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Soluble novel optically active poly(amide–imide)s derived from N,N ′‐(4,4′‐oxydiphthaloyl)‐bis‐ L ‐leucine diacid chloride and various aromatic diamines: Synthesis and characterization
Author(s) -
Mallakpour Shadpour,
Kowsari Elaheh
Publication year - 2005
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.21462
Subject(s) - condensation polymer , imide , inherent viscosity , thionyl chloride , specific rotation , polyamide , polymer chemistry , chloride , chemistry , amide , acetic anhydride , monomer , yield (engineering) , intrinsic viscosity , polymer , materials science , organic chemistry , catalysis , metallurgy
4,4′‐Oxydiphthalic anhydride ( 1 ) was reacted with L ‐leucine ( 2 ) in acetic acid, and the resulting imide‐acid ( 3 ) was obtained in high yield. The diacid chloride ( 4 ) was obtained from diacid derivative ( 3 ) by reaction with thionyl chloride. The polycondensation reaction of diacid chloride ( 4 ) with several aromatic diamines, such as 4,4′‐sulfonyldianiline ( 5a ), 4,4′‐diaminodiphenyl methane ( 5b ), 4,4′‐diaminodiphenylether ( 5c ), p ‐phenylenediamine ( 5d ), m‐phenylenediamine ( 5e ), and 4,4′‐diaminobiphenyl ( 5f ), was performed by two conventional methods: low temperature solution polycondensation and short period reflux conditions. To compare conventional solution polycondensation reaction methods with microwave‐assisted polycondensation, the reactions were also carried out under microwave conditions in the presence of a small amount of o ‐cresol that acts as a primary microwave absorber. The reaction mixture was irradiated for 6 min with 100% of radiation power. Several new optically active poly(amide–imide)s with inherent viscosity ranging from 0.25–0.52 dL/g were obtained with high yield. All of the above polymers were fully characterized by IR, elemental analyses, and specific rotation techniques. Some structural characterizations and physical properties of these new optically active poly(amide–imide)s are reported. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 96: 435–442, 2005