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

^*Corresponding author for this work

Kiilto Oy
University of Helsinki
Tampere University

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

16 Citations (Scopus)

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
Number of pages	13
Journal	Journal of Applied Polymer Science
Volume	140
Issue number	24
DOIs	https://doi.org/10.1002/app.53964
Publication status	Published - 20 Jun 2023
MoE 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

Access to Document

10.1002/app.53964

Cite this

@article{c5fa8e97a4f44f3f95bfc9034fba6121,

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.",

keywords = "cyclic carbonate, non-isocyanate polyurethane, self-polycondensation, urea",

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

note = "Funding Information: The authors would like to thank P{\"a}ivi Jokinen from Kiilto Oy for her support with the experiments, Atte Mikkelson from VTT for SEC analysis and Riina Paalij{\"a}rvi 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: {\textcopyright} 2023 Wiley Periodicals LLC.",

year = "2023",

month = jun,

day = "20",

doi = "10.1002/app.53964",

language = "English",

volume = "140",

journal = "Journal of Applied Polymer Science",

issn = "0021-8995",

publisher = "Wiley",

number = "24",

}

TY - JOUR

T1 - Cyclic carbonates as building blocks for non-isocyanate polyurethanes

AU - Kotanen, Soilikki

AU - Wirtanen, Tom

AU - Mahlberg, Riitta

AU - Anghelescu-Hakala, Adina

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 - 2023/6/20

Y1 - 2023/6/20

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.

KW - cyclic carbonate

KW - non-isocyanate polyurethane

KW - self-polycondensation

KW - urea

UR - https://www.scopus.com/pages/publications/85153362263

U2 - 10.1002/app.53964

DO - 10.1002/app.53964

M3 - Article

AN - SCOPUS:85153362263

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

Abstract

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Cite this