Synthetic routes to responsive polymers; co-polycondensation of tri-functional amino acids with diacylchlorides

• Published in: Reactive & functional polymers Vol. 42; no. 2; pp. 147 - 161
• Main Authors: Eccleston, M.E., Slater, N.K.H., Tighe, B.J.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 15-11-1999; Elsevier Science
• Subjects: Amino acids; Applied sciences; Biodegradable polyamides; Co-polycondensation; Equilibrium partition coefficient; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; Polycondensation; Preparation, kinetics, thermodynamics, mechanism and catalysts; Responsive polymers; Amino acids; Biodegradable polyamides; Responsive polymers; Equilibrium partition coefficient; Co-polycondensation; Solvent effect; Nylon; Solution polycondensation; Molecular structure; Experimental study; Functional polymer; Optimization; Aminoester; Medium effect; Aminoacid; Preparation; Amide copolymer; Copolycondensation; Interfacial polymerization; Polyacid; Processing parameter
• ISSN: 1381-5148
• DOI: 10.1016/S1381-5148(98)00073-X

The condensation of diamino acids and their derivatives such as
l-lysine,
l-lysine ethyl ester and
l-ornithine with aromatic and aliphatic diacyl chlorides was investigated. Linear polyamides bearing carboxylic acid or ester functional groups pendant to the backbone with reasonable molecular weight (
M
w 56–66 kDa) could be produced using either a single phase aqueous acetone solution method or a bi-phasic carbon tetrachloride/aqueous method. The effect of reaction conditions on product yield and molecular weight were also investigated. The molecular weight averages of polymers produced using a single phase aqueous acetone solution method were found to be comparable to those of similar polymers synthesized using interfacial polycondensation. In addition, esterified and non-esterified diamino acids could be copolymerised using the single phase technique whereas two distinct products were obtained when a bi-phasic method was used.