Synthesis of azidooxetane statistical polymers and copolymers

Garaev, I. Kh.; Kostochko, A. V.; Петров, А. И.; Ibragimov, E. N.; Голубев, А. Е.

doi:10.1134/s1070363216060384

Cited by 9 publications

(8 citation statements)

References 15 publications

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“…With the AMM, the propagating chain is uncharged and hydroxy-terminated, leading to less backbiting and other chain terminating reactions. This results in less cyclic oligomers, improved molecular weight, and end-group functionality as well as a narrower polydispersity. ,, While this system usually provides rather low molecular weights ( M W < 5000 g mol –1 ), TIBA is capable of providing linear polymers of especially high molecular weight. , Mechanistically, it is commonly assumed that an acidic complex forms between water and triisobutylaluminum to protonate a first monomer and thus forms an ion pair. The carbocation reacts with another monomer, causing chain growth.…”

Section: Resultsmentioning

confidence: 99%

“…Since azido compounds, which are popular in the field of energetic binders, are unstable toward radicals and strong acids and bases, the choice of the polymerization catalyst is limited using azido monomers. , For example, polymerization of 3-azidooxetane using triisobutylaluminum-water (TIBA) as a catalyst results in decomposition . In contrast, 3-tosyloxyoxetane and 3-mesyloxyoxetane provided the corresponding high-molecular-weight polymers using this catalyst. , Accordingly, it was possible for the first time to obtain a high-molecular-weight species of poly(3-azidooxetane) by subsequent azidation. The molecular weight and polydispersity of all parent polymers (pTsOx and pMsOx) were assessed by gel permeation chromatography to gain insight into the polymerization behavior and their suitability for the preparation of curable binders.…”

Section: Introductionmentioning

confidence: 99%

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A GAP Replacement, Part 2: Preparation of Poly(3-azidooxetane) via Azidation of Poly(3-tosyloxyoxetane) and Poly(3-mesyloxyoxetane)

Born

Göttemann²,

Plank

et al. 2022

J. Org. Chem.

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Despite the variety of energetic polyoxetane binders, the oxirane-based glycidyl azide polymer (GAP) has largely succeeded in the market due to its advantageous properties. Nevertheless, it suffers from various drawbacks such as non-uniform chain termination, possible chlorine content (flame retardant), and toxic epichlorohydrin required for its synthesis. These problems can be bypassed using the structurally related poly(3-azidooxetane). Unfortunately, it is only accessible in moderate yield by polymerization of 3-azidooxetane. Herein, we describe its synthesis by polymer-analogous transformation using the new polymers poly(3-tosyloxyoxetane) and poly(3-mesyloxyoxetane) as precursors. This results in a significantly increased yield and improved safety as handling of the very sensitive 3-azidooxetane is avoided. The aforementioned prepolymers were prepared using boron trifluoride etherate as well as triisobutylaluminum as catalysts. The latter provides polymers of particularly high molecular weight, and the corresponding poly(3-azidooxetane) species was obtained and studied for the first time. In order to shed light on the applicability of poly(3-azidooxetane) as a GAP substitute, it was thoroughly studied with regard to thermal behavior, energetic performance (EXPLO5), plasticizer compatibility, and curing. Moreover, the aquatic toxicity of all involved monomers was analyzed and compared to epichlorohydrin. Here, poly(3-azidooxetane) turned out as a fully adequate, if not more environmentally benign, substitute.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A GAP Replacement, Part 2: Preparation of Poly(3-azidooxetane) via Azidation of Poly(3-tosyloxyoxetane) and Poly(3-mesyloxyoxetane)

Born

Göttemann²,

Plank

et al. 2022

J. Org. Chem.

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“…Another novel energetic binder is the polymer of 3,3 -bis(azidomethyl)oxetane (PBAMO). In the case of PBAMO, both its density and heat of formation are higher than the respective values for GAP, but on the other hand, PBAMO exhibits poor mechanical properties (i.e., higher glass transition temperature) [20,26]. To overcome this problem, a lot of copolymers are synthesized (e.g., DFAMO/BAMO copolymer) [27].…”

Section: Use Of New Polymer Bindersmentioning

confidence: 99%

“…Materials 2021, 14, x FOR PEER REVIEW 4 of 18 [20,26]. To overcome this problem, a lot of copolymers are synthesized (e.g., DFAMO/BAMO copolymer) [27].…”

Section: Use Of New Polymer Bindersmentioning

confidence: 99%

Solid Propellant Formulations: A Review of Recent Progress and Utilized Components

2021

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“…Zhang et al 17 reported the response law of deflagration to detonation transition of P(BAMO/AMMO) based high energy propellants. Garaev et al 15 synthesized different mass ratio P(BAMO/AMMO) and found that while increasing fraction of PAMMO in the P(BAMO/AMMO) copolymers, the strength properties of the copolymers enhance and the degree of crystallinity decreases. However, there are few reports about modified P(BAMO/AMMO).…”

Section: Introductionmentioning

confidence: 99%

Molecular dynamic simulation of performance of modified BAMO/AMMO copolymers and their effects on mechanical properties of energetic materials

Wang¹,

Li²,

Li³

et al. 2020

Sci Rep

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Based on molecular dynamic method, densities, mechanical behavior and mechanical performance of P(BAMO/ AMMO) (Polymer 1) and two novel modified P(BAMO/AMMO) (Polymer 2: containing amino group, Polymer 3: containing nitro group), and their effects on mechanical properties of four energetic materials are investigated, the main results are as follow: Polymer 2 (1.235 g/cm3, 240 ± 5 K) and Polymer 3: 1.281 g/cm3, 181 ± 3 K) possess higher densities and lower glass transition temperatures than Polymer 1 (1.229 g/cm3, 247 ± 4 K). The modification makes Polymer 1 difficult to expand, improves its mechanical properties, but has few effect on its diffusion coefficient at same temperature and state. In addition, three binders are compatible with TNT, HMX and CL-20, and may react with DNTF. All polymers particularly improve rigidity of four energetic materials, and enhance their ductility except Polymer 2 on TNT. The ability of Polymer 2 and Polymer 3 improving rigidity (except Polymer 3 on HMX) and ductility of TNT and HMX is inferior to that of Polymer 1, but it is contrary for CL-20 and DNTF (except Polymer 2 on rigidity of DNTF). Moreover, Polymer 2-based interfacial crystals exhibit higher rigidity than Polymer 3-based interfacial crystals.

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Synthesis of azidooxetane statistical polymers and copolymers

Cited by 9 publications

References 15 publications

A GAP Replacement, Part 2: Preparation of Poly(3-azidooxetane) via Azidation of Poly(3-tosyloxyoxetane) and Poly(3-mesyloxyoxetane)

A GAP Replacement, Part 2: Preparation of Poly(3-azidooxetane) via Azidation of Poly(3-tosyloxyoxetane) and Poly(3-mesyloxyoxetane)

Solid Propellant Formulations: A Review of Recent Progress and Utilized Components

Molecular dynamic simulation of performance of modified BAMO/AMMO copolymers and their effects on mechanical properties of energetic materials

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