Polylactones derived from polymethacrolein and styrene–methacrolein copolymerizations

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Abstract
Emulsion polymerization of methacrolein produces a polyacetal which can be converted through the action of sodium hydroxide to an alternating copolymer of methallyl alcohol and sodium methacrylate. Support for the alternating structure was gained primarily through a study of the polylactone formed through subsequent acidification of the sodium salt. Thus, the poly(methallyl alcohol–sodium methacrylate) copolymer was acidified under selected conditions to give a soluble polylactone containing 14.2 mole‐% of residual acid and hydroxyl groups. This number agrees quite closely with the value of 13.5 mole‐% which one would predict from the random cyclization of a true alternating copolymer. Cyclization of a random copolymer of poly(methallyl alcohol–sodium methacrylate) in a random fashion would have resulted in a value of about 36.8 mole‐%. The results also support both the 1,2 vinyl polymerization of methacrolein and a nonrandom attack of the polymethacrolein by base. In a completely separate set of experiments, the value of r1 and r2 for the copolymerization of styrene (M1) and methacrolein (M2) were determined to be 0.22 ± 0.02 and 0.88 ± 0.02, respectively.