Reactivity of ADN with PolyButadiene in Air
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1 Reactivity of ADN with PolyButadiene in Air Simon Torry 1, Matthew Williamson 2, Don Fossey 2, David Tod 1 1 QinetiQ, Fort Halstead, Sevenoaks, Kent, TN14 7BP, UK 2 Roxel, Summerfield, Kidderminster, Worcestershire, DY11 7RZ, UK A presentation to: Insensitive Munitions and Energetic Materials Technology Symposium 1th October 213 QINETIQ/13/2125 1
2 Contents 1. Introduction 2. Bulk Ageing 3. Experimental 4. Aged HTPB (no stabiliser) 5. Aged HTPB + ADN (no stabiliser) 6. Effect of Antioxidant 7. Effect of Stabiliser and Antioxidant Type 8. Effect of Polybutadiene Type 9. Conclusions 2
3 1 Introduction MoD (UK) is funding a Novel Propellants programme developing rocket propellants Current composite rocket propellants usually contain ammonium perchlorate (AP) toxic stealth issues Aim to develop rocket propellants using chlorine-free oxidisers ammonium dinitramide (ADN) 1,1-diamino-2,2-dinitro-ethylene (FOX-7) Patrick Goede, Niklas Wingborg, ADN Solid Propellants, IVth Dinitramide & FOX 7 Seminar, September 29, Stockholm, Sweden. 3
4 1 Introduction Aim to measure and understand ageing of ADN in binders Advantageous to fill polybutadiene (HTPB) with ADN polymer has a proven track record as a binder system in AP composite propellants exhibits good mechanical properties low glass transition temperature Component Mass % ADN 69.4 Polybutadiene 3.6 Subjected HTPB/ADN composite to a minimal ageing trial three temperatures (6, 7 and 8 C) dry conditions 4
5 2 Bulk Ageing Oxidised at a faster rate than expected in air darkened rapidly (within two weeks) to form a hard skin inhomogeneous brown banding at the ADN/polybutadiene interface downward trend in the sol fraction oxidative crosslinking 5
6 2 Bulk Ageing Understand ageing Quantify rate Nature of reaction Identify additives Stabilisers Antioxidants Prolong life Decrease costs Increase safety 6
7 3 Experimental Diffuse reflectance infrared spectroscopy (DRIFTS) optimised for trans-flection Coated aluminium sample holder base with thin coat dried in vacuum for 1 minutes prior to kinetic measurement ADN/HTPB (uncured) ratio 5:5 heated in holder exposed to dry air collected IR spectrum every 5 minutes 7
8 Area hydroxyl band 4 Aged HTPB (no stabiliser) Cured HTPB undergoes autocatalytic oxidative crosslinking (4 microns thick) hours to days depending on temperature Forms new carbonyl and hydroxyl bearing species.6 Ageing Thin Polybutadiene Rubber, Dry Ageing 2.5 Linked spectrum at 1.99 min. 7oC IP DI/HTP B 2..5 Abs Maximum oxidation rate. Auto-oxidation 5 C 6 C 7 C Abs Linked spectrum at min. 7oC IP DI/HTP B Induction period Time / days Wavenumbers (cm-1 ) 2 1 8
9 Normalised Abs Difference 4 Aged HTPB (no antioxidant) R45M uncured with minor amounts of antioxidant (AO) 8 C, dry air, ~2.4 days maximum oxidation rate Fits autoxidation scheme Initial dip in the OH content due to hydrogen abstraction reactions of OH A k 2 1 ka1 A k B k k ka 2 a2 a1 B C A R45M Time / mins o S B C S OH Fit Diff 9
10 5 Aged HTPB + ADN (no stabiliser) Addition of ADN Abs degradation does not follow classic auto-oxidation scheme HTPB oxidises at a faster rate in the presence of ADN time to maximum auto-oxidation rate was ~ 9 minutes Different oxidation products carbon-multiple bond-nitrogen species (2223cm -1 ) probably a conjugated nitrile reaction of ADN with oxidising HTPB Abs orbanc e Linked s pec trum at min. 5oC Normalised Abs Time / mins Time / mins 7 C 6 C 5 C 6 C Fit Diff 3 2 Wavenumbers (cm-1 ) 1 1
11 6 Effect of Antioxidant Addition of Calco2246 AO Time/mins increased the time to maximum auto-oxidation linear BUT still a fast oxidation process at 8 C Mass % Calco2246 Time to max oxidation/days Normalised Peak Area Time/mins Time to max oxidation %.25%.5% 1% 2% Mass % AO 11
12 6 Effect of Antioxidant Extrapolation to lower temperatures (Arrhenius) still fast oxidation process Mass % AO Temperature/ C Time to max oxidation / days Time to max oxidation / years
13 Normalised Peak Area Normalised Peak Area Normalised Peak Area 7 Effect of Stabiliser and Antioxidant Type Addition of stabiliser pnma at 8 C.2% - no affect.5% appears to accelerate oxidation Time/mins.2% pnma+ 2NDPA none Time/mins.5% pnma+ 2NDPA none Change antioxidant to Irganox (4,6-bis (octylthiomethyl)-o-cresol) less efficient antioxidant than Calco Time/mins Calco2246 Irganox 13
14 Normalised Peak Area 8 Effect of Polybutadiene Type R45M 2% vinyl, 6% trans, 2% cis (minor antioxidant) Krasol LBH2 (vinyl-htpb) 65% vinyl, 22.5% trans, 12.5% cis (minor antioxidant) Aldrich HTPB (cis-htpb) 1% vinyl, 27% trans, 72% cis (no observable antioxidant) Reactivity Vinyl HTPB<<R45M<cis-HTPB Time/mins Aldrich R45M Krasol LBH2 14
15 CO Peak Area NC Peak Area 8 Effect of Polybutadiene Type Vinyl HTPB + minor AO - extrapolated oxidative ageing to room temperature longer life Disadvantage Vinyl HTPB higher glass transition temperature (-46 C versus -75 C for R45M) Formation of the conjugated nitrile after maximum oxidation rate Temperature/ C Time to max oxidation / days Time to max oxidation / years ~13 ~.4 5 ~64 ~.2 4 ~339 ~.9 3 ~21 ~5.5 2 ~13441 ~ Time/mins CO N-C 15
16 9 Conclusions HTPB/ADN propellant, with small amounts of antioxidant, ages rapidly highly inhomogeneous process Followed oxidation of thin ADN/HTPB R45M samples using IR spectroscopy does not follow the classic autoxidation kinetic scheme much faster than pure HTPB R45M evidence of ADN reaction with oxidising HTPB - formation of a conjugated nitrile species Addition of antioxidants mitigates degradation inefficient additives Stabiliser pnma does not improve oxidation rate Oxidation depends on polymer backbone vinyl HTPB<<R45M<cis HTPB 16
17 The authors thank the DSTL's Programme and Delivery Directorate (MoD, UK) for funding this work. Thank you for your attention! 17
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