Synthesis and characterization of polyamides obtained from tartaric acid and L-lysine
- 作者：Maj脙脙 ; M. Antonia ; Alla ; Abdelilah ; Bou ; Jordi J. ; Herranz ; Concepci脙脙n ; Mu脙脙oz-Guerra ; Sebasti脙脙n
- 关键词：l-lysine ; Optically active polyamides ; Renewable resources ; Tartaric acid
- 刊名：European Polymer Journal
- 出版年：2004
- 期刊代码：35_00143057
- 类别：ms
- 出版时间：December, 2004
- 卷：40
- 期：12
- 页码：2699-2708
- 文件大小：433 K
摘要
Two sets of AA脗脗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脗脗脗aminoacid and amide脗脗脗diamine monomeric precursors, respectively. These polyamides have intrinsic viscosities in the 0.50脗脗脗0.76dlg脗脗脗1 range, display optical activity, and are readily soluble in chloroform. They start to decompose well above 200脗脗C and display glass-transition temperatures at 100脗脗脗105脗脗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.