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Nitrile-oxide/dipolarophile cycloaddition polymers derived from renewable feedstocks
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Jones, Nyle Owen Saul (2020) Nitrile-oxide/dipolarophile cycloaddition polymers derived from renewable feedstocks. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b3520400~S15
Abstract
Polytriazoles formed by 1,3-dipolar cycloaddition have been widely reported in literature, including some derived from renewable feedstocks. The analogous nitrile oxide-alkyne cycloaddition has received limited attention as a polymerisation technique. This work explores the application of 1,3-dipolar nitrile oxide cycloadditions to the synthesis of renewably derived polymers.
Initial studies were carried out using commercially available dipolarophiles to assess the reproducibility of a polymerisation technique taken from a literature source. The polymerisation technique used molecular sieves as a mildly basic additive to form nitrile oxides from oximoyl chlorides in situ. After the technique was shown to successfully form polyisoxazolines, it was applied to dialkene and dialkyne acetamide monomers, these were used to model the behaviour of intended fatty acid derived monomers. Polyisoxazoles and polyisoxazolines were formed with low numbers of repeat units, attempts were therefore made to optimise the polymerisation conditions. Optimisation studies showed that a longer reaction time was required, moving forward this finding was applied to later polymerisations.
Dialkene and dialkyne monomers were derived from palmitic, stearic, oleic, linoleic and linolenic acid. They were used along with a di(oximoyl chloride) premonomer to form polyisoxazoles and polyisoxazolines. Unsaturated fatty chains demonstrated an ability to allow crosslinking to occur through cycloaddition with the cis-alkene. Finally, oximoyl chloride and dialkene monomers were derived from vanillin and used in conjunction with the fatty acid derived dipolarophiles to form bio-derived polyisoxazoles. Vanillin was also used to form a difunctional monomer which allowed for the formation of homopolymers by a solvent free polymerisation method.
Item Type: | Thesis (PhD) | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Ring formation (Chemistry), Polymerization, Chemistry, Organic | ||||
Official Date: | September 2020 | ||||
Dates: |
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Institution: | University of Warwick | ||||
Theses Department: | Department of Chemistry | ||||
Thesis Type: | PhD | ||||
Publication Status: | Unpublished | ||||
Supervisor(s)/Advisor: | Clark, Andrew J. (Professor) | ||||
Format of File: | |||||
Extent: | xxxi, 317 leaves : illustrations (some colour) | ||||
Language: | eng |
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