Journal
POLYMER JOURNAL
Volume 42, Issue 6, Pages 443-449Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/pj.2010.26
Keywords
allyl phenyl ether; Claisen condensation; graft polymerization; novolac; phenolic resin; polycondensation; polymer reaction
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Funding
- NEDO of Japan [04A23030, 09C46622]
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We report the direct synthesis of new functional novolacs having allyl ether (4) or bromoalkyl groups (5 and 6) in the side chain by the addition-condensation of allyl phenyl ether (1), 1-bromo-2-phenoxyethane (2) or 1-bromo-4-phenoxybutane (3) with formaldehyde. The structure of these novolacs was confirmed by Fourier transform infrared, (1)H NMR and (13)C NMR spectra. The number-average molecular weights (M(n)) of the obtained polymers were found to be similar to 1000-3000. In the case of the polymerization of 1 with formaldehyde using hydrated sulfuric acid as a catalyst, Claisen condensation did not occur with the polymerization; therefore, pure allylated novolac (4) without a phenol moiety was obtained. Thus, in this process, phenol formaldehyde condensation proceeded under such conditions that the functional group was not affected. These polymers (4-6) have considerable potential as reactive polymers in the field of materials science. Their applications are as follows: (i) a key reaction of a latent curing system: thermal stimuli-induced Claisen rearrangement of allylated novolac to generate phenolic hydroxyl groups; (ii) vinyl ether-modified novolac (7) prepared by 1-bromoethoxy-group-modified novolac; and (iii) an amphiphilic graft-shaped polymer prepared by bromoalkyl-group-modified novolac-initiated ring-opening polymerization of 2-methyl-2-oxazoline. Polymer Journal (2010) 42, 443-449; doi:10.1038/pj.2010.26; published online 14 April 2010
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