Citation: YOU Geyun, FENG Bin, FAN Fangfang, YANG Changjie, LIANG Cong. Synthesis of Phosphorus-Nitrogen Synergistic Flame-Retardant Compounds with Imide Structure and Their Flame Retardant Effect on Epoxy Resin[J]. Chinese Journal of Applied Chemistry, ;2020, 37(2): 144-154. doi: 10.11944/j.issn.1000-0518.2020.02.190213 shu

Synthesis of Phosphorus-Nitrogen Synergistic Flame-Retardant Compounds with Imide Structure and Their Flame Retardant Effect on Epoxy Resin

Key Laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi, College of Chemistry and Environment Engineering, Baise University, Baise, Guangxi 533000, China

Corresponding author: YOU Geyun, yougeyun1988@163.com
Received Date: 1 August 2019
Revised Date: 29 September 2019
Accepted Date: 28 October 2019

Fund Project: Supported by the Natural Science Foundation of Guangxi Province(No.2016GXNSFBA380072), the Middle-Aged and Young Teachers′ Basic Ability Promotion Project of Guangxi(No.2017KY0713), and the Science Research Foundation of Baise University(No.2015KAN05)the Natural Science Foundation of Guangxi Province 2016GXNSFBA380072the Middle-Aged and Young Teachers′ Basic Ability Promotion Project of Guangxi 2017KY0713the Science Research Foundation of Baise University 2015KAN05

Figures(6)

Two novel phosphate-imine bifunctional flame-retardant compounds (FR:N¹, N⁴-bis{[4-(5, 5-dimethyl-2-oxide-1, 3, 2-dioxaphosphinan-2-yl)oxy]benzylidene}benzene-1, 4-diamine(PNB); N¹, N²-bis{[4-(5, 5-dimethyl-2-oxide-1, 3, 2-dioxaphosphinan-2-yl)oxy]benzylidene}ethane-1, 2-diamine(PNE)) were synthesized via aldehyde amine condensation reaction using 4-(5, 5-dimethyl-1, 3-dioxygen heterocyclic phosphoryl) benzaldehyde (PCHO), p-phenylene diamine and ethylenediamine as raw materials, respectively. FRs were applied on a bisphenol-A diglycidyl ether type epoxy resin (DGEBA) cured by 4, 4'-diaminodiphenylsulfone (DDS) and the flame retarded mechanism was studied. The results showed that the introduction of FR greatly improved the char residues (R_c) of DGEBA/DDS at 700℃ and enhanced the flame retardant properties of epoxy resin systems. PNE with ethylene diamine unit presented a better flame retardant performance than PNB with p-phenylene diamine unit. With 1.5% phosphorus content, PNE-1.5/DGEBA/DDS could obtain R_c of 35.1% in nitrogen atmosphere and 14.4% in air, respectively, and a limiting oxygen index(LOI) value of 33.2%, reaching UL-94 Ⅴ-0 grade. At the same time, PNE-1.5/DGEBA/DDS maintained the bending strength and more than 76% of the impact strength compared to DGEBA/DDS, which is significantly superior to PNB-1.5/DGEBA/DDS. Analysis of flame retardant results showed that FR presented a comprehensive mechanism of condensed phase, gas phase and phosphorus-nitrogen synergistic effect in DGEBA/DDS system. In conclusion, phosphate-imine bifunctional compounds FR have excellent flame retardancy for epoxy resin systems and have potential applications.
- imide,
- phosphorus-nitrogen synergy,
- flame retardant,
- epoxy resin
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