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

doi:10.1021/acs.macromol.8b01747

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

Penn State New Kensington

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

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 language	English (US)
Pages (from-to)	8461-8468
Number of pages	8
Journal	Macromolecules
Volume	51
Issue number	21
DOIs	https://doi.org/10.1021/acs.macromol.8b01747
State	Published - Nov 13 2018

All Science Journal Classification (ASJC) codes

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Quantitative Measurements of Polymer Hydrophobicity Based on Functional Group Identity and Oligomer Length",

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.",

author = "Dharmaratne, {Nayanthara U.} and Jouaneh, {Terra Marie M.} and Kiesewetter, {Matthew K.} and Mathers, {Robert T.}",

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AU - Kiesewetter, Matthew K.

AU - Mathers, Robert T.

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N2 - 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.

AB - 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.

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

Abstract

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