Co-Oligomers of Renewable and “Inert”
2‑MeTHF and Propylene Oxide for Use in Bio-Based Adhesives
Posted on 2020-08-27 - 16:37
Commercial
polyether polyols are usually obtained by the ring-opening
polymerization of epoxides or tetrahydrofuran. 2-Methyl-tetrahydrofuran
(2-MeTHF) could be an alternative bio-based building block for the
synthesis of these polyols. Although 2-MeTHF cannot be polymerized,
we did achieve the copolymerization of 2-MeTHF with propylene oxide
(PO) using Lewis and Brønsted acids as catalysts and water or
diols as initiators. The resulting polyether polyols have a molecular
weight range, which allows their use as components for adhesives.
The molar content of 2-MeTHF in the oligomers can be up to 48%. A
1:1 copolymer of 2-MeTHF and PO is produced when stoichiometric amounts
of BF3·OEt2 are used. Here, the monomeric
units in the chains alternate, but also cyclic or other nondiol products
are formed that are detrimental to its further use in adhesives. Linear
dihydroxyl-terminated polyether chains were formed when the heteropolyacid
H3PW12O40·24H2O was
used as a catalyst and a diol as an initiator. The formation of cyclic
products can be drastically reduced when the accumulation of propylene
oxide during the reaction is avoided. 1H NMR experiments
indicate that the step of 2-MeTHF incorporation is the alkylation
of 2-MeTHF by protonated PO. It was shown that the 2-MeTHF/PO copolymer
had increased tensile strength compared to polypropylene glycol in
a two-component adhesive formulation.
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Stadler, Bernhard
M.; Tin, Sergey; Kux, Alexander; Grauke, Reni; Koy, Cornelia; Tiemersma-Wegman, Theodora D.; et al. (2020). Co-Oligomers of Renewable and “Inert”
2‑MeTHF and Propylene Oxide for Use in Bio-Based Adhesives. ACS Publications. Collection. https://doi.org/10.1021/acssuschemeng.0c04450
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AUTHORS (11)
BS
Bernhard
M. Stadler
ST
Sergey Tin
AK
Alexander Kux
RG
Reni Grauke
CK
Cornelia Koy
TT
Theodora D. Tiemersma-Wegman
SH
Sandra Hinze
HB
Horst Beck
MG
Michael O. Glocker
AB
Adrian Brandt
Jd
Johannes G. de Vries