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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
Author(s) -
Lamparth Iris,
Fischer Urs K.,
Pavlinec Juraj,
Kleinova Angela,
Moszner Norbert
Publication year - 2014
Publication title -
macromolecular materials and engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.913
H-Index - 96
eISSN - 1439-2054
pISSN - 1438-7492
DOI - 10.1002/mame.201300332
Subject(s) - phthalic acid , polymerization , monomer , radical initiator , polymer chemistry , radical polymerization , materials science , phthalic anhydride , hydrolysis , organic chemistry , chemistry , polymer , catalysis
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 1 H NMR, 13 C 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 E a is 66.2 kJ mol −1 .