US3898112A - Solid 5-aminotetrazole nitrate gas generating propellant with block copolymer binder - Google Patents

Solid 5-aminotetrazole nitrate gas generating propellant with block copolymer binder Download PDF

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US3898112A
US3898112A US074894A US7489470A US3898112A US 3898112 A US3898112 A US 3898112A US 074894 A US074894 A US 074894A US 7489470 A US7489470 A US 7489470A US 3898112 A US3898112 A US 3898112A
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styrene
gas generating
block copolymer
propellant composition
solid
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US074894A
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Ruediger A H Strecker
Hermann S Haiss
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US Department of Navy
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    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00—Compositions containing a nitrated organic compound
    • C06B25/04—Compositions containing a nitrated organic compound the nitrated compound being an aromatic
    • 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

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  • ABSTRACT A solid gas generating propellant based upon 5- aminotetrazole nitrate as the oxidant component and utilizing a binder matrix of a block eopolymer selected from the group consisting of styrene-butadiene-styrene and styrene-isoprene-styrene.
  • This invention relates generally to composite propellants and more particularly to a composite propellant especially useful as a gas generator.
  • ammonium nitrate As the oxidizing component, the ammonium nitrate based gas generators burn very slowly; i.e., about 0.10 inches/sec., even with the addition of burning rate modifiers.
  • ammonium perchlorate As the oxidant. Although these have higher burning rate characteristics than the ammonium nitrate based compositions, the ammonium perchlorate generators generate deleterious corrosive gases and therefore also have limited applicability.
  • Another object of the present invention is to provide a gas generating solid propellant composition based upon S-aminotetrazole nitrate which yields only noncorrosive gases upon combustion.
  • Still another object of this invention is to provide a gas generating solid propellant composition based upon S-aminotetrazole nitrate which possesses improved mechanical, physical and chemical characteristics.
  • a still further object of the instant invention is to provide a gas generating solid propellant composition DESCRIPTION OF THE PREFERRED EMBODIMENTS
  • the gas generating propellant compositions of this invention are based upon S-aminotetrazole nitrate, depicted by the structural formula below, as the oxidizing material ll II N c NH HNO3
  • the oxidizing compound of the formula is easily and conventionally prepared by the addition of nitric acid to S-aminotetrazole.
  • the 5- aminotetrazole nitrate is incorporated in a binder matrix which is a block copolymer of styrene and butadiene or styrene and isoprene.
  • the propellant composition of this invention is comprised of from about to about 87 percent by weight of the compound of formula l and from about 13 to about 25 percent by weight of the styrene-butadiene-styrene or styrene-isoprene-styrene binder.
  • the present propellant compositions are comprised of from about 84 to about 87 percent by weight of oxidant.
  • the styrene-butadiene-styrene and the styreneisoprene-styrene block copolymer binders of the pres ent invention have a molecular weight within the range of from about 60,000 to about 100,000 with a first block styrene molecular weight of from about 9,600 to about 13,600, a center block molecular weight (butadiene or isoprene) of from about 47,500 to about 69,800 and a second block styrene molecular weight of from about 9,400 to about 14,500.
  • the styrene content is preferably maintained within the range of from about 28 to about 29 percent by weight and more specifically about 28.6 percent by weight. Higher styrene contents tend to make the material too hard for propellant composition use.
  • the styrene-butadiene-styrene and styrene-isoprenestyrene block copolymers are rubbery materials and are commercially available as KRATON 1 102 and KRATON l 107 respectfully, manufactured by the Shell Chemical Company, Emeryville, California.
  • the gas generating solid propellant compositions of this invention are readily made by conventional mixing procedures.
  • the solid styrene-butadienestyrene or styrene-isoprene-styrene copolymer is dissolved in a suitable solvent such as cyclohexane, in a ratio of, for example, 1 part to 5 parts respectfully.
  • the 5- aminotetrazole nitrate and other additives such as for example anti-oxidants are added with mixing and under vacuum to the copolymer solution.
  • the dry mix is removed from the mixer and compression or extruded molded.
  • the composition does not require any curing and retains its elastic properties for an extended period of time.
  • the gas generating propellant compositions possess excellent aging characteristics and thus have long shelf-lives. Furthermore, the excellent m, values of less than 0.3, also characteristic of the present propellant compositions, are also attributed to the copolymer binder materials employed herein.
  • Organic anti-oxidants and plasticizing agents also may be added in minor amounts (about 3 to percent by weight) to the propellant compositions of this invention for additional improved aging and mechanical properties.
  • some anti-oxidants which are applicable herein include 2.2-methylenebis(4-methyl- 6-tertiarybutylphenol) and phenyl B-naphthylamine and the like
  • plasticizing agents include dioctyladipate, Conco oil (an aromatic hydrocarbon made by the Continental Oil Company, New York, New York,) Circolight oil (another aromatic hydrocarbon made by the Sun Oil Company of Phil., Pa.) and the like.
  • Conco oil an aromatic hydrocarbon made by the Continental Oil Company, New York, New York,
  • Circolight oil another aromatic hydrocarbon made by the Sun Oil Company of Phil., Pa.
  • Example 1 The composition of Example 1 exhibited a burning rate of 0.420 in./sec at 1000 psi and 77F.
  • the popular ammonium nitrate based gas generators generally burn only at about 0.10 inches/sec even with the addition of burning rate modifiers which add corrosive materials to the end combustion products.
  • the composition of Example 1 is further characterized by a burning rate exponent of 0.51 and a 11 valve of 0.296. This constant 'rr represents the burning rate dependency of a propellant upon changes in temperature and pressure.
  • a low Tl' value is generally desired since the burning rate of an ideal propellant composition would be completely independent of variations in temperature and pressure.
  • a 11 value of between 0.2 and 0.3 is therefore noteworthy.
  • composition of example 1 ignites at 168C and after constant heating at 120C it does not ignite or show any exotherm over a period of 24 hours, which clearly demonstrates the improved stability of the instant composition.
  • the gas generating compositions of this invention are especially useful, for instance, for actuating gas pres sure operated mechanical devices; e.g., for driving engines, electric generator motors, and turbines or for operating pneumatic tools, and for the propulsion and guidance of rockets or other gas escape reaction propelled devices.
  • a gas generating solid propellant composition comprising 5-aminotetrazole nitrate as the oxidant and a binder matrix selected from the group consisting of a styrene-butadiene-styrene block copolymer and a styrene-isoprene-styrene block copolymer.
  • the gas generating solid propellant composition of claim 3 which further includes a minor amount of a material selected from the group consisting of an organic anti-oxidant, an organic plasticizing agent and mixtures

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A solid gas generating propellant based upon 5-aminotetrazole nitrate as the oxidant component and utilizing a binder matrix of a block copolymer selected from the group consisting of styrenebutadiene-styrene and styrene-isoprene-styrene.

Description

United States Patent [191 Strecker et a1.
[ 51 Aug. 5, 1975 SOLID S-AMINOTETRAZOLE NITRATE GAS GENERATING PROPELLANT WITH BLOCK COPOLYMER BINDER [75] Inventors: Ruediger A. H. Strecker, Oxon Hill;
Hermann S. Haiss, Indian Head, both of Md.
[73] Assignee: The United States of America as represented by the Secretary of the Navy, Washington, DC.
22 Filed: Sept. 23, 1970 211 App1.No.:74,894
[52] US. Cl. l49/l9.9; 149/19.91; 149/92 [51] Int. Cl. .1 C06D 5/06 [58] Field of Search 149/19, 19.9, 19.91, 92
Primary Examiner-Benjamin R. Padgett Assistant ExaminerE. A. Miller Attorney, Agent, or Firm-R. S. Sciascia; .1. A. Cooke [57] ABSTRACT A solid gas generating propellant based upon 5- aminotetrazole nitrate as the oxidant component and utilizing a binder matrix of a block eopolymer selected from the group consisting of styrene-butadiene-styrene and styrene-isoprene-styrene.
5 Claims, N0 Drawings SOLID S-AMINOTETRAZOLE NITRATE GAS GENERATING PROPELLANT WITH BLOCK COPOLYMER BINDER BACKGROUND OF THE INVENTION This invention relates generally to composite propellants and more particularly to a composite propellant especially useful as a gas generator.
In the past, the mainstay of gas generating composite propellants has been based on ammonium nitrate as the oxidizing component. Although generally acceptable the ammonium nitrate based gas generators burn very slowly; i.e., about 0.10 inches/sec., even with the addition of burning rate modifiers.
Consequently, large volumes of gas are not produced quickly by these systems and thus they are not effective for purposes where total pressure is required immediately, for example, where the guidance of a missile is dependent upon instantaneous total pressurization.
Efforts have been made to improve the burning rates of ammonium nitrate gas generators, but have not been completely successful, since the addition of burning rate modifiers, while increasing the burning rate, cause additional problems, such as the erosion of hardware due to the formation of metal oxides not otherwise present in the system. However, a desirable characteristic of the ammonium nitrate compositions, also desirable for all gas generators, is its low flame temperature.
Another gas generating propellant composition which has been employed in the past is based upon ammonium perchlorate as the oxidant. Although these have higher burning rate characteristics than the ammonium nitrate based compositions, the ammonium perchlorate generators generate deleterious corrosive gases and therefore also have limited applicability.
ln US. application Ser. No. 883,327 by Moy et al. filed Nov. 28, 1969, a gas generating propellant composition based upon S-aminotetrazole nitrate as the oxidant was disclosed. This gas generator was found to be faster burning than the ammonium nitrate type and have a comparable low flame temperature.
Other characteristics, such as a low burning rate slope and a rr value of between 0.2 and 0.3, increased temperature stability, and good aging of the propellant composition, are also highly desirable properties for a solid propellant. Furthermore, the complete absence of inorganic additives, even small amounts that are often required as curing catalysts for the binder material or ballistic modifiers, is preferred to avoid any formation ofinorganic solids upon combustion, which are intolerable in some applications.
SUMMARY OF THE INVENTION Accordingly, it is one object of the present invention to provide an improved fast burning, gas generating solid propellant composition based upon 5- aminotetrazole nitrate.
Another object of the present invention is to provide a gas generating solid propellant composition based upon S-aminotetrazole nitrate which yields only noncorrosive gases upon combustion.
Still another object of this invention is to provide a gas generating solid propellant composition based upon S-aminotetrazole nitrate which possesses improved mechanical, physical and chemical characteristics.
A still further object of the instant invention is to provide a gas generating solid propellant composition DESCRIPTION OF THE PREFERRED EMBODIMENTS The gas generating propellant compositions of this invention are based upon S-aminotetrazole nitrate, depicted by the structural formula below, as the oxidizing material ll II N c NH HNO3 The oxidizing compound of the formula is easily and conventionally prepared by the addition of nitric acid to S-aminotetrazole.
For the purposes of this invention, the 5- aminotetrazole nitrate is incorporated in a binder matrix which is a block copolymer of styrene and butadiene or styrene and isoprene. Generally, the propellant composition of this invention is comprised of from about to about 87 percent by weight of the compound of formula l and from about 13 to about 25 percent by weight of the styrene-butadiene-styrene or styrene-isoprene-styrene binder. Preferably, the present propellant compositions are comprised of from about 84 to about 87 percent by weight of oxidant.
The styrene-butadiene-styrene and the styreneisoprene-styrene block copolymer binders of the pres ent invention have a molecular weight within the range of from about 60,000 to about 100,000 with a first block styrene molecular weight of from about 9,600 to about 13,600, a center block molecular weight (butadiene or isoprene) of from about 47,500 to about 69,800 and a second block styrene molecular weight of from about 9,400 to about 14,500. The styrene content is preferably maintained within the range of from about 28 to about 29 percent by weight and more specifically about 28.6 percent by weight. Higher styrene contents tend to make the material too hard for propellant composition use.
The styrene-butadiene-styrene and styrene-isoprenestyrene block copolymers are rubbery materials and are commercially available as KRATON 1 102 and KRATON l 107 respectfully, manufactured by the Shell Chemical Company, Emeryville, California.
The gas generating solid propellant compositions of this invention are readily made by conventional mixing procedures. For example, the solid styrene-butadienestyrene or styrene-isoprene-styrene copolymer is dissolved in a suitable solvent such as cyclohexane, in a ratio of, for example, 1 part to 5 parts respectfully.
Upon the substantial solution of the copolymer, the 5- aminotetrazole nitrate and other additives such as for example anti-oxidants are added with mixing and under vacuum to the copolymer solution. When all the solvent has been evaporated off, the dry mix is removed from the mixer and compression or extruded molded. The composition does not require any curing and retains its elastic properties for an extended period of time.
As a result of the low unsaturation (unsaturation is easily accessible to air oxidation), which is characteristic of the copolymer binders of the present invention, and the absence of any inorganic additives for curing purposes or ballistic modifying purposes, the gas generating propellant compositions possess excellent aging characteristics and thus have long shelf-lives. Furthermore, the excellent m, values of less than 0.3, also characteristic of the present propellant compositions, are also attributed to the copolymer binder materials employed herein.
Organic anti-oxidants and plasticizing agents also may be added in minor amounts (about 3 to percent by weight) to the propellant compositions of this invention for additional improved aging and mechanical properties. Specifically, some anti-oxidants which are applicable herein include 2.2-methylenebis(4-methyl- 6-tertiarybutylphenol) and phenyl B-naphthylamine and the like, while applicable plasticizing agents include dioctyladipate, Conco oil (an aromatic hydrocarbon made by the Continental Oil Company, New York, New York,) Circolight oil (another aromatic hydrocarbon made by the Sun Oil Company of Phil., Pa.) and the like. As herein before set forth the addition of inorganic materials, for example for curing purposes or ballistic modifying purposes, is not desirable. Their pres ence, however, is not beyond the scope of this invention.
Having generally described the invention the following example is given for purposes of illustration. It will be understood that the invention is not limited to this example, but is susceptible to different modifications that will be recognized by one of ordinary skill in the art.
butylphenol) The composition of Example 1 exhibited a burning rate of 0.420 in./sec at 1000 psi and 77F. The popular ammonium nitrate based gas generators generally burn only at about 0.10 inches/sec even with the addition of burning rate modifiers which add corrosive materials to the end combustion products. Furthermore, the composition of Example 1 is further characterized by a burning rate exponent of 0.51 and a 11 valve of 0.296. This constant 'rr represents the burning rate dependency of a propellant upon changes in temperature and pressure. Thus, a low Tl' value is generally desired since the burning rate of an ideal propellant composition would be completely independent of variations in temperature and pressure. A 11 value of between 0.2 and 0.3 is therefore noteworthy.
Furthermore, the composition of example 1 ignites at 168C and after constant heating at 120C it does not ignite or show any exotherm over a period of 24 hours, which clearly demonstrates the improved stability of the instant composition.
The gas generating compositions of this invention are especially useful, for instance, for actuating gas pres sure operated mechanical devices; e.g., for driving engines, electric generator motors, and turbines or for operating pneumatic tools, and for the propulsion and guidance of rockets or other gas escape reaction propelled devices.
Having thus described the invention, what is claimed and desired to be secured by Letters Patent of the United States is:
1. A gas generating solid propellant composition comprising 5-aminotetrazole nitrate as the oxidant and a binder matrix selected from the group consisting of a styrene-butadiene-styrene block copolymer and a styrene-isoprene-styrene block copolymer.
2. The gas generating solid propellant composition of claim 1 wherein said styrene-butadiene-styrene and said styrene-isoprene-styrene block copolymers have a molecular weight within the range of from about 60,000 to about 100,000 and a styrene content of from about 28 to 29 percent by weight.
3. The gas generating solid propellant composition of claim 2 wherein said S-aminotetrazole nitrate is present in an amount within the range of from about to 87 percent by weight and said block copolymer is present in an amount within the range of from about 13 to about 25 percent.
4. The gas generating solid propellant composition of claim 3 wherein said block copolymer is styrenebutadiene-styrene.
5. The gas generating solid propellant composition of claim 3 which further includes a minor amount of a material selected from the group consisting of an organic anti-oxidant, an organic plasticizing agent and mixtures

Claims (5)

1. A GAS GENERATING SOLID PROPELLANT COMPOSITION COMPRISING 5-AMINOTETRAZOLE NITRATE AS THE OXIDANT AND A BINDER MATRIX SELECTED FROM THE GROUP CONSISTING OF A STYRENE-BUTADIENE-STYRENE BLOCK COPOLYMER AND A STYRENE-ISOPRENE-STYRENE BLOCK COPOLYMER.
2. The gas generating solid propellant composition of claim 1 wherein said styrene-butadiene-styrene and said styrene-isoprene-styrene block copolymers have a molecular weight within the range of from about 60,000 to about 100,000 and a styRene content of from about 28 to 29 percent by weight.
3. The gas generating solid propellant composition of claim 2 wherein said 5-aminotetrazole nitrate is present in an amount within the range of from about 75 to 87 percent by weight and said block copolymer is present in an amount within the range of from about 13 to about 25 percent.
4. The gas generating solid propellant composition of claim 3 wherein said block copolymer is styrene-butadiene-styrene.
5. The gas generating solid propellant composition of claim 3 which further includes a minor amount of a material selected from the group consisting of an organic anti-oxidant, an organic plasticizing agent and mixtures thereof.
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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4028154A (en) * 1976-09-01 1977-06-07 The United States Of America As Represented By The United States Energy Research And Development Administration Ammonium 2,4,5-trinitroimidazole
US4919737A (en) * 1988-08-05 1990-04-24 Morton Thiokol Inc. Thermoplastic elastomer-based low vulnerability ammunition gun propellants
US4976794A (en) * 1988-08-05 1990-12-11 Morton Thiokol Inc. Thermoplastic elastomer-based low vulnerability ammunition gun propellants
EP0482755A1 (en) * 1990-10-23 1992-04-29 Automotive Systems Laboratory Inc. Ignition composition for inflator gas generators
US5160386A (en) * 1991-11-04 1992-11-03 Morton International, Inc. Gas generant formulations containing poly(nitrito) metal complexes as oxidants and method
US5197758A (en) * 1991-10-09 1993-03-30 Morton International, Inc. Non-azide gas generant formulation, method, and apparatus
DE4222953A1 (en) * 1992-07-13 1994-01-20 Buna Ag Further modifiable thermoplastic polymers prodn. - by copolymerisation of vinyl:aromatics and 2H-tetrazole(s) contg. vinyl:phenyl gps., opt. with other comonomers and graft-linking polymers
US5439251A (en) * 1992-11-30 1995-08-08 Toyo Kasei Kogyo Company Limited Method of tetrazole amine salts having improved physical properties for generating gas in airbags
US5451682A (en) * 1994-01-10 1995-09-19 Thiokol Corporation Method for synthesizing 5-aminotetrazole
US5468866A (en) * 1994-01-04 1995-11-21 Thiokol Corporation Methods for synthesizing and processing bis-(1(2)H-tetrazol-5-yl)-amine
US5472647A (en) * 1993-08-02 1995-12-05 Thiokol Corporation Method for preparing anhydrous tetrazole gas generant compositions
US5501823A (en) * 1993-08-02 1996-03-26 Thiokol Corporation Preparation of anhydrous tetrazole gas generant compositions
US5514230A (en) * 1995-04-14 1996-05-07 Automotive Systems Laboratory, Inc. Nonazide gas generating compositions with a built-in catalyst
US5516377A (en) * 1994-01-10 1996-05-14 Thiokol Corporation Gas generating compositions based on salts of 5-nitraminotetrazole
US5661261A (en) * 1996-02-23 1997-08-26 Breed Automotive Technology, Inc. Gas generating composition
US5844164A (en) * 1996-02-23 1998-12-01 Breed Automotive Technologies, Inc. Gas generating device with specific composition
US5847315A (en) * 1996-11-29 1998-12-08 Ecotech Solid solution vehicle airbag clean gas generator propellant
WO2000055106A1 (en) * 1999-03-01 2000-09-21 Automotive Systems Laboratory, Inc. Gas generant composition
WO2000060154A1 (en) * 1999-04-07 2000-10-12 Automotive Systems Laboratory, Inc. Method of formulating a gas generant composition
US6228192B1 (en) 1999-04-20 2001-05-08 Altantic Research Corporation Double base propellant containing 5-aminotetrazole
US6475312B1 (en) 1999-04-07 2002-11-05 Automotive Systems Laboratory, Inc. Method of formulating a gas generant composition
US6509473B1 (en) * 2000-10-16 2003-01-21 The United States Of America As Represented By The Secretary Of The Air Force Energetic triazolium salts
US20030066584A1 (en) * 2000-03-01 2003-04-10 Burns Sean P. Gas generant composition
US6620266B1 (en) * 1999-07-02 2003-09-16 Automotive Systems Laboratory, Inc. Gas generant compositions containing a silicone coating

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US3348985A (en) * 1965-08-14 1967-10-24 Dynamit Nobel Ag Gas-generating pyrotechnic composition consisting essentially of ammonium nitrate and aminotetrazole
US3501357A (en) * 1967-04-12 1970-03-17 Asahi Chemical Ind Composite propellants containing block copolymers
US3734789A (en) * 1969-11-28 1973-05-22 Us Navy Gas generating solid propellant containing 5-aminotetrazole nitrate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3348985A (en) * 1965-08-14 1967-10-24 Dynamit Nobel Ag Gas-generating pyrotechnic composition consisting essentially of ammonium nitrate and aminotetrazole
US3501357A (en) * 1967-04-12 1970-03-17 Asahi Chemical Ind Composite propellants containing block copolymers
US3734789A (en) * 1969-11-28 1973-05-22 Us Navy Gas generating solid propellant containing 5-aminotetrazole nitrate

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4028154A (en) * 1976-09-01 1977-06-07 The United States Of America As Represented By The United States Energy Research And Development Administration Ammonium 2,4,5-trinitroimidazole
US4919737A (en) * 1988-08-05 1990-04-24 Morton Thiokol Inc. Thermoplastic elastomer-based low vulnerability ammunition gun propellants
US4976794A (en) * 1988-08-05 1990-12-11 Morton Thiokol Inc. Thermoplastic elastomer-based low vulnerability ammunition gun propellants
EP0482755A1 (en) * 1990-10-23 1992-04-29 Automotive Systems Laboratory Inc. Ignition composition for inflator gas generators
US5197758A (en) * 1991-10-09 1993-03-30 Morton International, Inc. Non-azide gas generant formulation, method, and apparatus
US5160386A (en) * 1991-11-04 1992-11-03 Morton International, Inc. Gas generant formulations containing poly(nitrito) metal complexes as oxidants and method
DE4222953A1 (en) * 1992-07-13 1994-01-20 Buna Ag Further modifiable thermoplastic polymers prodn. - by copolymerisation of vinyl:aromatics and 2H-tetrazole(s) contg. vinyl:phenyl gps., opt. with other comonomers and graft-linking polymers
US5439251A (en) * 1992-11-30 1995-08-08 Toyo Kasei Kogyo Company Limited Method of tetrazole amine salts having improved physical properties for generating gas in airbags
US5472647A (en) * 1993-08-02 1995-12-05 Thiokol Corporation Method for preparing anhydrous tetrazole gas generant compositions
US5501823A (en) * 1993-08-02 1996-03-26 Thiokol Corporation Preparation of anhydrous tetrazole gas generant compositions
US5682014A (en) * 1993-08-02 1997-10-28 Thiokol Corporation Bitetrazoleamine gas generant compositions
US5468866A (en) * 1994-01-04 1995-11-21 Thiokol Corporation Methods for synthesizing and processing bis-(1(2)H-tetrazol-5-yl)-amine
US5451682A (en) * 1994-01-10 1995-09-19 Thiokol Corporation Method for synthesizing 5-aminotetrazole
US5516377A (en) * 1994-01-10 1996-05-14 Thiokol Corporation Gas generating compositions based on salts of 5-nitraminotetrazole
US5514230A (en) * 1995-04-14 1996-05-07 Automotive Systems Laboratory, Inc. Nonazide gas generating compositions with a built-in catalyst
US5661261A (en) * 1996-02-23 1997-08-26 Breed Automotive Technology, Inc. Gas generating composition
US5844164A (en) * 1996-02-23 1998-12-01 Breed Automotive Technologies, Inc. Gas generating device with specific composition
US5847315A (en) * 1996-11-29 1998-12-08 Ecotech Solid solution vehicle airbag clean gas generator propellant
EP1181262A1 (en) * 1999-03-01 2002-02-27 Automotive Systems Laboratory Inc. Gas generant composition
WO2000055106A1 (en) * 1999-03-01 2000-09-21 Automotive Systems Laboratory, Inc. Gas generant composition
EP1181262A4 (en) * 1999-03-01 2005-03-16 Automotive Systems Lab Gas generant composition
US6287400B1 (en) 1999-03-01 2001-09-11 Automotive Systems Laboratory, Inc. Gas generant composition
WO2000060154A1 (en) * 1999-04-07 2000-10-12 Automotive Systems Laboratory, Inc. Method of formulating a gas generant composition
US6475312B1 (en) 1999-04-07 2002-11-05 Automotive Systems Laboratory, Inc. Method of formulating a gas generant composition
US6228192B1 (en) 1999-04-20 2001-05-08 Altantic Research Corporation Double base propellant containing 5-aminotetrazole
US6620266B1 (en) * 1999-07-02 2003-09-16 Automotive Systems Laboratory, Inc. Gas generant compositions containing a silicone coating
US20030066584A1 (en) * 2000-03-01 2003-04-10 Burns Sean P. Gas generant composition
US20060118218A1 (en) * 2000-03-01 2006-06-08 Burns Sean P Gas generant composition
US6509473B1 (en) * 2000-10-16 2003-01-21 The United States Of America As Represented By The Secretary Of The Air Force Energetic triazolium salts

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