Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s

Cristina Maquilón; Arianna Brandolese; Christian Alter; Claas H. Hövelmann; Francesco Della Monica; Arjan W. Kleij

doi:10.1002/cssc.202201123

Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s

Cristina Maquilón, Arianna Brandolese, Christian Alter, Claas H. Hövelmann, Francesco Della Monica^*, Arjan W. Kleij^*

^*Corresponding author for this work

Chemistry

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

4 Citations (Scopus)

67 Downloads (Pure)

Abstract

Conversion of β-elemene into new β-elemene dicarbonates through epoxidation and halide salt-catalyzed CO₂ cycloaddition reactions is reported. Step-growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)s with 1.3≤M_n≤6.3 kDa and 1.3≤Ð≤2.1, and with glass transition temperatures ranging from −59 to 84 °C. The preparation of one selected polyhydroxyurethane material, obtained in the presence of Jeffamine® D-2010 was scaled-up to 43 g. The latter, when combined in a formulation using Irgacure® 2100 and Laromer® LR 9000 allowed the preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanes towards the preparation of commercially relevant materials.

Original language	English
Article number	e202201123
Number of pages	8
Journal	ChemSusChem
Volume	15
Issue number	17
Early online date	27 Jun 2022
DOIs	https://doi.org/10.1002/cssc.202201123
Publication status	Published - 7 Sept 2022

Bibliographical note

Funding Information:
We thank the Cerca program/Generalitat de Catalunya, ICREA and MINECO (PID2020-112684GB-100) for support. We also thank the Ministerio de Ciencia e Innovación for funding through Severo Ochoa Excellence Accreditation 2020–2023 (CEX2019-000925-S, MIC/AEI). F.D.M. kindly acknowledges the European Community for a postdoctoral fellowship through the European Union's Horizon 2020 research and innovation program under Marie Skłodowska-Curie Grant Agreement No. 840557. A.B. thanks the ERDF (European Regional Development Fund) for financial support through the POCTEFA Interreg program (EFA308/19 TRIPyr). We also thank Isobionics for a kind donation of beta-elemene. Open Access funding provided by Università degli Studi dell'Insubria within the CRUI-CARE Agreement.

Publisher Copyright:
© 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH.

Keywords

amine reagents
beta-elemene
carbon dioxide
cyclic carbonates
polyurethanes

ASJC Scopus subject areas

Environmental Chemistry
General Chemical Engineering
General Materials Science
General Energy

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1002/cssc.202201123Licence: Creative Commons: Attribution (CC BY)

MaquilónC2022RenewableFinal published version, 2.67 MBLicence: Creative Commons: Attribution (CC BY)

Cite this

@article{09a8d9725cb1458f8d3f5895b9597a99,

title = "Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s",

abstract = "Conversion of β-elemene into new β-elemene dicarbonates through epoxidation and halide salt-catalyzed CO2 cycloaddition reactions is reported. Step-growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)s with 1.3≤Mn≤6.3 kDa and 1.3≤{\DH}≤2.1, and with glass transition temperatures ranging from −59 to 84 °C. The preparation of one selected polyhydroxyurethane material, obtained in the presence of Jeffamine{\textregistered} D-2010 was scaled-up to 43 g. The latter, when combined in a formulation using Irgacure{\textregistered} 2100 and Laromer{\textregistered} LR 9000 allowed the preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanes towards the preparation of commercially relevant materials.",

keywords = "amine reagents, beta-elemene, carbon dioxide, cyclic carbonates, polyurethanes",

author = "Cristina Maquil{\'o}n and Arianna Brandolese and Christian Alter and H{\"o}velmann, {Claas H.} and {Della Monica}, Francesco and Kleij, {Arjan W.}",

note = "Funding Information: We thank the Cerca program/Generalitat de Catalunya, ICREA and MINECO (PID2020-112684GB-100) for support. We also thank the Ministerio de Ciencia e Innovaci{\'o}n for funding through Severo Ochoa Excellence Accreditation 2020–2023 (CEX2019-000925-S, MIC/AEI). F.D.M. kindly acknowledges the European Community for a postdoctoral fellowship through the European Union's Horizon 2020 research and innovation program under Marie Sk{\l}odowska-Curie Grant Agreement No. 840557. A.B. thanks the ERDF (European Regional Development Fund) for financial support through the POCTEFA Interreg program (EFA308/19 TRIPyr). We also thank Isobionics for a kind donation of beta-elemene. Open Access funding provided by Universit{\`a} degli Studi dell'Insubria within the CRUI-CARE Agreement. Publisher Copyright: {\textcopyright} 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH.",

year = "2022",

month = sep,

day = "7",

doi = "10.1002/cssc.202201123",

language = "English",

volume = "15",

journal = "ChemSusChem",

issn = "1864-5631",

publisher = "Wiley-VCH Verlag",

number = "17",

}

TY - JOUR

T1 - Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s

AU - Maquilón, Cristina

AU - Brandolese, Arianna

AU - Alter, Christian

AU - Hövelmann, Claas H.

AU - Della Monica, Francesco

AU - Kleij, Arjan W.

N1 - Funding Information: We thank the Cerca program/Generalitat de Catalunya, ICREA and MINECO (PID2020-112684GB-100) for support. We also thank the Ministerio de Ciencia e Innovación for funding through Severo Ochoa Excellence Accreditation 2020–2023 (CEX2019-000925-S, MIC/AEI). F.D.M. kindly acknowledges the European Community for a postdoctoral fellowship through the European Union's Horizon 2020 research and innovation program under Marie Skłodowska-Curie Grant Agreement No. 840557. A.B. thanks the ERDF (European Regional Development Fund) for financial support through the POCTEFA Interreg program (EFA308/19 TRIPyr). We also thank Isobionics for a kind donation of beta-elemene. Open Access funding provided by Università degli Studi dell'Insubria within the CRUI-CARE Agreement. Publisher Copyright: © 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH.

PY - 2022/9/7

Y1 - 2022/9/7

N2 - Conversion of β-elemene into new β-elemene dicarbonates through epoxidation and halide salt-catalyzed CO2 cycloaddition reactions is reported. Step-growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)s with 1.3≤Mn≤6.3 kDa and 1.3≤Ð≤2.1, and with glass transition temperatures ranging from −59 to 84 °C. The preparation of one selected polyhydroxyurethane material, obtained in the presence of Jeffamine® D-2010 was scaled-up to 43 g. The latter, when combined in a formulation using Irgacure® 2100 and Laromer® LR 9000 allowed the preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanes towards the preparation of commercially relevant materials.

AB - Conversion of β-elemene into new β-elemene dicarbonates through epoxidation and halide salt-catalyzed CO2 cycloaddition reactions is reported. Step-growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)s with 1.3≤Mn≤6.3 kDa and 1.3≤Ð≤2.1, and with glass transition temperatures ranging from −59 to 84 °C. The preparation of one selected polyhydroxyurethane material, obtained in the presence of Jeffamine® D-2010 was scaled-up to 43 g. The latter, when combined in a formulation using Irgacure® 2100 and Laromer® LR 9000 allowed the preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanes towards the preparation of commercially relevant materials.

KW - amine reagents

KW - beta-elemene

KW - carbon dioxide

KW - cyclic carbonates

KW - polyurethanes

UR - http://www.scopus.com/inward/record.url?scp=85134645005&partnerID=8YFLogxK

U2 - 10.1002/cssc.202201123

DO - 10.1002/cssc.202201123

M3 - Article

C2 - 35757910

AN - SCOPUS:85134645005

SN - 1864-5631

VL - 15

JO - ChemSusChem

JF - ChemSusChem

IS - 17

M1 - e202201123

ER -

Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Fingerprint

Cite this