Polyesteramides based on PET and nylon 2,T part 1. synthesis of the bisesterdiamide

K. Bouma, J.H.G.M. Lohmeijer, R.J. Gaymans

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Abstract

The synthesis of the bisesterdiamide T2T-dimethyl (one-and-a-half repeating unit of nylon 2,T) (benzoic acid, 4,4′-[1,2–ethanediylbis(iminocarbonyl)] bis-dimethyl ester, CAS no 7060-10-8) has been studied using dimethyl terephthalate (DMT) and 1,2-diaminoethane (DAE) as starting materials. T2T-dimethyl was synthesised in a solvent mixture of toluene/methanol at 65°C employing lithium or sodium methanolate as a catalyst. The progress of reaction was followed as function of time using liquid chomatrography and endgroup titrations. The products were analysed using 1H NMR, 13C NMR and differential scanning calorimeter. A high yield was obtained (90%), and after recrystallisation from NMP, the product was found to be of high purity. The pure T2T-dimethyl obtained had a melting onset of 312°C and a melting enthalpy of 165 J/g. T2T-dimethyl was also synthesised in absence of a catalyst at 100°C and using m-xylene as solvent and at a high concentration of reactants. The yield of this reaction was relatively low (34%). The addition of phenol to the reaction mixture had little effect on the yield and purity of the product.
Original languageUndefined
Pages (from-to)2719-2725
JournalPolymer
Volume41
Issue number8
DOIs
Publication statusPublished - 2000

Keywords

  • METIS-106557
  • IR-71825
  • Bisesterdiamide
  • 1
  • 2-Diaminoethane
  • Dimethyl terephthalate

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