Halliwell, Lauren (2013) Investigation and synthesis of alkyl cyanoacrylates and modification of x-ray contrast agents for incorporation into alkyl cyanoacrylate for use in medical devices. PhD thesis, University of Warwick.

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Abstract

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.

Item Type:	Thesis or Dissertation (PhD)
Subjects:	Q Science > QD Chemistry R Medicine > RC Internal medicine
Library of Congress Subject Headings (LCSH):	Cyanoacrylates -- Synthesis, Transesterification, Adhesion, Contrast media (Diagnostic imaging), Monomers
Official Date:	March 2013
Dates:	Date Event March 2013 Submitted
Institution:	University of Warwick
Theses Department:	Department of Chemistry
Thesis Type:	PhD
Publication Status:	Unpublished
Supervisor(s)/Advisor:	Clark, Andrew J.; Filik, Robert
Extent:	x, 233 leaves : illustrations.
Language:	eng

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