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Green chemistry in the design of safer anaerobic adhesives

Porter, Adam (2015) Green chemistry in the design of safer anaerobic adhesives. PhD thesis, Dublin City University.

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Abstract

New cure accelerators for anaerobic adhesives have been designed to offer less harmful alternatives to current industry standard accelerators. Accelerators in current use are comprised of compounds such as acetylphenylhydrazine (APH), diethyl-p- toluidine (DEpT), tetrahydroquinoline (THQ) and their derivatives, all of which can be classified as being acutely toxic or harmful to the user. Further to this, there is no consensus as to their mode of action within the curing of the adhesive and how they affect the radically initiated polymerisation mechanism. Safer alternative cure accelerators have been designed and added insight as to their mechanistic role gained through the conception, synthesis, and screening of “generations” of accelerators and structurally similar compounds for key properties such as anti-microbial toxicity, cytotoxicity, biodegradability, eco-toxicity, and cure activity. With the analysis of each generation, more information was gathered and the structure activity relationship for these properties further elucidated. This greatly aided the design of each succeeding generation of synthetic targets in order to maximise their accelerator activity whilst reducing their risk to the user and the environment. This approach not only yielded new ionic liquid based cure accelerators but also opened up new directions for their future development and design by identifying classes of compounds not previously used for this purpose. These saccharinate, acesulfamate, and phthalimate based compounds have been proven to possess activity equal to current industry benchmarks whilst being of low cytotoxicity and anti-microbial activity. Furthermore, these compounds offer significant room in their scope for derivitisation and development as custom designed cure catalysts.

Item Type:Thesis (PhD)
Date of Award:November 2015
Refereed:No
Supervisor(s):Kellett, Andrew and Gathergood, Nicholas and Kelleher, Brian
Uncontrolled Keywords:Green chemistry; Aerobic adhesives
Subjects:Physical Sciences > Organic chemistry
Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 3.0 License. View License
Funders:Irish Research Council for Science Engineering and Technology
ID Code:20829
Deposited On:24 Nov 2015 14:48 by Andrew Kellett. Last Modified 24 Nov 2015 14:48

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