An alternative pathway for the hydrolysis of epoxy ester compounds
- 作者：Sarah E. Shaw ; Tiziana Russo ; David H. Solomon ; Greg G. Qiao
- 关键词：Hydrophilic polymers ; Isomerization ; Radical polymerization
- 刊名：Polymer
- 出版年：2006
- 期刊代码：83_00323861
- 类别：ms
- 出版时间：22 November 2006
- 卷：47
- 期：25
- 页码：8247-8252
- 文件大小：391 K
摘要
The water-soluble polymer, poly(2,3-dihydroxypropyl methacrylate), also known as poly(glyceryl methacrylate), is known to isomerize and give a mixture of 2,3- and 1,3-isomers in both the monomeric and polymeric forms. The glyceryl methacrylate monomer was synthesized via acid-catalyzed hydrolysis of glycidyl methacrylate, which produced a mixture of 1,3- and 2,3-isomers in a ratio of 25%and 75%, respectively. This was surprising, as hydrolysis of epoxy compounds generally yields a 1,2-diol product. Furthermore, the level of 1,3-isomer at equilibrium is known to be 10%in both the glyceryl methacrylate monomer and polymer. An alternative hydrolysis pathway involving the ester and epoxy moieties was investigated for glycidyl methacrylate, and a mechanism was proposed.