Journal
MACROMOLECULAR RAPID COMMUNICATIONS
Volume 32, Issue 17, Pages 1319-1323Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.201100246
Keywords
furan-maleimide Diels-Alder polymers; renewable resources; thermoreversible polymerization; thiol-ene click chemistry; vegetable oil derivatives
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Funding
- Portuguese Foundation for Science and Technology (FCT) [SFRH/BD/44884/2008]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/44884/2008] Funding Source: FCT
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This investigation describes preliminary results related to the preparation of monomers based on vegetable oil derivatives bearing furan heterocycles appended through thiol-ene click chemistry, and their subsequent polymerization via the Diels-Alder (DA) polycondensation between furan and maleimide complementary moieties, i.e. a second type of click chemistry. Following the optimization of these interactions with model compounds, two basic approaches were considered for these DA polymerizations, namely (i) the use of monomers with two terminal furan rings in conjunction with bismaleimides (AA+BB systems) and (ii) the use of AB monomers incorporating both furan and maleimide end-groups. This ongoing study clearly showed that both approaches were successful, albeit with different outcomes, in terms of the nature of the products. The application of the retro-DA reaction confirmed their thermoreversible character, i.e. the clean-cut return to their respective starting monomers.
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