A Route Toward Multifunctional Polyurethanes Using Triple Click Reactions

Demirel E., DURMAZ H., Hızal G., TUNCA Ü.

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, vol.54, no.4, pp.480-486, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 4
  • Publication Date: 2016
  • Doi Number: 10.1002/pola.27796
  • Journal Name: JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.480-486
  • Keywords: active ester substitution, aliphatic polyurethane (PU), alkyne, anthracene, CuAAC, Diels-Alder reaction, differential scanning calorimetry (DSC), perfluorophenyl ester, polycondensation, UV, NMR, maleimide, azide, alkyl amine, ONE-POT, CHEMISTRY, POLYMERS, FUNCTIONALIZATION, POLYMERIZATION, CONJUGATION, OILS
  • Istanbul Technical University Affiliated: Yes

Abstract

The aliphatic polyurethane with pendant alkyne, perfluorophenyl, and anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracene, alkyne, and perfluorophenyl functional-diols with hexamethylenediisocyanate in the presence of dibutyltindilaurate (DBTL) in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-(anthraceneco-alkyne-co-perfluorophenyl) (M-n,M-GPC=15,400 g/mol, M-w/M-n=1.37, relative to PS standards) was sequentially clicked with benzyl azide, octylamine, and 4-(2-hydroxyethyl) 210-oxa-4-azatricyclo[5.2.1.02,6] dec-8-ene-3,5-dione (adduct alcohol) via copper-catalyzed azide-alkyne cycloaddition, active ester substitution and Diels-Alder reactions, respectively, to finally yield PU(hydroxyl-co-benzyltriazole-co-octylamine). The PUs were characterized using H-1 NMR, GPC, and DSC. (C) 2015 Wiley Periodicals, Inc.