Abstract
The interfacial polycondensation of (2R*,4S*)-4-chloroformyl-2-chloroformyl-methyl-2,4-dimethyl-4-butanolide (BC) with 1,6-hexanediamine (HDA) gives an unique 6,6-type polyamide (PA-6L) with partial hydrolytic cleavage of the lactone moiety. PA-6L containing at random both γ-lactone ring and hydrophilic groups such as carboxyl and hydroxyl groups was modified by the following three methods: 1) ring-opening of the lactone groups in PA-6L by chemical treatment, 2) incorporation of nylon-66 (PA-66) sequence into PA-6L chain by interfacial copolycondensation, and 3) crosslinking of PA-6L with methylene bis(4-phenylisocyanate) (MDI). The ring-opening ratio of PA-6L increased by treating with either acids or alkalis, whereas [η] decreased. In particular, the carboxylato-containing PA-6L prepared by the treatment with potassium hydroxide was highly soluble in water. In the interfacial copolycondensation of acid dichlorides, BC and adipoyl chloride (AC), with HDA, a methanol-soluble copolyamide PA-6L/66 was prepared at an [AC]/([BC]+[AC]) mole fraction of ca. 0.25. PA-6L crosslinked with MDI had a decomposition point of 303°C and showed a lower thermostability beyond 280°C than the original one.
Similar content being viewed by others
Article PDF
References
T. Kimura, H. Morimoto, E. Sasaki, K. Tanji, and M. Hamashima, Polym. J., 22, 1015 (1990).
T. Kimura, K. Tanji, and M. Minabe, Polym. J., 24, 1311 (1992).
H. G. Elias and R. Schumacher, Makromol. Chem., 76, 23 (1964).
P. W. Morgan and S. L. Kwolek, J. Chem. Ed., 36, 182 (1959).
Y. Ikeda, S. Kohjiya, S. Yamashita, N. Yamamoto, K. Hayashi, and I. Yamashita, Nippon Kagaku Kaishi, 699 (1986).
J. Burkus and C. F. Eckert, J. Am. Chem. Soc., 80, 5948 (1958).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kimura, T., Tanji, K., Sasaki, R. et al. Modification of 6,6-Type Polyamide Containing both γ-Lactone Ring and Hydrophilic Groups. Polym J 25, 267–273 (1993). https://doi.org/10.1295/polymj.25.267
Issue Date:
DOI: https://doi.org/10.1295/polymj.25.267