Synthesis of bicyclic bis(γ‐butyrolactone) derivatives bearing sulfide moieties and their alternating copolymers with epoxide |
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Authors: | Sousuke Ohsawa Kazuhide Morino Atsushi Sudo Takeshi Endo |
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Institution: | Molecular Engineering Institute, Kinki University, 11‐6 Kayanomori, Iizuka, Fukuoka, 820‐8555, Japan |
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Abstract: | A series of bicyclic bis(γ‐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. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 |
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Keywords: | alternating butyrolactone copolymerization polyester ring‐opening polymerization thiol‐en |
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