WHOLLY AROMATIC CHIRAL POLYAMIDES BEARING PENDANT PHTHALIMIDO AND L-ISOLEUCINE MOITIES  

作　　者：Shadpour Mallakpour Marziyeh Khani 

机构地区：[1]Organic Polymer Chemistry Research Laboratory,Department of Chemistry,Isfahan University of Technology

出　　处：《Chinese Journal of Polymer Science》2010年第6期859-867,共9页高分子科学（英文版）

基　　金：supported by the Research Affairs Division Isfahan University of Technology(IUT),Isfahan;National Elite Foundation(NEF) ;Center of Excellency in Sensors and Green Chemistry Research(IUT)

摘　　要：A potential biodegradable and optically active bulky chiral aromatic amide-imidic diacid monomer,（2S,3S）-5-（3- methyl-2-phthalimidylpentanoylarnino）isophthalic acid（7）,containing a rigid phthalimide and flexible L-isoleucine pendant group was synthesized in three steps.New aromatic polyamides including pendant phthalimido groups and flexible side spacers have been synthesized by direct polycondensation reaction of equimolar amounts of different aromatic diamines with an optically active diacid 7,using N-methyl-2-pyrrolidone（NMP） as a solvent and triphenyl phosphite/CaCl_2/pyridine as a condensing agent.These polyamides were characterized by FTIR,~1H-NMR spectroscopy,specific rotation, thermogravimetric and elemental analysis.The resulting polymers have inherent viscosities in the range of 0.21-0.45 dL/g. Amino acid existence in this backbone results in optically active polymers.Due to introduction of bulky and flexible groups in these polyamides,they show improved solubility in polar aprotic solvents such as NMP and dimethylacetamide and also good thermal stability（10%weight loss temperatures in excess of 330℃,and char yields at 600℃in nitrogen higher than 62%）.A potential biodegradable and optically active bulky chiral aromatic amide-imidic diacid monomer,（2S,3S）-5-（3- methyl-2-phthalimidylpentanoylarnino）isophthalic acid（7）,containing a rigid phthalimide and flexible L-isoleucine pendant group was synthesized in three steps.New aromatic polyamides including pendant phthalimido groups and flexible side spacers have been synthesized by direct polycondensation reaction of equimolar amounts of different aromatic diamines with an optically active diacid 7,using N-methyl-2-pyrrolidone（NMP） as a solvent and triphenyl phosphite/CaCl_2/pyridine as a condensing agent.These polyamides were characterized by FTIR,~1H-NMR spectroscopy,specific rotation, thermogravimetric and elemental analysis.The resulting polymers have inherent viscosities in the range of 0.21-0.45 dL/g. Amino acid existence in this backbone results in optically active polymers.Due to introduction of bulky and flexible groups in these polyamides,they show improved solubility in polar aprotic solvents such as NMP and dimethylacetamide and also good thermal stability（10%weight loss temperatures in excess of 330℃,and char yields at 600℃in nitrogen higher than 62%）.

关 键 词：Polyamides BIODEGRADABLE Thermally stable polymers Thermogravimetric analysis Polycondensation reaction 

分 类 号：O631.3[理学—高分子化学]