A series of new di(meth)acrylate monomers was synthesized from the reactions of methyl alpha-hydroxymethylacrylate (MHMA), ethyl alpha-hydroxymethylacrylate (EHMA), hydroxyethyl acrylate (HEA) and hydroxyethylmethacrylate (HEMA) with alpha,omega-C18 diacid chloride. The photopolymerization behavior and reaction kinetics of the synthesized monomers were investigated using photoinitiation with differential scanning calorimetry. The polymerization rates, conversions and kinetic constants for propagation and termination were determined for each of the monomers. The maximum rate of polymerizations of the diacrylate monomers was higher than that of the dimethacrylate monomers and followed the order: HDDA (1,6-hexanediol diacrylate) > HEA-C18 > EHMA-C18 similar to HEMA-C18 > MHMA-C18. The total conversions obtained were 78, 75, 72, 64 and 69% for MHMA-C18, EHMA-C18, HEMA-C18, HEA-C18 and HDDA, respectively, indicating comparable or higher conversions for methacrylates despite their lower rates of polymerization. Propagation and termination mechanisms of the monomers were investigated by plotting propagation and termination rate constants as a function of conversion.