Synthesis of Novel Chiral Poly(methacrylate)s Having Urea Moieties and (S)-Methylbenzyl or L-Phenylalanine Methyl Ester Groups and Their Chiral Recognition Abilities.

• Lee Yong-Kyung

  Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

• Hisamitsu Nobuo

  Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

• Onimura Kenjiro

  Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

• Tsutsumi Hiromori

  Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

• Oishi Tsutomu

  Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

抄録

New chiral methacrylates, (S)-methylbenzyl methacryloyloxyethyl urea (MBMOU) and (S)-methoxycarbonylbenzylmethyl methacryloyloxyethyl urea (MCMOU) were synthesized from 2-(methacryloyloxy)ethyl isocyanate (MOI) and (S)-methylbenzylamine and l-phenylalanine methyl ester, respectively. Radical polymerizations of MBMOU and MCMOU were performed under several conditions to obtain the corresponding polymers whose specific optical rotations ([α]²⁵₄₃₅) were -13.5^° to -10.9^° and 30.8^° to 31.5^°, respectively. From the results of radical copolymerizations of RMOU (MBMOU and MCMOU, M₁) with styrene (ST, M₂) or butyl methacrylate (BMA, M₂), monomer reactivity ratios (r1, r2) and Alfrey–Price Q-e were determined. The chiroptical properties of poly(MBMOU-co-M₂)s were strongly influenced by co-units. Poly(RMOU)-bonded-silica gel as chiral stationary phase (CSP) was prepared for high performance liquid chromatography (HPLC). The CSPs resolved some racemates such as ketoprofen and ethyl mandelate. The enantiorecognition ability may be based on higher-ordered structures of the polymer.

収録刊行物

• Polymer Journal

  Polymer Journal 34 (1), 9-17, 2002

  The Society of Polymer Science, Japan

キーワード

• 2-(Methacryloyloxy)ethyl isocyanate
• Radical Polymerization
• Monomer Reactivity Ratios
• Chiral Stationary Phase
• Optical Resolution

詳細情報

• CRID: 1390282681266697344
• NII論文ID: 10012292240
• NII書誌ID: AA00777013
• DOI: 10.1295/polymj.34.9
• COI: 1:CAS:528:DC%2BD38XptFSlsg%3D%3D
• ISSN: 13490540
• ISSN: 00323896
• NDL書誌ID: 6048586
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6048586
• 本文言語コード: en
• データソース種別:
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