Shape memory crosslinked polyurethanes containing thermoreversible Diels-Alder couplings

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10 Citations (Scopus)

Abstract

Crosslinked polyurethanes (PUs) containing irreversible (allophanate) and reversible Diels-Alder chemical bonds were synthesized using various diisocyanates (methylene diphenyl diisocyanate MDI, 1,6-hexamethylenediisocyanate HDI) and poly(ɛ-caprolactone) ((PCL) with different molecular weights (Mn = 10 kg/mol, 25 kg/mol, 50 kg/mol) as diol component. The melting/crystallization of PCL and the reversible DA bonds acted as temperature-activated switches for shape memory performances, while allophanate network provided the permanent crosslinks for these PUs. The reversible DA bonds were obtained by the reaction of diisocyanate-ended prepolymers with furfurylamine (FA) followed by the addition of bismaleimide (BMI). The permanent crosslinks between the linear chains containing DA bonds were achieved using additional amounts of diisocyanates (MDI or HDI). The above reaction path was supported by infrared spectroscopic results and swelling experiments. Tensile mechanical and shape memory properties in tension of the PUs were determined and discussed as a function of composition and crosslink densities deduced from swelling and dynamic mechanical analysis.

Original languageEnglish
Article number44145
JournalJournal of Applied Polymer Science
Volume133
Issue number43
DOIs
Publication statusPublished - Nov 15 2016

Fingerprint

Polyurethanes
Shape memory effect
Swelling
Chemical bonds
Dynamic mechanical analysis
Crystallization
Melting
Molecular weight
Switches
Infrared radiation
Chemical analysis
Experiments
Temperature
allophanic acid

Keywords

  • copolymers
  • crosslinking
  • morphology
  • polyurethanes
  • structure-property relations

ASJC Scopus subject areas

  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Polymers and Plastics
  • Materials Chemistry

Cite this

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abstract = "Crosslinked polyurethanes (PUs) containing irreversible (allophanate) and reversible Diels-Alder chemical bonds were synthesized using various diisocyanates (methylene diphenyl diisocyanate MDI, 1,6-hexamethylenediisocyanate HDI) and poly(ɛ-caprolactone) ((PCL) with different molecular weights (Mn = 10 kg/mol, 25 kg/mol, 50 kg/mol) as diol component. The melting/crystallization of PCL and the reversible DA bonds acted as temperature-activated switches for shape memory performances, while allophanate network provided the permanent crosslinks for these PUs. The reversible DA bonds were obtained by the reaction of diisocyanate-ended prepolymers with furfurylamine (FA) followed by the addition of bismaleimide (BMI). The permanent crosslinks between the linear chains containing DA bonds were achieved using additional amounts of diisocyanates (MDI or HDI). The above reaction path was supported by infrared spectroscopic results and swelling experiments. Tensile mechanical and shape memory properties in tension of the PUs were determined and discussed as a function of composition and crosslink densities deduced from swelling and dynamic mechanical analysis.",
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AU - Lakatos, Csilla

AU - Czifrák, K.

AU - Karger-Kocsis, J.

AU - Daróczi, L.

AU - Zsuga, M.

AU - Kéki, S.

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N2 - Crosslinked polyurethanes (PUs) containing irreversible (allophanate) and reversible Diels-Alder chemical bonds were synthesized using various diisocyanates (methylene diphenyl diisocyanate MDI, 1,6-hexamethylenediisocyanate HDI) and poly(ɛ-caprolactone) ((PCL) with different molecular weights (Mn = 10 kg/mol, 25 kg/mol, 50 kg/mol) as diol component. The melting/crystallization of PCL and the reversible DA bonds acted as temperature-activated switches for shape memory performances, while allophanate network provided the permanent crosslinks for these PUs. The reversible DA bonds were obtained by the reaction of diisocyanate-ended prepolymers with furfurylamine (FA) followed by the addition of bismaleimide (BMI). The permanent crosslinks between the linear chains containing DA bonds were achieved using additional amounts of diisocyanates (MDI or HDI). The above reaction path was supported by infrared spectroscopic results and swelling experiments. Tensile mechanical and shape memory properties in tension of the PUs were determined and discussed as a function of composition and crosslink densities deduced from swelling and dynamic mechanical analysis.

AB - Crosslinked polyurethanes (PUs) containing irreversible (allophanate) and reversible Diels-Alder chemical bonds were synthesized using various diisocyanates (methylene diphenyl diisocyanate MDI, 1,6-hexamethylenediisocyanate HDI) and poly(ɛ-caprolactone) ((PCL) with different molecular weights (Mn = 10 kg/mol, 25 kg/mol, 50 kg/mol) as diol component. The melting/crystallization of PCL and the reversible DA bonds acted as temperature-activated switches for shape memory performances, while allophanate network provided the permanent crosslinks for these PUs. The reversible DA bonds were obtained by the reaction of diisocyanate-ended prepolymers with furfurylamine (FA) followed by the addition of bismaleimide (BMI). The permanent crosslinks between the linear chains containing DA bonds were achieved using additional amounts of diisocyanates (MDI or HDI). The above reaction path was supported by infrared spectroscopic results and swelling experiments. Tensile mechanical and shape memory properties in tension of the PUs were determined and discussed as a function of composition and crosslink densities deduced from swelling and dynamic mechanical analysis.

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KW - structure-property relations

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