Functionalization of hydroxyl groups in segmented polyhydroxyurethane eliminates nanophase separation

Goliath Beniah, William H. Heath, John M. Torkelson*

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

The properties of segmented, nanophase-separated polyhydroxyurethane (PHUs) were investigated before and after hydroxyl group functionalization. Segmented PHU was synthesized using polytetramethylene oxide (PTMO)-based soft segment, divinylbenzene dicyclocarbonate (DVBDCC) as hard segment, and p-xylylene diamine as chain extender at 40 wt% hard-segment content. The pendant hydroxyl groups were subsequently functionalized with benzoyl chloride, and the properties of PHUs before and after functionalization were characterized with NMR spectroscopy, small-angle X-ray scattering (SAXS), and dynamic mechanical analysis (DMA). 1H and 13C NMR spectra confirm the successful attachment of the benzoyl group to the hydroxyl group. The FTIR spectra of PHU-Bz in the carbonyl region also show a higher proportion of free carbonyl relative to hydrogen-bonded carbonyl, indicative of phase mixing. These results show that hydroxyl group functionalization with side groups as small as an acetyl group or as large as a benzoyl group provides similar, substantial steric hindrance to interurethane hydrogen bonding, leading to phase mixing in these segmented, functionalized PHUs. SAXS experiments were performed using a Rigaku S-MAX 3000 SAXS system emitting X-rays with a wavelength of 0.154 nm.

Original languageEnglish (US)
Pages (from-to)3347-3351
Number of pages5
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume55
Issue number20
DOIs
StatePublished - Oct 15 2017

Keywords

  • nanophase separation
  • nonisocyanate polyurethane
  • polyhydroxyurethane

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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