Monomers for Adhesive Polymers, 14 Synthesis and Radical Polymerization of 4-[11-(Acryloyl-methyl-amino)-undecyloxy]-phthalic Acid and {10-[1,3-Bis(methacrylamido)-propoxy]-decyloxy}-phthalic Acid

The polymerizable phthalic acid derivatives 4-[11-(acryloyl-methyl-amino)-undecyloxy]-phthalic acid (1) and {10-[1,3-bis(methacrylamido)-propoxy]-decyloxy}-phthalic acid (2) are synthesized from the MOM-ester of 4-hydroxy-phthalic acid and the corresponding bromo-alkyl-(meth)acrylamides. The synthesized monomers are characterized by 1H NMR, 13C NMR, and IR spectroscopy. The acrylamide 1 is insusceptible toward hydrolysis in aqueous media, strongly acidic and highly reactive in free radical polymerization. With these characteristics, 1 fulfills important requirements for the application in water-based single-bottle adhesive formulations. A deviation from the standard reaction kinetics is found for the free-radical homopolymerization of 1 in methanol with AIBN as initiator. The overall activation energy Ea is 66.2 kJ mol−1.