SYNTHESES AND RADICAL POLYMERIZATIONS OF METHACRYLAMIDES DERIVED FROMOPTICALLY-ACTIVE AMINO-ALCOHOLS

Syntheses and radical polymerizations of methacrylamides derived from optically active amino alcohols were carried out. The monomers were pr epared by condensation of optically active amino alcohols and methacry lic acid using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochlo ride (EDC . HCl). Radical polymerizations of the monomers were carried out in the presence of 2,2-azoisobutyronitrile (AIBN) (3 mol-%) in me thanol and N,N-dimethylformamide (DMF) as solvents, resulting with goo d yields in polymers with (M) over bar(n)'s in the range 17 800-81 000 . The monomer reactivity ratios of N-(1-hydroxy-4-methyl-2-pentyl)meth acrylamide (MA-Lol) and methyl methacrylate (MMA) in the copolymerizat ion were estimated to be 0.50 and 2.38, respectively. The lower reacti vity of MA-Lol in comparison with MMA is similar to common methacrylam ide derivatives. The hydrophilicity of the polymers was evaluated by t he heat of fusion of water using differential scanning calorimetry (DS C). The determined order poly(MA-Aol) > poly(MA-Lol) > poly(MA-Fol) re flects the bulkiness of the side chains.