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

被引：0
|
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;
D O I：
暂无
中图分类号：
学科分类号：
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.
引用
收藏
页码：2699 / 2708
相关论文
共 50 条
  • [21] Alkaliphilic lysine decarboxylases for effective synthesis of cadaverine from L-lysine
    Seongwook Jeong
    Young Joo Yeon
    Eun-Gyu Choi
    Sungmin Byun
    DaeHaeng Cho
    Il Kwon Kim
    Yong Hwan Kim
    [J]. Korean Journal of Chemical Engineering, 2016, 33 : 1530 - 1533
  • [22] POLYAMIDES FROM DIKETOPIPERAZINES .I. CONDENSATION OF L-LYSINE DIKETOPIPERAZINE WITH ADIPYL CHLORIDE
    CRESCENZI, V
    GIANCOTTI, V
    QUADRIFOLIO, F
    [J]. MAKROMOLEKULARE CHEMIE-MACROMOLECULAR CHEMISTRY AND PHYSICS, 1968, 120 (DEC): : 220 - +
  • [23] Synthesis of novel chiral macrocyclic polyamides derived from L-/D-tartaric acid
    Li, BH
    Yang, XM
    Yang, K
    Fu, EQ
    [J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (19) : 2603 - 2608
  • [24] Synthesis and characterization of random and regular L-lysine-based polyamides
    Gachard, I
    Coutin, B
    Sekiguchi, H
    [J]. MACROMOLECULAR CHEMISTRY AND PHYSICS, 1997, 198 (05) : 1375 - 1389
  • [25] Obtaining the zwitterionic form of L-lysine from L-lysine monohydrochloride by electrodialysis
    Aghajanyan, A. E.
    Tsaturyan, A. O.
    Hambardzumyan, A. A.
    Saghyan, A. S.
    [J]. MEMBRANE AND WATER TREATMENT, 2013, 4 (01): : 1 - 9
  • [26] Production of L-lysine from L-lysine monohydrochloride by bipolar membrane electrodialysis
    Zhang, Yaping
    Chen, Yan
    Yue, Mingzhu
    Wang, Lei
    [J]. DESALINATION AND WATER TREATMENT, 2012, 41 (1-3) : 105 - 113
  • [27] OPTICALLY-ACTIVE POLYAMIDES DERIVED FROM L-TARTARIC ACID
    BOU, JJ
    RODRIGUEZGALAN, A
    MUNOZGUERRA, S
    [J]. MACROMOLECULES, 1993, 26 (21) : 5664 - 5670
  • [28] METHOD OF D,L-LYSINE SYNTHESIS
    SAMOILOVICH, TI
    POLYANSK.AS
    PEREKALI.VV
    [J]. DOKLADY AKADEMII NAUK SSSR, 1974, 217 (06): : 1335 - 1336
  • [29] Enzymatic synthesis and characterization of hydrophobized poly (L-lysine)-amylose conjugates
    Akiyoshi, Kazunari
    Yamazaki, Mio
    Morimoto, Noriyuki
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [30] DERIVATION OF PIPECOLIC ACID FROM L-LYSINE BY FAMILIAL HYPERLYSINEMICS
    WOODY, NC
    PUPENE, MB
    [J]. PEDIATRIC RESEARCH, 1971, 5 (10) : 511 - &
12345