Synthesis of Novel Formaldehyde Acetals Bearing Long Chain
Alkyl Groups for Use as Chain Transfer Agent†
Hajime NAGAHARA†, Keisuke YAJIMA and Junzo MASAMOTO*
Department of Polymer Science and Engineering, Kyoto Institute of Technology; Matsugasaki, Sakyo-ku, Kyoto-shi 606-8585 Japan
† Division of Research and Development, Asahi Chemical Industry Co. Ltd.; Yuraku-cho, Chiyoda-ku, Tokyo 100-8440 Japan
We synthesized novel formaldehyde acetals bearing long chain alkyl groups, which could be potential chain transfer agent for the polymerization of trioxane. We formerly reported the synthesis of a new poly(oxymethylene) with a long chain alkyl group using 1-octadecanol as a chain transfer agent. However, using 1-octadecanol, one of the end-groups of the obtained polymer is a thermally stable octadecyloxy group, and the other is thermally unstable hydroxy group, respectively. The polymer with thermally stable both end groups is desired. For this purpose, we synthesized formaldehyde methyl octadecyl acetal, formaldehyde bisoctadecyl acetal, starting from 1-octadecanol and formaldehyde dimethyl acetal as raw material using a cationic ion exchange resin as catalyst by acetal exchange reaction. Synthesized materials are confirmed with 1H-NMR, mass spectra and elemental analysis. We also synthesized formaldehyde acetal with a longer chain alkyl group starting from an alcohol of carbon number of 38.
† Synthesis of End-Group Modified Poly(oxymethylene) by Chain Transfer Reaction. Part 2.
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