Synthesis and Properties of Asymmetric Polyamidosulfoimides on the Basis of Dichloroanhydrides of Saccharin-5-Carboxylic Acids and Aliphatic Diamines
Abstract
By polycondensation of dichloroanhydride of saccharin-5-carboxylic acids with aliphatic diamines in dimethylacetamide at room temperature the asymmetric polyamidosulfoimide has been synthesized. The influence of nature of solvent, concentration of the initial reagents and reaction temperature on value of characteristic viscosity and also on solubility, thermal stability and deformation-strength properties of the synthesized polyamidosulfoimides has been investigated. It has been elucidated that a growth of a quantity of methylene groups in the polymer leads to the improvement of solubility of the polymers in dimethylformamide and dimethylacetamide, but at the same time leads to the relative deterioration of thermal stability.
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Introduction
In recent years, in the field of chemistry of high-molecular compounds, special attention is paid to the development of methods for the synthesis of high-thermostable polymers [1]. The aromatic and aliphatic polysulfoimides (polysaccharins) are the sulphur-containing analogs of polyimides. The polysulfoimides are differed from polyimides by availability of one carbonyl (С=О) and one sulfonyl (-SO2-) group in imide cycle. These polymers possess high thermal stability (500-650˚С), solubility, resistance to radiation, light, acidic and alkaline hydrolysis.
In this connection, taking into account the advantages of polysaccharins, it is appeared a need of development of the effective methods for synthesis of new monomers on the basis of saccharin-monocarboxylic acids.
It was known that due to solubility in amide solvents and sufficiently high mechanical, thermal and dielectrical properties the polyamidoimides find a wide application in microelectronics in creation of foil-coated dielectrics as the protective coatings. The polyamidoimides prepared on the basis of dichloroanhydrides of dicarboxylic acids possess sufficiently high molecular weight and are differed with thermal stability and also good physical-mechanical properties [2]. There are data about development of method of synthesis of the polyamidoimides containing side carboxyl groups by interaction of imidecontaining dichloroanhydrides of dicarboxylic acids with aromatic diamines [3]. We have previously synthesized the symmetric polyamidosulfoimides on the basis of dichloranhydride of saccharin-6-carboxylic acid and aliphatic and also aromatic diamines [4-6].
The purpose of work – synthesis of asymmetric polyamidosulfoimides (PASI) on the basis of dichloranhydrides of saccharin-5-carboxylic acids and aliphatic diamines.
Conclusion
By polycondensation of dichloroanhydride of saccharin-5-carboxylic acids with aliphatic diamines in dimethylacetamide at room temperature the asymmetric polyamidosulfoimide has been synthesized. It has been established the optimal condition of synthesis of the polyamidosulfimides: solvent – DMAA, acceptor – sodium carbonate, synthesis temperature – 20С, reagents concentration – 10-12 mass%.
It has been elucidated by methods of DTA and TGA that on thermal stability the prepared compounds depending on used diamine are located in the following series: ethylene diamine>tetramethylene diamine>hexamethylenje diamine. It has been established that the synthesized polyamidosulfoimides possess high physical-mechanical indices. On exploitation indices they are on the level of the industrial polyamidoimides. It has been revealed that the growth of quantity of methylene groups in the polymer leads to the improvement of the polymer solubility in aprotonic solvents, but also to the relative deterioration of their thermal stability.