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Synthesis of New Polyamides from Natural Monomers: L ‐Malic acid and L ‐Lysine
Author(s) -
Pascual Sagrario,
Gachard Isabelle,
Coutin Bernard,
Sekiguchi Hikaru
Publication year - 2001
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20010301)202:6<873::aid-macp873>3.0.co;2-k
Subject(s) - polyamide , malic acid , monomer , lysine , polymer chemistry , chemistry , organic chemistry , polymer , amino acid , biochemistry , citric acid
The synthesis of new polyamides from two natural compounds L ‐malic acid and L ‐lysine was carried out via the active ester polycondensation method (pentafluorophenyl ester). The hydroxyl and carboxylic side groups were orthogonally protected as tert‐ butyl ether and benzyl ester, respectively. High molecular masses (reaching 25 000 g/mol) were obtained at 60°C in tetrahydrofuran for fully protected polyamide. This polymer was soluble in chloroform. Total regeneration of hydroxyl groups was carried out in trifluoroacetic acid. Regeneration of the carboxylic group by hydrogenolysis led to a polyamide, soluble in Tris buffer solution (pH = 7.4). The polyamides bearing free hydroxyl and carboxyl groups were water‐soluble.