Rapid Hyperbranched Polythioether Synthesis Through Thiol-Michael Addition Reaction

Ozgun Daglar; Begum Gungor; Gulce Guric; Ufuk Saim Gunay; Gurkan Hizal; Umit Tunca; Hakan Durmaz

doi:10.1002/pol.20190279

Rapid Hyperbranched Polythioether Synthesis Through Thiol-Michael Addition Reaction

Ozgun Daglar, Begum Gungor, Gulce Guric, Ufuk Saim Gunay, Gurkan Hizal, Umit Tunca^*, Hakan Durmaz^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

In this study, two types of hyperbranched (HB) polythioether could readily be achieved in a short time at ambient temperature through a thiol-Michael addition reaction. Dimethyl acetylenedicarboxylate (DMADC) or methyl propiolate (A₂) and trimethylolpropane tris(3-mercaptopropionate) (B₃) monomers were reacted using an organobase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst in chloroform at room temperature to provide subsequent HB polythioethers. The effect of TBD concentration on the polymerization was studied for the DMDAC case monitoring the molecular weight evolution against time. HB polythioethers were characterized using spectroscopic (nuclear magnetic resonance) and chromatographic (gel permeation chromatography with refractive index and light-scattering detectors) techniques.

Original language	English
Pages (from-to)	824-830
Number of pages	7
Journal	Journal of Polymer Science
Volume	58
Issue number	6
DOIs	https://doi.org/10.1002/pol.20190279
Publication status	Published - 15 Mar 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley Periodicals, Inc.

Funding

This work was supported by the Research Fund of Istanbul Technical University (Project Number: TGA‐2019‐42295).

Funders	Funder number
Istanbul Teknik Üniversitesi	TGA‐2019‐42295

Keywords

hyperbranched
hyperbranched polymer
organocatalyst
polysulfides
polythioether
step-growth polymerization
thiol-Michael

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abstract = "In this study, two types of hyperbranched (HB) polythioether could readily be achieved in a short time at ambient temperature through a thiol-Michael addition reaction. Dimethyl acetylenedicarboxylate (DMADC) or methyl propiolate (A2) and trimethylolpropane tris(3-mercaptopropionate) (B3) monomers were reacted using an organobase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst in chloroform at room temperature to provide subsequent HB polythioethers. The effect of TBD concentration on the polymerization was studied for the DMDAC case monitoring the molecular weight evolution against time. HB polythioethers were characterized using spectroscopic (nuclear magnetic resonance) and chromatographic (gel permeation chromatography with refractive index and light-scattering detectors) techniques.",

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AU - Daglar, Ozgun

AU - Gungor, Begum

AU - Guric, Gulce

AU - Gunay, Ufuk Saim

AU - Hizal, Gurkan

AU - Tunca, Umit

AU - Durmaz, Hakan

PY - 2020/3/15

Y1 - 2020/3/15

N2 - In this study, two types of hyperbranched (HB) polythioether could readily be achieved in a short time at ambient temperature through a thiol-Michael addition reaction. Dimethyl acetylenedicarboxylate (DMADC) or methyl propiolate (A2) and trimethylolpropane tris(3-mercaptopropionate) (B3) monomers were reacted using an organobase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst in chloroform at room temperature to provide subsequent HB polythioethers. The effect of TBD concentration on the polymerization was studied for the DMDAC case monitoring the molecular weight evolution against time. HB polythioethers were characterized using spectroscopic (nuclear magnetic resonance) and chromatographic (gel permeation chromatography with refractive index and light-scattering detectors) techniques.

AB - In this study, two types of hyperbranched (HB) polythioether could readily be achieved in a short time at ambient temperature through a thiol-Michael addition reaction. Dimethyl acetylenedicarboxylate (DMADC) or methyl propiolate (A2) and trimethylolpropane tris(3-mercaptopropionate) (B3) monomers were reacted using an organobase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst in chloroform at room temperature to provide subsequent HB polythioethers. The effect of TBD concentration on the polymerization was studied for the DMDAC case monitoring the molecular weight evolution against time. HB polythioethers were characterized using spectroscopic (nuclear magnetic resonance) and chromatographic (gel permeation chromatography with refractive index and light-scattering detectors) techniques.

KW - hyperbranched

KW - hyperbranched polymer

KW - organocatalyst

KW - polysulfides

KW - polythioether

KW - step-growth polymerization

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IS - 6

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Rapid Hyperbranched Polythioether Synthesis Through Thiol-Michael Addition Reaction

Abstract

Bibliographical note

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Keywords

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