Phosphorus-containing epoxy curing agents via imine linkage

被引:52
作者
Lin, Ching Hsuan [1 ]
Hwang, Ting Yu [1 ]
Taso, Ya Ru [1 ]
Lin, Tsung Li [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem Engn, Taichung 402, Taiwan
关键词
diastereomers; epoxy curing agents; imines; phosphorus; thermosets;
D O I
10.1002/macp.200700253
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Two new phenol-type curing agents, (3) and (4), were synthesized by the condensation of 4 (or 2)-hydroxybenzaldehyde and 4-aminophenol, followed by the addition of DOPO to the resulting imine linkage. Two reaction mechanisms, conjugate-addition and carbocation mechanisms, were proposed. The fact that the ratio of the configuration of the two diastereomers depends on the reaction solvent indicates that the carbocation mechanism is the more reasonable one. (3) and (4) served as curing agents for epoxy resins, and the resulting epoxy thermosets exhibited good flame retardancy, and moderate T-g and thermal stability. The nitrogen-phosphorus synergistic effect explains the high flame retardancy.
引用
收藏
页码:2628 / 2641
页数:14
相关论文
共 50 条
[31]   NOVEL SILICON AND PHOSPHORUS-CONTAINING HETEROCYCLES [J].
KARSCH, HH ;
RICHTER, R ;
SCHIER, A ;
HECKEL, M ;
FICKER, R ;
HILLER, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 501 (1-2) :167-177
[32]   Phosphorus-Containing Polycyclic Aromatic Hydrocarbons [J].
Szucs, Rozsa ;
Bouit, Pierre-Antoine ;
Nyulaszi, Laszlo ;
Hissler, Muriel .
CHEMPHYSCHEM, 2017, 18 (19) :2618-2630
[33]   Chemoselective polyalkylations of phosphorus-containing dendrimers [J].
Larre, C ;
Caminade, AM ;
Majoral, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (06) :596-&
[34]   Preparation and properties of halogen-free flame retardant epoxy resins with phosphorus-containing siloxanes [J].
Ding, Jiapei ;
Tao, Zhiqiang ;
Zuo, Xiaobiao ;
Fan, Lin ;
Yang, Shiyong .
POLYMER BULLETIN, 2009, 62 (06) :829-841
[35]   Stable cubic phosphorus-containing radicals [J].
Armstrong, A ;
Chivers, T ;
Parvez, M ;
Boeré, RT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (04) :502-505
[36]   Preparation and properties of halogen-free flame retardant epoxy resins with phosphorus-containing siloxanes [J].
Jiapei Ding ;
Zhiqiang Tao ;
Xiaobiao Zuo ;
Lin Fan ;
Shiyong Yang .
Polymer Bulletin, 2009, 62 :829-841
[37]   Improving the Flame Retardancy of Polybenzoxazines with a Reactive Phosphorus-Containing Compound [J].
Ling, Hong ;
Gu, Yi .
JOURNAL OF MACROMOLECULAR SCIENCE PART B-PHYSICS, 2011, 50 (12) :2393-2404
[38]   Synthesis and application of a benzoxazine-type phosphorus-containing monomer on epoxy/benzoxazine copolymer: Thermal stability and compatibility with liquid oxygen [J].
Peng, Cong ;
Gao, Chang ;
Yuan, Yuhuan ;
Wu, Zhanjun ;
Zhou, Dayu .
POLYMER DEGRADATION AND STABILITY, 2018, 157 :131-142
[39]   Determination of Phosphorus Content in Phosphorus-containing Feed by EDXRF Method [J].
Deng Y. ;
Liu Y. ;
Zhao T. ;
Meng D. ;
Yu G. .
Nongye Jixie Xuebao/Transactions of the Chinese Society for Agricultural Machinery, 2020, 51 (03) :358-362and222
[40]   Synthesis of eugenol-based phosphorus-containing epoxy for enhancing the flame-retardancy and mechanical performance of DGEBA epoxy resin [J].
Zhou, Wei ;
Lv, Dongxuan ;
Ding, Hui ;
Xu, Pengwu ;
Zhang, Congjian ;
Ren, Yuezhang ;
Yang, Weijun ;
Ma, Piming .
REACTIVE & FUNCTIONAL POLYMERS, 2022, 180