Synthesis and characterization of poly(succinimide-co-6-aminocaproic acid) by acid-catalyzed polycondensation of L-aspartic acid, and 6-aminocaproic acid

The polycondensation of L-aspartic acid (ASP) with 6-aminocaproic acid (ACA) using o-phosphoric acid produced poly(succinimide-co-6-aminocaproic acid). The yield of the MeOH-insoluble copolymer decreased from 99 to 52% and that of the MeOH-soluble one increased from 9 to 47%, with increasing molar ratio of ACA in the monomer feed. The compositions of the succinimide (SCI) unit in the MeOH-insoluble and -soluble copolymers tended to be higher than those of ASP in the monomer feed. The copolymers with the 35 mol % SCI units or above were soluble in DMSO, DMF, and conc-H2SO4, but those with the 20 and 21 mol % SCI units were soluble only in conc-H2SO4. The melting temperature appeared for the copolymers with less than 76 mol % SCI units. Poly(succinimide-co-6-aminocaproic acid) was easily hydrolyzed to yield poly(aspartic acid-co-6-aminocaproic acid), and it exhibited biodegradability toward activated sludge. (C) 1997 John Wiley & Sons, Inc.