The interest in renewable natural resources, including plant oils, has become increasingly appealing due to the oil abundance, availability, and wide range of applications for polymers and polymeric materials thereof. In this dissertation, a library of plant oil-based acrylic monomers (POBMs) with a broad range of unsaturation was synthesized using a one-step transesterification. It is demonstrated that the unsaturation degree of plant oil remains preserved during the synthesis and determines the structure and properties of POBMs. The life cycle assessment (LCA) was conducted in this study to evaluate the environmental impact of soybean oil-based acrylic monomer (SBM) production. LCA was applied to provide guidance for SBM synthesis optimization, including the type of catalyst, the ratio between reactants, renewable sources (soybean oil/biodiesel), and solvent recycling. The performed LCA shows the positive effect of the inclusion of the solvent recycling step in the SBM synthesis. This study shows that POBMs behave as conventional vinyl monomers in free radical polymerization and copolymerization. The monomer unsaturation impacts polymerization rate and molecular weight of resulted polymers decreasing as follows: poly(OVM) > poly(SFM) > poly(SBM) > poly(LSM), due allylic termination presented during polymerization. A series of stable POBM-based latexes with high solid content (40-45 %) and monomer conversion (95-97 %) were synthesized using miniemulsion process. The incorporation of POBMs fragments provides the plasticizing effect on the resulting latex polymers, as seen by a noticeable decrease in their glass transition temperature (Tg). The crosslink density of POBM-based latex films follows the linear dependence vs. monomer feed unsaturation, providing a tool for controlling latex mechanical properties, including hardness, toughness, Young's modulus, etc. Besides, the presence of highly hydrophobic POBM fragments enhances water resistivity of latex coatings and films. Following the "greener" vector of research, a variety of stable latexes from high oleic soybean oil-based monomer (HOSBM) and cardanol, eugenol, and guaiacol derivatives were synthesized in miniemulsion. Resulting polymeric materials advantageously combine flexibility provided by HOSBM fragments with strength facilitated by aromatic biobased units.