Synthesis and characterization of polyamides obtained from tartaric acid and L-lysine

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作者
Majó, M. Antonia [1 ]
Alla, Abdelilah [1 ]
Bou, Jordi J. [1 ]
Herranz, Concepción [1 ]
Muñoz-Guerra, Sebastián [1 ]
机构
[1] Dept. d'Enginyeria Química, Univ. Politèc. de Catalunya, ETSEIB, Diagonal 647, 08028 Barcelona, Spain
来源
European Polymer Journal | 2004年 / 40卷 / 12期
关键词
Crystallization - Differential scanning calorimetry - Glass transition - Monomers - Organic acids - Synthesis (chemical) - X ray diffraction analysis;
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摘要
Two sets of AA &middot BB-type polyamides (PLyTA) were synthesized from natural compounds L-lysine and D- or L-tartaric acid via the active ester polycondensation method. The carboxyl and hydroxyl side groups were orthogonally protected as methyl ester and methyl ether, respectively. Direct reaction of methyl L-lysinate dihydrochloride with bis(pentachlorophenyl) di-O-methyl tartaric acid led to the aregic polyamide ar-PLyTA, whereas isoregic (ir-PLyTA) and syndioregic (sr-PLyTA) polyamides were obtained by polycondensation of specifically designed amide-aminoacid and amide-diamine monomeric precursors, respectively. These polyamides have intrinsic viscosities in the 0.50-0.76dl g-1 range, display optical activity, and are readily soluble in chloroform. They start to decompose well above 200°C and display glass-transition temperatures at 100-105°C. DSC and X-ray diffraction results indicated that these polyamides are not crystalline but they seem to adopt a partially ordered phase. No differences in properties other than optical rotation were observed between PLyTA made of D- and L-tartaric acid. © 2004 Elsevier Ltd. All rights reserved.
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页码:2699 / 2708
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