Synthesis of methylene butyrolactone polymers from itaconic acid

ABSTRACT Herein, we report the transformation of β‐monomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high‐value monomer α‐methylene‐γ,γ‐dimethyl‐γ‐butyrolactone (Me2MBL) through a selective addition strategy. This strategy is also applied to the synthe...

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Published in:Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2017-09, Vol.55 (17), p.2730-2737
Main Authors: Trotta, Jacob T., Jin, Mengyuan, Stawiasz, Katherine J., Michaudel, Quentin, Chen, Wei‐Liang, Fors, Brett P.
Format: Article
Language:English
Subjects:
Addition polymerization
biorenewable
Butyrolactone
Chains (polymeric)
Chemical synthesis
controlled radical polymerization
Fragmentation
Glass transition temperature
Itaconic acid
Materials selection
Methylene
Physical properties
Polymerization
radical polymerization
Refractivity
renewable resources
reversible addition‐fragmentation chain‐transfer (RAFT)
Temperature
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Summary:ABSTRACT Herein, we report the transformation of β‐monomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high‐value monomer α‐methylene‐γ,γ‐dimethyl‐γ‐butyrolactone (Me2MBL) through a selective addition strategy. This strategy is also applied to the synthesis of α‐methylene‐γ‐butyrolactone (MBL, tulipalin A), a monomer that can be polymerized to give materials with desirable properties (high decomposition temperature, glass transition temperature, and refractive index). Subsequent polymerization of both Me2MBL and MBL through reversible addition‐fragmentation chain‐transfer polymerization generates well‐defined poly(Me2MBL) and poly(MBL) (PMBL). Physical characterization of poly(Me2MBL) shows good physical properties comparable with known PMBL materials. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2730–2737 A selective addition strategy is used to convert β‐monomethyl itaconate (β‐MMI), a cheap and biorenewable alternative to petroleum feedstocks, to the high value monomers α‐methylene‐γ,γ‐dimethyl‐γ‐butyrolactone (Me2MBL) and α‐methylene‐γ‐butyrolactone (MBL, Tulipalin A). Poly(Me2MBL) and poly(MBL) were synthesized with reversible addition‐fragmentation chain‐transfer (RAFT) polymerization to give materials with desirable properties (high Td, Tg, and refractive index).
ISSN:0887-624X
1099-0518
DOI:10.1002/pola.28654