The syntheses of functional benzoxazine monomers based on phenol and either propargyl amine or allyl amine were carried out to investigate the effect of introducing benzoxazines into thiol-alkyne or thiol-alkene networks on the thermal and mechanical properties of the networks. The thiol-alkyne polymer networks were modified by utilizing the ability of the benzoxazine to undergo heat-induced ring-opening polymerization, adjusting the properties of the networks by varying the functionality of the thiol. The kinetics of the thiol-benzoxazine reaction were determined to compete with thiol-alkyne polymerization, and so the properties of the final networks were influenced by both factors, resulting in broad glass transitions and mechanically fragile samples above the glass transition temperatures. Thermal stability, however, was intermediate compared to neat thiol-alkyne polymers and polybenzoxazines. The thiol-alkene polymer networks were modified by reacting the benzoxazine directly into the polymer matrix, taking advantage of the thiol-benzoxazine reaction. The thermal and mechanical properties were studied with respect to the fraction of thiol-benzoxazine crosslinker introduced into the polymer, showing trends such as slower kinetics, lower initial thermal stability, lower Young's modulus, tunable glass transition temperatures, and higher strain at break.
","abstract_html":"<p>The syntheses of functional benzoxazine monomers based on phenol and either propargyl amine or allyl amine were carried out to investigate the effect of introducing benzoxazines into thiol-alkyne or thiol-alkene networks on the thermal and mechanical properties of the networks. The thiol-alkyne polymer networks were modified by utilizing the ability of the benzoxazine to undergo heat-induced ring-opening polymerization, adjusting the properties of the networks by varying the functionality of the thiol. The kinetics of the thiol-benzoxazine reaction were determined to compete with thiol-alkyne polymerization, and so the properties of the final networks were influenced by both factors, resulting in broad glass transitions and mechanically fragile samples above the glass transition temperatures. Thermal stability, however, was intermediate compared to neat thiol-alkyne polymers and polybenzoxazines. The thiol-alkene polymer networks were modified by reacting the benzoxazine directly into the polymer matrix, taking advantage of the thiol-benzoxazine reaction. The thermal and mechanical properties were studied with respect to the fraction of thiol-benzoxazine crosslinker introduced into the polymer, showing trends such as slower kinetics, lower initial thermal stability, lower Young's modulus, tunable glass transition temperatures, and higher strain at break.</p>","abstract_has_math":false,"creators":["Jungman, Matthew James"],"institution":null,"degree_name":"Master of Science (MS)","degree_level":"Masters Thesis","degree_discipline":"Polymers and High Performance Materials","degree_department":null,"school":null,"contributors":["Derek Patton"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-05-01T07:00:00Z","date_published":"2013-05-01T07:00:00Z","updated_at":"2026-07-24T05:45:06Z","subjects":[],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://aquila.usm.edu/masters_theses/532","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Derek Patton"]},{"key":"dc:creator","label":"Author","values":["Jungman, Matthew James"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2018-11-15T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Polymers and High Performance Materials"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Masters Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MS)"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://aquila.usm.edu/masters_theses/532"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The syntheses of functional benzoxazine monomers based on phenol and either propargyl amine or allyl amine were carried out to investigate the effect of introducing benzoxazines into thiol-alkyne or thiol-alkene networks on the thermal and mechanical properties of the networks. The thiol-alkyne polymer networks were modified by utilizing the ability of the benzoxazine to undergo heat-induced ring-opening polymerization, adjusting the properties of the networks by varying the functionality of the thiol. The kinetics of the thiol-benzoxazine reaction were determined to compete with thiol-alkyne polymerization, and so the properties of the final networks were influenced by both factors, resulting in broad glass transitions and mechanically fragile samples above the glass transition temperatures. Thermal stability, however, was intermediate compared to neat thiol-alkyne polymers and polybenzoxazines. The thiol-alkene polymer networks were modified by reacting the benzoxazine directly into the polymer matrix, taking advantage of the thiol-benzoxazine reaction. The thermal and mechanical properties were studied with respect to the fraction of thiol-benzoxazine crosslinker introduced into the polymer, showing trends such as slower kinetics, lower initial thermal stability, lower Young's modulus, tunable glass transition temperatures, and higher strain at break.
"]},{"key":"dc:title","label":"Title","values":["Design of Functional Benzoxazine Materials Via Thiol-Mediated Reactions"]}]}],"canonical_facts":{"dc:contributor":["Derek Patton"],"dc:creator":["Jungman, Matthew James"],"dc:date.available":["2018-11-15T08:00:00Z"],"dc:description.abstract":["The syntheses of functional benzoxazine monomers based on phenol and either propargyl amine or allyl amine were carried out to investigate the effect of introducing benzoxazines into thiol-alkyne or thiol-alkene networks on the thermal and mechanical properties of the networks. The thiol-alkyne polymer networks were modified by utilizing the ability of the benzoxazine to undergo heat-induced ring-opening polymerization, adjusting the properties of the networks by varying the functionality of the thiol. The kinetics of the thiol-benzoxazine reaction were determined to compete with thiol-alkyne polymerization, and so the properties of the final networks were influenced by both factors, resulting in broad glass transitions and mechanically fragile samples above the glass transition temperatures. Thermal stability, however, was intermediate compared to neat thiol-alkyne polymers and polybenzoxazines. The thiol-alkene polymer networks were modified by reacting the benzoxazine directly into the polymer matrix, taking advantage of the thiol-benzoxazine reaction. The thermal and mechanical properties were studied with respect to the fraction of thiol-benzoxazine crosslinker introduced into the polymer, showing trends such as slower kinetics, lower initial thermal stability, lower Young's modulus, tunable glass transition temperatures, and higher strain at break.
"],"dc:identifier":["https://aquila.usm.edu/masters_theses/532"],"dc:title":["Design of Functional Benzoxazine Materials Via Thiol-Mediated Reactions"],"thesis:degree_discipline":["Polymers and High Performance Materials"],"thesis:degree_level":["Masters Thesis"],"thesis:degree_name":["Master of Science (MS)"]},"updated_at":"2026-07-24T05:45:06Z"}