Functional Poly(ester-alt-sulfide)s
Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization
of Oxiranes and γ‑Thiobutyrolactones
Posted on 2020-06-30 - 16:23
The copolymerization of tert-butyl glycidyl ether
(tBuGE), allyl glycidyl ether (AGE), ethoxyethyl
glycidyl ether (EEGE) and 1,2-epoxybutane (BO) with γ-thiobutyrolactone
was investigated using benzyl alcohol–phosphazene bases as
initiating systems. The prepared copolymers display perfect (poly(ester-alt-sulfide)) alternating structures for all epoxide monomers
as evidenced by 1H, 13C, and 2D NMR and MALDI–TOF
mass spectrometry. A marked influence of the reaction temperature
on the occurrence of transesterification side reactions has been evidenced.
In particular, at elevated temperature, transesterification reactions
led to the formation of alternating macrocycles. The choice of the
phosphazene base (tBuP4, tBuP2, or tBuP1) has a strong
impact on the system reactivity and on the control of the polymerization.
The use of tBuP1 led to very slow polymerization
rates. The polymerization is much faster in the presence of tBuP2 even at low temperature. The use of tBuP4 shows an intermediate polymerization rate
and enabled a good polymerization control at moderate temperatures.
Finally, the synthesis of well-defined polyether-block-poly(ester-alt-sulfide) and the polymerization
of a challenging substituted γ-thiolactone were proven to be
feasible.
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Puchelle, Valentin; Latreyte, Yannick; Girardot, Mélanie; Garnotel, Laura; Levesque, Léa; Coutelier, Olivier; et al. (2020). Functional Poly(ester-alt-sulfide)s
Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization
of Oxiranes and γ‑Thiobutyrolactones. ACS Publications. Collection. https://doi.org/10.1021/acs.macromol.0c00261