Green Colorants Based on Energetic Azole Borates

Glück, Johann; Klapötke, Thomas M.; Rusan, Magdalena; Stierstorfer, Jörg

doi:10.1002/chem.201403451

Cited by 11 publications

(9 citation statements)

References 38 publications

(76 reference statements)

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“…A novel family of N–boron functionalized nitroazole-based energetic salts was studied for pyrotechnic applications (Scheme b), which illustrate their promising performance as green colorants. In contrast to the environmentally hazardous barium(II) nitrate-based pyrotechnic formulations, these energetic azole borates are potential candidates for less-toxic green pyrotechnic colorants.…”

Section: Synthesis Of High-energy Density Materials Involving An N–ha...mentioning

confidence: 99%

“…Earlier we reported an effective approach to azolium poly(1,2,4-triazolyl)borate salts (Scheme 18a) 58 including some nitrogen-rich compounds exhibiting favorable stabilities, densities, viscosities, and ignition delay times, which might be potential propellant fuels for replacement of toxic hydrazine. 59,60 A novel family of N−boron functionalized nitroazolebased energetic salts was studied for pyrotechnic applications (Scheme 18b), 61 which illustrate their promising performance as green colorants. In contrast to the environmentally hazardous barium(II) nitrate-based pyrotechnic formulations, these energetic azole borates are potential candidates for less-toxic green pyrotechnic colorants.…”

Section: ■ Introductionmentioning

confidence: 99%

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Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

2015

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Nitrogen-rich heterocycles represent a unique class of energetic frameworks featuring high heats of formation and high nitrogen content, which have generated considerable research interest in the field of high energy density materials (HEDMs). Although traditional C-functionalization methodology of aromatic hydrocarbons has been fully established, studies on N-functionalization strategies of nitrogen-containing heterocycles still have great potential to be exploited by virtue of forming diverse N-X bonds (X = C, N, O, B, halogen, etc.), which are capable of regulating energy performance and the stability of the resulting energetic compounds. In this sense, versatile N-functionalization of N-heterocyclic frameworks offers a flexible strategy to meet the requirements of developing new-generation HEDMs. In this Account, the role of strategic N-functionalization in designing new energetic frameworks, including the formation of N-C, N-N, N-O, N-B and N-halogen bonds, is emphasized. In the family of N-functionalized HEDMs, energetic derivatives, by virtue of forming N-C bonds, are the most widely used type due to the good nucleophilic capacity of most heterocyclic backbones. Although introduction of carbon tends to decrease energetic performance, significant improvement in material sensitivity makes this strategy attractive for safety concerns. More importantly, most "explosophores" can be readily introduced into the N-C linkage, thus providing a promising route to various HEDMs. Formation of additional N-N bonds typically gives rise to higher heats of formation, implying the potential enhancement in detonation performance. In many cases, the increased hydrogen bonding interactions within N-N functionalized heterocycles also improve thermal stability accordingly. Introduction of a single N,N'-azo bridge into several azole moieties leads to an extended nitrogen chain, demonstrating a new strategy for designing high-nitrogen compounds. The strategy of N-O functionalization has become an increasingly efficient tool for exploring new HEDMs with both high energy and low sensitivity. As a highly dense building block, introduction of oxygen not only improves density significantly but also gives rise to a better oxygen balance. Furthermore, the N-O functionalized strategy is highly suitable for a broad variety of N-heterocycles including five-membered azoles and six-membered azines. Newly explored N-halogen and N-B functionalization strategies have endowed the resulting HEDMs with some new energetic characteristics. Typical examples include the N-halogenated fused triazole and FOX-7 as potential hypergolic oxidizers with very short ignition delay times. In addition, some exploratory studies of N-B functionalized heterocycles have expanded energetic applications as hypergolic ionic liquids, green pyrotechnic colorants, and high-oxygen carriers. Overall, flexible N-functionalization methodologies involving different N-X bond formation have not only provided an efficient approach to diverse energetic ingredients but also expanded...

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Section: Synthesis Of High-energy Density Materials Involving An N–ha...mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

2015

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“…A lot of work was done to deepen the understanding of the underlying phenomena during the 1950s to 1960s , though without affecting much of the products already in use. The main driving force in development in recent years has been focused on eliminating certain unwanted ingredients and to a certain degree improving flame color depth .…”

Section: Introductionmentioning

confidence: 99%

The Performance of Red Flare Pyrotechnic Compositions Modified with Gas Generating Additives

Juknelevicius

Alenfelt

Ramanavičius

2020

Propellants Explo Pyrotec

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In this work, an effective, but still not well‐explored area of red flare pyrotechnic formulations was investigated. High magnesium content (40–60 % w.t.) and the presence of conventional gas generating materials were the specific features of formulations explored herein. Such illuminant compositions possessed a low burning rate and high specific luminous intensity. The investigated system was based on strontium nitrate, rounded magnesium powder, chlorinated rubber, binder and gas generating additives. Emission spectra, light intensity and burning time have been measured during the experiment and recalculated to the specific luminous intensity and color purity. Additives in the form of 2‐cyanoguanidine, Melamine, Azodicarbonamide, Calcium resinate, Shellac, Strontium oxalate, Lactose, Dextrin, Phenolic resin, Lignin sulfonate, 5‐aminotetrazole, Urea, Guanidinium nitrate (GN), Hexamine and Sulfur were evaluated in Mg‐rich flare compositions. The use of GN was studied more carefully as an exceptionally efficient additive that increased the flares light intensity by 60 %, in comparison to the standard GN‐free composition, while maintaining high color purity of 90–97 %.

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“…[5d], A possible solution for “greener“ pyrotechnics is the application of high‐nitrogen compounds. [5a], [5b], High‐nitrogen energetic salts derive their energy from their high positive heat of formation upon release of non‐toxic dinitrogen gas as a main combustion product . This is beneficial to achieve brilliant colors and a good color performance…”

Section: Introductionmentioning

confidence: 99%

Metal Salts of 3,3′‐Diamino‐4,4′‐dinitramino‐5,5′‐bi‐1,2,4‐triazole in Pyrotechnic Compositions

Glück

Gospodinov

Klapötke

et al. 2018

Zeitschrift anorg allge chemie

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Green Colorants Based on Energetic Azole Borates

Cited by 11 publications

References 38 publications

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

The Performance of Red Flare Pyrotechnic Compositions Modified with Gas Generating Additives

Metal Salts of 3,3′‐Diamino‐4,4′‐dinitramino‐5,5′‐bi‐1,2,4‐triazole in Pyrotechnic Compositions

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