Acid-labile polyvinylamine micro- and nanogel capsules

Hollow nanoparticles represent an emerging area of development for the encapsulation of active ingredients. Expanding the capabilities of these nanomaterials will require continued efforts to infill properties such as size control, biodegradability, and environmental responsiveness. Acid-labile poly(N-vinylformamide) (PNVF) nanocapsules were synthesized by free radical polymerization of N-vinylformamide on the surface of silica nanoparticles. Polymerization in the presence of a novel cross-linker that contains an acid-labile ketal facilitated stable etching of silica nanoparticle templates using sodium hydroxide and recovery of degradable PNVF nanocapsules. The formamide side group of PNVF was then hydrolyzed by extended exposure to sodium hydroxide to produce polyvinylamine (PVAm) micro- and nanocapsules. Both capsule types demonstrated an increasing dissolution rate as pH decreased. In addition, PVAm nanocapsules exhibited swelling in proportion to the relative charge density of the PVAm network (a function of the degree of formamide hydrolysis and pH), presumably due to the repulsion of positively charged amine groups within the elastic shell network. The synthetic approaches reported provide methods to endow nanocapsules with key attributes such as size control, pH sensitive degradation, swelling in response to pH, and amine functionality.