Vanillin based polymers: V. Poly(hydrovanilloin–urethane)

Abstract

Renewable resources based hydrovanilloin [1,2- bis(4-hydroxy-3-methoxyphenyl)-1,2-ethanediol] was synthesized in 86% yield by electrochemical dimerization of vanillin in aqueous NaOH. This symmetrical bis-phenol monomer was then used for the preparation of urethane polymers by two different methods. In the first method a 1:2 mole ratio mixture of hydrovanilloin and diisocyanate was polymerized in DMF using 1,4-diazabicyclo[2,2,2]octane as the catalyst at 60°C, for 1 h to give poly(hydrovanilloin–urethane)s. In the second method diisocyanates were first reacted with polyethylene glycol-400 to give pre-polymers. Then prepolymers were reacted with equivalent amount of hydrovanilloin at 60°C for 4 days to produce poly(hydrovanilloin-ethylene glycol-urethane)s. The first method resulted hard poly(hydrovanilloin–urethane)s showing Tg values in the range of 121–172°C. The second method yielded softer poly(hydrovanilloin-ethylene glycol-urethane)s and these polymers failed to show distinct glass transition temperatures in the DSC analysis. However, poly(hydrovanilloin-ethylene glycol-urethane)s showed better thermal stabilities than polymers without polyethylene glycol units.

Drug delivery systems based on renewable polymers: A conceptual short review

“…The journal of “Polymers from Renewable Resources” has been a leading journal in this field that discusses synthesizing and applications of sustainable polymers. 24,79,80 However, most of sustainable polymers have been considered as alternatives to commodity fossil-derived polymers in applications such as packaging. 81 Current paper discusses the huge potential of such renewable polymers for biomedical field.…”

“…[20][21][22] The third class of renewable polymers are those that their monomers are extracted from renewable resources, for example, terpenes, sugar and fermentation products of carbohydrate sources. 23,24 In addition, sustainable monomers can be obtained by depolymerization and/or fermentation of PSAs as schematically illustrated in Figure 1.…”

“…20–22 The third class of renewable polymers are those that their monomers are extracted from renewable resources, for example, terpenes, sugar and fermentation products of carbohydrate sources. 23,24 In addition, sustainable monomers can be obtained by depolymerization and/or fermentation of PSAs as schematically illustrated in Figure 1.

Figure 1.Renewable polymers origin, classification, and examples (PHFA: polydihydroferulic acid; SynBio: synthetic biology; MGE: metabolic glycoengineering; GelMA: Gelatin methacryloyl; SF: Silk fibroin; PLGA: poly(lactic-co-glycolic acid); PBS: Polybutylene succinate; PHAs: polyhydroxyalkanoates). Sustainable delivery platforms based on renewable polymers.

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