their structure, uses and synthesis, as well as the current treatments for brain aneurysms. Chapter 2 focuses on the modification of several iodinated contrast agents in order to increase solubility in ethyl cyanoacrylate. Three existing contrast agents were protected using a variety of different protecting groups and tested for solubility in ethyl cyanoacrylate. Partition coefficients were calculated for the successfully modified compounds. Chapter 3 outlines the development of the anthracene protected route for the synthesis of cyanoacrylate monomers, utilising the Diels- Alder and retro-Diels-Alder reactions of anthracene. This route was subsequently used to synthesis a range of cyanoacrylate monomers. Polymerisation of these monomers gave a range of polymers which were tested to determine their rate of degradation through formaldehyde detection. Chapter 4 further details the first and final step of the anthracene protected route developed in chapter 3. It involved 1H NMR experiments to determine how substitution at the 9 and 10 position of anthracene affects the rate of reaction of the forward and retro-Diels-Alder reaction.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry ; RC Internal medicine