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. Issue 7 (20th January 2014)

• Record Type: Journal Article
• Authors: Lamparth, Iris; Fischer, Urs K.; Pavlinec, Juraj; Kleinova, Angela; Moszner, Norbert
• Is Part Of: Macromolecular materials and engineering. Volume 299:Issue 7(2014:Jul.)
• Page Start: 834
• Page End: 842
• Publication Date: 2014-01-20
• Subjects: Plastics -- Periodicals; Polymers -- Periodicals; Polymerization -- Periodicals; 547.705
• DOI: 10.1002/mame.201300332
• Languages: English
• ISSNs: 1438-7492

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <sec id="mame201300332-sec-0001" sec-type="section"> <p>The polymerizable phthalic acid derivatives 4‐[11‐(acryloyl‐methyl‐amino)‐undecyloxy]‐phthalic acid (<bold>1</bold>) and {10‐[1, 3‐bis(methacrylamido)‐propoxy]‐decyloxy}‐phthalic acid (<bold>2</bold>) 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 <bold>1</bold> is insusceptible toward hydrolysis in aqueous media, strongly acidic and highly reactive in free radical polymerization. With these characteristics, <bold>1</bold> 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 <bold>1</bold> in methanol with AIBN as initiator. The overall activation energy <italic>E</italic>_a is 66.2 kJ mol⁻¹.<inline-graphic xlink:href="ark:/27927/pghqpm6p7j" content-type="mame201300332-gra-0001" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></p> </sec> </abstract>