US3762972A - Reaction product of phosphine oxide with carboxylic acids - Google Patents

Reaction product of phosphine oxide with carboxylic acids Download PDF

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US3762972A
US3762972A US00851137A US3762972DA US3762972A US 3762972 A US3762972 A US 3762972A US 00851137 A US00851137 A US 00851137A US 3762972D A US3762972D A US 3762972DA US 3762972 A US3762972 A US 3762972A
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reaction product
propellant
phosphine oxide
binder
acid
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • 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
    • C06B23/001—Fillers, gelling and thickening agents (e.g. fibres), absorbents for nitroglycerine
    • 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
    • C06B45/18—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component
    • C06B45/30—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an inorganic explosive or an inorganic thermic component
    • C06B45/32—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an inorganic explosive or an inorganic thermic component the coating containing an organic compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/564—Three-membered rings
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/69—Polymers of conjugated dienes

Definitions

  • the propellant grain usually has an internal perforation parallel to the longest axis of the motor case. Since the propellant and the metal case are bonded together, and since the coefficients of thermal expansion of metal and propellant differ greatly, and since the metal case is rigid, lowering the temperature of the motor induces strain in the propellant proportional to the amount of temperature change. Such strain is usually greatest at the surface of the internal perforation of the propellant grain. If such strain exceeds the strain capability of the propellant, the grain will crack open and thus expose more surface for burning upon ignition. The motor is a hazard in such condition, and must be discarded. Thus it is extremely important that the propellant have ample strain capability to withstand such strains as may be imposed.
  • a still further object of this invention is to provide a reaction product that can be crosslinked with other binder ingredients to increase the strain capability of the solid propellant composition.
  • a binder type reaction product is produced by reacting in the presence of an organic solvent dior trifunctional aziridinyl phosphine oxides or their derivatives with organic molecules which are polyfunctional with respect to carboxyl groups and which also contain an alkyl structure that may contain one or more hydroxyl groups.
  • the reaction product is used to coat oxidizer material such as ammonium perchlorate or in a propellant composition that contains ammonium perchlorate.
  • oxidizer material such as ammonium perchlorate or in a propellant composition that contains ammonium perchlorate.
  • the active hydrogen atoms of the reaction product are linked to the rest of the binder ingredients during the cure of the propellant to increase the strain capability of the propellant.
  • the binder cure reactions are usually between hydroxyl groups and isocyanate groups to form a urethane linkage, although other groups may be used in curing without affecting the usefulness of the invention. Examples of such other groups are active hydrogen containing groups such as amine and thiol.
  • X eprese n a ns s a 9 the t i and Q and Q are either hydrogen or alkyl groups of one to four carbon atoms (Q, and 0: may be the same or different), X may be the same as X, or may be an organic radical such as phenyl, benzyl, methyl, ethyl, etc., R is an alkyl that contains at least one active hydrogen atom or an organic entity of molecules that contain one or more hydroxyl groups, and n is 2, 3, or 4. Since both reactants are polyfunctional, the reaction product must necessarily be a mixture of compounds. However, the nominal structure may be represented by the following general formula:
  • the optimum amounts of reactants are such that essentially all carboxyl groups in (II) are reacted and nominally one aziridine group in (I) is reacted. Thus one mole of (I) is required for each carboxyl equivalent of (II).
  • the use of less than one mole of (I) per carboxyl equivalent of (II) will result in a polymeric form of (III), while the use of more than one mole of (I) per carboxyl equivalent of (II) will result in essentially (III) plus unreacted (I).
  • Such variations from the optimum ratio of (I) to (II) can be tolerated to a certain extent without seriously affecting the effectiveness of the invention.
  • a second acid (IV) may be used of the same general formula as (ll) except that no hydroxyl groups are contained in its structure.
  • (II) and (IV) can be mixed in any desired proportion prior to reacting with (I), with the optimum amount of reactants being one mole of (I) per the sum of the carboxyl equivalents of (II) and IV).
  • the reaction product is produced by dissolving the reactants in a suitable inert solvent such as methanol, ethanol, methylene chloride, tetrahydrofuran, diethyl ether, or mixtures of these. It has been found to be preferable that methanol or ethanol comprise at least a part of the solvent.
  • Reaction temperature is not critical, and may range from 70F to 200F for such time as is needed for essentially all carboxyl groups in (II) [and (IV) if used] to be reacted.
  • the solvent is then removed by any suitable means, such as evaporation under vacuum at elevated temperatures. The residue is the reaction product which is usually straw-colored and quite viscous.
  • reaction product enhances the mechanical properties of such a propellant
  • the ammonium perchlorate catalyzes the homopolymerization of the remaining aziridine rings in the reaction product, thus linking the molecules together in a highly cross-linked network structure.
  • the film of the reaction product on the AP surfaces becomes a hard, tear-resistant layer which adheres strongly to the surface, and which can react chemically with the curative through the active hydrogen atoms which are contained in the structure of the reaction product.
  • a propellant when stressed after cure, must fail in large part by tearing the binder rather than by separation of the binder from the filler particles. As stated earlier, this is very desirable, and imparts greatly increased strain capability and tensile strength to the propellant, thus the invention accomplishes the desired objectives. Specific examples of the invention are given below:
  • EXAMPLE I 21.5 grams (0.10 moles of tris-l-(2-methyl aziridinyl) phosphine oxide and 7.5 grams (0.10 equivalent) of tartaric acid were dissolved in 200 ml of methanol. The solution was kept at room temperature (about F) for 3 days, at which time essentially all carboxyl groups in the tartaric acid were reacted, as evidenced by infrared spectra and titration. The methanol was removed under 0.1 mm vacuum at 70C to a constant weight.
  • This reaction product (A) was added in the amount of 0.3 percent by weight of the total to a propellant mix consisting of 68 percent by weight ammonium perchlorate of which half was 17 micron nominal diameter, and half was 200 micron nominal diameter, 16 percent by weight of a powdered metal fuel (alumimum), and 16 percent by weight of binder ingredients of which the additive (A) was part.
  • the remaining binder ingredients were a hydroxy-terminated liquid polybutadiene, toluene diisocyanate, and a plasticizer (dioctyl adipate).
  • the cured propellant had greatly improved strain capability and resistance to separation of the binder from the filler as compared to a similar propellant without additive. More specifically, the propellant containing 0.5 percent of (B) exhibited 73 percent strain at failure at 40F whereas the similar propellant without additive exhibited 13 percent strain at failure at 40F.
  • EXAMPLE III 0.10 moles of bis-l-(2-methyl aziridinyl) phenyl phosphine oxide, 0.05 equivalents of malic acid and 0.05 equivalents of succinic acid were reacted 4 hours at reflux in a mixture of ml of methanol and 100 ml of methylene chloride. The solvents were removed under heat and vacuum to a constant weight.
  • This reac- EXAMPLE IV 0.10 moles of tris-l-(2-methyl aziridinyl) phosphine oxide, 0.04 equivalents of citric acid and 0.06 equivalents of sebacic acid were reacted as in Example I.
  • This reaction product (D) was added to a propellant mix as in Example I in the amount of 0.75 percent by weight of the total. The strain capability of the resulting propellant was greatly improved as compared to a similar propellant without additive.
  • reaction product formed by reacting phosphine oxides of the general formula 0 X1I.LX2
  • reaction product of claim 1 wherein said phosphine oxides and said organic molecules are reacted in a ratio of one mole of the phosphine oxide to one carboxyl equivalent of the organic molecules, said organic solvent is selected from the group consisting of methanol, ethanol, methylene chloride, tetrahydrofuran, diethyl ether, and mixtures thereof, and said phosphine oxides are selected from the group consisting of tris-l- (2-methyl aziridinyl) phosphine oxide and bis-l-(2- methyl aziridinyl) phenyl phosphine oxide.
  • reaction product of claim 2 wherein said organic molecules are succinic acid and said organic solvent is a mixture of methanol and methylene chloride.
  • reaction product of claim 2 wherein said organic molecules are malic acid and succinic acid, said organic solvent is a mixture of methanol and methylene chloride, and said phosphine oxide is bis-l-(Z-methyl aziridinyl) phenyl phosphine oxide.
  • reaction product of claim 2 wherein said organic molecules are a mixture of citric acid and sebacic acid, said organic solvent is methanol, and said phosphine oxide is tris-l-(2-methyl aziridinyl) phosphine oxide.
  • reaction product of claim 2 wherein said organic molecules are adipic acid, said organic solvent is methanol, and said phosphine oxide is tris-l-(2-methyl aziridinyl) phosphine oxide.

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  • Molecular Biology (AREA)
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Abstract

THE REACTION PRODUCTS OF DI- OR TRI- FUNCTIONAL AZIRIDINYL PHOSPHINE OXIDES OR THEIR DERIVATIVES WITH POLYFUNCTIONAL CARBOXYLIC ACIDS, AND THE COMBINATION OF THE REACTION PRODUCTS WITH OTHER PROPELLANT INGREDIENTS SUCH AS INORGANIC OXIDIZER, BINDER, PLASTICIZER, METAL FUEL AND ETC.

Description

United States Patent [191 Allen REACTION PRODUCT OF PHOSPHINE OXIDE WITH CARBOXYLIC ACIDS [75] Inventor: Henry C. Allen, Decatur, Ala.
[7 3 Assignee: The United States of America as represented by the Secretary of the Army [22] Filed: July 30, 1969 [21] App]. No.: 851,137
[52] US. Cl 149/109, 149/7, 149/19,
149/44, 149/76, 260/239 EP [51] Int. Cl. C06h 7/00, C07d 23/06 [58] Field of Search 260/2 EN, 78.4 R,
[56] References Cited UNITED STATES PATENTS 4/1966 Christena et al 260/239 EP 3,507,839 4/1970 Christena et a] 260/239 E? X Primary Examiner-Leland A. Sebastian Attorney-Harry M. Saragovitz, Edward J. Kelly, Herbert Berl and James T. Deaton [57] ABSTRACT 11 Claims, No Drawings REACTION PRODUCT OF PHOSPI-IINE OXIDE WITH CARBOXYLIC ACIDS BACKGROUND OF THE INVENTION Rocket motors consisting of a solid propellant grain bonded to a rigid metal case are widely used both in military missilery and in non-military applications. The propellant grain usually has an internal perforation parallel to the longest axis of the motor case. Since the propellant and the metal case are bonded together, and since the coefficients of thermal expansion of metal and propellant differ greatly, and since the metal case is rigid, lowering the temperature of the motor induces strain in the propellant proportional to the amount of temperature change. Such strain is usually greatest at the surface of the internal perforation of the propellant grain. If such strain exceeds the strain capability of the propellant, the grain will crack open and thus expose more surface for burning upon ignition. The motor is a hazard in such condition, and must be discarded. Thus it is extremely important that the propellant have ample strain capability to withstand such strains as may be imposed.
Until recently, the relationship between the strain capability of a composite propellant and the extensibility of its binder was not understood. It was known from empirical data that binders with excellant extensibility often made propellants with low strain capability, but the reason for this was unknown. In recent work by the present inventor, it has been discovered that binderfiller physical interactions are a large factor in propellant mechanical properties, and further that a high level of adhesion of binder to filler is necessary to fully utilize the extensibility of a binder in achieving good strain capability in the propellant. Consequently, it is very desirable to use a binder which adheresstrongly to the oxidizer and other solid particles of a composite propellant.
Further study of binder-filler interactions have shown that even further improvement in propellant strain capability can be achieved if a thin tear-resistant layer of binder is deposited on the surfaces of the filler particles prior to final binder cure, provided this layer becomes chemically bonded to the rest of the binder during the cure cycle. This layer prevents microscopic voids (which form in the strained cured propellant) from reaching the particle surfaces and causing early separation of binder from the tiller.
- Therefore, it is an object of this invention to provide a novel reaction product that'is produced by reacting dior tri functional aziridinyl phosphine oxides or their derivatives with organic molecules which are polyfunctional with respect to carboxyl groups and some of Still another object of this invention is to provide a reaction product that can be used in a propellant composition to increase the strain capability thereof.
A still further object of this invention is to provide a reaction product that can be crosslinked with other binder ingredients to increase the strain capability of the solid propellant composition.
SUMMARY OF THE INVENTION In accordance with this invention, a binder type reaction product is produced by reacting in the presence of an organic solvent dior trifunctional aziridinyl phosphine oxides or their derivatives with organic molecules which are polyfunctional with respect to carboxyl groups and which also contain an alkyl structure that may contain one or more hydroxyl groups.
The reaction product is used to coat oxidizer material such as ammonium perchlorate or in a propellant composition that contains ammonium perchlorate. In the propellant composition, the active hydrogen atoms of the reaction product are linked to the rest of the binder ingredients during the cure of the propellant to increase the strain capability of the propellant. The binder cure reactions are usually between hydroxyl groups and isocyanate groups to form a urethane linkage, although other groups may be used in curing without affecting the usefulness of the invention. Examples of such other groups are active hydrogen containing groups such as amine and thiol.
DETAILED DESCRIPTION OF THE INVENTION consists of the reaction products of dior trifunctional aziridinyl phosphine oxide or its derivatives with organic molecules which are polyfunctional with respect to carboxyl groups and which may contain one or more hydroxyl groups in their structures. The starting compounds or reactants may be represented as follows:
where X eprese n a ns s a 9 the t i and Q and Q, are either hydrogen or alkyl groups of one to four carbon atoms (Q, and 0: may be the same or different), X may be the same as X, or may be an organic radical such as phenyl, benzyl, methyl, ethyl, etc., R is an alkyl that contains at least one active hydrogen atom or an organic entity of molecules that contain one or more hydroxyl groups, and n is 2, 3, or 4. Since both reactants are polyfunctional, the reaction product must necessarily be a mixture of compounds. However, the nominal structure may be represented by the following general formula:
(III) where X X Q Q R and n are as already defined.
The optimum amounts of reactants are such that essentially all carboxyl groups in (II) are reacted and nominally one aziridine group in (I) is reacted. Thus one mole of (I) is required for each carboxyl equivalent of (II). The use of less than one mole of (I) per carboxyl equivalent of (II) will result in a polymeric form of (III), while the use of more than one mole of (I) per carboxyl equivalent of (II) will result in essentially (III) plus unreacted (I). Such variations from the optimum ratio of (I) to (II) can be tolerated to a certain extent without seriously affecting the effectiveness of the invention. Further, if it is desired to increase the ratio of aziridine groups to hydroxyl groups in (III), a second acid (IV) may be used of the same general formula as (ll) except that no hydroxyl groups are contained in its structure. Thus (II) and (IV) can be mixed in any desired proportion prior to reacting with (I), with the optimum amount of reactants being one mole of (I) per the sum of the carboxyl equivalents of (II) and IV).
The reaction product is produced by dissolving the reactants in a suitable inert solvent such as methanol, ethanol, methylene chloride, tetrahydrofuran, diethyl ether, or mixtures of these. It has been found to be preferable that methanol or ethanol comprise at least a part of the solvent. Reaction temperature is not critical, and may range from 70F to 200F for such time as is needed for essentially all carboxyl groups in (II) [and (IV) if used] to be reacted. The solvent is then removed by any suitable means, such as evaporation under vacuum at elevated temperatures. The residue is the reaction product which is usually straw-colored and quite viscous.
In propellants in which ammonium perchlorate is the principal oxidizer, addition of 0.05 to L percent of the reaction product greatly enhances the strain capability of the cured propellant. In preparing such a propellant, it is common practice to first place in a suitable mechanical mixer the liquid polymer, plasticizer, antioxidant and any other binder ingredient except the curing agent. The reaction product may also be added at this time. Metal powder, if used, is added next and mixed into the binder ingredients. Then the oxidizer being principally ammonium perchlorate is added and mixed in. After the oxidizer has been thoroughly incorporated by mixing, the curing agent is added to initiate the reaction which in time changes the liquid propellant slurry into a flexible solid propellant. The rate of the cure reaction must be slow enough to allow time for casting the propellant into motors or other receptacles before the viscosity of the liquid slurry becomes unmanageable.
It is postulated that the manner in which the reaction product enhances the mechanical properties of such a propellant is as follows: The compound of the reaction product has a polar character due to the P=O groups, and this polarity causes it to migrate preferentially to the polar surface of the ammonium perchlorate oxidizer, thus coating it with a film of the reaction product. The ammonium perchlorate catalyzes the homopolymerization of the remaining aziridine rings in the reaction product, thus linking the molecules together in a highly cross-linked network structure. Thus the film of the reaction product on the AP surfaces becomes a hard, tear-resistant layer which adheres strongly to the surface, and which can react chemically with the curative through the active hydrogen atoms which are contained in the structure of the reaction product. Such a propellant, when stressed after cure, must fail in large part by tearing the binder rather than by separation of the binder from the filler particles. As stated earlier, this is very desirable, and imparts greatly increased strain capability and tensile strength to the propellant, thus the invention accomplishes the desired objectives. Specific examples of the invention are given below:
EXAMPLE I 21.5 grams (0.10 moles of tris-l-(2-methyl aziridinyl) phosphine oxide and 7.5 grams (0.10 equivalent) of tartaric acid were dissolved in 200 ml of methanol. The solution was kept at room temperature (about F) for 3 days, at which time essentially all carboxyl groups in the tartaric acid were reacted, as evidenced by infrared spectra and titration. The methanol was removed under 0.1 mm vacuum at 70C to a constant weight. This reaction product (A) was added in the amount of 0.3 percent by weight of the total to a propellant mix consisting of 68 percent by weight ammonium perchlorate of which half was 17 micron nominal diameter, and half was 200 micron nominal diameter, 16 percent by weight of a powdered metal fuel (alumimum), and 16 percent by weight of binder ingredients of which the additive (A) was part. The remaining binder ingredients were a hydroxy-terminated liquid polybutadiene, toluene diisocyanate, and a plasticizer (dioctyl adipate). After cure, the propellant exhibited much improved mechanical properties as compared to a similar propellant without (A), as tabulated below:
Strain at break.% Tensile strength, psi
21.5 grams (0.10 moles) of tris-l-(2-methyl aziridinyl) phosphine oxide, 2.25 grams (0.03 equivalents) of tartaric acid and 5.11 grams (0.07 equivalents) of adipic acid were dissolved in 200 ml. of ethanol. The solution was warmed to about 120F for 24 hours, at which (time essentially all the carboxyl groups in the tartaric and adipic acids were reacted. The ethanol was removed under heat and vacuum to a constant weight. This reaction product (B) was added in the amount of 0.5 percent of the total to a propellant mix as described in Example I. The cured propellant had greatly improved strain capability and resistance to separation of the binder from the filler as compared to a similar propellant without additive. More specifically, the propellant containing 0.5 percent of (B) exhibited 73 percent strain at failure at 40F whereas the similar propellant without additive exhibited 13 percent strain at failure at 40F.
EXAMPLE III 0.10 moles of bis-l-(2-methyl aziridinyl) phenyl phosphine oxide, 0.05 equivalents of malic acid and 0.05 equivalents of succinic acid were reacted 4 hours at reflux in a mixture of ml of methanol and 100 ml of methylene chloride. The solvents were removed under heat and vacuum to a constant weight. This reac- EXAMPLE IV 0.10 moles of tris-l-(2-methyl aziridinyl) phosphine oxide, 0.04 equivalents of citric acid and 0.06 equivalents of sebacic acid were reacted as in Example I. This reaction product (D) was added to a propellant mix as in Example I in the amount of 0.75 percent by weight of the total. The strain capability of the resulting propellant was greatly improved as compared to a similar propellant without additive.
EXAMPLE V s ai atmakrft s a strcngthtpsi Additive 712R 40 F 77 "F 40 "F None 19.7 25.5 54 120 0.15% (B) 24.2 39.7 152 270 This and other data show that the effectiveness of the invention is not affected by the solids concentration or plasticizer type.
EXAMPLE VI 21.5 grams (0.10 moles) of tris-l-(2-methyl aziridinyl) phosphine oxide and 7.3 grams (0.10 equivalents) of adipic acid were reacted in 200 ml. of methanol at reflux for four hours. The methanol was then removed under vacuum to constant weight, and this reaction product (E) was added in the amount of 0.20 percent to a propellant as described in Example 1. The strain capability and tensile strength of the resulting propellant was greatly improved as compared to a similar propellant without additive, butthe improvement was not as much as when a hydroxyl-containing polyacid, such as tartaric acid, comprised part of the reaction product.
I claim:
1. The reaction product formed by reacting phosphine oxides of the general formula 0 X1I.LX2
or 7.77. 1 V V. with organic molecules selected from the group consisting of adipic acid, citric acid, malic acid, sebacic acid, succinic acid and tartaric acid in the presence of an organic solvent, and wherein X, represents an aziridine group of the structure and Q and Q are selected from the group consisting of hydrogen or alkyl groups of one to four carbon atoms, and X is an organic radical selected from the group consisting of phenyl, benzyl, methyl, ethyl, and an aziridine group represented by those set forth for X 2. The reaction product of claim 1 wherein said phosphine oxides and said organic molecules are reacted in a ratio of one mole of the phosphine oxide to one carboxyl equivalent of the organic molecules, said organic solvent is selected from the group consisting of methanol, ethanol, methylene chloride, tetrahydrofuran, diethyl ether, and mixtures thereof, and said phosphine oxides are selected from the group consisting of tris-l- (2-methyl aziridinyl) phosphine oxide and bis-l-(2- methyl aziridinyl) phenyl phosphine oxide.
3. The reaction product of claim 2 wherein said organic molecules are a mixture of tartaric acid and adipic acid, and said organic solvent is methanol.
4. The reaction product of claim 2 wherein said organic molecules are a mixture of tartaric acid and adipic acid, and said organic solvent is ethanol.
5. The reaction product of claim 2 wherein said organic molecules are succinic acid and said organic solvent is a mixture of methanol and methylene chloride.
6. The reaction product of claim 2 wherein said organic molecules are citric acid and sebacic acid.
7. The reaction produce of claim 2 wherein said organic molecules are tartaric acid, said organic solvent is methanol, and said phosphine oxide is tris-l-(2- methyl aziridinyl) phosphine oxide.
8. The reaction product of claim 2 wherein said organic molecules are tartaric acid and adipic acid, said organic solvent is ethanol, and said phosphine oxide is tris-l-(2-methyl aziridinyl) phosphine oxide.
9. The reaction product of claim 2 wherein said organic molecules are malic acid and succinic acid, said organic solvent is a mixture of methanol and methylene chloride, and said phosphine oxide is bis-l-(Z-methyl aziridinyl) phenyl phosphine oxide.
10. The reaction product of claim 2 wherein said organic molecules are a mixture of citric acid and sebacic acid, said organic solvent is methanol, and said phosphine oxide is tris-l-(2-methyl aziridinyl) phosphine oxide.
11. The reaction product of claim 2 wherein said organic molecules are adipic acid, said organic solvent is methanol, and said phosphine oxide is tris-l-(2-methyl aziridinyl) phosphine oxide.
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953257A (en) * 1973-09-07 1976-04-27 The United States Of America As Represented By The Secretary Of The Army Method for preparing small particle size coated ammonium perchlorate
US3974004A (en) * 1974-02-04 1976-08-10 The United States Of America As Represented By The Secretary Of The Army Extension of pot life of HTPB composite propellants by phosphine oxides
US4070213A (en) * 1976-06-30 1978-01-24 The United States Of America As Represented By The Secretary Of The Army Dispersing aids for MT-4
US4427468A (en) 1976-01-16 1984-01-24 Her Majesty The Queen In Right Of Canada Curable propellant binding systems with bonding agent combination
US4517035A (en) * 1976-01-16 1985-05-14 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Method of making a castable propellant
FR2587329A1 (en) * 1985-09-19 1987-03-20 Poudres & Explosifs Ste Nale BINDER-LOADING ADHESION AGENT AND PROPULSIVE COMPOSITION CONTAINING THE SAME
US5273785A (en) * 1991-08-15 1993-12-28 Thiokol Corporation Methods and compositions for bonding propellants within rocket motors
EP0655429A1 (en) * 1993-11-17 1995-05-31 Morton International, Inc. Improved PVC-based gas generant for hybrid gas generators
US5928687A (en) * 1994-01-14 1999-07-27 Long Trail Enterprises, Inc. Rumen by-pass feed supplement

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953257A (en) * 1973-09-07 1976-04-27 The United States Of America As Represented By The Secretary Of The Army Method for preparing small particle size coated ammonium perchlorate
US3974004A (en) * 1974-02-04 1976-08-10 The United States Of America As Represented By The Secretary Of The Army Extension of pot life of HTPB composite propellants by phosphine oxides
US4427468A (en) 1976-01-16 1984-01-24 Her Majesty The Queen In Right Of Canada Curable propellant binding systems with bonding agent combination
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