Synthesis of polymers in aqueous solutions: Esterification reaction of poly(methacrylic acid) with alkyl halides using DBU in aqueous solutions

✍ Scribed by Tadatomi Nishikubo; Atsushi Kameyama; Youji Yamada; Yuichi Yoshida

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 577 KB
• Volume: 34
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(199612)34:17<3531::aid-pola7>3.0.co;2-x

✦ Synopsis

A convenient esterification reaction of poly(methacry1ic acid) (PMAA) with certain alkyl halides was performed using 1,8-diazabicyclo-[5.4.0] -7-undecene (DBU) as a base in aqueous solution or in water. The esterification reaction of PMAA with propargyl bromide (PB) proceeded very smoothly and quantitatively at 30°C to give corresponding poly(propargy1 methacrylate), although the rate of the reaction decreased with increasing water. The reaction of PMAA with benzyl bromide, o-nitrobenzyl bromide, and p-nitrobenzyl bromide gave corresponding poly(methacry1ic ester)s using DBU under suitable reaction conditions in water. The esterification reactions of PMAA with PB were carried out using certain organic bases such as triethylamine, 4(N,N-dimethylamino)pyridine and pyridine. Inorganic bases such as sodium carbonate, sodium hydroxide, potassium carbonate, and potassium hydroxide were also tried under the same conditions as with DBU. However, the degrees of estrification with all these bases was much lower than that with DBU.