Journal
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 55, Issue 17, Pages 2730-2737Publisher
WILEY
DOI: 10.1002/pola.28654
Keywords
biorenewable; controlled radical polymerization; itaconic acid; radical polymerization; reversible addition-fragmentation chain-transfer (RAFT); renewable resources
Categories
Funding
- NSF through Center for Sustainable Polymers [CHE-1413862]
- NSF MRSEC [DMR-1120296]
- 3M
- NSF [CHE-1531632]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1413862] Funding Source: National Science Foundation
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Herein, we report the transformation of beta-monomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high-value monomer alpha-methylene-gamma,gamma-dimethyl-gamma-butyrolactone (Me2MBL) through a selective addition strategy. This strategy is also applied to the synthesis of alpha-methylene-gamma-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. (C) 2017 Wiley Periodicals, Inc.
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