Chemical modification of chain end in nylon 4 and improvement of its thermal stability

Two kinds of nylon 4 having an acyllactam group at one or both chain ends were synthesized by the anionic ring‐opening polymerization of 2‐pyrrolidone using N‐benzoyl‐2‐pyrrolidone (BP) or N,N′‐isophthaloylbis‐2‐pyrrolidone (IPP) and potassium tert‐butoxide as an initiator and a catalyst, respectively, and carefully isolated with the suppression of moisture adsorption. The acyllactam at one chain end in the low molecular weight of nylon 4 was quantitatively converted to other functional groups such as carboxy, amine and so on, which were confirmed by matrix‐assisted laser desorption/ionization time‐of‐flight (MALDI TOF) mass spectroscopy. Terminal acyllactam groups telechelating in the nylon 4 at both chain ends were also modified to carboxy and amino groups. From the thermogravimetric analysis (TGA), thermal decomposition point of the modified nylon 4 was increased in comparison with that of the original acyllactam‐type nylon 4, although the acyllactam chain end caused the backbiting depolymerization accompanied with the generation of 2‐pyrrolidone monomer. The direct heating of the acyllactam‐telechelic low molecular weight of nylon 4 mixed with the diamine in bulk also led to improve its thermal stability significantly by the chain extension through the polyaddition reaction. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011