Oxidative Cross-Coupling between Phenolic Polymer and Phenol-Containing Cellulose:  Synthesis of a New Class of Artificial Wood Polymers

• Published in: Macromolecules 2004-10, Vol.37 (21), p.7901-7905
• Main Authors: Tonami, Hiroyuki, Uyama, Hiroshi, Kobayashi, Shiro
• Format: Article
• Language: English
• Subjects: Applied sciences; Cellulose and derivatives; Exact sciences and technology; Natural polymers; Physicochemistry of polymers
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/ma049420p

Oxidative cross-coupling of phenolic polymers, mainly poly(bisphenol A) including poly(m-cresol) and poly(p-tert-butylphenol), onto a phenol-containing cellulose has been performed in pyridine at room temperature under air to produce cellulose−phenolic polymer hybrids, cellulose-graft-phenolic polymers, which is a new synthetic method utilizing phenolic polymers as substrates. Iron salen complex and hydrogen peroxide were used as a catalyst and an oxidizing agent, respectively. During the reaction, the cross-coupling between the cellulose derivative and the phenolic polymer as well as the homocoupling of the phenolic polymer took place. The resultant cellulose−phenolic polymer hybrid was isolated by reprecipitation. Characterization of the hybrid was performed by 1H NMR, SEC, UV, and elemental analysis. The coupled amount of the phenolic polymer on the cellulose could be controlled by the feed ratio. The present study provides a new method for hybrid polymer synthesis by oxidative coupling, leading to production of a new type of biopolymers from abundant renewable resources.