Synthesis and Photo-degradation of Polyphthalaldehydes with Oxime Ether Terminals

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  • Hayashi Hirokazu
    Research Division of Applied Material Chemistry, Izumi Center, Osaka Research Institute of Industrial Science and Technology (ORIST)
  • Tachi Hideki
    Research Division of Polymer Functional Materials, Izumi Center, Osaka Research Institute of Industrial Science and Technology (ORIST)
  • Suyama Kanji
    Faculty of Liberal Arts and Sciences, Osaka Prefecture University

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<p>The degradation and recycling of polymeric materials are growing public interests recently, and the molecular design of degradable polymers is highly important. Herein the syntheses and photochemical behavior of photolabile polyphthalaldehydes (PPAs) with oxime ether terminals are reported. o-Phthalaldehyde (o-PA) was polymerized with 1 or 2-acetonaphthone oxime as initiators in the presence of DBU at low temperature and terminated with acetic anhydride. The incorporation of naphthyl oxime ether units and acetyl terminals was confirmed by NMR, UV, and IR spectral measurements. The repeating units of obtained PPAs were about 100. When PPAs were irradiated with UV light (>310 nm) in CHCl3, peaks due to o-PA appeared. On irradiation of PPA films, peaks appeared around 1775 cm-1 in IR spectra, suggesting the formation of phthalide which could be derived from photo-transformation of o-PA. These spectral changes clearly indicated the proceeding of photo-depolymerization of PPAs. In order to analyze the mechanical property changes of PPA films on irradiation, nanoindentation technique was attempted. It was found that reduced modulus of PPAs decreased on irradiation, which supported the photo-depolymerization as observed in spectral analyses.</p>

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