Water → alpha-Methylene-gamma-Valerolactone Acrylic Acid

Participants

Reaction Conditions

Reaction Steps

To a 150 mL round bottom flask equipped with a magnetic stir bar was added 11.730 g (0.651 mol) water and 0.140 g (4.85×10−4 mol) sodium dodecyl sulfate (20% aqueous solution). The mixture was heated under flowing nitrogen to 71° C., at which time a monomer mixture consisting of 5.561 g (4.91×10−2 mol) α-methylene-γ-valerolactone, 0.290 g (4.83×10−3 mol) acrylic acid, and either 0.2%, 0.5%, or 1.0% by weight of pentaerythritol allyl ether crosslinker (70% purity) were added dropwise over 110 minutes. After 5 minutes of monomer mixture addition, an aqueous mixture consisting of 22.270 g (1.237 mol) water, 0.355 g (1.23×10−3 mol) sodium dodecyl sulfate (20% aqueous solution), 0.039 g (1.63×10−4 mol) sodium persulfate, and 0.053 g of a 20% aqueous sodium hydroxide solution was also added dropwise over 110 minutes. After both the monomer and aqueous mixtures were added completely, the emulsion was allowed to stir for an additional 60 minutes, after which the reaction was cooled to room temperature and dried for 16 hours at 90° C. under vacuum. In each experiment, a 100-fold excess of DMF was added to the polymer sample and allowed to sit on a platform shaker for 22 hours. The DMF was then decanted and the solvent removed under vacuum to determine the mass of the soluble chains. The insoluble portion was also dried under vacuum to determine the insoluble fraction.

Provenance & Evidence