巯基-烯点击反应制备含不同功能端基的环三磷腈衍生物

王海侨,刘卫卫,叶俊,乔志,李琦,李效玉*

化工新型材料 ›› 2019, Vol. 47 ›› Issue (3) : 108 -112.

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化工新型材料 ›› 2019, Vol. 47 ›› Issue (3) : 108-112.
新材料与新技术

巯基-烯点击反应制备含不同功能端基的环三磷腈衍生物

    王海侨,刘卫卫,叶俊,乔志,李琦,李效玉*
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Preparation of cyclotriphosphazene derivative with different functional terminal groups via thiol-ene click

  • Wang Haiqiao ,Liu Weiwei ,Ye Jun ,Qiao Zhi,Li Qi ,Li Xiaoyu
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摘要

环三磷腈衍生物在阻燃添加剂、生物医药材料、电解液和液压油等领域有着广泛的应用前景,因此,近年来环三磷腈衍生物的功能化改性研究受到越来越多的关注。利用巯基化合物与丁香酚氧基环三磷腈在紫外光下的巯基-烯点击反应,制备了末端分别含有烷基、羟基和羧基等不同功能基团的系列环三磷腈衍生物,研究了反应时间、投料比和巯基反应物所带的端基官能团对反应的影响规律。发现此方法具有反应条件温和,反应时间短(≤30min),反应产率高(≥95%),可批量制备的优点;同时还可以将具有不同结构的功能基团定量的引入到目标产物中。对产物的热性能表征结果表明,C—S键的引入降低了环三磷腈衍生物的热稳定性,但产物的起始分解温度依然保持在300℃以上;末端基团的种类对产物的热稳定性和受热分解后的残炭量有一定影响。

Abstract

Cyclotriphosphazene derivatives have drawn increasing attention because they have significant potential applications in flame-retardant additives,biomedical material,electrolyte and hydraulic fluid,etc.A series of cyclotriphosphazene derivatives with different functional terminal groups,such as alkyl,hydroxyl or carboxyl,were synthesized through thiol-ene click reaction between thiol compounds with different functional terminal groups and cyclotriphosphazene with eugenol oxygen groups under the UV light.The effect of reaction times,feed ratios and terminal groups of thiol reactants were studied.The results revealed that this strategy for preparing cyclotriphosphazene derivatives possessed many advantages,such as mild reaction conditions,fast reaction times (≤30min),high reaction yields (≥95%) and easy to mass-producton.Moreover,the functional terminal groups can be introduced quantitatively.The measurement on the thermal properties demonstrated that the introduced C—S bond reduced the thermal stability of targeted produces,but the onset decomposition temperature still keeps on above 300℃.Moreover,the kinds of terminal groups affected the thermal stability and the char forming of products.

关键词

巯基-烯点击反应 / 环三磷腈衍生物 / 末端功能化 / 热分解

Key words

thiol-ene click reaction / cyclotriphosphazene derivative / terminal functionalization / thermolysis

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巯基-烯点击反应制备含不同功能端基的环三磷腈衍生物[J]. 化工新型材料, 2019, 47(3): 108-112 DOI:

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参考文献

[1] 元东海,唐安斌,黄杰.环磷腈阻燃剂的开发与应用研究进展[J].化工新型材料,2012,40(4):17-19.
[2] Liu H,Wang X D,Wu D Z.Novel cyclotriphosphazene-based epoxy compound and its application in halogen-free epoxy thermosetting systems:synthesis,curing behaviors,and flame retardancy[J].Polymer Degradation and Stability,2014(5),103:96-112.
[3] 游歌云,程之泉,彭浩,等.环三磷腈类阻燃剂的合成及应用研究进展[J].应用化学,2014,31(9):993-1009.
[4] 贺攀,胡玲霞,方仕江.含硅环磷腈的合成与表征研究[J].化工新型材料,2014,42(2):149-151.
[5] Sun J,Wang X D,Wu D Z.Novel spirocyclic phosphazene-based epoxy resin for halogen-free fire resistance:synthesis,cuing behaviors,and flammability characteristics[J].ACS Applied Materials & Interfaces,2012,4(8):4047-4061.
[6] Liu J,Tang J Y,Wang X D,et al.Synthesis,characterization and curing properties of a novel cyclolinear phosphazene-based epoxy resin for halogen-free flame retardancy and high performance[J].RSC Advances,2012,2(13):5789-5799.
[7] 李晓丽.环三磷腈衍生物制备与自组装行为及其药物负载应用研究[D].哈尔滨:东北林业大学,2012,23-28.
[8] 刘榛,尚玉明,王莉,等.环三磷腈在锂离子电池中的应用研究现状[J].储能科学与技术,2016,5(2):181-187.
[9] 高维全,唐淑娟,孙德,等.羟基环三磷腈衍生物阻燃剂的合成和性能研究[J].染整技术,2008,30(9):11-14.
[10] 凌雅静.基于环三磷腈羧酸类配体构筑的金属-有机骨架化合物的合成、结构及性能研究[D].金华:浙江师范大学,2016,17-42.
[11] Kolb H C,Finn M G,Sharpless K B.C1ick chemistry:diverse chemical function from a few good reactions[J].Angewandte Chemie International Edition Angew,2001,40(11):2004-2021.
[12] 徐源鸿,熊兴泉,蔡雷,等.巯基-烯点击化学[J].化学进展,2012,24(3):385-394.
[13] Zhang X F,Akram R,Zhang S K,et al.Hexa(eugenol)cyclotriphosphazene modified bismaleimide resins with unique thermal stability and flame retardancy[J].Reactive and Functional Polymers,2017,113(4):77-84.
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