New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties
An N-glycidyl-5-aminotetrazole homopolymer was synthesized herein by nucleophilic substitution of 5-aminotetrazole heterocycles for chlorine atoms in poly-(epichlorohydrin)-butanediol. Copolymers of N-glycidyl-5-aminotetrazole and glycidyl azide with a varied ratio of energetic elements were synthes...
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MDPI AG
2022-10-01
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| Online Access: | https://www.mdpi.com/1996-1944/15/19/6936 |
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| author | Gennady T. Sukhanov Konstantin K. Bosov Yulia V. Filippova Anna G. Sukhanova Irina A. Krupnova Ekaterina V. Pivovarova |
| author_facet | Gennady T. Sukhanov Konstantin K. Bosov Yulia V. Filippova Anna G. Sukhanova Irina A. Krupnova Ekaterina V. Pivovarova |
| author_sort | Gennady T. Sukhanov |
| collection | DOAJ |
| description | An N-glycidyl-5-aminotetrazole homopolymer was synthesized herein by nucleophilic substitution of 5-aminotetrazole heterocycles for chlorine atoms in poly-(epichlorohydrin)-butanediol. Copolymers of N-glycidyl-5-aminotetrazole and glycidyl azide with a varied ratio of energetic elements were synthesized by simultaneously reacting the 5-aminotetrazole sodium salt and the azide ion with the starting polymeric matrix. The 5-aminotetrazole-based homopolymer was nitrated to furnish a polymer whose macromolecule is enriched additionally with energy-rich terminal ONO<sub>2</sub> groups and nitrate anions. The structures of the synthesized polymers were characterized by <sup>1</sup>H and <sup>13</sup>C NMR and IR spectroscopies, elemental analysis and gel-permeation chromatography. The densities were experimentally measured, and thermal stability data were acquired by differential scanning calorimetry. The insertion of aminotetrazole heterocycles into the polymeric chain and their modification via nitration provides an acceptable thermal stability and a considerable enhancement in density and nitrogen content compared to azide homopolymer GAP. By the 1.3-dipolar cycloaddition reaction, we demonstrated the conceptual possibility of preparing spatially branched, energy-rich polymeric binders bearing 5-aminotetrazole and 1,2,3-triazole heterocycles starting from the plasticized azide copolymers. The presence of the aforesaid advantages makes the reported polymers attractive candidates for use as a scaffold of energetic binders. |
| first_indexed | 2024-03-09T21:29:51Z |
| format | Article |
| id | doaj.art-b952cdc78e1149ddb4d57258806a98b4 |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-09T21:29:51Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-b952cdc78e1149ddb4d57258806a98b42023-11-23T20:59:15ZengMDPI AGMaterials1996-19442022-10-011519693610.3390/ma15196936New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and PropertiesGennady T. Sukhanov0Konstantin K. Bosov1Yulia V. Filippova2Anna G. Sukhanova3Irina A. Krupnova4Ekaterina V. Pivovarova5Laboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, RussiaLaboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, RussiaLaboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, RussiaLaboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, RussiaLaboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, RussiaLaboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, RussiaAn N-glycidyl-5-aminotetrazole homopolymer was synthesized herein by nucleophilic substitution of 5-aminotetrazole heterocycles for chlorine atoms in poly-(epichlorohydrin)-butanediol. Copolymers of N-glycidyl-5-aminotetrazole and glycidyl azide with a varied ratio of energetic elements were synthesized by simultaneously reacting the 5-aminotetrazole sodium salt and the azide ion with the starting polymeric matrix. The 5-aminotetrazole-based homopolymer was nitrated to furnish a polymer whose macromolecule is enriched additionally with energy-rich terminal ONO<sub>2</sub> groups and nitrate anions. The structures of the synthesized polymers were characterized by <sup>1</sup>H and <sup>13</sup>C NMR and IR spectroscopies, elemental analysis and gel-permeation chromatography. The densities were experimentally measured, and thermal stability data were acquired by differential scanning calorimetry. The insertion of aminotetrazole heterocycles into the polymeric chain and their modification via nitration provides an acceptable thermal stability and a considerable enhancement in density and nitrogen content compared to azide homopolymer GAP. By the 1.3-dipolar cycloaddition reaction, we demonstrated the conceptual possibility of preparing spatially branched, energy-rich polymeric binders bearing 5-aminotetrazole and 1,2,3-triazole heterocycles starting from the plasticized azide copolymers. The presence of the aforesaid advantages makes the reported polymers attractive candidates for use as a scaffold of energetic binders.https://www.mdpi.com/1996-1944/15/19/6936energetic polymers5-aminotetrazoleGAPnucleophilic substitutionnitration |
| spellingShingle | Gennady T. Sukhanov Konstantin K. Bosov Yulia V. Filippova Anna G. Sukhanova Irina A. Krupnova Ekaterina V. Pivovarova New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties Materials energetic polymers 5-aminotetrazole GAP nucleophilic substitution nitration |
| title | New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties |
| title_full | New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties |
| title_fullStr | New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties |
| title_full_unstemmed | New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties |
| title_short | New 5-Aminotetrazole-Based Energetic Polymers: Synthesis, Structure and Properties |
| title_sort | new 5 aminotetrazole based energetic polymers synthesis structure and properties |
| topic | energetic polymers 5-aminotetrazole GAP nucleophilic substitution nitration |
| url | https://www.mdpi.com/1996-1944/15/19/6936 |
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