New insight: Nitrosation of n-phenyl-β-naphthylamine in the early stage of nitroplasticizer aging

Chen, Kitmin; Kress, Joel D.; Yang, Dali

doi:10.1016/j.polymdegradstab.2023.110541

New insight: Nitrosation of n-phenyl-β-naphthylamine in the early stage of nitroplasticizer aging

Journal Article · Sat Sep 23 00:00:00 EDT 2023 · Polymer Degradation and Stability

DOI:https://doi.org/10.1016/j.polymdegradstab.2023.110541· OSTI ID:2006715

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Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Antioxidants are additives and used for inhibiting oxidative degradation of many polymeric materials. Likewise, to maintain long-term stability of nitroplasticizer (NP) used in the formulation of a polymer-bonded energetic material, 0.1 wt.% of an arylamine antioxidant, n-phenyl-β-naphthylamine (PBNA) was added. Recently, the detection of PBNA nitration has brought forth the mechanistic complexity of antioxidant chemistry and created a path to understand how NP naturally degrades over time. Through a short-term aging experiment and with optimized LC-QTOF analysis, a reaction between PBNA and nitrous acid (HONO) that precedes the nitration event has been found, known as nitrosation. The identification of nitroso-PBNA has solidified the HONO elimination mechanism in NP degradation and provided new insight on the role of this arylamine antioxidant. It also shows how stabilizer reactions with key intermediate degradation species can be a contributing process in polymer degradation.

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Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: 89233218CNA000001

OSTI ID:: 2006715

Alternate ID(s):: OSTI ID: 2329252

Report Number(s):: LA-UR-23-29968

Journal Information:: Polymer Degradation and Stability, Vol. 217; ISSN 0141-3910

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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