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Synthesis of Substituted Phenyl Esters of Amino Acids and Polycondensation in Langmuirblodgett Films
Authors:Kenji Hanabusa  Takekazu Oumi  Toshiki Koyama  Hirofusa Shirai  Tadao Hayakawa  Akio Kurose
Affiliation:1. Department of Functional , Polymer Science Shinshu University Ueda , 386, Japan;2. Institute of High Polymer Research Shinshu University Ueda , 386, Japan;3. Konan Women's Junior College , Konan, 483, Japan
Abstract:Long-alkyl-chain phenyl esters of β-alanine, glycine, and L-valine were prepared, and their monolayer properties were correlated with their molecular structures. These compounds formed stable monolayers on acidic subphases. In particular, the p-hexadecylphenyl esters of β-alanine and glycine were remarkably stable, and their monolayers could be deposited on calcium fluoride plates as Y-type film by Blodgett's technique. The polycondensation of multilayers under an atmosphere saturated with triethylamine was investigated by changes in the IR spectra. It was determined that the polycondensation proceeded by a first-order reaction mechanism in the initial stage and that the rate in multilayers was faster than that in the bulk crystalline powder. These results suggest that the polycondensation is accelerated by a regular arrangement of the monomer in the multilayers, where the active sites are concentrated and located better for the polycondensation. In the case of the polycondensation in multilayers of the glycine ester, two kinds of condensation proceeded to afford poly(glycine) and 2,5-piperazinedione.
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