Copolymers of 4-Adamantylphenyl Methacrylate Derivatives with Methyl Methacrylate and Styrene
Document Type
Article
Publication Date
7-1-2001
Department
Polymers and High Performance Materials
Abstract
Three 4-(I-adamantyl)phenyl methacrylate monomers were synthesized from 4-(l-adamantyl)phenol derivatives which were obtained by Friedel-Crafts alkylation of phenol, 2-methylphenol and 2,6-dimethylphenol with 1-bromoadamantane. Characterization of the monomers by IR, H-1 and C-13 NMR, GC and elemental analysis confirmed structures and purities. Copolymers of these new monomers with styrene were synthesized using free radical techniques. One series of 4-(1-adamantyl)phenyl methacrylate was also prepared with methyl methacrylate (MMA). Copolymer compositions were evaluated by H-1 and C-13 solution NMR, and with FTIR. Reactivity ratios were estimated to have values of r(1) = 0.22 and r(2) = 1.51 for styrene and 4-(1-adamantyl)phenyl methacrylate copolymers; r(1) = 0.31 and r(2) = 2.44 for styrene and 2-methyl-4-(1-adamantyl)phenyl methacrylate; and r(1) = 0.97 and r(2) = 0 for styrene and 4-(1-adamantyl)-2,6-dimethylphenyl methacrylate copolymers (J Polym Sci A 3 (1965) 369-87, J Macromol Sci Rev C4 (1970) 281). All homo- and copolymers were characterized using DSC and TGA to determine copolymer composition effects on T-g and thermal stability. The estimated T-g for the homopolymer of 4-(l-adamantyl)phenyl methacrylate was 253 degreesC and the onset of decomposition was 250 degreesC in nitrogen. The homopolymer of 2-methyl-4-(1-adamantyl)phenyl methacrylate had a T-g of 250 degreesC which was at the onset of decomposition in nitrogen. The homopolymer of 4-(1-adamantyl)-2,6-dimethylphenyl methacrylate could not be obtained by free-radical polymerization. 4-(Adamantyl)phenyl methacrylate was incorporated into styrene copolymers at 1-30 mol% and gave T-g increases of cs. 5-60 degreesC over that of polystyrene, respectively. Incorporation of this monomer into MMA copolymers (0.75-35 mol%) resulted in T-g increases of ca. 6-70 degreesC over that of poly(methyl methacylate). (C) 2001 Elsevier Science Ltd. All rights reserved.
Publication Title
Polymer
Volume
42
Issue
15
First Page
6527
Last Page
6537
Recommended Citation
Mathias, L. J.,
Jensen, J.,
Thigpen, K.,
McGowen, J.,
McCormick, D.,
Somlai, L.
(2001). Copolymers of 4-Adamantylphenyl Methacrylate Derivatives with Methyl Methacrylate and Styrene. Polymer, 42(15), 6527-6537.
Available at: https://aquila.usm.edu/fac_pubs/3858