Long-chain aliphatic polyesters from plant oils for injection molding, film extrusion and electrospinning

被引：89
作者：
Stempfle, Florian [1 ]
Ritter, Benjamin S. [2 ,3 ]
Muelhaupt, Rolf [2 ,3 ]
Mecking, Stefan [1 ]
机构：
[1] Univ Konstanz, Dept Chem, Chair Chem Mat Sci, D-78457 Constance, Germany
[2] Freiburg Mat Res Ctr FMF, D-79104 Freiburg, Germany
[3] Univ Freiburg, Inst Macromol Chem, D-79104 Freiburg, Germany
来源：
GREEN CHEMISTRY | 2014年 / 16卷 / 04期
关键词：
RING-OPENING POLYMERIZATION; MOLECULAR-WEIGHT; FATTY-ACIDS; POLYMERS; MONOMERS; METATHESIS; POLYETHYLENE; ESTERS;
D O I：
10.1039/c4gc00114a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The polycondensation of long-chain alpha,omega-diesters with long-chain alpha,omega-diols, prepared by means of catalytic conversion of plant oils, affords linear aliphatic polyesters. They contain both long crystallizable polyethylene-like hydrocarbon segments and ester moieties in the backbone. In a convenient catalytic one-step process a high-purity polycondensation grade dimethyl-1,19-nonadecanedioate monomer is obtained directly from the technical grade methyl ester of high oleic sunflower oil. Likewise, dimethyl1,23- tricosanedioate is derived from methyl erucate. The successful scale-up renders both intermediates available on a 100 g scale. Injection molded parts of polyester-19.19 and -23.23 with a number average molecular mass of M-n = 3 x 10(4) g mol(-1) possess an elongation at break of >600% and a Young's modulus of 400 MPa. Electrospinning produces non-woven meshes. The polyesters prepared even enable film extrusion and represent new blend components for a variety of thermoplastics including polyethylene.
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收藏
页码：2008 / 2014
页数：7
相关论文
共 33 条
[1]  
Baann H., 1996, Borealis A/S, Patent No. [WO 1996/9622328A1, 19969622328]
[2]   Oils and Fats as Renewable Raw Materials in Chemistry [J].
Biermann, Ursula ;
Bornscheuer, Uwe ;
Meier, Michael A. R. ;
Metzger, Juergen O. ;
Schaefer, Hans J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) :3854-3871
[3]   Effects of molecular weight on poly(ω-pentadecalactone) mechanical and thermal properties [J].
Cai, Jiali ;
Liu, Chen ;
Cai, Minmin ;
Zhu, Jie ;
Zuo, Feng ;
Hsiao, Benjamin S. ;
Gross, Richard A. .
POLYMER, 2010, 51 (05) :1088-1099
[4]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[5]   Refining of Plant Oils to Chemicals by Olefin Metathesis [J].
Chikkali, Samir ;
Mecking, Stefan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5802-5808
[6]   Poly(triacontamethylene triacontanedioate) as polyethylene analogue: Properties and enzymatic degradation [J].
Cho, I ;
Lee, K .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 1997, 198 (03) :861-869
[7]  
Cohen S A, 2011, WO, Patent No. [2011/046872, 2011046872]
[8]   Performance polymers from renewable monomers: high molecular weight poly(pentadecalactone) for fiber applications [J].
de Geus, Matthijs ;
van der Meulen, Inge ;
Goderis, Bart ;
van Hecke, Kristof ;
Dorschu, Marko ;
van der Werff, Harm ;
Koning, Cor E. ;
Heise, Andreas .
POLYMER CHEMISTRY, 2010, 1 (04) :525-533
[9]  
Dinger MB, 2002, ADV SYNTH CATAL, V344, P671, DOI 10.1002/1615-4169(200208)344:6/7<671::AID-ADSC671>3.0.CO
[10]  
2-G
1234