Tuneable N-Substituted Polyamides with High Biomass Content via Ugi 4 Component Polymerization. MacKinnon, D., Zhao, T., & Becer, C. R. MACROMOLECULAR CHEMISTRY AND PHYSICS, July, 2022. doi abstract bibtex Ugi 4-component reaction (Ugi 4CR) is an efficient tool which benefits from high atom efficiency, compatibility with green solvents such as methanol, simple purification, and a water side-product. By using two bifunctional starting materials for Ugi 4CR, N-substituted polyamides can be prepared via a step-growth process. As polyamides play important roles in applications including films, and adhesives, the preparation of N-substituted functional polyamides from largely sustainable monomers is investigated. Herein, the combination of renewable diamine, diacid, and aldehydes with commercially available isocyanides yield polyamides with tuneable side chain functionalities and approximate to 80% biomass content. Relatively high yields (up to 96%) are recorded for polymers of moderate molecular weights (M-w up to 8100 g mol(-1)). The prepared polyamides possess backbones which exhibit excellent thermal stability (T-d(eg) = 440 +/- 10 degrees C), while functional side chains result in additional lower-temperature degradations (215-285 degrees C). Side-group variation enables shifting of the glass transition temperature (T-g) between 9 and 38 degrees C and causes variation in hydrophobicity resulting in water contact angles ranging from 47 (o) to 105 (o). This work presents a reliable approach to prepare sustainable polymers with diverse side chain functionalities in a short reaction time and without need for catalysts or complicated purifications.
@article{mackinnon_tuneable_2022,
title = {Tuneable {N}-{Substituted} {Polyamides} with {High} {Biomass} {Content} via {Ugi} 4 {Component} {Polymerization}},
volume = {223},
issn = {1022-1352},
doi = {10.1002/macp.202100408},
abstract = {Ugi 4-component reaction (Ugi 4CR) is an efficient tool which benefits from high atom efficiency, compatibility with green solvents such as methanol, simple purification, and a water side-product. By using two bifunctional starting materials for Ugi 4CR, N-substituted polyamides can be prepared via a step-growth process. As polyamides play important roles in applications including films, and adhesives, the preparation of N-substituted functional polyamides from largely sustainable monomers is investigated. Herein, the combination of renewable diamine, diacid, and aldehydes with commercially available isocyanides yield polyamides with tuneable side chain functionalities and approximate to 80\% biomass content. Relatively high yields (up to 96\%) are recorded for polymers of moderate molecular weights (M-w up to 8100 g mol(-1)). The prepared polyamides possess backbones which exhibit excellent thermal stability (T-d(eg) = 440 +/- 10 degrees C), while functional side chains result in additional lower-temperature degradations (215-285 degrees C). Side-group variation enables shifting of the glass transition temperature (T-g) between 9 and 38 degrees C and causes variation in hydrophobicity resulting in water contact angles ranging from 47 (o) to 105 (o). This work presents a reliable approach to prepare sustainable polymers with diverse side chain functionalities in a short reaction time and without need for catalysts or complicated purifications.},
number = {13},
urldate = {2022-01-12},
journal = {MACROMOLECULAR CHEMISTRY AND PHYSICS},
author = {MacKinnon, Daniel and Zhao, Tieshuai and Becer, C. Remzi},
month = jul,
year = {2022},
}
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Herein, the combination of renewable diamine, diacid, and aldehydes with commercially available isocyanides yield polyamides with tuneable side chain functionalities and approximate to 80% biomass content. Relatively high yields (up to 96%) are recorded for polymers of moderate molecular weights (M-w up to 8100 g mol(-1)). The prepared polyamides possess backbones which exhibit excellent thermal stability (T-d(eg) = 440 +/- 10 degrees C), while functional side chains result in additional lower-temperature degradations (215-285 degrees C). Side-group variation enables shifting of the glass transition temperature (T-g) between 9 and 38 degrees C and causes variation in hydrophobicity resulting in water contact angles ranging from 47 (o) to 105 (o). 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Side-group variation enables shifting of the glass transition temperature (T-g) between 9 and 38 degrees C and causes variation in hydrophobicity resulting in water contact angles ranging from 47 (o) to 105 (o). This work presents a reliable approach to prepare sustainable polymers with diverse side chain functionalities in a short reaction time and without need for catalysts or complicated purifications.},\n\tnumber = {13},\n\turldate = {2022-01-12},\n\tjournal = {MACROMOLECULAR CHEMISTRY AND PHYSICS},\n\tauthor = {MacKinnon, Daniel and Zhao, Tieshuai and Becer, C. Remzi},\n\tmonth = jul,\n\tyear = {2022},\n}\n\n","author_short":["MacKinnon, D.","Zhao, T.","Becer, C. 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