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A simple and efficient way to synthesize optically active polyamides by solution polycondensation of di‐ O ‐methyl‐ L ‐tartaryl chloride with diamines
Author(s) -
Wu Zuolin,
Huang Yanjiong,
Zhang Chunhua,
Zhu Danyang,
Bian Zheng,
Ding Mengxian,
Gao Lianxun,
Yang Zhenghua
Publication year - 2010
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.32264
Subject(s) - condensation polymer , polyamide , polymer chemistry , interfacial polymerization , monomer , thermal stability , terephthalic acid , chemistry , diamine , chloride , gel permeation chromatography , hydrolysis , organic chemistry , polymer , polyester
A series of optically active polyamides containing di‐ O ‐methyl‐ L ‐tartaryl moieties in the main chain were synthesized by polycondensation of di‐ O ‐methyl‐ L ‐tartaryl chloride 5 with diamines and characterized by gel permeation chromatography, UV–vis, circular dichroism (CD), IR, and NMR spectroscopies. The polycondensation reaction could be carried out under mild conditions and the reaction time was short (2–3 h). The key monomer 5 prepared from L ‐tartaric acid via esterification, etherification, hydrolysis, and chlorination was easily purified by vacuum sublimation. These polyamides with number average molecular weights ranging from 14,000 to 35,000, displayed large optical activity in dimethyl sulfoxide solution, and their specific optical rotations oscillated between 87.2° and 210.7° depending on the structures of the diamines. The glass transition temperatures of these polyamides were in the range of 106–191°C, and the 10% mass loss occurred at temperature above 300°C. The polyamides derived from aromatic diamines exhibited higher T g and thermal stability than those derived from aliphatic diamines. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010