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Bis-spirocyclic diol monomers and polyurethanes derived from citric acid: synthesis, properties, electrospinnability, and evaluation of chemical recyclability

Liblikas, Ilme ; Bonjour, Olivier LU ; Savest, Natalja ; Krumme, Andres ; Jannasch, Patric LU orcid and Vares, Lauri (2025) In Chemical Engineering Journal 515.
Abstract
A series of rigid spiro-acetal-containing diol monomers derived from citric acid were synthesized and reacted with five different diisocyanates to form partially biobased thermoplastic polyurethanes (PUs) with different chemical and physical properties. The PUs had a renewable carbon content between 48 and 71%, and all formed transparent and colorless films with glass-transition temperatures between 48 and 145 °C, and thermal stability at least up to 254 °C. Copolymers with polytetrahydrofuran were also prepared to further expand the range of properties. The PUs showed good electrospinnability, and electrospun fiber mats exhibited a maximum stress of 11.5 MPa and a strain of ca. 47%. Hydrolytic degradation studies indicated that the... (More)
A series of rigid spiro-acetal-containing diol monomers derived from citric acid were synthesized and reacted with five different diisocyanates to form partially biobased thermoplastic polyurethanes (PUs) with different chemical and physical properties. The PUs had a renewable carbon content between 48 and 71%, and all formed transparent and colorless films with glass-transition temperatures between 48 and 145 °C, and thermal stability at least up to 254 °C. Copolymers with polytetrahydrofuran were also prepared to further expand the range of properties. The PUs showed good electrospinnability, and electrospun fiber mats exhibited a maximum stress of 11.5 MPa and a strain of ca. 47%. Hydrolytic degradation studies indicated that the acetal-functional groups in PUs were selectively and efficiently hydrolyzed in acidic aqueous acetone or DMSO, as well as under mechanochemical treatment. This indicated possible chemical recycling pathways of this new family of versatile polymer materials. (Less)
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemical Engineering Journal
volume
515
article number
163525
pages
12 pages
publisher
Elsevier
external identifiers
  • scopus:105004659774
ISSN
1385-8947
DOI
10.1016/j.cej.2025.163525
language
English
LU publication?
yes
id
4ea8eeb1-3d40-494d-9fec-6f91c0bce6b8
date added to LUP
2025-04-01 15:58:09
date last changed
2025-07-04 04:01:15
@article{4ea8eeb1-3d40-494d-9fec-6f91c0bce6b8,
  abstract     = {{A series of rigid spiro-acetal-containing diol monomers derived from citric acid were synthesized and reacted with five different diisocyanates to form partially biobased thermoplastic polyurethanes (PUs) with different chemical and physical properties. The PUs had a renewable carbon content between 48 and 71%, and all formed transparent and colorless films with glass-transition temperatures between 48 and 145 °C, and thermal stability at least up to 254 °C. Copolymers with polytetrahydrofuran were also prepared to further expand the range of properties. The PUs showed good electrospinnability, and electrospun fiber mats exhibited a maximum stress of 11.5 MPa and a strain of ca. 47%. Hydrolytic degradation studies indicated that the acetal-functional groups in PUs were selectively and efficiently hydrolyzed in acidic aqueous acetone or DMSO, as well as under mechanochemical treatment. This indicated possible chemical recycling pathways of this new family of versatile polymer materials.}},
  author       = {{Liblikas, Ilme and Bonjour, Olivier and Savest, Natalja and Krumme, Andres and Jannasch, Patric and Vares, Lauri}},
  issn         = {{1385-8947}},
  language     = {{eng}},
  publisher    = {{Elsevier}},
  series       = {{Chemical Engineering Journal}},
  title        = {{Bis-spirocyclic diol monomers and polyurethanes derived from citric acid: synthesis, properties, electrospinnability, and evaluation of chemical recyclability}},
  url          = {{http://dx.doi.org/10.1016/j.cej.2025.163525}},
  doi          = {{10.1016/j.cej.2025.163525}},
  volume       = {{515}},
  year         = {{2025}},
}