Free radical polymerization of caffeine-containing methacrylate monomers

Ashley M. Nelson, Sean T. Hemp, Jessica Chau, Timothy Edward Long

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The incorporation of acrylic functionality into caffeine enables the preparation of a vast array of novel thermoplastics and thermosets. A two-step derivatization provided a novel caffeine-containing methacrylate monomer capable of free radical polymerization. Copolymers of 2-ethylhexyl methacrylate and caffeine methacrylate (CMA) allowed for a systematic study of the effect of covalently bound caffeine on polymer properties. 1H NMR and UV-vis spectroscopy confirmed caffeine incorporation at 5 and 13 mol %, and SEC revealed the formation of high molecular weight (co)polymers (>40,000 g/mol). CMA incorporation resulted in a multistep degradation profile with initial mass loss closely correlating to caffeine content. Differential scanning calorimetry, rheological, and thermomechanical analysis demonstrated that relatively low levels of CMA increased the glass transition temperature, resulting in higher moduli and elucidating the benefits of incorporating caffeine into polymers.

Original languageEnglish
Pages (from-to)2829-2837
Number of pages9
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume53
Issue number24
DOIs
Publication statusPublished - 2015 Dec 15
Externally publishedYes

Fingerprint

Caffeine
Methacrylates
Free radical polymerization
Monomers
Polymers
Thermosets
Ultraviolet spectroscopy
Thermoplastics
Acrylics
Differential scanning calorimetry
Copolymers
Molecular weight
Nuclear magnetic resonance
Degradation

Keywords

  • photochemistry
  • renewable resources
  • structure-property relations

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Free radical polymerization of caffeine-containing methacrylate monomers. / Nelson, Ashley M.; Hemp, Sean T.; Chau, Jessica; Long, Timothy Edward.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 53, No. 24, 15.12.2015, p. 2829-2837.

Research output: Contribution to journalArticle

Nelson, Ashley M. ; Hemp, Sean T. ; Chau, Jessica ; Long, Timothy Edward. / Free radical polymerization of caffeine-containing methacrylate monomers. In: Journal of Polymer Science, Part A: Polymer Chemistry. 2015 ; Vol. 53, No. 24. pp. 2829-2837.
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