Quantitative Measurements of Polymer Hydrophobicity Based on Functional Group Identity and Oligomer Length

Nayanthara U. Dharmaratne, Terra Marie M. Jouaneh, Matthew K. Kiesewetter, Robert T. Mathers

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Abstract

A combined experimental and computational investigation revealed a hydrophobicity trend for oxygen-containing functional groups commonly encountered in monomers and polymers. Based on solvatochromatic dye experiments, HPLC retention times, and theoretical LogP values, the arrangement of the three oxygen atoms in carbonates results in more hydrophobicity than other permutations like anhydrides. Another trend emerged for functional groups with two oxygen atoms (acetals > esters). Overall, when comparing aliphatic polymers with similarly sized monomers, hydrophobicity decreased as follows: carbonates > acetals > esters > anhydrides. These trends have important implications for degradation, conductivity, and many other applications.

Original languageEnglish (US)
Pages (from-to)8461-8468
Number of pages8
JournalMacromolecules
Volume51
Issue number21
DOIs
StatePublished - Nov 13 2018

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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