화학공학소재연구정보센터
Journal of Polymer Science Part A: Polymer Chemistry, Vol.52, No.3, 360-365, 2014
Synthesis of Well-Defined, Soluble Poly(3-alkyl-4-benzamide) by Chain-Growth Condensation Polymerization
Well-defined poly(3-alkyl-4-benzamide) was synthesized by means of chain-growth condensation polymerization of phenyl 3-octyl-4-(4-octyloxybenzyl(OOB)amino)benzoate (1c) from initiator 2, followed by removal of the OOB groups on amide nitrogen of poly1c. Polymerization of 1c with phenyl 4-(trifluoromethyl)benzoate (2b) in the presence of 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS) and LiCl in THF at -10 degrees C gave poly1c with a narrow molecular weight distribution (M-w/M-n 1.08) and a well-defined molecular weight (M-n = 4480-12,700) determined by the feed ratio of monomer to initiator (from 10 to 30). The OOB groups of poly1c were removed with H2SO4 to give the corresponding N-unsubstituted poly(p-benzamide) (poly1c) with low polydispersity. The solublity of poly1c in polar organic solvents was dramatically higher than that of poly(p-benzamide), demonstrating that introduction of an alkyl group on the aromatic ring is very effective for improving the solubility of poly(p-benzamide). (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 360-365