US3447981A - Solid propellant compositions and method of modifying propellant burning rate using ferrocene derivatives - Google Patents
Solid propellant compositions and method of modifying propellant burning rate using ferrocene derivatives Download PDFInfo
- Publication number
- US3447981A US3447981A US235601A US3447981DA US3447981A US 3447981 A US3447981 A US 3447981A US 235601 A US235601 A US 235601A US 3447981D A US3447981D A US 3447981DA US 3447981 A US3447981 A US 3447981A
- Authority
- US
- United States
- Prior art keywords
- cyclopentadienyl
- iron
- propellant
- burning rate
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 34
- 239000004449 solid propellant Substances 0.000 title claims description 14
- 239000003380 propellant Substances 0.000 title description 19
- 238000000034 method Methods 0.000 title description 7
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 title description 2
- -1 BIS(CYCLOPENTADIENYL) IRON Chemical compound 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- NJPGTUIMEAOISI-UHFFFAOYSA-N cyclopentane;1-cyclopentylethanol;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.CC(O)[C]1[CH][CH][CH][CH]1 NJPGTUIMEAOISI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical class [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 claims 2
- 239000004615 ingredient Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- OTVPWGHMBHYUAX-UHFFFAOYSA-N [Fe].[CH]1C=CC=C1 Chemical compound [Fe].[CH]1C=CC=C1 OTVPWGHMBHYUAX-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011872 intimate mixture Substances 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 2
- IZBYGQZNHUXSFU-UHFFFAOYSA-N C(=O)(O)[Fe](C1C=CC=C1)C1C=CC=C1 Chemical compound C(=O)(O)[Fe](C1C=CC=C1)C1C=CC=C1 IZBYGQZNHUXSFU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- JWIWTUFLYLUADU-UHFFFAOYSA-N N(=C=O)C=1C(C=CC=1)[Fe]C1C=CC=C1 Chemical compound N(=C=O)C=1C(C=CC=1)[Fe]C1C=CC=C1 JWIWTUFLYLUADU-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- FZHCFNGSGGGXEH-UHFFFAOYSA-N ruthenocene Chemical compound [Ru+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 FZHCFNGSGGGXEH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
- C06B23/007—Ballistic modifiers, burning rate catalysts, burning rate depressing agents, e.g. for gas generating
Definitions
- This invention relates to an improvement in solid propellants and more specifically to bis(cyclopentadienyl)iron derivatives containing reactive functional groups which act as burning rate accelerators in solid propellants.
- bis(cyclopentadienyl)iron in solid propellant compositions as a burning rate accelerator is well known in the art.
- this compound has inherent shortcomings which limit its usefulness.
- the first of these faults is that the bis(cyclopentadienyl)iron does not react with any of the ingredients in the propellant composition thereby lending itself to easy loss from the composition. This loss may occur during compounding by entrainment in vaporizing liquids or it may occur by sublimation after the propellant has undergone polymerization.
- Another fault of bis(cyclopentadienyl) iron is its poor compatibility with other ingredients in the propellant composition.
- This invention employs bis(cyclopentadienyl) iron derivatives containing reactive functional groups to overcome these aforementioned shortcomings. These compounds can be used in solid propellant fuels to replace bis(cyclopentadienyl)iron which is currently utilized as a burning rate modifier.
- the bis(cyclopentadienyl) iron derivatives disclosed in this invention have many advantages over the previously used bis(cyclopentadienyl)iron. In addition to being as effective as a burning rate accelerator as bis(cyclopentadienyl)iron, these additives react with the cross linking agents of the propellant composition during curing to form an integral segment of the polymeric binder and result in a propellant composition having more uniform and more reproducible burning rate characteristics.
- these compounds are not lost from the propellant composition during the compounding step. Also, they are not lost by sublimation after the propellant has undergone polymerization. Finally, these compounds are more compatible with the other ingredients in propellant compositions than is bis(cyclopentadienyl)iron.
- One other object of the instant invention is to provide burning rate modifiers which, when used in propellant compositions, are more compatible with the other ingredients of the propellant composition than bis(cyclopentadienyl)iron.
- Another object of the instant invention is to provide an improved method of modifying the burning rate of solid propellant compositions wherein bis(cyclopentadienyl) iron has previously been employed.
- the bis(cyclopentadienylfiron derivatives used in the instant invention are known in the art and may be obtained according to prior art techniques.
- Example I Formulation: Wt. percent Polybutadiene-acrylic acid prepolymer 15 Tris(methylaziradinyl)phosphinic oxide 2.5 Ammonium perchlorate 66.5 Aluminum powder 15.0 Cyclopentadienyl [2 (1 hydroxyethyD-cyclopentadienyl]iron The formulation is mixed in any manner to insure thorough mingling of the ingredients and cured at The formulation is mixed and cured as in Example I.
- compositions employing bis(cyclopentadienyl)iron as the burning rate accelerator, the improvement in these compositions which comprises the substitution of a compound selected from the group consisting of cyclopentadienyl [2-( l-hydroxyethyl)-cyclopentadienyl1iron, 2 carboxycyclopentadienyl(cyclopentadienyl)iron, 2 isocyanatocyclopentadienyl(cyclopentadienyl)iron for said bis(cyclopentadienyl)iron.
- composition of claim 5 wherein said compound is cyclopentadienyl [2 (1 hydroxyethyl) cyclopentadienyl] iron.
- composition of claim 5 wherein said compound is 2-carboxycyclopentadienyl(cyclopentadienyl)iron.
- composition of claim 5 wherein said compound is 2-isocyanatocyclopentadienyl(cyclopentadienyl)iron.
- a solid propellant composition consisting essentially of a cured intimate mixture of about 15 weight percent polybutadiene-acrylic acid copolymer, about 2.5 weight 4 percent tris(methylaziradinyl) phosphinic oxide, about 66.5 weight percent ammonium perchlorate, about 15 weight percent aluminum powder, and about 1 weight percent cyclopentadienyl [2 (1 hydroxyethyl) cyclopentadienyl] iron.
- a solid propellant composition consisting essentially of a cured intimate mixture of about 62 weight percent ammonium perchlorate, about 20 weight percent aluminum powder, about 14 weight percent polyurethane polymer, about 2 weight percent hydroxyl-terminated polypropylene ether, about 0.01 weight percent triethanolamine, and about 2 weight percent Z-isocyanatocyclopentadienyl (cyclopentadienyl) iron.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
United States Patent O 3,447,981 SOLID PROPELLANT COMPOSITIONS AND METHOD OF MODIFYING PROPELLANT BURNING RATE USING FERROCENE DERIVATIVES David C. Sayles, Huntsville, Ala., assiguor to the Umted States of America as represented by the Secretary of the Army No Drawing. Filed Nov. 1, 1962, Ser. No. 235,601 Int. Cl. C06b 11/00 U.S. Cl. 149-19 11 Claims The invention described herein may be manufactured and used by or for the Government for governmental purposes without the payment of any royalty thereon.
This invention relates to an improvement in solid propellants and more specifically to bis(cyclopentadienyl)iron derivatives containing reactive functional groups which act as burning rate accelerators in solid propellants.
The use of bis(cyclopentadienyl)iron in solid propellant compositions as a burning rate accelerator is well known in the art. However, this compound has inherent shortcomings which limit its usefulness. The first of these faults is that the bis(cyclopentadienyl)iron does not react with any of the ingredients in the propellant composition thereby lending itself to easy loss from the composition. This loss may occur during compounding by entrainment in vaporizing liquids or it may occur by sublimation after the propellant has undergone polymerization. Another fault of bis(cyclopentadienyl) iron is its poor compatibility with other ingredients in the propellant composition.
This invention employs bis(cyclopentadienyl) iron derivatives containing reactive functional groups to overcome these aforementioned shortcomings. These compounds can be used in solid propellant fuels to replace bis(cyclopentadienyl)iron which is currently utilized as a burning rate modifier. The bis(cyclopentadienyl) iron derivatives disclosed in this invention have many advantages over the previously used bis(cyclopentadienyl)iron. In addition to being as effective as a burning rate accelerator as bis(cyclopentadienyl)iron, these additives react with the cross linking agents of the propellant composition during curing to form an integral segment of the polymeric binder and result in a propellant composition having more uniform and more reproducible burning rate characteristics. Unlike bis(cyclopentadienyl)iron, these compounds are not lost from the propellant composition during the compounding step. Also, they are not lost by sublimation after the propellant has undergone polymerization. Finally, these compounds are more compatible with the other ingredients in propellant compositions than is bis(cyclopentadienyl)iron.
Therefore it is an object of this invention to provide burning-rate modifiers which form an integral segment of the polymer binder and result in a propellant composition having more uniform and reproducible burning rate characteristics.
It is a further object of this invention to provide burning rate modifiers which are not lost from the propellant composition by mechanical entrainment or sublimation. One other object of the instant invention is to provide burning rate modifiers which, when used in propellant compositions, are more compatible with the other ingredients of the propellant composition than bis(cyclopentadienyl)iron.
Another object of the instant invention is to provide an improved method of modifying the burning rate of solid propellant compositions wherein bis(cyclopentadienyl) iron has previously been employed.
These and other objects will become apparent to one skilled in the art upon reading the more detailed discussion presented hereinafter.
3,447,981 Patented June 3, 1969 The objects of this invention are accomplished by the substitution of a compound selected from the group consisting of cyclopentadienyl-[2(l-hydroxyethyl)-cyclopentadienyl]iron, 2 carboxycyclopentadienyl(cyclopen'tadienyl)iron, and 2 isocyanatocyclopentadienyl(cyclopentadienyl)iron for bis(cyclopentadienyl)iron when it is used in solid propellant compositions as a burning rate accelerator. These derivatives are employed in the propellant composition in quantities of 1% to 2% by weight.
The bis(cyclopentadienylfiron derivatives used in the instant invention are known in the art and may be obtained according to prior art techniques.
Other rnetallocenes, such as ruthenocene and osmocene, will undergo a similar series of reactions and function similarly as propellant burning rate modifiers.
The invention is further illustrated by the following examples of suitable propellant compositions. In the examples listed the bis(cyclopentadienyl)iron derivative reacts with the cross linking agent, such as tris(me'thylaziradinyl)phosphinic oxide since it has three functional groups. However, this cross linking agent can be replaced by any other tri-functional agent. Furthermore, it is not necessary that a tri-functional cross linking agent be present since the bis(cyclopentadienyl)iron derivative can react with any functional group in the propellant compositiqn thereby becoming an integral part of the composition. It is to be understood that these examples are for purpose of exemplification and that the invention is not limited thereto.
Example I Formulation: Wt. percent Polybutadiene-acrylic acid prepolymer 15 Tris(methylaziradinyl)phosphinic oxide 2.5 Ammonium perchlorate 66.5 Aluminum powder 15.0 Cyclopentadienyl [2 (1 hydroxyethyD-cyclopentadienyl]iron The formulation is mixed in any manner to insure thorough mingling of the ingredients and cured at The formulation is mixed and cured as in Example I.
As many possible embodiments can be made of this invention without departing from the scope thereof, it is to be understood that all matter herein set forth is to be interpreted as illustrative and that the invenion is limited only by the appended claims.
I claim:
1. In the method of accelerating the burning rate of solid propellant compositions with bis(cyclopentadienyl) iron as the burning rate accelerator, the improvement in said method which comprises the substitution in said propellant composition of a compound selected from the group consisting of cyclopentadienyl-[2-(1-hydroxyethyl)- cyclopentadienyl]iron, 2 carboxycyclopentadienyl(cyclopentadienyl)iron, and 2 isocyanatocyclopentadienyl(cyclopentadienyl)iron for said bis(cyclopentadieny1)iron.
2. The method of claim 1 wherein said compound is cyclopentadienyl [2 (1 hydroxyethyl) cyclopentadienyl]iron.
3. The method of claim 1 wherein said compound is 2- carboxycyclopentadienyl (cyclopentadienyl iron.
4. The mehtod of claim 1 wherein said compound is 2-isocyanatocyclopentadienyl (cyclopentadienyl iron.
5. In solid propellant compositions employing bis(cyclopentadienyl)iron as the burning rate accelerator, the improvement in these compositions which comprises the substitution of a compound selected from the group consisting of cyclopentadienyl [2-( l-hydroxyethyl)-cyclopentadienyl1iron, 2 carboxycyclopentadienyl(cyclopentadienyl)iron, 2 isocyanatocyclopentadienyl(cyclopentadienyl)iron for said bis(cyclopentadienyl)iron.
6. The composition of claim 5 wherein said compound is cyclopentadienyl [2 (1 hydroxyethyl) cyclopentadienyl] iron.
7. The composition of claim 5 wherein said compound is 2-carboxycyclopentadienyl(cyclopentadienyl)iron.
8. The composition of claim 5 wherein said compound is 2-isocyanatocyclopentadienyl(cyclopentadienyl)iron.
9. A solid propellant composition consisting essentially of a cured intimate mixture of about 15 weight percent polybutadiene-acrylic acid copolymer, about 2.5 weight 4 percent tris(methylaziradinyl) phosphinic oxide, about 66.5 weight percent ammonium perchlorate, about 15 weight percent aluminum powder, and about 1 weight percent cyclopentadienyl [2 (1 hydroxyethyl) cyclopentadienyl] iron.
10. A solid propellant composition consisting essentially of a cured intimate mixture of about 62 weight percent ammonium perchlorate, about 20 weight percent aluminum powder, about 14 weight percent polyurethane polymer, about 2 weight percent hydroxyl-terminated polypropylene ether, about 0.01 weight percent triethanolamine, and about 2 weight percent Z-isocyanatocyclopentadienyl (cyclopentadienyl) iron.
11. A solid propellant composition consisting essentially of a cured intimate mixture of about 15 weight percent polybutadiene-acrylic acid copolymer, about 2.5 weight percent tris(methylaziradinyl) phosphinic oxide, about 66.5 weight percent ammonium perchlorate, about 15 weight percent aluminum powder, and about 1 weight percent 2-carboxycyclopentadienyl (cyclopentadienyl) iron.
References Cited UNITED STATES PATENTS 3,002,830 10/1961 Barr 149-19 3,038,299 6/ 1962 Pedersen 149-74 X BENJAMIN R. PADGETT, Primary Examiner.
US. Cl. X.R. 149-109, 44
Claims (1)
- 5. IN SOLID PROPELLANT COMPOSITIONS EMPLOYING BIS(CYCLOPENTADIENYL) IRON AS THE BURNING RATE ACCELERATOR, THE IMPROVEMENT IN THESE COMPOSITIONS WHICH COMPRISES THE SUBSTITUTION OF A COMPOUND SELECTED FROM THE GROUP CONSISING OF CYCLOPENTADIENYL(2-(1-HYDROXYETHYL)-CYCLOPENTADIENYL)IRON, 2-CARBOXYCLOPENTADIENYL(CYCLOPENTADIENYL)IRON, 2-ISOCYANATOCYCLOENTADIENYL(CYCLOPENTADIENYL)IRON FOR SAID BIS(CYCLOPENTADIENYL)IRON.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23560162A | 1962-11-01 | 1962-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3447981A true US3447981A (en) | 1969-06-03 |
Family
ID=22886191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US235601A Expired - Lifetime US3447981A (en) | 1962-11-01 | 1962-11-01 | Solid propellant compositions and method of modifying propellant burning rate using ferrocene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3447981A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3718633A (en) * | 1969-11-25 | 1973-02-27 | Us Army | Hydroxy-terminated copolymers of butadiene and ferrocene derivatives |
| US3765965A (en) * | 1972-07-12 | 1973-10-16 | Us Army | Composite propellant composition with ferrocene compound as bonding agent and ballistic modifier |
| US3881969A (en) * | 1969-11-25 | 1975-05-06 | Us Army | Solid propellant with hydroxy-terminated butadiene-ferrocenyl methyl acrylate copolymer binder |
| US3951703A (en) * | 1971-06-15 | 1976-04-20 | The United States Of America As Represented By The Secretary Of The Army | Ballistic modification of composite propellants by use of 2-ferrocenyltetrahydrofuran novel liquid compound |
| US3954527A (en) * | 1970-03-24 | 1976-05-04 | The United States Of America As Represented By The Secretary Of The Army | Solid propellant with iron-carbonyl containing polymer binder |
| US4034675A (en) * | 1970-08-20 | 1977-07-12 | The United States Of America As Represented By The Secretary Of The Army | Catalysts - containing ablative resonance suppressors |
| US4070212A (en) * | 1964-11-23 | 1978-01-24 | Thiokol Corporation | High performance fast burning solid propellant |
| EP0741119A1 (en) * | 1995-05-05 | 1996-11-06 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Composite propellant and process for the manufacture thereof |
| US6039819A (en) * | 1982-03-04 | 2000-03-21 | Atlantic Research Corporation | Solid propellant containing ferrocenyl phosphine derivatives |
| US10196324B2 (en) | 2014-12-08 | 2019-02-05 | Raytheon Company | Ferrocenyl bonding agent oxidizers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3002830A (en) * | 1959-01-02 | 1961-10-03 | Olin Mathieson | Method of manufacturing solid propellants having a polymeric fuel-binder using a plurality of crosslinking agents |
| US3038299A (en) * | 1953-12-15 | 1962-06-12 | Du Pont | Fuels and process for burning them |
-
1962
- 1962-11-01 US US235601A patent/US3447981A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3038299A (en) * | 1953-12-15 | 1962-06-12 | Du Pont | Fuels and process for burning them |
| US3002830A (en) * | 1959-01-02 | 1961-10-03 | Olin Mathieson | Method of manufacturing solid propellants having a polymeric fuel-binder using a plurality of crosslinking agents |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070212A (en) * | 1964-11-23 | 1978-01-24 | Thiokol Corporation | High performance fast burning solid propellant |
| US3718633A (en) * | 1969-11-25 | 1973-02-27 | Us Army | Hydroxy-terminated copolymers of butadiene and ferrocene derivatives |
| US3881969A (en) * | 1969-11-25 | 1975-05-06 | Us Army | Solid propellant with hydroxy-terminated butadiene-ferrocenyl methyl acrylate copolymer binder |
| US3954527A (en) * | 1970-03-24 | 1976-05-04 | The United States Of America As Represented By The Secretary Of The Army | Solid propellant with iron-carbonyl containing polymer binder |
| US4034675A (en) * | 1970-08-20 | 1977-07-12 | The United States Of America As Represented By The Secretary Of The Army | Catalysts - containing ablative resonance suppressors |
| US3951703A (en) * | 1971-06-15 | 1976-04-20 | The United States Of America As Represented By The Secretary Of The Army | Ballistic modification of composite propellants by use of 2-ferrocenyltetrahydrofuran novel liquid compound |
| US3765965A (en) * | 1972-07-12 | 1973-10-16 | Us Army | Composite propellant composition with ferrocene compound as bonding agent and ballistic modifier |
| US6039819A (en) * | 1982-03-04 | 2000-03-21 | Atlantic Research Corporation | Solid propellant containing ferrocenyl phosphine derivatives |
| EP0741119A1 (en) * | 1995-05-05 | 1996-11-06 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Composite propellant and process for the manufacture thereof |
| US10196324B2 (en) | 2014-12-08 | 2019-02-05 | Raytheon Company | Ferrocenyl bonding agent oxidizers |
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