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Polyalkylenehydroxybenzoates (PAHBs): Biorenewable Aromatic/Aliphatic Polyesters from Lignin
Author(s) -
Mialon Laurent,
Vanderhenst Rob,
Pemba Alexander G.,
Miller Stephen A.
Publication year - 2011
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201100242
Subject(s) - vanillic acid , syringic acid , polyester , thermogravimetric analysis , differential scanning calorimetry , monomer , alkylation , lignin , organic chemistry , chemistry , catalysis , vanillin , polymer chemistry , materials science , polymer , antioxidant , gallic acid , physics , thermodynamics
Polyalkylenehydroxybenzoates (PAHBs) are a new class of thermoplastic, biorenewable aromatic/aliphatic polyester having the general formula H‐[O‐(CH 2 ) n ‐O‐4‐(3‐X, 5‐Y‐C 6 H 2 )‐CO] z ‐OH. These are synthesized from the lignin‐derived aromatics 4‐hydroxybenzoic acid (X = Y = H), vanillic acid (X = OMe; Y = H), and syringic acid (X = Y = OMe). Alkylation of these with several chloroalkanols affords hydroxy‐acid monomers suitable for polyesterification under dynamic vacuum between 150 and 250 °C with 1 mol% Sb 2 O 3 as catalyst. Thus, polyalkylene 4‐hydroxybenzoates, polyalkylene vanillates, and polyalkylene syringates are prepared, characterized, and subjected to thermal property comparisons by differential scanning calorimetry and thermogravimetric analysis.