聚三唑酯树脂的合成及其性能

doi:10.12034/j.issn.1009-606X.218145

过程工程学报 ›› 2019, Vol. 19 ›› Issue (1): 181-188.DOI: 10.12034/j.issn.1009-606X.218145

聚三唑酯树脂的合成及其性能

潘博^1,2 ，王露雨¹，王海军¹，江松达¹，万里强¹，郝旭峰²，田杰²，黄发荣^1*

1. 华东理工大学特种功能高分子材料及相关技术教育部重点实验室，上海 200237 2. 上海复合材料科技有限公司，上海 201112

收稿日期:2018-03-09 修回日期:2018-04-26 出版日期:2019-02-22 发布日期:2019-02-12
通讯作者: 潘博 13120516603@163.com
基金资助:
中央高校基本科研业务费专项基金

Synthesis and properties of poly(triazole ester) resins

Bo PAN^1,2, Luyu WANG¹, Haijun WANG¹, Songda JIANG¹, Liqiang WAN¹, Xufeng HAO², Jie TIAN², Farong HUANG^1*

1. Key Laboratory of Specially Functional Polymeric Materials and Related Technology, Ministry of Education, East China University of Science and Technology, Shanghai 200237, China 2. Shanghai Composites Science and Technology Co., Ltd., Shanghai 201112, China

Received:2018-03-09 Revised:2018-04-26 Online:2019-02-22 Published:2019-02-12
Contact: Bo Pan 13120516603@163.com
Supported by:
the Fundamental Research Funds for the Central Universities

摘要/Abstract

摘要： 通过酯化反应合成丁二酸二炔丙醇酯(DPS)、间苯二甲酸二炔丙醇酯(DPIP)、对苯二甲酸二炔丙醇酯(DPP)，与三官能团叠氮化合物(TAMTMB)反应，制备了3种热固性聚三唑酯(PTAE)树脂，研究了树脂的加工特性、固化行为、树脂固化物的力学性能，制备和表征了T700单向碳纤维增强PTAE树脂复合材料。结果表明，PTAE树脂具有良好的加工性能，可在较低温度(80℃)下固化；固化后的PTAE树脂的玻璃化转变温度(Tg)受主链结构影响，3种树脂的Tg均高于140℃，浇铸体弯曲强度高于170 MPa，T700单向纤维增强PTAE树脂复合材料的常温弯曲强度高于1500 MPa。

关键词: 点击化学反应, 聚三唑, 聚酯, 低温固化, 高力学性能

Abstract: As a new kind of resin system, polytriazole resin has lots of excellent properties, including excellent low temperature curing property, excellent thermal property and low vacuum outgassing rate, which is expected to be used as matrix resins in the application of satellites. In recent years, we have carried out a series of studies on the polytriazole resin systems. Different kinds of polytriazole resin are prepared by changing the chemical structure of azides and alkynyl compounds, reaction degree, main chain or side chain, etc. In this work, we hope to explore the effect of ester groups on curing behavior and thermodynamic properties of polytriazole resin system. Comparing the properties of three new polytriazole resin, we try to find a way for the development of a higher performance polytriazole resin. Dipropargyl succinate (DPS), dipropargyl isophthalate (DPIP) and dipropargyl phthalate (DPP) were synthesized by esterification. Three kinds of poly(triazole ester) (PTAE) resins were designed and synthesized from DPS, DPIP, DPP and multifunctional azides (TAMTMB) through thermal polymerization. T700 carbon fiber-reinforced PTAE composites were prepared and characterized. The processing properties, curing behaviors and mechanical properties of resins were investigated. The results revealed that PTAE resins had good processing properties and could be cured at a low temperature (80℃) . The glass transition temperatures (Tg) of the cured PTAE resins were greatly influenced by the structure of the crosslinked backbone, which was higher than 140℃. Flexural strength of the cured PTAE resins was higher than 170 MPa. Flexural strength of the T700 carbon fiber-reinforced PTAE composited at ambient temperature arrived at over 1500 MPa. From the above results, the introduction of ester group did not change the low temperature curing characteristics of polytriazole resin, and the mechanical properties of polytriazole resin did not change remarkably. Three kinds of poly(triazole ester) were expected to be used as the resin matrix of high performance composites.

Key words: “click&rdquo, reaction, polytriazole, polyester, curing at low temperature, high mechanical properties

潘博王露雨王海军江松达万里强郝旭峰田杰黄发荣. 聚三唑酯树脂的合成及其性能[J]. 过程工程学报, 2019, 19(1): 181-188.

Bo PAN Luyu WANG Haijun WANG Songda JIANG Liqiang WAN Xufeng HAO Jie TIAN Farong HUANG. Synthesis and properties of poly(triazole ester) resins[J]. Chin. J. Process Eng., 2019, 19(1): 181-188.

参考文献

[1]Michael A.Ueber die einwirkung von diazobenzolimid auf acetylendicarbons?uremethylester[J].Advanced Synthesis & Catalysis, 1893, 48(1):94-95
[2]Kolb C, Finn G, Sharpless B.Click chemistry: Diverse chemical function from a few good reactions[J].Angwandte Chemie(International Edition), 2001, 40(11):2004-2021
[3]Rostovtsev V V, Green L G, Fokin V V, et al.A stepwise huisgen cycloaddition process: copper (I)-catalyzed regioselective “ligation” of azides and terminal alkynes[J].Angewandte Chemie, 2002, 114(14):2708-2711
[4]Ackermann L, Potukuchi HK, Landsberg D et al.Copper-catalyzed "click" reactiondirect arylation sequence: modular syntheses of 1,2,3-triazoles[J].Organic Letters, 2008, 10(14):3081-3084
[5] Um J E, Song S G, Yoo P J, et al.Large-scale separation of single-walled carbon nanotubes by electronic type usingclick chemistry[J].[J].Applied Surface Science, 2017, 429:278-283
[6]Liu H, Li S, Zhang M, et al.Facile synthesis of ABCDE‐type H‐shaped quintopolymers by combination of ATRP,ROP,and click chemistry and their potential applications as drug carriers[J].Journal of Polymer Science, Part A: Polymer Chemistry, 2015, 50(22):4705-4716
[7]Lee K S, Park S Y, Moon H C, et al.Thermal stability of ester linkage in the presence of 1,2,3‐Triazole moiety generated by click reaction[J].Journal of Polymer Science, Part A: Polymer Chemistry, 2017, 55(3):427-436
[8]Thibault R J, Takizawa K, Lowenheilm P, et al.A versatile new monomer family: functionalized 4-vinyl-1,2,3-triazoles via click chemistry[J].Journal of the American Chemical Society, 2006, 128(37):12084-12085
[9]Li H, Li L, Wu H, et al.Ferrocene-based poly(aroxycarbonyltriazole)s: synthesis by metal-free click polymerization and use as precursors to magnetic ceramics[J].Polymer Chemistry, 2013, 4(22):5537-5541
[10] Tang J, Wan L, Zhou Y, et al.Strong and efficient self-healing adhesives based on dynamic quaternization cross-links[J][J]..Journal of Materials Chemistry A, 2017, 5: 21169-21177
[11]Ye L, Wan L, Huang F.A class of polytriazole metallogels via CuAAC polymerization: preparation and properties[J].New Journal of Chemistry, 2017, 41(11):4424-4430
[12]Li Y, Zhou H, E Y, et al.Synthesis and characterization of a new series of rigid polytriazole resins[J].Designed Monomers & Polymers, 2013, 16(6):556-563
[13] 刘强, 万里强, 张路路, 等.聚三唑/石墨烯复合材料的制备与性能研究[J][J].热固性树脂, 2017, 1:33-38
[14]Liu Q, Wan L Q, Zhang L, et al.Preparation and properties of polytriazole/graphene composites[J].[J].Thermosetting Resin, 2017, 1:33-38
[15]Xu Z, Du L, Wan L, et al.Synthesis and characterization of a novel thermostable polyether-based elastomeric polytriazole via click reaction[J].Soft Materials, 2013, 11(3):254-260
[16]Huang J, Wan L, Zhang J, et al.Synthesis and characterization of a novel silicon-containing polytriazole resin[J].Journal of Applied Polymer Science, 2009, 114(3):1725-1730
[17] Xu Z, Du L, Wan L, et al.Synthesis and characterization of a novel linear benzoxazine-containing polytriazole via metal-free click reaction and its self-crosslinking behavior[J][J].Advanced Materials Research, 2012, 557-559:557-559
[18]E Y, Wan L, Huang F, et al.New heat-resistant polytriazole adhesives: investigation of adhesion of polytriazole resins to metals[J].Journal of Adhesion Science & Technology, 2013, 27(16):1767-1777
[19]Nagao Y, Takasu A.Click polyester: synthesis of polyesters containing triazole units in the main chain by Click chemistry and improved thermal property[J].Macromolecular Rapid Communications, 2009, 30(3):199-203
[20]Katritzky A, Meher N, Hanci S, et al.Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes[J].Journal of Polymer Science, Part A: Polymer Chemistry, 2010, 46(1):238-256

聚三唑酯树脂的合成及其性能

Synthesis and properties of poly(triazole ester) resins

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