An Azido Ester Plasticizer, 1,3‐Di(Azidoacetoxy)‐2,2‐Di(Azidomethyl)Propane (PEAA): Synthesis, Characterization and Thermal Properties

Abstract

A polyazido compound, 1,3-di(azidoacetoxy)-2,2-di(azidomethyl)propane (PEAA) was synthesized and identified. Thermal properties of PEAA, such as the glass transition temperature (T g ), differential scanning calorimetry (DSC) and thermogravimetric analysis (DTG) were investigated in detail. Two steps in the course of thermal decomposition of PEAA were observed clearly, and some gases, carbon monoxide, carbon dioxide, nitrogen, hydrocyanic acid, methane and 2-methyl-1,3-butadiene were identified as decomposition products by in situ cell FTIR. The pyrolysis mechanism was also proposed.

Studies on the Effect of a Covalently Bonded PGN Based Reactive Plasticizer on the Thermal Decomposition Behavior of Glycidyl Azide Polymer

“…The M n values of GAP-g-PGN was around 950 g/mol, with a PDI value of 1.9. Considerable data have been produced for the effect of plasticizer on the T g values of polymer systems and have appeared in the literature [20][21][22][23][24]. PTMPGN is a reactive energetic plasticizer.…”

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].…”

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

“…At the rst step, all azido groups decomposed to produce nitrogen and at the second step, ester groups (-CH 2 OCO-) followed by carbon backbone were found to be decomposed. 36 Generally, organic azide decomposes stepwise during slow heating rate. However, the main exothermicity of the thermal decomposition is related only to the rst mass loss step which corresponds well with the release of molecular nitrogen as a result of azide decomposition.…”

“…Various multi azido-ester plasticizers are like-bis(2-azidoethyl)adipate (BAEA), ethylene glycol bis azido acetate (EGBAA), diethylene glycol bis azido acetate (DEGBAA), trimethylol nitro methane triazido acetate (TMNTA), pentaerythritol tetrakis azido acetate (PETKAA), bis azido diethyl phthalate (BADEP), bis azido dipropyl phthalate (BADPP), bis azido dibutyl phthalate (BADBP), tris(azido acetoxy methyl)propane (TAAMP), bis (azido acetoxy) bis(azido methyl)propane (BABAMP), di(azido acetoxy) di(azido methyl) propane (PEAA), bis(1,3-diazido prop-2-yl)malonate, bis(1,3-diazido prop-2-yl) glutarate, and dendritic azido esters have been reported. [31][32][33][34][35][36][37][38] All these reported azido esters, except dendrimers, are synthesized along with similar route of ester formation by reux reaction followed by substitution of halogen with azide anion (shown in Scheme 1). Usually esterication process involves mixing of acid, alcohol and catalytic amount of sulphuric acid or p-toluene sulfonic acid and reuxed.…”