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Synthesis and thermal polymerization of aromatic 2‐oxazolines containing carboxylic groups
Author(s) -
Jakisch Lothar,
Böhme Frank,
Komber Hartmut,
Pompe Gisela
Publication year - 1999
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/(sici)1521-3927(19990501)20:5<256::aid-marc256>3.0.co;2-j
Subject(s) - triethylamine , oxazoline , polymerization , differential scanning calorimetry , polymer chemistry , amide , chemistry , ring opening polymerization , polymer , condensation polymer , hydrochloride , polyamide , materials science , organic chemistry , catalysis , physics , thermodynamics
2‐(4‐Carboxyphenyl)‐1,3‐oxazoline ( 2 a ), 2‐(3‐carboxyphenyl)‐1,3‐oxazoline ( 2 b ), and 2‐(6‐carboxynaphthyl‐2‐yl)‐1,3‐oxazoline ( 2 c ) were synthesized by reaction of monomethyl ester chlorides of aromatic dicarboxylic acids with 2‐chloroethylamine hydrochloride in the presence of triethylamine followed by cyclization with methanolic KOH. Thermal polymerization in bulk within a few minutes at 200–220°C resulted in new linear poly(ester amide)s 3 a – 3 c without significant side reactions. The polymerization occurred in the melt phase ( 2 b ) or in the solid state ( 2 a , 2 c ) and the resulting polymers are amorphous ( 3 b ) or semi‐crystalline ( 3 a , 3 c ). The polyaddition reactions were investigated by means of differential scanning calorimetry (DSC) and 1 H NMR spectroscopy.