alpha-Exomethylene Lactone Possessing Acetal-Ester Linkage: Polymerization and Postpolymerization Modification for Water-Soluble Polymer

作者：Kohsaka Yasuhiro^*; Matsumoto Yusuke; Zhang Tianyi; Matsuhashi Yosuke; Kitayama Tatsuki^*

来源：Journal of Polymer Science Part A: Polymer Chemistry , 2016, 54(7): 955-961.

DOI：10.1002/pola.27931

• alpha-substituted acrylate
• anionic polymerization
• radical polymerization
• trifunctional monomer
• water-soluble polymers

2,6-Dimethyl-5-methylene-1,3-dioxa-4-one (DMDO), a cyclic acrylate possessing acetal-ester linkage, was obtained as a mixture of cis- and trans-isomers (95:5) from Baylis-Hillman reaction of an aryl acrylate. The radical and anionic polymerizations of DMDO yielded the corresponding vinyl polymers without any side reactions such as cleavage of the acetal-ester linkage. The polymerization behaviors were significantly different from that of the acyclic acrylate, alpha-(hydroxymethyl) acrylic acid, which was expected inactive against polymerization due to the steric hindrance around the vinylidene group by the alpha-substituent. The acetal-ester linkage of the obtained polymer (P1) was completely cleaved via acid hydrolysis to afford a water soluble polymer, P2.

• 出版日期2016-4-1