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Author: Subject: Energetic binders
DubaiAmateurRocketry
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[*] posted on 5-11-2013 at 08:22
Energetic binders


First this site need an auto-save thing, I miss clicked something and it all went gone, so annoying.. Anyways..

I realized there are almost little discussion about energetic binders, so I thought I want to start one.

Binders often decrease performance significantly, however these ones, are not too expensive, and I personally most look forward to the energetic BAMO for propellants, BNMO for binder bonded explosives, and Nitrated--HTPB for properties.

Here are their structures




Here are some papers I saved on my computer.

Energetic binder, plasticizer systems.

Compatibility between GAP and HTPB
http://sci-hub.org/pdfcache/071d8d5d23a853352d5c211afcf576dc...

Good idea ! Hydroxyl diazodotriazene terminated poly butadiene.
http://www.ias.ac.in/matersci/bmsjul2011/745.pdf

Well written and informative. Synthesis and thermal decomposition of GAP and Poly(BAMO) copolymer
http://libgen.org/scimag2/10.1016/j.polymdegradstab.2007.03....

Alkaabi synthesis -
Well written and informative. GAP, GTP complete guide
GAP Glycidyl Azide Polymer + HT-GAP (Hydroxyl terminated Glycidyl Azide Polymer) + other nitrogenous polymer.
https://www.google.ae/url?sa=t&rct=j&q=&esrc=s&a...

Recent trends in Enegetic polymers and plasticizers
1. http://www.dtic.mil/dtic/tr/fulltext/u2/a377866.pdf

2. http://www.dsto.defence.gov.au/publications/2210/DSTO-TR-096...

3.http://www.smf.phy.cam.ac.uk/fsp/Publications/Energetics%20papers/211EMAgrawalPECS24.pdf

List of azide, nitrated plasticizers. Well written.
http://libgen.org/scimag4/10.1134/S207997801203003X.pdf

Direct conversion of epichlorohydrin to glycidyl azide polymer
https://docs.google.com/viewer?url=patentimages.storage.goog...

Heat of formation of some Azide containing Oxetane
Monomers and Polymers
https://e-reports-ext.llnl.gov/pdf/244050.pdf

Azide terminated azido compounds for plasticizer.
https://docs.google.com/viewer?url=patentimages.storage.goog...

Diisocyanate terminated azido compounds.
https://docs.google.com/viewer?url=patentimages.storage.goog...

An azide terminated GAP useful plasticizer
https://docs.google.com/viewer?url=patentimages.storage.goog...

Hydroxyl terminated GAP
http://worldwide.espacenet.com/publicationDetails/originalDo...

HT-azide containign polyers.
https://docs.google.com/viewer?url=patentimages.storage.goog...

Poly-BAMO copolymers
http://www.jatm.com.br/papers/vol2_n3/JATMv2n3_p307-322_Synt...

Poly-BAMO + Poly-AMMO characteristics
http://onlinelibrary.wiley.com/doi/10.1002/prep.200600054/pd...

NCO-(CH2)6-[GAP]n-(CH2)6-NCO isocyanate functional GAP !
https://docs.google.com/viewer?url=patentimages.storage.goog...

nitrated compounds with isocyanates.
https://docs.google.com/viewer?url=patentimages.storage.goog...

Nitrated HTPB - NHTPB
https://attachment.fbsbx.com/file_download.php?id=1420082624...

Advanced propellant chemistry-Gould R.F.-
http://www.libgen.net/view.php?id=853382

Energetics binders, book.
http://books.google.ae/books?id=ykVXPCaiRtYC&pg=PA27&...




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[*] posted on 5-11-2013 at 12:38


Something easy to manufacture, with common materials ? And as less toxic as possible? I am also interested in cause of the rocketry theme, not only about the HE

Maybe we could also find a good comp for AN based propellants with those binders...
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[*] posted on 6-11-2013 at 08:39


Quote: Originally posted by underground  
Something easy to manufacture, with common materials ? And as less toxic as possible? I am also interested in cause of the rocketry theme, not only about the HE

Maybe we could also find a good comp for AN based propellants with those binders...


AN is not energetic at all, at least AP to begin with. I want to find a stable tetrazole oxidizer.

and for binders, the N-HTPB and BNMO meets your requirements. NHPTB can be easily made in 2 steps from commerical HTPB you can buy from many suppliers since it is used in plastics.

NHTPB have a higher density, around 1.3, depending on the level of nitration.

the more nitration on HTPB, the mechanical properties goes down, the optimum is around 10% nitration, gives a good margin between oxygen balance, density, cost, and performance.




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[*] posted on 6-11-2013 at 10:13


when SHN (Sorbitol Hexa Nitrate) is succesfully nitrated (yeah good luck!! :D) a sirup of mixed nitrates is found, this is then redissolved in ethanol or other solvent and crystallized out by being poured into water..
i suppose the sirup COULD be used as a sort of plasticizer?? of what ive read it has significant use in the gunpowder propellants industry, probably even in military grade propellants aswell?




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
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[*] posted on 6-11-2013 at 10:33


Quote: Originally posted by Antiswat  
when SHN (Sorbitol Hexa Nitrate) is succesfully nitrated (yeah good luck!! :D) a sirup of mixed nitrates is found, this is then redissolved in ethanol or other solvent and crystallized out by being poured into water..
i suppose the sirup COULD be used as a sort of plasticizer?? of what ive read it has significant use in the gunpowder propellants industry, probably even in military grade propellants aswell?


I have read little about SHN, and I am not sure what the sirup, you're talking about, is.

for plasticizers, I have linked few papers on my post you can find.




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[*] posted on 7-11-2013 at 03:34


nice collection of papers there. ill be reading through some of them for sure the concept of energetic binders+plasticizers have always intrigued me.it always seemed counter productive to add a non energetic element to explosive, altering some of the more desirable properties they have thanks for posting the wealth of info. much apreciated. NP



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[*] posted on 7-11-2013 at 05:06


I'd like to disagree that AN is not suitable as a propellant base. I have experimented with an AN/silicone rubber/Al propellant which was extremely energetic. The idea (for me) came from a topic here on SM some years ago, but is really an old notion. I used phase stabilized AN and 3 um Al along with silicone rubber.
Later, I altered both the formulation and the procedure by including a granulated NC/NG propellant and dissolving the (un-hardened) silicone rubber in detergent gasoline, mixing in the other ingredients and evaporating the solvent under agitation. This gave a molding powder that I pressed into a motor case around a special coring tool with a "+" cross section (made in my hobbyist machine shop). Then I added a nozzle with a very small throat (steel).
These rockets (12 mm OD, 50 mm long) were fairly difficult to ignite (one reason I added the NC/NG was for greater ease of ignition) but once they were, they accelerated fast enough that I think you could use them as kinetic penetrators (like the gyro-jet).
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[*] posted on 7-11-2013 at 05:22


Quote: Originally posted by Microtek  
I'd like to disagree that AN is not suitable as a propellant base. I have experimented with an AN/silicone rubber/Al propellant which was extremely energetic. The idea (for me) came from a topic here on SM some years ago, but is really an old notion. I used phase stabilized AN and 3 um Al along with silicone rubber.
Later, I altered both the formulation and the procedure by including a granulated NC/NG propellant and dissolving the (un-hardened) silicone rubber in detergent gasoline, mixing in the other ingredients and evaporating the solvent under agitation. This gave a molding powder that I pressed into a motor case around a special coring tool with a "+" cross section (made in my hobbyist machine shop). Then I added a nozzle with a very small throat (steel).
These rockets (12 mm OD, 50 mm long) were fairly difficult to ignite (one reason I added the NC/NG was for greater ease of ignition) but once they were, they accelerated fast enough that I think you could use them as kinetic penetrators (like the gyro-jet).


AN compared to old old fuels like black powder, yes it then is energetic since it produce a lot of gas. However... It has a very low density, just above 1.7.

Its decomposition is also not as exothermic as ammonium perchlorate, It can not even burn with polyurethane without the addition of magnesium, titanium, or maybe silicone since it worked for you. Even aluminum does not combust with ammonium nitrate without energetic binders.





This is AP vs AN. and ANCP are very oxygen negative and also much less dense than APCP.




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[*] posted on 7-11-2013 at 05:57


@DubaiAmateurRocketry

Microteck replied to your statement that ammonium nitrate is not energetic at all. Now AN is not as performant as AP, yes we all agree. However, and based on the graph that you just post, i see that AN propellant composition (based on specific impulse) are interesting for an amateur. for example, an Isp of 238 s for 62% AN-20%Mg-18%R45 (@ 1000 psi) is not too low compared to high performance AP composition. Also, AN is far less expensive than AP.

Dany.
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[*] posted on 7-11-2013 at 06:12


@Dany

Hey I apologize for any exaggerations, but I said that while replying to underground.

Underground:
Quote:

Maybe we could also find a good comp for AN based propellants with those binders...


I said that because AP is not expensive nor hard to find, so using AN on these expensive binders which take hours or days to make, is kind of a waste.


Finally, AN IS actually a bad oxidizer for rocket fuels. It has one of the slowest burn rates and only a moderate combustion temperature. It is also uncompatible with many fuels, mixtures of AN with Sugar, PU, HTPB, hexamine can not even ignite.
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[*] posted on 7-11-2013 at 07:42


Excerpt from one of the papers below. Can someone explain what ecombn kcal/mol is?

Density -- kcal/mol -- ecombn kcal/mol -- OB -- Tg C

Nitroglycerine (NG)
1.60 –83.97 368.4 +3.5 –68

Diethyleneglycol bis(azidoacetate)
(DEGBAA)
1.00 –329 1081.07 –100 –63.3

Trimethylolnitromethane(triazidoace
tate) (TMNTA)
1.45 –230 1294.04 –72 –34.1

Pentaerythritol tetrakis(azidoacetate)
(PETKAA)
1.39 –215 1714.76 –89 –35.4
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[*] posted on 7-11-2013 at 08:23


Quote: Originally posted by malford  
Excerpt from one of the papers below. Can someone explain what ecombn kcal/mol is?


??
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[*] posted on 7-11-2013 at 10:39


Quote: Originally posted by malford  
Excerpt from one of the papers below. Can someone explain what ecombn kcal/mol is?


Although im not sure what is the ecombn, maybe it shows how much heat is given off when it is completely burned ? or decompose ? I am not sure.

Any ways, what do you guys think are most promising ? The Nitrated HTPB is also miscible with all polar liquids, which means, finally, these energetic plasticizers can be mixed into NHTPB which i think is not hard to produce on industrial scale.

Ethyleneglycol bis(idoacetate) (EGBAA)
Density 1.34
HOF –167.36
HOC 796.26
OB –84.15
Tg –70.8

Tg -71 is amazing, and it has a good density, however the more traditional DTTN, although with higher Tg, is more cheap to produce, and ... it has a much higher density 1.5(in paper) or a lower density 1.2(wikipedia). If its 1.5, I think DTTN would need no replacement. I think the wikipedia one is wrong.
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[*] posted on 7-11-2013 at 11:19


Dany, perhaps I worded my statement in a confusing manner. I meant, below was an excerpt from one of the papers in the original post. I selected those compounds because they had the highest kcal/mol from one of the charts in the paper to which I linked. That chart has two columns, one for kcal/mol and another for ecombn kcal/mol. I don't know what ecombn kcal/mol is and was hoping someone could tell me.

DubaiAmateurRocketry, EGBAA has a high HOF, but DEGBAA is significantly higher. Compare -167 to -329. If I had more free time right now, I'd find more information about these compounds and build a chart which shows kJ/cm3. I believe comparison based on volume is more beneficial because rocket motors and their igniters will be limited by volume not weight.
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[*] posted on 7-11-2013 at 11:24


Quote: Originally posted by malford  

DubaiAmateurRocketry, EGBAA has a high HOF, but DEGBAA is significantly higher. Compare -167 to -329. If I had more free time right now, I'd find more information about these compounds and build a chart which shows kJ/cm3. I believe comparison based on volume is more beneficial because rocket motors and their igniters will be limited by volume not weight.


Umm, do you mean lower ? Its negative so the smaller the number the larger.

So EGBAA > DEGBAA in HOF, Density, and Tg.
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[*] posted on 7-11-2013 at 12:00


Quote: Originally posted by malford  
Dany, perhaps I worded my statement in a confusing manner. I meant, below was an excerpt from one of the papers in the original post. I selected those compounds because they had the highest kcal/mol from one of the charts in the paper to which I linked. That chart has two columns, one for kcal/mol and another for ecombn kcal/mol. I don't know what ecombn kcal/mol is and was hoping someone could tell me.


well, first it is Ecombn and not ecombn. What the authors mean by that is the Energy or heat of combustion. So the heat of combustion of nitroglycerine is Ecombn= 368.4 kcal/mol.

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[*] posted on 7-11-2013 at 12:39


Quote: Originally posted by Dany  
Quote: Originally posted by malford  
Dany, perhaps I worded my statement in a confusing manner. I meant, below was an excerpt from one of the papers in the original post. I selected those compounds because they had the highest kcal/mol from one of the charts in the paper to which I linked. That chart has two columns, one for kcal/mol and another for ecombn kcal/mol. I don't know what ecombn kcal/mol is and was hoping someone could tell me.


well, first it is Ecombn and not ecombn. What the authors mean by that is the Energy or heat of combustion. So the heat of combustion of nitroglycerine is Ecombn= 368.4 kcal/mol.

Dany.


Thank you, Dany, for pointing that out. Since heat of combustion is defined as the difference between the heat of formation of the products and reactants, and since these compounds consist of homogenous molecules rather than mixtures of fuel and oxidizer, how, then, is the heat of combustion not the same as the inverse of the heat of formation? I am strictly referring to the compounds in the chart in the aforementioned paper.

Also, Dany, I'd like to return the critical favor. The beginning of your post should be capitalized. You should have used "Well" instead of "well". Also, you are missing a comma after "So". It should look like "So, the heat...". Lastly, your signature, currently "Dany." aspires to be what is known as a sentence in the body of rules called English grammar by displaying the period. It, sadly, falls short. "Dany" would be more appropriate.

Have a nice day.
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[*] posted on 7-11-2013 at 13:15


with or without capitalization, with or without comma, at least you are understanding what is written. However, we will spend all the day to understand ecombn. Here, we are on a science forum so the most important thing is the scientific language. Grammar and poetry is secondary. Sadly, a lazy person put ecombn instead of Ecombn...

Back to your question: heat of formation and heat of combustion are different.

"Heat of formation is the is the heat of reaction or enthalpy change involved in making a particular compound, or molecule, from its elements where both the elements and compound are at standard-state condition" for more information see Explosive engineering for Paul W.Cooper.

"The heat of combustion of a specified substance is the heat
evolved when it is converted to the standard oxidation products
by means of molecular oxygen" see M.H. Keshavarz et al. / Journal of Hazardous Materials 185 (2011) 1086–1106 (and reference therein).

Dany.

[Edited on 7-11-2013 by Dany]
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[*] posted on 8-11-2013 at 01:15


I moved some offtopic drivel to detritus. Please stay on topic and stop derailing the thread.



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Want to wonder? Look at http://www.oelen.net/science
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[*] posted on 8-11-2013 at 04:46


woelen, I appreciate your fervor for keeping the information on the forum relevant and useful. I actually took the time to go to detritus and see what was moved and found only the image I had posted. You may not have read the image and understood the purpose of it. The point of the image is not made out of the context of this thread. For your convenience, I will show it again in this post which is now on topic and contains further contribution below to the thread's OP. Also, if you'd like to clean up off-topic bickering, all of the posts regarding AN are entirely unrelated.



Dany, I understand the definitions of the combustion enthalpy and formation enthalpy, but my question was specific to this list of compound which are not mixtures. How can combustion occur with homogenous compounds? Logically, I see the only route for combustion would be once the molecule decomposes, the decomposition products combust. If this is the case, I still don't see how the absolute value of enthalpy change of some decomposition products combusting would be larger than the total enthalpy change of the formation from elements.

[Edited on 8-11-2013 by malford]

[Edited on 8-11-2013 by malford]
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[*] posted on 8-11-2013 at 08:05


well, DubaiAmateurRocketry .. sorry for late reply..
the product you get from nitration is a mix of nitrates, which is somewhat oily and sticky, meaning you can stick this to a solid without making it worse as in properties..
ratios can be fixed..
if you want to have a rocketfuel thats OB and you dont wanna mess more with the OB you can make EGDN which has a PERFECT OB meaning you dont need to regulate oxidizer / fuel in the rocketfuel and can just add until you think its enough




~25 drops = 1mL @dH2O viscocity - STP
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[*] posted on 8-11-2013 at 15:51


Quote: Originally posted by malford  
Dany, I understand the definitions of the combustion enthalpy and formation enthalpy, but my question was specific to this list of compound which are not mixtures. How can combustion occur with homogenous compounds? Logically, I see the only route for combustion would be once the molecule decomposes, the decomposition products combust. If this is the case, I still don't see how the absolute value of enthalpy change of some decomposition products combusting would be larger than the total enthalpy change of the formation from elements.


As i explained above the "Heat of formation is the is the heat of reaction or enthalpy change involved in making a particular compound, or molecule, from its elements" since the heat of formation of the element is zero (e.g., carbon, Oxygen, fluorine, O2, F2...) so the heat of formation is the energy content of the molecule just formed, whereas the heat of combustion (when a molecule burn with O2 to form CO2, H2O...) is the heat difference between heat of formation of the products (CO2, H2O...which is not equal to zero) and the heat of formation of the compound which undergoes the combustion (e.g, TNT, a propellant...). This mean you can calculate the heat of formation if you know the heat of combustion (heat of formation and heat of combustion are not equal!). An example is illustrated in [1] page 644 where the authors determine the heat of formation of TNT from the known heat of combustion of TNT with oxygen, a reaction that yield CO2, H2O and N2. The heat of formation of CO2 and H2O are well known from thermochemical tables (see, http://webbook.nist.gov/chemistry/name-ser.html). Since we know the heat of combustion of the reaction (which is measured in a bomb calorimeter) the heat of formation of TNT= heat of combustion (of the reaction) minus heat of formation of reaction products. As you can see, heat of formation and heat of combustion are not equal.

a case where the heat of formation equal the heat of combustion [2] is the combustion of elements (e.g., C+O2----> CO2) since the heat of formation of carbon and oxygen (or other element like for example aluminum etc...) is equal to zero so here the heat of combustion is equal to the heat of formation of the products (in this case it is CO2)

[1] Chemistry and Physics of Energetic Materials, editor Surya N. Bulusu.
[2] Propellants and Explosives, Thermochemical Aspects of Combustion, Naminosuke Kubota (see page 280 under Heats of Combustion of Elements)

Dany.

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[*] posted on 17-11-2013 at 07:23


A method of curing azido-polymers where the amount of interlinked bonds can be controled.

This method of curing is also iso-cyanate free. It seems very interesting.


open file with adobe reader
Attachment: phpy4Z0DR (259kB)
This file has been downloaded 1494 times

[Edited on 17-11-2013 by DubaiAmateurRocketry]
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[*] posted on 10-12-2013 at 19:54


Interested by the reaction on page 68

https://smartech.gatech.edu/bitstream/handle/1853/7597/arons...

I think we can graft ''energetic'' tetrazoles onto GAP. This seems interesting !

Im not sure about if the mix acid will kick the tetrazole out and form Poly-GLYN or perform nitration on the COOH. and sorry for my bad drawing of polymers.




However this compound seems like it have a melting point at around room temperature with high viscousity and might not serve good as a ''binder'', however partial reactions still can be done to increase the density and oxygen balance.

If nitration fails, I really do think Trinitro-acetonenitrile can make the above compound. or polymer.

I have found little information about Trinitro-acetonenitrile however if it is a liquid and not a solid, and is compatible with some oxidizers and metal powders, it can be used to Cure GAP while giving oxygen balance during mixing ! making GAP propellant manufacturing crafting easier.

references for the above reaction.

Ralf Haiges * and Karl O. Christe Inorg. Chem., 2013, 52 May 31, 2013

and the paper i already posted.

[Edited on 11-12-2013 by DubaiAmateurRocketry]


[Edited on 11-12-2013 by DubaiAmateurRocketry]

[Edited on 11-12-2013 by DubaiAmateurRocketry]
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[*] posted on 1-2-2014 at 07:33


Has any thought ever been given to a partial polymerization of glycerol, and then forming a nitrate ester with the remaining hydroxyl groups? Or would the nitrating split the oligomers apart to form NG?
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