Synthesis and Characterization of First Generation Dendritic Azidoesters

Pant, Chandra Shekhar; Wagh, R. M.; Nair, J. K.; Gore, G. M.; Thekkekara, Mukundan; Venugopalan, S.

doi:10.1002/prep.200700050

Cited by 23 publications

(19 citation statements)

References 6 publications

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“…Thus, researchers have also begun the preliminary study of hyperbranched energetic polymers. In previous work, azido‐terminated dendritic esters were synthesized in a four‐step process as new energetic additives . On this basis, Wang and co‐workers prepared azide‐terminated hyperbranched polyesters using a three‐step process, and optimized the reaction conditions .…”

Section: Introductionmentioning

confidence: 99%

“…In previous work, azido-terminated dendritic esters were synthesized in a four-step process as new energetic additives. 29,30 On this basis, Wang and co-workers prepared azide-terminated hyperbranched polyesters using a three-step process, and optimized the reaction conditions. 31,32 Malkov et al obtained nitrogen-rich hyperbranched polymers -poly( 1-3 triazole 1,3,5 triazine)s -through 'click' chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…36 Hence, it is an ideal candidate as a hyperbranched structure for hybridization with linear energetic materials. Inspired by the literature, 17,22,29,30,35,36,38 GAPs copolymerized with hyperbranched polyether are a desirable alternative. Therefore, much more efforts should be made to improve this promising method in the field of energetic materials.…”

Section: Introductionmentioning

confidence: 99%

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Core–shell type multi‐arm azide polymers based on hyperbranched copolyether as potential energetic materials in solid propellants

Zhang

et al. 2017

Polymer International

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A series of novel multi-arm azide copolymers (POGs) with the same hyperbranched poly[3-ethyl-3-(hydroxymethyl)oxetane] core (PEHO-c) and different content of linear glycidyl azide polymer shell (GAP-s) have been synthesized by sequential cationic ring-opening polymerization and azidation. Detailed structural information of these copolyethers was deduced from Fourier transform infrared, 1 H NMR and inverse gated decoupled 13 C NMR spectroscopies, matrix-assisted laser desorption ionization time-of-flight mass spectrometry, gel permeation chromatography and elemental analysis. The molecular weight of POG having GAP-s and PEHO-c with a molar ratio 14.95:1 (R s/c ) was around 31 000 g mol −1 , far above that of linear GAP (around 4000 g mol −1 ). The apparent viscosity and glass transition temperature (−51 to −23 ∘ C) decreased first and then slightly increased with increasing molecular weight. Thermal analysis revealed that all the obtained POGs exhibited excellent resistance to thermal decomposition up to 220 ∘ C. Moreover, the energetic properties, investigated using oxygen bomb calorimetric measurements, indicated that the enthalpy of formation of the POGs was higher than that of general linear GAP, but similar to that of branched GAP under reasonable R s/c . The compatibilities of the POGs with common materials used in solid propellants were studied using differential scanning calorimetry and the results indicated that the POGs had good compatibility with these materials.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Core–shell type multi‐arm azide polymers based on hyperbranched copolyether as potential energetic materials in solid propellants

Zhang

et al. 2017

Polymer International

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“…Consequently, we explored the synthesis of a variety of azido-esters by using a simple and easy protocol such as esterification [12] and azidation (Scheme 1) with non-hazardous and low cost reagents. These molecules (1a-6a) have di-, tri-or tetra-azido groups along with the aliphatic or bicyclic esters ( Figure 2).…”

Section: -6 1a-6amentioning

confidence: 99%

Design and Evaluation of the Thermal Properties of Di-, Tri- and Tetra-Azido-Esters

Kumar¹,

Kumar²,

Yamajala³

et al. 2017

Cent. Eur. J. Energ. Mater.

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A group of polycyclic and aliphatic azido-esters (as energetic plasticizers) have been synthesized by simple synthetic routes and their molecular structures were confirmed by spectroscopic techniques. In addition, their thermal and rheological properties have been determined utilizing DSC, TGA, viscosity, and contact angle. Computational studies of these plasticizers have been performed by means of DFT (B3LYP/6-31G*) to estimate possible stable structures, energies, heat of formation, bond dissociation energies, IR and NMR spectra etc. Their compatibility with glycidyl azide polymer (GAP) binder was studied to explore their applicability in propellants. All of these molecules are novel and have been synthesized with the possibility of scale up.

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“…[13][14][15][16][17] Compared with general organic azido compounds, energetic azido ester plasticizers provided with better lubricant effect and thermal stability, lower sensitivity and glass transition temperature. [18][19][20] Previous work have reported the synthesis and properties of some energetic azido ester plasticizers such as bis(2-azido-1-(azidomethyl)ethyl) malonate (BAEM), bis(2-azido-1-(azidomethyl)ethyl) glutarate (BAEG), 1,3-bis(azidoacetoxy)-2,2-bis-(azidomethyl)propane (BABAMP) and triazidopentaerythrite acetate (TAP-Ac) (Scheme 1). [4,12,[21][22][23][24] However, the most conspicuous drawback of these azido ester plasticizers is their low level of nitrogen content, oxygen balance, density and energy.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer

et al. 2019

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This study reports the synthesis and characterization of a novel azido ester plasticizer, 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition temperature were determined to be 1.326 g ⋅ cm−3, 16 J, 324 N, 235.9 °C and −50.4 °C, respectively. The plasticizing effect of ABAMPA on glycidyl azide polymer (GAP) was calculated by molecular dynamics, the solubility parameter difference value was 1.7(J ⋅ cm−3)0.5, and the glass transition temperature of GAP was reduced from −35 °C to −43 °C when the weight ratio of ABAMPA and GAP was 50 : 50. The new azido ester exhibits high energy, remarkable thermostability and good compatibility with GAP, which indicates that it would have potential application in explosive and propellant formulations.

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Synthesis and Characterization of First Generation Dendritic Azidoesters

Cited by 23 publications

References 6 publications

Core–shell type multi‐arm azide polymers based on hyperbranched copolyether as potential energetic materials in solid propellants

Core–shell type multi‐arm azide polymers based on hyperbranched copolyether as potential energetic materials in solid propellants

Design and Evaluation of the Thermal Properties of Di-, Tri- and Tetra-Azido-Esters

Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer

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