Triboelectrification of small polymer particles (< 10 microns) in which various functional groups are introduced by addition of substituted comonomers is studied. The particles are produced by suspension polymerization and mechanical crushing of larger particles. The effect of the different production methods on the particle is described. The particles produced by the polymerization method have a spherical shape with a smooth surface, and those produced by the crushing method have an irregular shape. Studies show that particles that have easily ionizable functional groups are charged more effectively. It is believed the ion-transfer route is the dominant mechanism in the triboelectrification charging of the particle. The magnitude of charge becomes saturated after 0.5% addition of substituted comonomers in the particle. The particles produced by the polymerization method have a tendency to be charged effectively compared with those produced by the crushing method.