Synthesis and characterization of telechelic macromers containing fatty acid derivatives

Telechelic macromers end-capped with (meth)acrylic functionalities are the most commonly used materials in rigid, dental formulations. In order to provide higher flexibility to the final product (not necessarily for dental applications), long chain aliphatic fatty acid derivatives may be chosen. Thus, new telechelic macromers comprising methacrylic functionalities and dimer fatty acid derivatives have been synthesized for the first time, and their chemical structure is discussed in detail. Six different systems comprising ester, anhydride and urethane bonds were synthesized from non-toxic raw materials. FTIR spectroscopy and NMR analysis were used to evaluate chemical structure of new systems. Their molecular masses were estimated from GPC measurements and from an analytical method based on iodine value determination. The latter one proved to be very accurate in determining molecular masses of methacrylated telechelics according to a new method developed in this work. We demonstrated that, via simple organic chemistry, different architectures of telechelic macromers comprising commercially available, long chain derivatives of fatty acid, mainly linoleic acid, with α,ω-dihydroxy, α,ω-dicarboxy or α,ω-diamino functionalities were successfully synthesized. These macromers facilitate the development of new reactive (preferably, photocurable) flexible systems for potential biomedical applications.