Journal
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 50, Issue 22, Pages 4666-4673Publisher
WILEY
DOI: 10.1002/pola.26278
Keywords
alternating; butyrolactone; copolymerization; polyester; ring-opening polymerization; thiol-en
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Funding
- JSR Corporation
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A series of bicyclic bis(?-butyrolactone)s (BBL) bearing sulfide moiety 2 were readily synthesized from a precursor BBL bearing isopropenyl group 1. This efficient and versatile synthesis of 2 was achieved by a highly reliable radical addition reaction of thiols to the C-C double bond in the isopropenyl group 2 underwent anionic copolymerization with glycidyl phenyl ether in a 1:1 alternating manner to give a series of the corresponding polyester 3, of which side chains inherited the sulfide group from 2. The glass transition temperatures (Tg) of 3 showed clear dependence on the flexibility of the sulfide side chains. The scope of this copolymerization system was further expanded by synthesizing a bifunctional BBL 4 from 1 with using hexanedithiol and performing its copolymerization with bisphenol A diglycidyl ether 5. The copolymerization gave the corresponding networked polymer in high yield. During the copolymerization, the volume expanding nature of the double ring-opening reaction of 4 contributed to the efficient compensation of the intrinsic volume shrinkage of the ring-opening of epoxide to achieve a shrinkage-free curing system. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
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