Synthetic approach to novel azido esters and their utility as energetic plasticizers

Abstract

A modular approach towards a series of novel di azido, tetra azido and hexa azido esters is introduced here.

Understanding the Compatibility of the Energetic Binder PolyNIMMO with Energetic Plasticizers: Experimental and DFT Studies

“…The glass transition temperature (T g )o fs ome mixtures of polymer and plasticizer for the effect of monomer mixture on the T g 's of copolymers systemsh ave been studied in the literature [12,[46][47][48][49][50][51].S ince, the molecular flexibility of the plasticizer is an importantm echanism for altering the brittleness of polymers via plasticization, the implication of this observation can be obtainedf rom the deviations of T g .I n the presented study,t he effect of adding plasticizer was observedi nt ermso fT g of polyNIMMO, which again indicates the compatibility of plasticizers with polyNIMMO. Maximum lowering of T g (À52 8C) was observed in the cases of BuNENA and DEGDN, where as BDNPAh as shown minimum lowering of T g at À38.85 8C ( Figure 2).…”

“…BTTNa nd DNDA-57h ave shown moderate lowering of T g at À46.41 8Ca nd À43.12 8C, respectively,A ll these polyNIM-MO/plasticizer blendsg ive single and reduced glass transition temperatures, which confirms the compatibility of pol-yNIMMO binder with the plasticizers. The reductioni nc ohesive forceso fa ttraction between polymer chains increases chain mobility leading to lowering of T g when plasticizers are incorporated in to the polymer.T hus, it is the plasticizer's function to reducet he forces between the macromoleculesa nd thereby increase chain mobility, reduce viscosity,w hich, in turn, leads to a" softening" or "plasticization" of the polymeric material [12,47,48].T he single T g value for all combinations has further confirms the presenceo fasingle phaseh omogeneouss ystema nd the thermodynamic compatibility of energetic binderw ith energetic plasticizers [41,49,50].…”

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

“…Energetic plasticizers (EPs) are often preferred to inert plasticizers because EPs perform a dual task: retaining reasonable sensitivity, suppressing chemical reactivity, and ensuring a high thermal stability as one approaches oxygen balanced materials, creating the densest material possible. In order to increase the energy level of propellants, energetic groups such as nitro, difluoramino, nitramino, and azido groups are introduced into some molecular structures to design novel high energetic plasticizers …”

“…In order to increase the energy level of propellants, energetic groups such as nitro, difluoramino, nitramino, and azido groups are introduced into some molecular structures to design novel high energetic plasticizers. [6][7][8][9][10][11][12] Organic azido compounds are one of the application prospect energetic plasticizers, which have the advantage of delivering extra energy on combustion combined with minimum smoke and good mixing compatibility with established energetic binders, like glycidyl azide polymer (GAP) and poly(3nitratomethyl-3-methyloxetan) (polyNIMMO). [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.…”

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

“…Their role is to improve the mechanical properties and processability [2] of a composite propellant. In order to increase the energy content of propellants [3], few research groups have ventured to replace inert plasticizers with plasticizers containing energetic groups [2,[4][5][6], with positive heats of explosion [7]. These energetic plasticizers generally contain functional groups such as nitro-, di-fluoramino-, nitramino-, and azido-groups, which contain bonds such as N−N, N−O or N−F, wherein each atom is covalently bonded and has lone pairs of electrons in p-orbitals.…”