Aryl acrylate based high-internal-phase emulsions as precursors for reactive monolithic polymer supports

Peter Krajnc, Dejan Stefanec, Jane F. Brown, Neil R. Cameron

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56 Citations (Scopus)

Abstract

Water-in-oil high-internal-phase emulsions (HIPEs), containing 4-nitrophenyl acrylate and 2,4,6-trichlorophenyl acrylate as reactive monomers, were prepared and polymerized, and highly porous monolithic materials resulted. The novel materials were studied by combustion analysis, Fourier transform infrared spectroscopy scanning electron microscopy, mercury porosimetry, and N2 adsorption/desorption analysis. With both esters, cellular macroporous monolithic polymers were obtained; the use of 4-nitrophenyl acrylate resulted in a cellular material with void diameters between 3 and 7 μm and approximately 3-μm interconnects, whereas the use of 2,4,6-trichlorophenyl acrylate yielded a foam with void diameters between 2 and 5 μm, most interconnects being around 1 μm. The resulting monoliths proved to be very reactive toward nucleophiles, and possibilities of functionalizing the novel polymer supports were demonstrated via reactions with amines bearing additional functional groups and via the synthesis of an acid chloride derivative. Tris(hydroxymethyl)aminomethane and tris(2-aminoethyl)amine derivatives were obtained. The hydrolysis of 4-nitrophenylacrylate removed the nitrophenyl group, yielding a monolithic acrylic acid polymer. Furthermore, functionalization to immobilized acid chloride was performed very efficiently, with more than 95% of the acid groups reacting. The measurement of the nitrogen content in 4-nitrophenyl acrylate poly(HIPE)s after various times of hydrolysis showed the influence of the total pore volume of the monolithic polymers on the velocity of the reaction, which was faster with the more porous polymer.

Original languageEnglish
Pages (from-to)296-303
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume43
Issue number2
DOIs
Publication statusPublished - 15 Jan 2005
Externally publishedYes

Keywords

  • Foams
  • Functionalization of polymers
  • High-internal-phase emulsions
  • Macroporous polymers
  • Monolithic polymers

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