화학공학소재연구정보센터
Journal of Polymer Science Part A: Polymer Chemistry, Vol.36, No.8, 1233-1241, 1998
Anionic synthesis of aromatic amide and carboxyl functionalized polymers. Chain-end functionalization of poly(styryl)lithium with N,N-diisopropyl-4-(1-phenylethenyl)benzamide
The novel syntheses of N,N-diisopropyl-4-benzoylbenzamide, N,N-diisopropyl-4-(1-hydroxy-1-phenylethyl)benzamide, and N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1) are described, omega-Amidopolystyrene (2) was synthesized in quantitative yields by the reaction of poly(styryl)lithium with stoichiometric amounts of N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1) in toluene/tetrahydrofuran (4:1 v/v) at -78 degrees C. Deblocking of the amide protecting group by acid hydrolysis quantitatively provides the corresponding aromatic carboxyl chain-end functionalized polystyrene (3). The functionalization agent and functionalized polymers were characterized by HPLC, thin-layer chromatography, size exclusion chromatography, vapor phase osmometry, spectroscopy (H-1-NMR, C-13-NMR, and FTIR), potentiometry, and elemental analysis.