Recyclable and Malleable Epoxy Thermoset Bearing Aromatic Imine Bonds

被引：335

作者：

Zhao, Shou ^{[1
]}

Abu-Omar, Mandi M. ^{[1
,2
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[2] Univ Calif Santa Barbara, Dept Chem Engn, Santa Barbara, CA 93106 USA

来源：

MACROMOLECULES | 2018年 / 51卷 / 23期

基金：

美国国家科学基金会;

关键词：

COVALENT ADAPTABLE NETWORKS; REVERSIBLE CROSS-LINKING; SELECTIVE CLEAVAGE; DYNAMIC EXCHANGE; RESIN COMPOSITES; POLYMER NETWORKS; SHAPE-MEMORY; LINKAGES; DENSITY; SOLVENT;

D O I：

10.1021/acs.macromol.8b01976

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

A method for preparing reprocessable epoxy thermoset is presented. The process is composed of synthesis of a bisphenol monomer bridged by an imine bond, glycidylation of the bisphenol, and cross-linking with a hardener to form thermoset. The resulting epoxy thermoset possesses comparable properties to conventional high-performance thermosets made from bisphenol A. However, when treated by a stimulus like acid, temperature, and/or water, the described thermoset exhibits reprocessability. Degradation and recycling involve hydrolysis and re-formation of imine bonds; reshaping and repairing of the thermoset are realized through imine exchange reactions. All the described processes require no metal catalyst, press heating, or additional monomer, which significantly widens thermoset reprocessing.

引用

页码：9816 / 9824

页数：9

共 56 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] Aromatic disulfide crosslinks in polymer systems: Self-healing, reprocessability, recyclability and more [J].

Azcune, Itxaso ;

Odriozola, Ibon .

EUROPEAN POLYMER JOURNAL, 2016, 84 :147-160

[3] Synthesis of a diamine cross-linker containing Diels-Alder adducts to produce self-healing thermosetting epoxy polymer from a widely used epoxy monomer [J].

Bai, Nan ;

Saito, Kei ;

Simon, George P. .

POLYMER CHEMISTRY, 2013, 4 (03) :724-730

[4] Covalent Adaptable Networks: Reversible Bond Structures Incorporated in Polymer Networks [J].

Bowman, Christopher N. ;

Kloxin, Christopher J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (18) :4272-4274

[5] Self-Healing Materials Based on Disulfide Links [J].

Canadell, Judit ;

Goossens, Han ;

Klumperman, Bert .

MACROMOLECULES, 2011, 44 (08) :2536-2541

[6] Metal-Catalyzed Transesterification for Healing and Assembling of Thermosets [J].

Capelot, Mathieu ;

Montarnal, Damien ;

Tournilhac, Francois ;

Leibler, Ludwik .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (18) :7664-7667

[7] Dynamic Covalent Polymer Networks Based on Degenerative Imine Bond Exchange: Tuning the Malleability and Self-Healing Properties by Solvent [J].

Chao, Albert ;

Negulescu, Joan ;

Zhang, Donghui .

MACROMOLECULES, 2016, 49 (17) :6277-6284

[8] Effect of Cross-Link Density on Photoplasticity of Epoxide Networks Containing Allylic Dithioether Moieties [J].

Cook, Wayne D. ;

Schiller, Tara L. ;

Chen, Fei ;

Moorhoff, Cornelis ;

Thang, San H. ;

Bowman, Christopher N. ;

Scott, Timothy F. .

MACROMOLECULES, 2012, 45 (24) :9734-9741

[9] Chemical recycling of glass fiber reinforced epoxy resin cured with amine using nitric acid [J].

Dang, WR ;

Kubouchi, M ;

Sembokuya, H ;

Tsuda, K .

POLYMER, 2005, 46 (06) :1905-1912

[10] An approach to chemical recycling of epoxy resin cured with amine using nitric acid [J].

Dang, WR ;

Kubouchi, M ;

Yamamoto, S ;

Sembokuya, H ;

Tsuda, K .

POLYMER, 2002, 43 (10) :2953-2958

← 1 2 3 4 5 6 →