One-pot synthesis and characterization of novel shape-memory poly(ε-Caprolactone) based polyurethane-epoxy co-networks with Diels-Alder couplings

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Abstract

The present work aimed at the preparation and investigation of different epoxypolyurethane (EP-PU) co-networks. The EP-PU co-networks were obtained by applying two different synthetic strategies, in which the coupling element, the Diels-Alder (DA) adduct, was prepared previously or formed "in situ" in the reaction between furan functionalized polyurethane and furfuryl amine-diglycidyl ether bisphenol-A oligomers (FA_DGEBA). For the synthesis of these EP-PU networks, poly(ε-caprolactone)-diol (PCD, Mn = 2 kg/mol) and poly("-caprolactone) (PCL) with different molecular weights (Mn = 10, 25 and 50 kg/mol) and 1,6-hexamethylenediisocyanate (HDI) were used. The EP-PU co-networks were characterized by Attenuated Total Reflectance Fourier-Transform Infrared spectroscopy (AT-FT-IR), differential scanning calorimetry (DSC) and dynamical mechanical analysis (DMA). Scanning electron microscopy (SEM) was applied to assess the morphology of the EP-PU samples. It was demonstrated that the stress-strain curves for the EP-PUs could be interpreted based on the Standard Linear Solid (SLS) model. The DMA traces of some EP-PUs (depending on the composition and the synthetic method) revealed a plateau-like region above the melting temperature (Tm) of PCL confirming the presence of cross-linked structure. This feature predicted shape memory (SM) behavior for these EP-PU samples. Indeed, very good shape fixity and moderate shape recovery were obtained. The shape recovery processes of these EP-PU samples were described using double exponential decay functions.

Original languageEnglish
Article number504
JournalPolymers
Volume10
Issue number5
DOIs
Publication statusPublished - May 6 2018

Fingerprint

Polyurethanes
Shape memory effect
Recovery
Stress-strain curves
Oligomers
Amines
Fourier transform infrared spectroscopy
Melting point
Differential scanning calorimetry
Ethers
Molecular weight
Scanning electron microscopy
Chemical analysis
polycaprolactone
2,2-bis(4-glycidyloxyphenyl)propane
furan

Keywords

  • Co-network
  • Diels-Alder adduct
  • Epoxy resin
  • Modeling
  • Polycaprolactone
  • Polyester polyurethane
  • Shape recovery
  • Stress-strain behavior

ASJC Scopus subject areas

  • Chemistry(all)
  • Polymers and Plastics

Cite this

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title = "One-pot synthesis and characterization of novel shape-memory poly(ε-Caprolactone) based polyurethane-epoxy co-networks with Diels-Alder couplings",
abstract = "The present work aimed at the preparation and investigation of different epoxypolyurethane (EP-PU) co-networks. The EP-PU co-networks were obtained by applying two different synthetic strategies, in which the coupling element, the Diels-Alder (DA) adduct, was prepared previously or formed {"}in situ{"} in the reaction between furan functionalized polyurethane and furfuryl amine-diglycidyl ether bisphenol-A oligomers (FA_DGEBA). For the synthesis of these EP-PU networks, poly(ε-caprolactone)-diol (PCD, Mn = 2 kg/mol) and poly({"}-caprolactone) (PCL) with different molecular weights (Mn = 10, 25 and 50 kg/mol) and 1,6-hexamethylenediisocyanate (HDI) were used. The EP-PU co-networks were characterized by Attenuated Total Reflectance Fourier-Transform Infrared spectroscopy (AT-FT-IR), differential scanning calorimetry (DSC) and dynamical mechanical analysis (DMA). Scanning electron microscopy (SEM) was applied to assess the morphology of the EP-PU samples. It was demonstrated that the stress-strain curves for the EP-PUs could be interpreted based on the Standard Linear Solid (SLS) model. The DMA traces of some EP-PUs (depending on the composition and the synthetic method) revealed a plateau-like region above the melting temperature (Tm) of PCL confirming the presence of cross-linked structure. This feature predicted shape memory (SM) behavior for these EP-PU samples. Indeed, very good shape fixity and moderate shape recovery were obtained. The shape recovery processes of these EP-PU samples were described using double exponential decay functions.",
keywords = "Co-network, Diels-Alder adduct, Epoxy resin, Modeling, Polycaprolactone, Polyester polyurethane, Shape recovery, Stress-strain behavior",
author = "K. Czifr{\'a}k and Csilla Lakatos and J. Karger-Kocsis and L. Dar{\'o}czi and M. Zsuga and S. K{\'e}ki",
year = "2018",
month = "5",
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T1 - One-pot synthesis and characterization of novel shape-memory poly(ε-Caprolactone) based polyurethane-epoxy co-networks with Diels-Alder couplings

AU - Czifrák, K.

AU - Lakatos, Csilla

AU - Karger-Kocsis, J.

AU - Daróczi, L.

AU - Zsuga, M.

AU - Kéki, S.

PY - 2018/5/6

Y1 - 2018/5/6

N2 - The present work aimed at the preparation and investigation of different epoxypolyurethane (EP-PU) co-networks. The EP-PU co-networks were obtained by applying two different synthetic strategies, in which the coupling element, the Diels-Alder (DA) adduct, was prepared previously or formed "in situ" in the reaction between furan functionalized polyurethane and furfuryl amine-diglycidyl ether bisphenol-A oligomers (FA_DGEBA). For the synthesis of these EP-PU networks, poly(ε-caprolactone)-diol (PCD, Mn = 2 kg/mol) and poly("-caprolactone) (PCL) with different molecular weights (Mn = 10, 25 and 50 kg/mol) and 1,6-hexamethylenediisocyanate (HDI) were used. The EP-PU co-networks were characterized by Attenuated Total Reflectance Fourier-Transform Infrared spectroscopy (AT-FT-IR), differential scanning calorimetry (DSC) and dynamical mechanical analysis (DMA). Scanning electron microscopy (SEM) was applied to assess the morphology of the EP-PU samples. It was demonstrated that the stress-strain curves for the EP-PUs could be interpreted based on the Standard Linear Solid (SLS) model. The DMA traces of some EP-PUs (depending on the composition and the synthetic method) revealed a plateau-like region above the melting temperature (Tm) of PCL confirming the presence of cross-linked structure. This feature predicted shape memory (SM) behavior for these EP-PU samples. Indeed, very good shape fixity and moderate shape recovery were obtained. The shape recovery processes of these EP-PU samples were described using double exponential decay functions.

AB - The present work aimed at the preparation and investigation of different epoxypolyurethane (EP-PU) co-networks. The EP-PU co-networks were obtained by applying two different synthetic strategies, in which the coupling element, the Diels-Alder (DA) adduct, was prepared previously or formed "in situ" in the reaction between furan functionalized polyurethane and furfuryl amine-diglycidyl ether bisphenol-A oligomers (FA_DGEBA). For the synthesis of these EP-PU networks, poly(ε-caprolactone)-diol (PCD, Mn = 2 kg/mol) and poly("-caprolactone) (PCL) with different molecular weights (Mn = 10, 25 and 50 kg/mol) and 1,6-hexamethylenediisocyanate (HDI) were used. The EP-PU co-networks were characterized by Attenuated Total Reflectance Fourier-Transform Infrared spectroscopy (AT-FT-IR), differential scanning calorimetry (DSC) and dynamical mechanical analysis (DMA). Scanning electron microscopy (SEM) was applied to assess the morphology of the EP-PU samples. It was demonstrated that the stress-strain curves for the EP-PUs could be interpreted based on the Standard Linear Solid (SLS) model. The DMA traces of some EP-PUs (depending on the composition and the synthetic method) revealed a plateau-like region above the melting temperature (Tm) of PCL confirming the presence of cross-linked structure. This feature predicted shape memory (SM) behavior for these EP-PU samples. Indeed, very good shape fixity and moderate shape recovery were obtained. The shape recovery processes of these EP-PU samples were described using double exponential decay functions.

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KW - Diels-Alder adduct

KW - Epoxy resin

KW - Modeling

KW - Polycaprolactone

KW - Polyester polyurethane

KW - Shape recovery

KW - Stress-strain behavior

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