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

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New chiral methacrylates, (<I>S</I>)-methylbenzyl methacryloyloxyethyl urea (MBMOU) and (<I>S</I>)-methoxycarbonylbenzylmethyl methacryloyloxyethyl urea (MCMOU) were synthesized from 2-(methacryloyloxy)ethyl isocyanate (MOI) and (<I>S</I>)-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]<FONT SIZE="-1"><SUP>25</SUP></FONT><FONT SIZE="-1"><SUB>435</SUB></FONT>) were -13.5<FONT SIZE="-1"><SUP>°</SUP></FONT> to -10.9<FONT SIZE="-1"><SUP>°</SUP></FONT> and 30.8<FONT SIZE="-1"><SUP>°</SUP></FONT> to 31.5<FONT SIZE="-1"><SUP>°</SUP></FONT>, respectively. From the results of radical copolymerizations of RMOU (MBMOU and MCMOU, M<FONT SIZE="-1"><SUB>1</SUB></FONT>) with styrene (ST, M<FONT SIZE="-1"><SUB>2</SUB></FONT>) or butyl methacrylate (BMA, M<FONT SIZE="-1"><SUB>2</SUB></FONT>), monomer reactivity ratios (<I>r<FONT SIZE="-1"><SUB></I>1</SUB></FONT>, <I>r<FONT SIZE="-1"><SUB></I>2</SUB></FONT>) and Alfrey–Price <I>Q</I>-<I>e</I> were determined. The chiroptical properties of poly(MBMOU-<I>co</I>-M<FONT SIZE="-1"><SUB>2</SUB></FONT>)s were strongly influenced by <I>co</I>-units. Poly(RMOU)-<I>bonded</I>-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, 2002-01-15

    社団法人 高分子学会

参考文献:  28件中 1-28件 を表示

  • <no title>

    MATSUHIRO S.

    Konbatekku 5, 8, 1997

    被引用文献3件

  • <no title>

    KAMOGAWA H.

    J. Polym. Sci., Part A: Polym. Chem. 27, 487, 1989

    被引用文献4件

  • <no title>

    DECKER C.

    Eur. Polym. J. 27, 881, 1991

    被引用文献4件

  • <no title>

    FRANCIS I.

    J. Polym. Sci., Part A: Polym. Chem. 31, 239, 1993

    被引用文献3件

  • <no title>

    ALBRECHT H.

    Angew. Makromol. Chem. 145/146, 89, 1986

    被引用文献3件

  • <no title>

    SAVASKAN S.

    Angew. Makromol. Chem. 239, 13, 1996

    被引用文献3件

  • <no title>

    OISHI T.

    Polym. J. 33, 81, 2001

    被引用文献3件

  • <no title>

    BAMFORD C. H.

    Bull. Soc. Chim. Belg. 99, 919, 1990

    被引用文献3件

  • <no title>

    KIMITSUKA Y.

    JPN. Kokai Tokkyo Koho JP 6-308108, 1994

    被引用文献2件

  • <no title>

    LEE Y. K.

    J. Polym. Sci., Part A: Polym. Chem. 38, 4315, 2000

    被引用文献4件

  • <no title>

    LEE Y. K.

    Polym. J. 32, 1007, 2000

    被引用文献3件

  • <no title>

    LEE Y. K.

    Polym. J. 33, 411, 2001

    被引用文献3件

  • <no title>

    ALLENMARK S. G.

    Chromatographic Enantioseparation, 1988

    被引用文献6件

  • <no title>

    OKAMOTO Y.

    CHEMTECH 176, 1987

    被引用文献3件

  • <no title>

    LIU J. H.

    J. Appl. Polym. Sci. 72, 677, 1999

    被引用文献3件

  • <no title>

    TAMAI Y.

    Bull. Chem. Soc. Jpn. 65, 817, 1992

    被引用文献6件

  • <no title>

    BLASCHKE G.

    Angew. Chem. Int. Ed. Eng. 19, 13, 1980

    被引用文献1件

  • <no title>

    BLASCHKE G.

    Angew. Chem. Int. Ed. Eng. 25, 830, 1986

    被引用文献1件

  • <no title>

    ARLT D.

    Angew. Chem. Int. Ed. Eng. 30, 1662, 1991

    被引用文献1件

  • <no title>

    OTSU T.

    Koubunshigousei Jikkenhou, 69-91, 1972

    被引用文献3件

  • <no title>

    IZUMIYA N.

    Pepuchidogousei no Kiso to Jikken, 50-51, 1985

    被引用文献1件

  • <no title>

    OKAMOTO Y.

    Bull. Chem. Soc. Jpn. 61, 255, 1988

    被引用文献1件

  • <no title>

    TUDOS F.

    J. Macromol. Sci., Chem. A10, 1513, 1976

    被引用文献9件

  • <no title>

    ALFREY T.

    J. Polym. Sci. 2, 101, 1947

    被引用文献5件

  • <no title>

    HARWOOD H. J.

    J. Polym. Sci., Polym. Lett. Ed. 2, 601, 1964

    被引用文献3件

  • <no title>

    KUROKAWA M.

    J. Polym. Sci., Chem. Ed. 17, 2241, 1979

    被引用文献1件

  • <no title>

    MAJUMDAR R. N.

    Makromol. Chem. 183, 2047, 1982

    被引用文献3件

  • <no title>

    MONZNER N.

    Angew. Makromol. Chem. 245, 155, 1997

    被引用文献3件

各種コード

  • NII論文ID(NAID)
    10012292240
  • NII書誌ID(NCID)
    AA00777013
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00323896
  • NDL 記事登録ID
    6048586
  • NDL 雑誌分類
    ZP16(科学技術--化学・化学工業--高分子化学・高分子化学工業)
  • NDL 請求記号
    Z53-R487
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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