US3886007A - Solid propellant having a ferrocene containing polyester fuel binder - Google Patents

Solid propellant having a ferrocene containing polyester fuel binder Download PDF

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US3886007A
US3886007A US358568A US35856873A US3886007A US 3886007 A US3886007 A US 3886007A US 358568 A US358568 A US 358568A US 35856873 A US35856873 A US 35856873A US 3886007 A US3886007 A US 3886007A
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ferrocene
solid propellant
polymeric binder
solid
binder
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US358568A
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Jr Charles S Combs
Charles I Ashmore
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ATK Launch Systems LLC
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Thiokol Corp
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
    • C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
    • C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
    • C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen

Definitions

  • Ferrocene and ferrocene derivatives have been used to give improved combustion stability and increased burn rates.
  • One of the long recognized problems associated with the use of these compounds has been the relatively high mobility and vapor pressure of ferrocene and ferrocene derivatives. Associated with this problem is the fact that this high mobility and high vapor pressure limits the amount of ferrocene compound which can be used in a practical propellant since losses through volatility and bleeding are severe at high levels of incorporation of organometallic compounds.
  • nonvolatile solid ferrocene derivatives are used to give decreased mobility and volatility. When the object of the additive is to obtain high burning rates, large amounts of ferrocene compounds must be used.
  • the instant invention was developed whereby high burning rates were made available without the extra expense involved in producing oxidizer having very small particle sizes.
  • This invention relates, therefore, to the area of composite solid propellants and solid propellant binders in which ferrocene types compounds are used to give stable combustion and increased burning rates, and more specifically to polyester propellant binders in which organometallic moieties are included as integral parts of the binder.
  • the primary object of this invention is to provide ferrocene polyesters that will give composite solid propellants stable combustion and increased burning rates.
  • Another object of the invention is to provide ferrocene polyester binders in which organometallic moieties are included as integral parts of the binder.
  • Liquid plasticizable, curable ferrocene containing polyesters have been prepared conveniently and in good yield.
  • the polymers are prepared from the appropriate acid and the appropriate glycol according to the reaction shown:
  • one of the comonomers is a difunctional alcohol of the general structure I-IO(R)OI-I in which (R) is an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, or alkynyl group, and may be substituted by one or more ferrocenyl or substituted ferrocenyl groups, and in which the carbon chain may contain or may be substituted by groups containing sulfur, oxygen, halogen, nitrogen, or metallic atoms, and in which one of the comonomers is a difunctional acid of the general structure:
  • (R) is as described above and in which one or more comonomers contain at least one ferrocenyl or substituted ferrocenyl group as an integral part of one of the repeating units.
  • the polyester is terminated by hydroxyl or carboxyl groups, or both, according to the conditions of the reaction. In the instance of termination by carboxylic acid groups, the polyester is cured by means of common aziridinyl or epoxide-type curing agents. When the polyester is terminated by hydroxyl groups, the polyester is cured by means of common isocyanate or carboxylic acid anhydride curing agents.
  • Fc represents ferrocenyl
  • the (ferrocenylmethylthio)succinic acid prepared above (11.48 g, 0.033 mole), 2-butene-l,4-diol (2.64 g., 0.030 mole), and p-toluenesulfonic acid monohydrate (0.07 g., 0.5 percent of the other constituents by weight) were placed in 80 ml. of toluene and allowed to reflux for four hours. The orange solution was filtered, while hot, through glass wool into approximately 250 ml. of n-hexane. The polymer separated to the bottom on standing, and the supernatent liquid was decanted.
  • the polymer was taken up in acetone and poured into n-hexane after which the precipitationdecantation procedure was repeated.
  • the polymer was taken up in acetone and the solution poured through a column containing a small amount of alumina (acid washed). Residual polymer was eluted with more acetone, the solutions combined, and the solvent removed in vacuo with heat (approximately 40C).
  • a clear, orange, viscous but mobile polymer was recovered in an amount equal to 76 percent (9.94 g.) of the sum of the monomers less the theoretical amount of water evolved.
  • Infrared analysis agreed with the structural assignment:
  • carboxyl content was found by titration to be 0.1076 eq/ 100 g. for the polymer obtained by this preparation. Assuming the functionality to equal 2, the molecular weight is calculated to be 1,859. The following analysis was obtained, by ashing, for iron: found Fe, 14.7 percent; calculated Fe, 14.4 percent.
  • the resulting polyester was similar in appearance and physical properties to the previously described polymer.
  • an excellent solid propellant composition comprising the following ingredients: 2 to 90 percent of a solid oxidizer such as ammonium perchlorate, ammonium nitrate or RDX; 2 to 40 percent of a polymeric binder, as embodied in the instant invention, to 50 percent of a metallie fuel, 0 to 25 percent ofa'dd-itives such as plasticizers, burning rate catalysts, cure catalysts, combustion stabilizers, and 0 to 30 percent of a non-metal containing polymeric fuel binder such as a hydrocarbon polymer.
  • a solid oxidizer such as ammonium perchlorate, ammonium nitrate or RDX
  • 2 to 40 percent of a polymeric binder as embodied in the instant invention, to 50 percent of a metallie fuel, 0 to 25 percent ofa'dd-itives such as plasticizers, burning rate catalysts, cure catalysts, combustion stabilizers, and 0 to 30 percent of a non-metal containing polymeric fuel binder such as
  • an oxidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising:
  • said binder comprising a ferrocene polyester consisting essentially of the reaction product of 2-butane- 1,4-diol and (ferrocenylmethylthio) succinic acid.
  • a composite solid propellant composition comprising a solid ozidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising:
  • said polymeric binder being a ferrocene polyester consisting essentially of the reaction product of 1,5-pentanediol and (ferrocenylmethylthio) succinic acid.
  • a solid propellant composition comprising a solid oxidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising:
  • said polymeric binder being a ferrocene polyester consisting essentially of the reaction product of 1,5-pentanediol, ethylene glycol, and (ferrocenylmethylthio) succinic acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Abstract

Ferrocene Polyesters that are prepared by the equation: HO2C(R)CO2H+HO(R)OH -> HO2C ((R)-CO2(R)-O2C)xRCO2H wherein HO(R)-OH is a difunctional alcohol and HO2C(R)CO2H is a difunctional acid, and (R) belongs to the group comprising alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl or alkynyl radicals which may be substituted by one or more ferrocenyl groups.

Description

United States Patent Combs, Jr. et al.
[ 51 May 27, 1975 SOLID PROPELLANT HAVING A FERROCENE CONTAINING POLYESTER FUEL BINDER Inventors: Charles S. Combs, Jr., Huntsville; Charles I. Ashmore, Owens Cross Roads, both of Ala.
Assignee: Thiokol Corporation, Bristol, Pa.
Filed: May 9, 1973 Appl. N0.: 358,568
' Related U.S. Application Data 7 V a Division of Ser. No. 730,633, May 20, 1968, abandoned.
U.S. Cl. 149/19.2; 149/19.5; 149/20 Int. Cl C06d 5/06 Field of Search 149/19, 20, 38, 44, 19.2,
[56] References Cited UNITED STATES PATENTS 3,598,850 8/1971 Dewey 149/19 X 3,739,004 6/1973 Ponder et a1. 149/19 X Primary ExaminerBenjamin R. Padgett Attorney, Agent, or Firm--Thomas W. Brennan [57] ABSTRACT 4 Claims, No Drawings SOLID PROPELLANT HAVING A FERROCENE CONTAINING POLYESTER FUEL BINDER This a division of application Ser. No. 730,633 now abandoned filed May 20, 1968.
BACKGROUND OF THE INVENTION l. Field of the Invention Ferrocene and ferrocene derivatives have been used to give improved combustion stability and increased burn rates. One of the long recognized problems associated with the use of these compounds has been the relatively high mobility and vapor pressure of ferrocene and ferrocene derivatives. Associated with this problem is the fact that this high mobility and high vapor pressure limits the amount of ferrocene compound which can be used in a practical propellant since losses through volatility and bleeding are severe at high levels of incorporation of organometallic compounds. In some instances nonvolatile solid ferrocene derivatives are used to give decreased mobility and volatility. When the object of the additive is to obtain high burning rates, large amounts of ferrocene compounds must be used. However, large amounts of solid ferrocene or solid ferrocene derivatives are used to the detriment of practical processability. This invention solves the problems associated with volatility and bleeding out of ferrocene derivatives by incorporating the catalysts as an agent which is chemically bonded into the propellant binder. The catalytic agent is thereby prevented from being lost except by rupture of a bond by a chemical reaction.
2. Description of the Prior Art One of the greatest problems to be overcome in this particular field of endeavor is producing either chemically or mechanically, procedures that will increase the burning rate of a composite solid propellant in a solid propellant rocket motor to increase the efficiency of the solid propellant rocket motor during operational flights. One of the procedures previously followed related to particle size of the particular oxidizer that was used in the composite solid propellant and it had been found that it was necessary to use very small particles of oxidizer in the composite solid propellant in order to achieve high burning rates.
In order to overcome the extra expense involved in producing the fine particles of oxidizer, the instant invention was developed whereby high burning rates were made available without the extra expense involved in producing oxidizer having very small particle sizes.
SUMMARY OF THE INVENTION This invention relates, therefore, to the area of composite solid propellants and solid propellant binders in which ferrocene types compounds are used to give stable combustion and increased burning rates, and more specifically to polyester propellant binders in which organometallic moieties are included as integral parts of the binder.
One of the most important advantages which accrue from the instant invention is that in addition to the ferrocene unit which is chemically bonded into the propellant binder, other solid or liquid ferrocene compounds may be added up to levels which induce problems with processing, bleeding or volatility. In this manner much larger amounts of burning rate catalysts may be incorporated in the composite solid propellant, and
extremely high burning rates may be achieved without the problems previously encountered.
The primary object of this invention, therefore, is to provide ferrocene polyesters that will give composite solid propellants stable combustion and increased burning rates.
Another object of the invention is to provide ferrocene polyester binders in which organometallic moieties are included as integral parts of the binder.
While only certain objects and advantages of the invention have been set forth, it is believed that other objects and advantages will become apparent to one skilled in the art from the following detailed description and discussion.
DESCRIPTION OF THE PREFERRED EMBODIMENTS Liquid plasticizable, curable ferrocene containing polyesters have been prepared conveniently and in good yield. In general, the polymers are prepared from the appropriate acid and the appropriate glycol according to the reaction shown:
in which one of the comonomers is a difunctional alcohol of the general structure I-IO(R)OI-I in which (R) is an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, or alkynyl group, and may be substituted by one or more ferrocenyl or substituted ferrocenyl groups, and in which the carbon chain may contain or may be substituted by groups containing sulfur, oxygen, halogen, nitrogen, or metallic atoms, and in which one of the comonomers is a difunctional acid of the general structure:
in which (R) is as described above and in which one or more comonomers contain at least one ferrocenyl or substituted ferrocenyl group as an integral part of one of the repeating units. The polyester is terminated by hydroxyl or carboxyl groups, or both, according to the conditions of the reaction. In the instance of termination by carboxylic acid groups, the polyester is cured by means of common aziridinyl or epoxide-type curing agents. When the polyester is terminated by hydroxyl groups, the polyester is cured by means of common isocyanate or carboxylic acid anhydride curing agents.
The preparation of the ferrocene containing polyester embodying the invention is illustrated by the following:
EXAMPLES A mixture of (hydroxymethyhferrocene (21.6 g., 0.100 mole) and mercaptosuccinic acid (30.0 g., 0.200 mole) contained in 200 ml. of water was stirred and brought to the reflux temperature, after which it was allowed to stand until it reached room temperature. The resulting solid was recovered by vacuum filtration and washed several times with water. The solid was taken up in ether and extracted several times with 5 percent aqueous sodium bicarbonate. The extractions were combined, gravity filtered, and neutralized by addition to 10 percent hydrochloric acid. The precipitate which resulted was extracted with ether. The ethereal solution was washed with water until neutral to litmus. The ether layer was dried over anhydrous magnesium sulfate, filtered (gravity) and the solvent removed in vacuo. (Ferrocenylmethylthio)succinic acid, M.P. l77l79, was recovered in an amount equal to 78 percent (27.7 g) of the theoretical yield. Infrared analysis agreed with the structural assignment:
where Fc represents ferrocenyl.
The (ferrocenylmethylthio)succinic acid prepared above (11.48 g, 0.033 mole), 2-butene-l,4-diol (2.64 g., 0.030 mole), and p-toluenesulfonic acid monohydrate (0.07 g., 0.5 percent of the other constituents by weight) were placed in 80 ml. of toluene and allowed to reflux for four hours. The orange solution was filtered, while hot, through glass wool into approximately 250 ml. of n-hexane. The polymer separated to the bottom on standing, and the supernatent liquid was decanted. The polymer was taken up in acetone and poured into n-hexane after which the precipitationdecantation procedure was repeated. The polymer was taken up in acetone and the solution poured through a column containing a small amount of alumina (acid washed). Residual polymer was eluted with more acetone, the solutions combined, and the solvent removed in vacuo with heat (approximately 40C). A clear, orange, viscous but mobile polymer was recovered in an amount equal to 76 percent (9.94 g.) of the sum of the monomers less the theoretical amount of water evolved. Infrared analysis agreed with the structural assignment:
carboxyl content was found by titration to be 0.1076 eq/ 100 g. for the polymer obtained by this preparation. Assuming the functionality to equal 2, the molecular weight is calculated to be 1,859. The following analysis was obtained, by ashing, for iron: found Fe, 14.7 percent; calculated Fe, 14.4 percent.
In a similar manner a mixture of 1, S-pentanediol and ethylene glycol (75/25 by mole percent) was allowed to react with (ferrocenylmethylthio)succinic acid to afford a ferrocene containing polyester which exemplitied a product prepared from a reaction in which more than one polyfunctional alcohol was used.
The resulting polyester was similar in appearance and physical properties to the previously described polymer.
It was also determined that an excellent solid propellant composition comprising the following ingredients could be provided: 2 to 90 percent of a solid oxidizer such as ammonium perchlorate, ammonium nitrate or RDX; 2 to 40 percent of a polymeric binder, as embodied in the instant invention, to 50 percent of a metallie fuel, 0 to 25 percent ofa'dd-itives such as plasticizers, burning rate catalysts, cure catalysts, combustion stabilizers, and 0 to 30 percent of a non-metal containing polymeric fuel binder such as a hydrocarbon polymer.
It was also determined that tris-(2 methylaziridinyl)- phosphine oxide and dibutylcarbutol formal could be used in the foregoing composition to provide excellent results as a curing agent and as a plasticizer respectively. It was also determined that the solid propellant composition possessed good physical properties.
It is to be understood, therefore. that while the present invention has been described by means of the foregoing examples, many obvious modifications and variations will occur to those with ordinary skill in the art and it is to be further understood that such variations and modifications may be adhered to without departing from the original spirit of the invention, and the scope of the appended claims.
What is claimed is:
1. In a solid propellant composition comprising;
an oxidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising:
said binder comprising a ferrocene polyester consisting essentially of the reaction product of 2-butane- 1,4-diol and (ferrocenylmethylthio) succinic acid.
2. A solid Propellant composition as in claim 1, wherein the polymeric binder is wherein x is equal to a number resulting in moleculare weight of 1.859.
3. A composite solid propellant composition comprising a solid ozidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising:
said polymeric binder being a ferrocene polyester consisting essentially of the reaction product of 1,5-pentanediol and (ferrocenylmethylthio) succinic acid.
4. In a solid propellant composition comprising a solid oxidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising:
said polymeric binder being a ferrocene polyester consisting essentially of the reaction product of 1,5-pentanediol, ethylene glycol, and (ferrocenylmethylthio) succinic acid.

Claims (4)

1. IN A SOLID PROPELLANT COMPOSITION COMPRISING, AN OXIDIZER SELECTED FROM THE GROUP CONSISTING OF AMMONIUM PERCHLORATE, AMMONIUM NITRATE AND RDX, A METALLIC FUEL AND A POLYMERIC BINDER, THE IMPROVEMENT COMPRISING: SAID BINDER COMPRISING A FERROCENE POLYESTER CONSISTING ESSENTIALLY OF THE REACTION PRODUCT OF 2-BUTANE-1,4-DIOL AND (FERROCENYLMETHYLTHIO) SUCCINIC ACID.
2. A solid Propellant composition as in claim 1, wherein the polymeric binder is HO2C-CH2CH (SCH2Fc) CO2CH2CH CHCH2O2xCH2CH(SCH2Fc)CO2H wherein x is equal to a number resulting in moleculare weight of 1.859.
3. A composite solid propellant composition comprising a solid ozidizer selected from the group consisting of ammonium perchlorate, ammOnium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising: said polymeric binder being a ferrocene polyester consisting essentially of the reaction product of 1,5-pentanediol and (ferrocenylmethylthio) succinic acid.
4. In a solid propellant composition comprising a solid oxidizer selected from the group consisting of ammonium perchlorate, ammonium nitrate and RDX, a metallic fuel and a polymeric binder, the improvement comprising: said polymeric binder being a ferrocene polyester consisting essentially of the reaction product of 1,5-pentanediol, ethylene glycol, and (ferrocenylmethylthio) succinic acid.
US358568A 1968-05-20 1973-05-09 Solid propellant having a ferrocene containing polyester fuel binder Expired - Lifetime US3886007A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5235936A (en) * 1992-12-04 1993-08-17 Kracklauer John J Ferrocene injection system
US5386804A (en) * 1991-11-21 1995-02-07 Veba Oel Aktiengesellschaft Process for the addition of ferrocene to combustion or motor fuels
US6969434B1 (en) * 2002-12-23 2005-11-29 The United States Of America As Represented By The Secretary Of The Navy Castable thermobaric explosive formulations
CN110423184A (en) * 2019-08-01 2019-11-08 上海航天化工应用研究所 A kind of solid propellant rocket propellant and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3598850A (en) * 1969-06-11 1971-08-10 Us Air Force Ferrocene polyglycols
US3739004A (en) * 1971-10-01 1973-06-12 Us Army Synthesis ferrocenyl butadiene compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3598850A (en) * 1969-06-11 1971-08-10 Us Air Force Ferrocene polyglycols
US3739004A (en) * 1971-10-01 1973-06-12 Us Army Synthesis ferrocenyl butadiene compounds

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5386804A (en) * 1991-11-21 1995-02-07 Veba Oel Aktiengesellschaft Process for the addition of ferrocene to combustion or motor fuels
US5235936A (en) * 1992-12-04 1993-08-17 Kracklauer John J Ferrocene injection system
US6969434B1 (en) * 2002-12-23 2005-11-29 The United States Of America As Represented By The Secretary Of The Navy Castable thermobaric explosive formulations
CN110423184A (en) * 2019-08-01 2019-11-08 上海航天化工应用研究所 A kind of solid propellant rocket propellant and preparation method thereof
CN110423184B (en) * 2019-08-01 2021-07-13 上海航天化工应用研究所 Propellant for solid rocket engine and preparation method thereof

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