Diglycidylether of iso-eugenol: a suitable lignin-derived synthon for epoxy thermoset applications

被引：37
作者：
Francois, Camille [1 ]
Pourchet, Sylvie [1 ]
Boni, Gilles [1 ]
Fontaine, Stephane [2 ]
Gaillard, Yves [3 ]
Placet, Vincent [3 ]
Galkin, Maxim V. [4 ]
Orebom, Alexander [4 ]
Samec, Joseph [4 ]
Plasseraud, Laurent [1 ]
机构：
[1] Univ Bourgogne Franche Comte, CNRS, UMR 6302, ICMUB Inst,Dept Electrochem Mol Mat & Devices, 9 Ave Alain Savary, F-21078 Dijon, France
[2] Inst Super Automobile & Transports, DRIVE Lab, 49 Rue Melle Bourgeois, F-58027 Nevers, France
[3] Univ Franche Comte, CNRS, UMR 6174, FEMTO Inst,Appl Mech Dept, 24 Chemin Epitaphe, F-25000 Besancon, France
[4] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
来源：
RSC ADVANCES | 2016年 / 6卷 / 73期
关键词：
BISPHENOL-A; RENEWABLE RESOURCES; BIOBASED POLYMERS; VANILLIN; BEHAVIOR; MONOMER; BIOMASS; ACID; PROGRESS; BLENDS;
D O I：
10.1039/c6ra15200g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel lignin-based synthon, diglycidylether of iso-eugenol (DGE-isoEu) is used as a prepolymer for the preparation of thermosetting resins. DGE-isoEu is synthesized in a two-step procedure with a satisfactory yield from bio-based iso-eugenol (isoEu, 2-methoxy-4-(1-propenyl)phenol) catalytically fragmented from lignin in an organosolv process. DGE-isoEu was fully characterized by NMR, MS and FTIR. Curing of the DGE-isoEu monomer has then been investigated in the presence of several carboxylic acid derivatives hardeners. The thermal and mechanical properties of each material were recorded showing, in particular, a high T-g and instantaneous modulus values in the range of 78-120 degrees C and 4.6-5.5 GPa, respectively. The lignin derived new materials give very attractive thermo-mechanical properties comparable to that of common BPA-containing epoxy resins.
引用
收藏
页码：68732 / 68738
页数：7
相关论文
共 32 条
[1]   Biobased Thermosetting Epoxy: Present and Future [J].
Auvergne, Remi ;
Caillol, Sylvain ;
David, Ghislain ;
Boutevin, Bernard ;
Pascault, Jean-Pierre .
CHEMICAL REVIEWS, 2014, 114 (02) :1082-1115
[2]   Glycerin as a renewable feedstock for epichlorohydrin production. The GTE process [J].
Bell, Bruce M. ;
Briggs, John R. ;
Campbell, Robert M. ;
Chambers, Susanne M. ;
Gaarenstroom, Phil D. ;
Hippler, Jeffrey G. ;
Hook, Bruce D. ;
Kearns, Kenneth ;
Kenney, John M. ;
Kruper, William J. ;
Schreck, D. James ;
Theriault, Curt N. ;
Wolfe, Charles P. .
CLEAN-SOIL AIR WATER, 2008, 36 (08) :657-661
[3]   Conversion of Biomass into Chemicals over Metal Catalysts [J].
Besson, Michele ;
Gallezot, Pierre ;
Pinel, Catherine .
CHEMICAL REVIEWS, 2014, 114 (03) :1827-1870
[4]   Undecylenic acid: A tunable bio-based synthon for materials applications [J].
Bigot, Sandra ;
Daghrir, Mohamed ;
Mhanna, Ali ;
Boni, Gilles ;
Pourchet, Sylvie ;
Lecamp, Laurence ;
Plasseraud, Laurent .
EUROPEAN POLYMER JOURNAL, 2016, 74 :26-37
[5]   Identification of the viscoplastic behavior of a polycarbonate based on experiments and numerical modeling of the nano-indentation test [J].
Bucaille, JL ;
Felder, E ;
Hochstetter, G .
JOURNAL OF MATERIALS SCIENCE, 2002, 37 (18) :3999-4011
[6]   Recent Developments on Biobased Curing Agents: A Review of Their Preparation and Use [J].
Ding, Cheng ;
Matharu, Avtar S. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (10) :2217-2236
[7]  
DUSEK K, 1986, ADV POLYM SCI, V78, P1
[8]   Biobased epoxy thermosets from vanillin-derived oligomers [J].
Fache, Maxence ;
Viola, Arnaud ;
Auvergne, Remi ;
Boutevin, Bernard ;
Caillol, Sylvain .
EUROPEAN POLYMER JOURNAL, 2015, 68 :526-535
[9]   Vanillin, a key-intermediate of biobased polymers [J].
Fache, Maxence ;
Boutevin, Bernard ;
Caillol, Sylvain .
EUROPEAN POLYMER JOURNAL, 2015, 68 :488-502
[10]   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
1234