Synthesis and characterization of renewable polyesters based on vanillic acid

被引:31
作者
Zhang, Silong [1 ]
Cheng, Zhengzai [1 ]
Zeng, Sheng [2 ]
Li, Guangyao [3 ]
Xiong, Jing [3 ]
Ding, Ling [1 ]
Gauthier, Mario [4 ]
机构
[1] Wuhan Univ Sci & Technol, Coal Convers & New Carbon Mat Hubei Key Lab, Wuhan 430081, Peoples R China
[2] WuXi AppTec Wuhan, Wuhan, Peoples R China
[3] Wuhan Univ Sci & Technol, Res Inst Fine Organ Chem & Organ Mat, Sch Chem & Chem Engn, Wuhan, Peoples R China
[4] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada
基金
中国国家自然科学基金;
关键词
polycondensation; polyesters; structure-property relationships; BIODEGRADABLE PLASTICS; DEGRADATION;
D O I
10.1002/app.49189
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Vanillic acid, potentially derived from biosourced feedstocks, was used as starting material in the synthesis of novel polyesters. A diester obtained by esterification and etherification of vanillic acid served as first monomer, in combination with resorcinol bis(2-hydroxyethyl) ether, hydroquinone bis(2-hydroxyethyl) ether, or aliphatic diols with different carbon chain lengths as second monomers, and antimony trioxide as catalyst to synthesize a series of polyesters by melt polymerization. The materials obtained had polystyrene-equivalentM(n)= 10,000-19,500 g/mol andM(w)= 19,300-39,500 g/mol. Thermal analysis yielded melting temperatures of 76-114 degrees C and onset decomposition temperaturesT(5%)= 321-360 degrees C. Dynamic mechanical and tensile testing confirmed that polyesters derived from vanillic acid have properties superior to poly(ethylene terephthalate) (PET). Aqueous degradation experiments with bulk polyester samples at different pH over 16 weeks led to intrinsic viscosity decreases of 9-23% under neutral conditions (pH 7), 10-26% under acidic conditions (pH 3), and 7-19% under alkaline conditions (pH 12). The results obtained show that the good thermal stability and degradability of vanillic acid-based polyesters, and the tunability of the properties of these materials through selection of the diol monomer used in their synthesis, make them excellent biosourced replacements for commercial polyesters such as PET.
引用
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页数:10
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共 22 条
[1]   Plastics and microplastics in the oceans: From emerging pollutants to emerged threat [J].
Avio, Carlo Giacomo ;
Gorbi, Stefania ;
Regoli, Francesco .
MARINE ENVIRONMENTAL RESEARCH, 2017, 128 :2-11
[2]   Degradation of agricultural biodegradable plastics in the soil under laboratory conditions [J].
Barragan, D. H. ;
Pelacho, A. M. ;
Martin-Closas, L. .
SOIL RESEARCH, 2016, 54 (02) :216-224
[3]   A crossroads for bioplastics: exploring product developers' challenges to move beyond petroleum-based plastics [J].
Brockhaus, Sebastian ;
Petersen, Moritz ;
Kersten, Wolfgang .
JOURNAL OF CLEANER PRODUCTION, 2016, 127 :84-95
[4]   SANS Investigation of Global and Segmental Structures of Hyperbranched Aliphatic-Aromatic Polyesters [J].
Burchard, W. ;
Khalyavina, A. ;
Lindner, P. ;
Schweins, R. ;
Friedel, P. ;
Wiemann, M. ;
Lederer, A. .
MACROMOLECULES, 2012, 45 (07) :3177-3187
[5]   The Neuropeptides FLP-2 and PDF-1 Act in Concert To Arouse Caenorhabditis elegans Locomotion [J].
Chen, Didi ;
Taylor, Kelsey P. ;
Hall, Qi ;
Kaplan, Joshua M. .
GENETICS, 2016, 204 (03) :1151-+
[6]   Biodegradation rate of biodegradable plastics at molecular level [J].
Chinaglia, Selene ;
Tosin, Maurizio ;
Degli-Innocenti, Francesco .
POLYMER DEGRADATION AND STABILITY, 2018, 147 :237-244
[7]   Vanillin Production from Lignin and Its Use as a Renewable Chemical [J].
Fache, Maxence ;
Boutevin, Bernard ;
Caillol, Sylvain .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (01) :35-46
[8]   Vanillin, a promising biobased building-block for monomer synthesis [J].
Fache, Maxence ;
Darroman, Emilie ;
Besse, Vincent ;
Auvergne, Remi ;
Caillol, Sylvain ;
Boutevin, Bernard .
GREEN CHEMISTRY, 2014, 16 (04) :1987-1998
[9]   Cellulose, hemicellulose and lignin slow steam pyrolysis: Thermal decomposition of biomass components mixtures [J].
Giudicianni, Paola ;
Cardone, Giuseppe ;
Ragucci, Raffaele .
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2013, 100 :213-222
[10]   Mechanism and kinetics of the enzymatic hydrolysis of polyester nanoparticles by lipases [J].
Herzog, K. ;
Mueller, R. -J. ;
Deckwer, W. -D. .
POLYMER DEGRADATION AND STABILITY, 2006, 91 (10) :2486-2498