Synthesis and radical polymerization of styrene derivative bearing kojic acid moieties

✍ Scribed by Ikuyoshi Tomita; Kenji Mitsuhashi; Takeshi Endo

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 408 KB
• Volume: 34
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19960130)34:2<271::aid-pola13>3.0.co;2-n

✦ Synopsis

A styrene derivative (1) bearing kojic acid moieties was prepared by t h e base-catalyzed reaction of p-formylstyrene with kojic acid. Hydroxyl groups in 1 were subjected to acetylation. Although 1 did not undergo radical polymerization, the acetylated styrene derivative (2) showed good radical homo-and copolymerizability. For instance, a polymer having the number average molecular weight ( M , ) of 60,000 was obtained in almost quantitative yield (97%) by the polymerization of 2 in chloroform (1.5 M ) a t 60°C for 36 h using cw,a'-azobis(isobutyronitri1e) (AIBN, 5 mol %) as a n initiator. Under similar conditions, copolymers of 2 with styrene were also obtained in high yield. By partial deacetylation of the copolymer with a triethylamine catalyst, a copolymer containing a-hydroxyketone structures originated from kojic acid moieties was successfully regenerated. T h e deacetylated copolymer can be crosslinked by complexation with metal salts such as A13+.