ABSTRACT:(2R*,4S*)-4-chloroformyl-2-chloroformylmethyl-2,4-dimethyl-4-butanolide was prepared by the chemical transformation of I-butyl methacrylate dimer telomerized using bromotrichloromethane. The interfacial polycondensation of this acid dichloride with hexamethylenediamine was accompanined by a partial hydrolytic cleavage of the lactone ring and gave an unique 6,6-type polyamide containing both lactone rings and hydrophilic groups such as carboxyl-and hydroxyl-groups. To determine the optimal conditions for interfacial polycondensation, the influence of the following factors on yield, value of intrinsic viscosity, and ring-opening ratio of polyamide was studied: volume of phase solvent, molar ratio of diamine to acid dichloride, molar ratio of sodium hydroxide as a hydrogen chloride acceptor to acid dichloride, temperature of reaction, the kinds of hydrogen chloride acceptors and organic phases, and contribution of stirring. The resulting polyamide was highly soluble in methanol, which is a poor solvent for conventional polyamides. A transparent and flexible film prepared from the methanol solution by a casting technique had a glass transition temperature of 88°C and a water absorption of ca. 30% at 95% relative humidity. Furthermore, the carboxylato-containing polyamide modified by treatment with potassium hydroxide was very soluble in water. In previous papers, 1 we reported the free radical telomerization of methacrylate monomers using bromotrichloromethane (BTCM) as a telogen. The effects of the substituent in the ester group on the telomerization and characteristics of the resulting n: 1-[methacrylate monomer]: [BTCM] adducts were studied systema ti call y. KEY WORDS

ABSTRACT:The interfacial polycondensation of (2R* ,4S*)-4-chloroformyl-2-chloroformylmethyl-2,4-dimethyl-4-butanolide (BC) with 1,6-hexanediamine (HOA) gives an unique 6,6-type polyamide (PA-6L) with partial hydrolytic cleavage of the lactone moiety. PA-6L containing at random both y-lactone ring and hydrophilic groups such as carboxyl and hydroxyl groups was modified by the following three methods: l) ring-opening of the lactone groups in PA-6L by chemical treatment, 2) incorporation ofnylon-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 [I/] 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 ( with MDI had a decomposition point of 303°C and showed a lower thermostability beyond 280°C than the original one.

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