Synthesis Methods of Saccharin-6-Carboxylic Acid Triglyceride
Abstract
One and two-step methods for the synthesis of saccharin-6-carboxylic acid triglyceride were studied. The reesterification reactions of 2-hydroxypropyl-1,3-bis-ethersulfoimide of this acid and glycerol with some aliphatic saccharin6-carboxylic acid esters were carried out. The resulting products are characterized by elemental analysis and IR spectroscopy and size exclusion chromatography. It was found that when using a two-step method, the end product is obtained with the highest yield (85%).
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Introduction
Aromatic and aliphatic polysulfoimides (polysaccharines) are sulfur-containing analogues of polyimides. Polysulfoimides differ from polyimides by the presence in the imide cycle of one carbonyl (C=O) and one sulfonyl (-SO2-) group [1]. These polymers possess high thermal stability (500-650°C), solubility, stability to radiation and light, acid and alkaline hydrolysis [2].
Polymer composite materials made based on compounds which contain epoxy and sulfoimide groups have high physicomechanical and thermal properties [3]. Epoxyimide oligomers possess the highest heat resistance, in which glycidyl groups are directly adjacent to the imide cycle [4]. In this regard, they are widely used as high-strength and heat-resistant construction materials.
It is known that epoxy resins, in particular dianes, are used after the introduction of hardening agents. Considering that the majority of epoxy composite materials in hardened form have brittleness that impairs the physicomechanical properties of the obtained material, often compounds with a plasticizing property are introduced into the composition, for example, esters and compounds containing groups capable of hardening by epoxy groups of the resin [5-7].
In this regard, given the advantages of polysaccharines, there is a need to develop effective methods for the synthesis of new monomers (prepolymers) based on saccharin monocarboxylic acids [8]. There is evidence of the use of diimidodicarboxylic acids as monomers in the synthesis of polyetherimides. The properties of these polymers can change due to the introduction of various fragment groups into their molecule [9, 10].
There is data in the literature on the synthesis of diesterodisulfoimides by reesterification of the methyl ester of saccharinmonocarboxylic acids with aliphatic and aromatic glycols [11, 12].
This paper describes one- and two-step methods for the synthesis of saccharin-6-carboxylic acid triglyceride.
The aim of the work is the synthesis of new monomers based on saccharin-6-carboxylic acid, for their further use in the preparation of highly branched and net heat-resistant polymers.
Conclusion
Thus, based on the research, the following conclusions can be drawn. One- and two-step methods for the synthesis of saccharin-6-carboxylic acid triglyceride have been developed; it was found that in the synthesis of triglyceride by the twostep method, the end product is obtained with the highest yield – 85%; the synthesized saccharin-6-carboxylic acid triglyceride is of interest for its use as a monomer in the production of highly branched and cross-linked sulfoimidecontaining polymers and epoxy resins, and also as a hardener-plasticizer of industrial epoxy resins.