Synthesis of N,N-dimethylaminoalkyl esters of butanoic and pentanoic acids and study of their activity in the polymerization reaction of diglycidyl ethers

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2025-03-25 DOI:10.1007/s11172-025-4512-y

M. A. Barabanov, V. A. Osipova, A. V. Mekhaev, O. V. Koryakova, D. I. Vichuzhanin, S. V. Smirnov, A. V. Pestov

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Abstract

A number of dimethylaminoalkyl esters of butanoic and pentanoic acids were obtained by the acylation reaction of N,N-dimethylaminoalkanols. 3-(Dimethylamino)propyl butanoate, 3-(dimethylamino)ethyl- and 2-(dimethylamino)propyl pentanoates are described for the first time. The structures of all synthesized compounds are confirmed by NMR spectroscopy and elemental analysis. 2-(Dimethylamino)ethyl pentanoate and 3-(dimethylamino)propyl pentanoate are obtained in 66% yield. It was found using the data of DTA, FTIR spectroscopy, as well as taking into account the value of the gel-fraction content in the cured compositions, that with a decrease in the length of the hydrocarbon fragment linked to nitrogen and oxygen atoms, and with an increase in the total nitrogen content in the amino ester molecule, the activity in the epoxy resin curing reaction increases. An assessment of the bonding strength of St3 steel and aluminum alloy D16 with ED-20 epoxy resin cured with amino esters demonstrated that all synthesized compounds provide more effective bonding than the standard polyethylene polyamine hardener.

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丁酸和戊酸N，N-二甲氨基烷基酯的合成及其在二缩水甘油醚聚合反应中的活性研究

通过N，N-二甲氨基醇酰化反应，得到了丁酸和戊酸的二甲基氨基烷基酯。3-（二甲氨基）丙基丁酸盐、3-（二甲氨基）乙基戊酸盐和2-（二甲氨基）丙基戊酸盐均为首次报道。所有合成化合物的结构均经核磁共振波谱和元素分析证实。以66%的收率得到2-（二甲氨基）戊酸乙酯和3-（二甲氨基）戊酸丙酯。利用差热分析（DTA）和傅里叶红外光谱（FTIR）的数据，并考虑到固化产物中凝胶组分的含量，发现随着与氮、氧原子相连的烃片段长度的减少，随着氨基酯分子中总氮含量的增加，环氧树脂固化反应的活性增加。对ED-20环氧树脂与氨基酯固化后的St3钢和D16铝合金的结合强度进行了评估，结果表明，所有合成的化合物都比标准的聚乙烯多胺固化剂具有更有效的结合效果。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.