Senior Project Advisor
Dr. Mike Larsen
Document Type
Project
Publication Date
Spring 2022
Keywords
Covalent Adaptable Networks, statistical copolymer, uncontrolled free radical copolymerization, Thermal Guanidine Metathesis, organic synthesis
Abstract
Covalent adaptable networks (CANs) are a newly emerging class of polymers that uniquely bridge the gap between traditional thermosets and thermoplastics. The distinguishing characteristic of these polymer networks is that they contain reversible crosslink bonds that allows these materials to be recycled. Two of the currently best-understood CAN systems include those based on Diels-Alder1 and transesterification2 reactions, both of which involve dissociative exchange mechanisms. Our group aimed to create a novel CAN system based on the thermal guanidine metathesis (TGM) reaction3 by using a guanidine functional group as a crosslinker. In order to create a guanidine-crosslinked network, our research took a postpolymerization modification approach wherein we synthesized a precursor polymer containing pendant reactive carbodiimide functionalities which, upon reaction with a multifunctional amine, are reversibly converted into guanidine crosslinks. The carbodiimide-containing polymer is synthesized using free-radical copolymerization with styrene and a carbodiimide (CDI)-containing monomer with a styrenic substituent. The CDI-containing monomer is synthesized via creation and subsequent dehydrosulfurization of a thiourea-based pre-monomer. This research presents a comprehensive overview of the process of creating a reliable, scalable, 4-step synthetic plan to create a covalent adaptable network which uses a dissociable guanidine functional group as a covalent crosslink.
Recommended Citation
Houck, Hayden, "Synthetic Development of Carbodiimide-Containing Polymers as Precursors to Guanidine-Based Covalent Adaptable Networks" (2022). WWU Honors College Senior Projects. 562.
https://cedar.wwu.edu/wwu_honors/562
Subjects - Topical (LCSH)
Organic compounds--Synthesis; Polymers; Carbodiimides; Guanidine
Genre/Form
essays
Type
Text
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.
Language
English
Format
application/pdf