FOX-7,FOX-7, anan IMIM IngredientIngredient CandidateCandidate –– WhereWhere AreAre WeWe Today?Today?

HelenaHelena Bergman,Bergman, AnnaAnna PetterssonPettersson andand HenricHenric Östmark,Östmark, SwedishSwedish DefenceDefence ResearchResearch Agency,Agency, FOIFOI

HelenHelen StenmarkStenmark andand CarinaCarina Bergvall-LaitalaBergvall-Laitala EurencoEurenco BoforsBofors ABAB

2009 Insensitive Munitions and Energetic Materials Technology Symposium OutlineOutline

WhyWhy newnew EnergeticEnergetic MoleculesMolecules FOX-7FOX-7 BasicsBasics FOX-7FOX-7 CrystalsCrystals FOX-7FOX-7 FormulationsFormulations andand ApplicationsApplications ConclusionsConclusions

2009 Insensitive Munitions and Energetic Materials Technology Symposium WaysWays toto InsensitiveInsensitive Munitions..Munitions..

Modify the energetic material Modify the composition Modify the munition

Modify the ammunition depot or storage Modify the packaging

2009 Insensitive Munitions and Energetic Materials Technology Symposium WaysWays toto InsensitiveInsensitive Munitions..Munitions..

Modify the energetic material Modify the composition Modify the munition

FOI activities

Modify the ammunition depot or storage Modify the packaging

2009 Insensitive Munitions and Energetic Materials Technology Symposium FOX-7FOX-7

1,1-Diamino-2,2-dinitroethylene1,1-Diamino-2,2-dinitroethylene DevelopedDeveloped atat FOIFOI inin 1997--1997-- WOWO PatentPatent No.No. 99038189903818 ProducedProduced byby EURENCOEURENCO BoforsBofors ABAB underunder licencelicence byby SwedishSwedish GovernmentGovernment O2NNO2 OO OO H2N NO2 H+, H O HNO3/H2SO4 2 NNH 5-10oC HN NH

H2N NO2 88%

O2NNO2

2009 Insensitive Munitions and Energetic Materials Technology Symposium FOX-7FOX-7 BasicsBasics

LowLow sensitivitysensitivity explosivesexplosives SimpleSimple synthesissynthesis

Crystal Structure

O2N NO2 O H N NO HNO /H SO 2 2 3 3 2 4 aq NH3 Density (crist): 1.885 g/cm NNH HN NH

Heat of Formation: -32 kcal/mole H2N NO2 Sensitivity: drop weight 70 cm (RDX 38 cm) O2NNO2 FOX-7 friction > 350 N (RDX 120 N) o Explosion Temperature: 215 C (RDX 220 oC) Synthesis Detonation Pressure (calc): 33.96 GPa (RDX 34.63 GPa) Detonation Velocity (meas.): 8870 m/s (RDX 8930 m/s)

ImpactImpact andand FrictionFriction SensitivitySensitivity ofof FOX-7FOX-7

Sample Drop height Friction (cm) (N) FOX-7 (recryst., 250–355 μm) 79

FOX-7 (recryst., < 70 μm) 63 >340

RDX 38 126 FOX-7:FOX-7: DSCDSC

60 3 Ea=234 kJ/mole (56 kcal/mole) 50 2

40 1 W) ln (R) ln 

30 0

20 -1 1.94 1.96 1.98 2.00 2.02 2.04 1000/T 10 Heat Flow (

0

100 150 200 250 300 350 Temperature (oC) FOX-7:FOX-7: SSGTSSGT

25.4 mm

Detonator DENSITY Attenuator Holder 12.7 mm (g/cc) Thickness (mm) 38.1 mm Donor (RDX 98/1/1) Tetryl 1.65 8.36 Attenuator (PMMA) 3.59 - 12.73 mm 5.11 mm HNS II 1.635 7.19 38.1 mm Acceptor (FOX-7) TNT 0.92*TMD 6.4 HMX 0.92*TMD 10.3 38.1 mm Witness block RDX 0.92*TMD 9.33 FOX-7 1.634 6.22 76.2 mm FOX-7FOX-7

Small-scaleSmall-scale gapgap testtest

Name Density Distance (50% probability point)

3 FOX-7 1.63 g/cm (86% of TMD) 6.2 mm TNT 1.53 g/cm3 (92% of TMD) 6.4 mm RDX 1.66 g/cm3 (92% of TMD) 9.3 mm

AirAir gapgap testtest

Name Density Distance (50% probability point)

3 TNT 1.51 g/cm (91% of TMD) 34 – 35 mm FOX-7 1.72 g/cm3 (91% of TMD) 35 – 37.5 mm

Composition B 1.59 g/cm3 (91% of TMD) 60 – 62.5 mm

H. Östmark et al. Int. Det. Symp. (1998) R. Adolfsson et al. FOI-R-0668-SE (2003) 2009 Insensitive Munitions and Energetic Materials Technology Symposium FOX-7:FOX-7: IgnitionIgnition TemperatureTemperature (Wood’s(Wood’s metalmetal bath)bath)

250

o 200 No reaction when T < 215 C (RDX ignites at 220°C)

150

100 Time to reaction [s] reaction to Time 50

0 210 220 230 240 250 260 270

Temperature of metal bath [ C] FOX-7:FOX-7: KOENENKOENEN TESTTEST (Steel(Steel sleevesleeve test)test)

Type “F” reaction at nozzle plate diameter 6 mm RDX explodes at nozzle plate diameter 8 mm

FOX-7:FOX-7: CompatibilityCompatibility byby HFCHFC

Polymer Ea (J/g/week) Cab (J/g/week) CAB (BF900) 0.38 -0.38  EE ba EC abab  Estane 0.27 -0.26 2 GAP (SNPE) 2.57 -0.44 HTPB (R-45 HT) 1.89 3.89 Incompatible: HTPB (Krasol LBH) 0.24 0.13 C>20 J/g/week Viton 0.10 0.03 Slightly Incompatible: Isocyanate 10 J/g/week H12MDI 0.70 0.41

detail image

Pcj E0 A B R1 R2 w (Gpa) (kJ/cc) (Gpa) (Gpa) 27.9 8.663 998.6 8.78 4.93 1.12 0.40

Data for FOX-7 + 1.5 w% wax, δ = 1.756 g/cc The detonation velocity was estimated to 8.335 ± 0.025 mm/μs; A Cheetah calculation, BKWC, gave a velocity of 8.266 mm/μs, which is in good agreement with the experimental value.

2009 Insensitive Munitions and Energetic Materials Technology Symposium FOX-7FOX-7

250250 µm µm CandidateCandidate forfor ingridientsingridients inin BoostersBoosters ShapeShape ChargeCharge warheadswarheads HighHigh performanceperformance warheadswarheads RocketRocket andand gungun propellantspropellants ParticleParticle sizesize andand particleparticle quallityquallity isis veryvery importantimportant forfor sensitivitysensitivity andand processingprocessing propertiesproperties

2009 Insensitive Munitions and Energetic Materials Technology Symposium NSF 110 (20 – 40 µm) is the smallest particle size available which also gives a relatively low bulk density, < 0.6 g/cm3 according to Hall measurements. Below, a SEM-photo with a1000 times magnification is shown together with a particle size distribution measured by Malvern is shown.

2009 Insensitive Munitions and Energetic Materials Technology Symposium NSF 120 (50 – 100 µm) gives a bulk density of approximately 0.7 g/cm3 according to Hall. The picture shows a 200 times magnification of the particles and a particle size distribution measured by Malvern.

2009 Insensitive Munitions and Energetic Materials Technology Symposium NSF 130 (100 – 200 µm) gives a bulk density of approximately 0.85 g/cm3. The SEM photo is a 70 times magnification and the particle size distribution is a Malvern measurement.

2009 Insensitive Munitions and Energetic Materials Technology Symposium 100%

90%

>75µ 80% 150-75µm

300-150 µm 70% >300µm

60%

50%

40%

30%

20%

10%

0%

39 53 38 7 7 0 5 6 7 3 3 0 04 04 08

NSF 140 (250 – 350 µm) is the largest particle size available at present. This quality has a bulk density of approximately 0.95 according to Hall. The SEM photograph is 70 times magnification and sieving results for a couple of batches are shown a long side.

2009 Insensitive Munitions and Energetic Materials Technology Symposium ScalingScaling upup ofof FOXFOX--77

•• EurencoEurenco BoforsBofors ABAB hashas producedproduced nerlynerly 10001000 kgkg (7(7 kgkg batches,batches, 11 toto 3per3per day)day)

ofof FOX-7FOX-7 inin itsits ownown pilotpilot plantplant •• MolarMolar yield 80 % for nitration step •• VeryVery smallsmall particleparticle sizesize hashas causedcaused problemsproblems toto washwash thethe filterfilter cake.cake. AA

separateseparate washingwashing stepstep hashas beenbeen introducedintroduced toto obtainobtain purepure productproduct •• HPLC-purityHPLC-purity isis moremore thanthan 9999 %% forfor washedwashed productproduct

2009 Insensitive Munitions and Energetic Materials Technology Symposium InsensitiveInsensitive FormulationsFormulations andand ApplicationsApplications

2009 Insensitive Munitions and Energetic Materials Technology Symposium PressedPressed ExplosivesExplosives

PressedPressed FOX-7/waxFOX-7/wax (97.8/2.2(97.8/2.2 wt%)wt%) InvestigatedInvestigated asas anan explosiveexplosive forfor useuse inin shapeshape chargecharge applicationsapplications

A. Helte et al. 23rd Int Symp on Ballistics, Spain (2006) A. Helte et al. FOI-R-1780-SE (2005)

PressedPressed ExplosivesExplosives

 JetJet straightnessstraightness  JetJet velocityvelocity  FragmentationFragmentation timetime FOX-7FOX-7 >> CompComp BB

 PenetrationPenetration (ARMOX(ARMOX 300S)300S) FOX-7FOX-7 230 230 mmmm (2.9(2.9 cal)cal) CompComp BB 265 265 mmmm (3.3(3.3 cal)cal)

A. Helte et al. 23rd Int Symp on Ballistics, Spain (2006) A. Helte et al. FOI-R-1780-SE (2005)

FOF-2FOF-2

FOX7FOX7 (255-350mm)(255-350mm) 5050 wt%wt% FOX7FOX7 (<(< 70mm)70mm) 2020 wt%wt% PolyGlyNPolyGlyN 21wt%21wt% Butyl-NENAButyl-NENA 55 wt%wt% H12MDIH12MDI (Desmodur-W)(Desmodur-W) 44 wt%wt% DBTDLDBTDL 0.030.03 wt%wt%

TgTg == -35°C-35°C ThermallyThermally stablestable atat 65°C65°C (14(14 days)days)

2009 Insensitive Munitions and Energetic Materials Technology Symposium Small-scaleSmall-scale slowslow cook-offcook-off

100-400°C Heating rate: 3.3°C/hour Small-scaleSmall-scale slowslow cook-offcook-off -- ResultsResults

FOF-2

T 220°C (Type V reaction) RDX/TNT 60/40 Tcook-off 220°C (Type V reaction)

Tcook-off 207°C (Type I reaction)

AA NewNew ExplosivesExplosives FormulationFormulation -- FOF-5FOF-5

FOX-7FOX-7 (238µm)(238µm) 38.138.1 %% FOX-7FOX-7 (32µm)(32µm) 25.425.4 %% HMXHMX (22(22 µm)µm) 16.516.5 %% EnergeticEnergetic binderbinder 20%20% PolyGlyNPolyGlyN 7.27.2 %% GAPGAP 7.27.2 %% Butyl-NENAButyl-NENA 3.63.6 %%

HH1212MDIMDI (Desmodur-W)(Desmodur-W) 2.02.0 %%

DBTDLDBTDL

2009 Insensitive Munitions and Energetic Materials Technology Symposium SlowSlow HeatingHeating (Slow(Slow Cook-Off)Cook-Off)

FirstFirst testtest (inert(inert fuze)fuze)  TypeType VV responseresponse (fire)(fire) SecondSecond testtest (HNS(HNS II-basedII-based fuze)fuze)  TypeType IVIV responseresponse (deflagration)(deflagration) CompositionComposition BB  TypeType II responseresponse (detonation)(detonation) FastFast Heating/FuelHeating/Fuel FireFire (Fast(Fast Cook-Off)Cook-Off)

BlastBlast pressurepressure (max(max 160160 Pa)Pa) andand nono significantsignificant heatheat radiationradiation  TypeType IVIV responseresponse (fire)(fire) DebrisDebris (fuze)(fuze) recoveredrecovered atat >> 2424 metersmeters fromfrom testtest standstand  TypeType IVIV responseresponse (deflagration)(deflagration) CompositionComposition BB  TypeType II responseresponse (detonation)(detonation) BulletBullet ImpactImpact

DebrisDebris (fuze)(fuze) recoveredrecovered lessless thanthan 1515 metersmeters fromfrom testtest standstand  TypeType VV responseresponse (fire)(fire) CompositionComposition BB  TypeType II responseresponse (detonation)(detonation) AA PotentialPotential IMIM Explosive?Explosive?

•• FOF-5FOF-5 isis aa cast-curedcast-cured explosiveexplosive basedbased onon FOX-7FOX-7 andand HMXHMX withwith thethe samesame performanceperformance (calc.)(calc.) asas CompositionComposition BB (RDX/TNT(RDX/TNT 60/40).60/40). •• InitialInitial IMIM testingtesting ofof ammunitionammunition containingcontaining FOF-5FOF-5 -- results:results: Slow Cook-Off Fast Cook-Off Bullet Impact FOF-5 Fire (1st test) Deflagration Fire (Batch No. 1) Fire/Defl (2nd test) Composition B Detonation Detonation Detonation CompositeComposite propellantspropellants FOX-12/RDXFOX-12/RDX andand FOX-7/HMXFOX-7/HMX basedbased compositionscompositions EnergeticEnergetic binderbinder

1200 600

1150 400 FOX-12 based propellant JA 2 1100 XM 39 200 ( ) 1050

100 1000 0.73 80 y = 3.82P 60 950 Force (J/g) 40 1.32 0.90 900 Burn rate (mm/s) y=0.81P y = 0.09P

20 850 FOX-7 based propellant FOX-12 based propellant

800 10 2000 2200 2400 2600 2800 3000 3200 3400 10 20 40 60 80 100 200 400 Temperature (K) Pressure (MPa)

2009 Insensitive Munitions and Energetic Materials Technology Symposium LowLow SensitivitySensitivity ExplosivesExplosives HEHE

NO2

H N NH 2 2 + - NH2 O

NO2

O N NO 2 2 N H2NNNH2

NH2 NO2 TATB H O N N NO 2 2 FOX-12

H H2N N NH2

N O N H2N NO2 O LLM-105

N H2NNO2 NO2 H NTO FOX-7

2009 Insensitive Munitions and Energetic Materials Technology Symposium ConclusionsConclusions FOX-7FOX-7 isis veryvery insensitive.insensitive. FOX-7FOX-7 makesmakes itit possiblepossible toto producesproduces lowlow sensitivitysensitivity chargescharges withwith highhigh performance,performance, asas exemplifiedexemplified byby thethe shapedshaped chargecharge andand 40mm40mm smallsmall calibercaliber examples.examples. TheThe availabilityavailability ofof moremore andand betterbetter characterizedcharacterized particleparticle sizessizes willwill enableenable anan easiereasier developmentdevelopment ofof newnew lowlow sensitivity,sensitivity, highhigh performanceperformance applications.applications. FOX-7FOX-7 isis availableavailable inin largelarge quantitiesquantities

2009 Insensitive Munitions and Energetic Materials Technology Symposium