Cyclic carbonates as building blocks for non-isocyanate polyurethanes

Soilikki Kotanen; Tom Wirtanen; Riitta Mahlberg; Adina Anghelescu-Hakala; Tapani Harjunalanen; Pia Willberg-Keyrilainen; Timo Laaksonen; Essi Sarlin

doi:10.1002/app.53964

Cyclic carbonates as building blocks for non-isocyanate polyurethanes

Soilikki Kotanen, Tom Wirtanen, Riitta Mahlberg, Adina Anghelescu-Hakala, Tapani Harjunalanen, Pia Willberg-Keyrilainen, Timo Laaksonen, Essi Sarlin

Materials Science and Environmental Engineering

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

6 Citations (Scopus)

19 Downloads (Pure)

Abstract

Three different cyclic carbonates (ethylene, propylene, and butylene carbonate) that can be derived from CO₂ were successfully polymerized with hexamethylenediamine to form non-isocyanate polyurethanes (NIPUs) via self-polycondensation route without the use of harmful di-isocyanates. Three different catalysts were compared for their performance in self-polycondensation. Increasing the side chain length in cyclic carbonate increased the amount of urea side reaction and decreased the solubility of the final product. The increased amount of urea lead to a more thermoset behavior as the melting and decomposition took place simultaneously. Furthermore, the extent of urea side reaction and melting behavior were adjustable with the selection of the catalyst or polymerization parameters. With ethylene and propylene carbonate based precursors, it was possible to obtain promising melting temperatures and lap shear strength for the NIPUs when optimized polymerization parameters and catalyst were used.

Original language	English
Article number	e53964
Journal	Journal of Applied Polymer Science
Volume	140
Issue number	24
DOIs	https://doi.org/10.1002/app.53964
Publication status	Published - 2023
Publication type	A1 Journal article-refereed

Funding

The authors would like to thank Päivi Jokinen from Kiilto Oy for her support with the experiments, Atte Mikkelson from VTT for SEC analysis and Riina Paalijärvi and Antti Pasanen from VTT for TGA analysis. The work was carried out in parallel with the BECCU research project coordinated by the VTT Technical Research Centre of Finland Ltd. with main funding from Business Finland (Funding decision number 3834/31/2019).

Keywords

cyclic carbonate
non-isocyanate polyurethane
self-polycondensation
urea

Publication forum classification

Publication forum level 1

ASJC Scopus subject areas

General Chemistry
Surfaces, Coatings and Films
Polymers and Plastics
Materials Chemistry

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title = "Cyclic carbonates as building blocks for non-isocyanate polyurethanes",

abstract = "Three different cyclic carbonates (ethylene, propylene, and butylene carbonate) that can be derived from CO2 were successfully polymerized with hexamethylenediamine to form non-isocyanate polyurethanes (NIPUs) via self-polycondensation route without the use of harmful di-isocyanates. Three different catalysts were compared for their performance in self-polycondensation. Increasing the side chain length in cyclic carbonate increased the amount of urea side reaction and decreased the solubility of the final product. The increased amount of urea lead to a more thermoset behavior as the melting and decomposition took place simultaneously. Furthermore, the extent of urea side reaction and melting behavior were adjustable with the selection of the catalyst or polymerization parameters. With ethylene and propylene carbonate based precursors, it was possible to obtain promising melting temperatures and lap shear strength for the NIPUs when optimized polymerization parameters and catalyst were used.",

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AU - Kotanen, Soilikki

AU - Wirtanen, Tom

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AU - Harjunalanen, Tapani

AU - Willberg-Keyrilainen, Pia

AU - Laaksonen, Timo

AU - Sarlin, Essi

N1 - Funding Information: The authors would like to thank Päivi Jokinen from Kiilto Oy for her support with the experiments, Atte Mikkelson from VTT for SEC analysis and Riina Paalijärvi and Antti Pasanen from VTT for TGA analysis. The work was carried out in parallel with the BECCU research project coordinated by the VTT Technical Research Centre of Finland Ltd. with main funding from Business Finland (Funding decision number 3834/31/2019). Publisher Copyright: © 2023 Wiley Periodicals LLC.

PY - 2023

Y1 - 2023

N2 - Three different cyclic carbonates (ethylene, propylene, and butylene carbonate) that can be derived from CO2 were successfully polymerized with hexamethylenediamine to form non-isocyanate polyurethanes (NIPUs) via self-polycondensation route without the use of harmful di-isocyanates. Three different catalysts were compared for their performance in self-polycondensation. Increasing the side chain length in cyclic carbonate increased the amount of urea side reaction and decreased the solubility of the final product. The increased amount of urea lead to a more thermoset behavior as the melting and decomposition took place simultaneously. Furthermore, the extent of urea side reaction and melting behavior were adjustable with the selection of the catalyst or polymerization parameters. With ethylene and propylene carbonate based precursors, it was possible to obtain promising melting temperatures and lap shear strength for the NIPUs when optimized polymerization parameters and catalyst were used.

AB - Three different cyclic carbonates (ethylene, propylene, and butylene carbonate) that can be derived from CO2 were successfully polymerized with hexamethylenediamine to form non-isocyanate polyurethanes (NIPUs) via self-polycondensation route without the use of harmful di-isocyanates. Three different catalysts were compared for their performance in self-polycondensation. Increasing the side chain length in cyclic carbonate increased the amount of urea side reaction and decreased the solubility of the final product. The increased amount of urea lead to a more thermoset behavior as the melting and decomposition took place simultaneously. Furthermore, the extent of urea side reaction and melting behavior were adjustable with the selection of the catalyst or polymerization parameters. With ethylene and propylene carbonate based precursors, it was possible to obtain promising melting temperatures and lap shear strength for the NIPUs when optimized polymerization parameters and catalyst were used.

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KW - non-isocyanate polyurethane

KW - self-polycondensation

KW - urea

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SN - 0021-8995

VL - 140

JO - Journal of Applied Polymer Science

JF - Journal of Applied Polymer Science

IS - 24

M1 - e53964

ER -

Cyclic carbonates as building blocks for non-isocyanate polyurethanes

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