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Syntheses and radical polymerizations of methacrylamides derived from optically active amino alcohols
Author(s) -
Koyama Emiko,
Sanda Fumio,
Endo Takeshi
Publication year - 1997
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1997.021981130
Subject(s) - methacrylamide , chemistry , polymer chemistry , monomer , methyl methacrylate , radical polymerization , reactivity (psychology) , copolymer , dimethylformamide , radical initiator , methacrylic acid , polymer , organic chemistry , acrylamide , medicine , alternative medicine , pathology , solvent
Syntheses and radical polymerizations of methacrylamides derived from optically active amino alcohols were carried out. The monomers were prepared by condensation of optically active amino alcohols and methacrylic acid using 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide hydrochloride (EDC · HCl). Radical polymerizations of the monomers were carried out in the presence of 2,2‐azoisobutyronitrile (AIBN) (3 mol‐%) in methanol and N,N ‐dimethylformamide (DMF) as solvents, resulting with good yields in polymers with M n 's in the range 17 800–81 000. The monomer reactivity ratios of N ‐(1‐hydroxy‐4‐methyl‐2‐pentyl)methacrylamide (MA‐Lol) and methyl methacrylate (MMA) in the copolymerization were estimated to be 0.50 and 2.38, respectively. The lower reactivity of MA‐Lol in comparison with MMA is similar to common methacrylamide derivatives. The hydrophilicity of the polymers was evaluated by the heat of fusion of water using differential scanning calorimetry (DSC). The determined order poly(MA‐Aol) > poly(MA‐Lol) > poly(MA‐Fol) reflects the bulkiness of the side chains.