Synthesis of isosorbide based polyurethanes: An isocyanate free method

被引:153
作者
Besse, Vincent [1 ]
Auvergne, Remi [1 ]
Carlotti, Stephane [3 ]
Boutevin, Gilles [2 ]
Otazaghine, Belkacem [4 ]
Caillol, Sylvain [1 ]
Pascault, Jean-Pierre [5 ]
Boutevin, Bernard [1 ]
机构
[1] Ecole Super Chim Montpellier, Inst Charles Gerhardt Montpellier, Equipe Ingn & Architectures Macromol, UMR 5253, F-34296 Montpellier 5, France
[2] Specif Polymers, F-34830 Clapiers, France
[3] Univ Bordeaux 1, Ecole Natl Super Chim Biol & Phys, CNRS, Lab Chim Polymeres Organ,UMR 5629, F-33607 Pessac, France
[4] Ctr Mat Grande Diffus, Ecole Mines Ales, F-30319 Ales, France
[5] Univ Lyon, INSA Lyon, IMP, UMR5223, F-69621 Villeurbanne, France
关键词
Polyhydroxyurethane; Isosorbide; Renewable resources; Thermal stability; Carbonate; CYCLIC CARBONATES; POLYADDITION; TRANSESTERIFICATION; DIISOCYANATE; REACTIVITY; EFFICIENT; NETWORKS; DIAMINES; AMINES; DIOLS;
D O I
10.1016/j.reactfunctpolym.2013.01.002
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The synthesis of isocyanate free polyurethanes is a major concern. This paper first reports the synthesis of new biobased isosorbide dicyclocarbonates from isosorbide. Then polyhydroxyurethanes (PHUs) were synthesized by a cyclocarbonate-amine step growth polyaddition with four commercial diamines (e.g. jeffamine D-400, 1,10 diaminodecane, diethylenetriamine and isophoronediamine). These unprecedented products, obtained with high yield, were characterized by H-1 NMR, FTIR, DSC, SEC and TGA analyses. PHUs exhibited glass transition temperatures from -8 degrees C to 59 degrees C, and degradation temperatures (Td 5%) between 234 degrees C and 255 degrees C. Last but not least, the compounds produced during the degradation of these PHUs were analyzed by ATG-IR technique and showed that carbon dioxide and secondary amines are released. (C) 2013 Elsevier Ltd. All rights reserved.
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页码:588 / 594
页数:7
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