USH365H - New energetic polymer, P-DEND - Google Patents
New energetic polymer, P-DEND Download PDFInfo
- Publication number
- USH365H USH365H US07/008,511 US851187A USH365H US H365 H USH365 H US H365H US 851187 A US851187 A US 851187A US H365 H USH365 H US H365H
- Authority
- US
- United States
- Prior art keywords
- diethylene glycol
- dend
- dinitrazadecane
- dioate
- dmdnd
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title description 16
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006845 Michael addition reaction Methods 0.000 claims abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- QCOXCILKVHKOGO-UHFFFAOYSA-N n-(2-nitramidoethyl)nitramide Chemical compound [O-][N+](=O)NCCN[N+]([O-])=O QCOXCILKVHKOGO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000741 silica gel Substances 0.000 claims abstract description 4
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 abstract description 15
- 229960003711 glyceryl trinitrate Drugs 0.000 abstract description 14
- 239000003380 propellant Substances 0.000 abstract description 6
- 239000000006 Nitroglycerin Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 229920005596 polymer binder Polymers 0.000 abstract 1
- 239000002491 polymer binding agent Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004449 solid propellant Substances 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 nitrate ester Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/02—N-nitro compounds
-
- 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
- C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive
-
- 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
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
Definitions
- Solid propellant binders which employ inert polymers yield a lower specific impulse as compared with solid propellant binders which employ energetic binders.
- inert or nonenergetic polymers are polyglycol adipate (PGA), polyethylene glycol (PEG), and polycaprolactone (PCL).
- PGA polyglycol adipate
- PEG polyethylene glycol
- PCL polycaprolactone
- An alternate consideration for achieving high performance propellants for future tactical and strategic systems includes obtaining high performance by employing high solids of oxidizers such as cyclotetramethylenetetranitramine (HMX) or cyclotrimethylenetrinitramine (RDX) and/or high content of high energy plasticizers such as nitroglycerine (NG).
- oxidizers such as cyclotetramethylenetetranitramine (HMX) or cyclotrimethylenetrinitramine (RDX) and/or high content of high energy plasticizers such as nitroglycerine (NG).
- HMX cyclotetramethylenetetranitramine
- RDX cyclotrimethylenetrinitramine
- NG nitroglycerine
- This alternate approach particularly, which involves high solids of HMX or RDX and increasing the high energy plasticizer content leads to other changes such as degradation of mechanical properties and processability and changes to shock sensitivity which makes the approach of improving performance
- an object of this invention is to provide a method for synthesis of an energetic polymer for use in nitrate ester plasticized propellants.
- Another object of this invention is to provide a method for synthesis of an energetic polymer which is very compatible with nitroglycerin.
- the energetic polymer poly(diethylene glycol-4,7-dinitrazadecane-dioate) (P-DEND) is synthesized in a two-step process.
- the first synthesis step is the Michael addition of ethylene dinitramine to methyl acrylate to yield the intermediate compound dimethyl-4,7-dinitrazadecane-dioate (DMDND).
- DMDND dimethyl-4,7-dinitrazadecane-dioate
- Polymer formation is achieved by the reaction of DMDND with diethylene glycol (DEG) using an elevated temperature and a catalyst of p-toluenesulfonic acid.
- a 15:1 mole ratio of DEG to DMDND is reacted at 85° C. for 18 hours, under vacuum, to remove the methanol which is generated. After the excess DEG is removed by high vacuum distillation, the mother liquid is further heated at 80° C., under high vacuum, so that polymerization proceeds. The product is subsequently purified by passing it through a silica gel column using methylene chloride as solvent.
- the average molecular weight of P-DEND obtained by this method ranges from 1500-2000.
- Poly(diethylene glycol-4,7-dinitrazadecane-dioate) (P-DEND), is synthesized by the Michael addition of ethylene dinitramine to methyl acrylate to yield the intermediate compound dimethyl-4,7-dinitrazadecane-dioate (DMDND).
- DMDND dimethyl-4,7-dinitrazadecane-dioate
- Polymer formation is achieved by the reaction of DMDND with diethylene glycol (DEG) using an elevated temperature and a catalyst of p-toluenesulfonic acid.
- a mole ratio of 15 of DEG to 1 of DMDND is preferred for polymer formation wherein the reaction is first achieved at 85° C. for about 18 hours and under vacuum conditions to remove the methanol which is generated. Excess DEG is then removed by high vacuum distillation. The liquid product remaining is further heated at 80° C., under high vacuum, so that polymerization proceeds.
- the product (P-DEND) is purified by passing it through a silica gel column using methylene chloride as solvent.
- the average molecular weight of the purified product ranges from about 1500-2000.
- the P-DEND is very compatible with nitroglycerin (NG), which is used as a plasticizer in high energy propellants.
- NG nitroglycerin
- Table I the total pressure of gas generated in three weeks time, for the mixture of P-DEND with NG is comparable to that generated by NG (99/1) alone.
- This test which has been performed several times, demonstrates that purified P-DEND is compatible with NG.
- Table II the tensile strengths of P-DEND binder and PGA binder (inert polymer control binder) are the same, while the P-DEND binder has higher modulus and lower elongation.
- the higher modulus for the P-DEND binder is attributed to the shorter chain length and resultant higher crosslink density than the PGA binder.
- the equivalent weights of P-DEND (X443-62) and PGA (S1011-35) are 846 and 1480, respectively.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
Abstract
Poly(diethylene glycol-4,7-dinitrazadecane-dioate), P-DEND), is synthesizedy the Michael addition of ethylene dinitramine to methyl acrylate to yield the intermediate compound dimethyl-4,7-dinitrazadecane-dioate (DMDND). DMDND is reacted for a period of about 18 hours with diethylene glycol (DEG) at about 85° C. in presence of a p-toluenesulfonic acid catalyst to yield P-DEND. The product (P-DEND) is purified by passing it through a silica gel column using methylene chloride as solvent. The average molecular weight of P-DEND ranges from about 1500-2000. P-DEND is shown to be compatible with stabilized nitroglycerin for use as an energetic polymer binder for high performance propellants.
Description
The invention described herein was made in the course of or under a contract or subcontract thereunder with the Government; therefore, the invention described herein may be manufactured, used and licensed by or for the government for governmental purposes without the payment to me of any royalties thereon.
Solid propellant binders which employ inert polymers yield a lower specific impulse as compared with solid propellant binders which employ energetic binders. Examples of inert or nonenergetic polymers are polyglycol adipate (PGA), polyethylene glycol (PEG), and polycaprolactone (PCL). Thus, the replacement of inert polymers by energetic polymers will improve the performance in both tactical and strategic propellants while maintaining good mechanical properties and processability.
An alternate consideration for achieving high performance propellants for future tactical and strategic systems includes obtaining high performance by employing high solids of oxidizers such as cyclotetramethylenetetranitramine (HMX) or cyclotrimethylenetrinitramine (RDX) and/or high content of high energy plasticizers such as nitroglycerine (NG). This alternate approach particularly, which involves high solids of HMX or RDX and increasing the high energy plasticizer content leads to other changes such as degradation of mechanical properties and processability and changes to shock sensitivity which makes the approach of improving performance by replacing of inert polymers (PGA or PEG) with energetic polymers a more desirable approach to increasing specific impulse. Energetic polymers which are compatible with nitroglycerin is an additional, attractive benefit.
Therefore, an object of this invention is to provide a method for synthesis of an energetic polymer for use in nitrate ester plasticized propellants.
Another object of this invention is to provide a method for synthesis of an energetic polymer which is very compatible with nitroglycerin.
The energetic polymer, poly(diethylene glycol-4,7-dinitrazadecane-dioate) (P-DEND), is synthesized in a two-step process. The first synthesis step is the Michael addition of ethylene dinitramine to methyl acrylate to yield the intermediate compound dimethyl-4,7-dinitrazadecane-dioate (DMDND). Polymer formation is achieved by the reaction of DMDND with diethylene glycol (DEG) using an elevated temperature and a catalyst of p-toluenesulfonic acid.
A 15:1 mole ratio of DEG to DMDND is reacted at 85° C. for 18 hours, under vacuum, to remove the methanol which is generated. After the excess DEG is removed by high vacuum distillation, the mother liquid is further heated at 80° C., under high vacuum, so that polymerization proceeds. The product is subsequently purified by passing it through a silica gel column using methylene chloride as solvent. The average molecular weight of P-DEND obtained by this method ranges from 1500-2000.
Poly(diethylene glycol-4,7-dinitrazadecane-dioate) (P-DEND), is synthesized by the Michael addition of ethylene dinitramine to methyl acrylate to yield the intermediate compound dimethyl-4,7-dinitrazadecane-dioate (DMDND). Polymer formation is achieved by the reaction of DMDND with diethylene glycol (DEG) using an elevated temperature and a catalyst of p-toluenesulfonic acid.
A mole ratio of 15 of DEG to 1 of DMDND is preferred for polymer formation wherein the reaction is first achieved at 85° C. for about 18 hours and under vacuum conditions to remove the methanol which is generated. Excess DEG is then removed by high vacuum distillation. The liquid product remaining is further heated at 80° C., under high vacuum, so that polymerization proceeds.
The product (P-DEND) is purified by passing it through a silica gel column using methylene chloride as solvent. The average molecular weight of the purified product ranges from about 1500-2000.
The P-DEND is very compatible with nitroglycerin (NG), which is used as a plasticizer in high energy propellants. In gas generation tests (at 70° C.), as shown in Table I, the total pressure of gas generated in three weeks time, for the mixture of P-DEND with NG is comparable to that generated by NG (99/1) alone. This test, which has been performed several times, demonstrates that purified P-DEND is compatible with NG. In a binder mechanical property study, as shown in Table II, the tensile strengths of P-DEND binder and PGA binder (inert polymer control binder) are the same, while the P-DEND binder has higher modulus and lower elongation. The higher modulus for the P-DEND binder is attributed to the shorter chain length and resultant higher crosslink density than the PGA binder. The equivalent weights of P-DEND (X443-62) and PGA (S1011-35) are 846 and 1480, respectively. These tests indicate, therefore, that P-DEND will perform as an energetic binder for high energy propellants having a good service life and good mechanical properties.
TABLE I
______________________________________
P-DEND GASSING STUDY AT 70° C.
Total Pressure (mmHg/g)
Aging Time
P-DEND Weight 1 2 3
Sample M. Wt. Ratio Week Weeks Weeks
______________________________________
(1) P-DEND 1900 20/80 1.23 2.11 2.66
(78-2)/NG
(99/1)*
(2) P-DEND 1500 20/80 1.83 1.94 2.55
(85-2)/NG
(99/1)
(3) NG(99/1) alone
-- 100 1.96 2.71 3.13
______________________________________
*NG(99/1) = nitroglycerin 99 parts and 1 part stabilizer
TABLE II
______________________________________
BINDER MECHANICAL PROPERTIES
Eq Mechanical Properties-*
Prepolymer
Wt. Pl/Po NCO/OH E.sub.ο (psi)
σ (psi)
ε (%)
______________________________________
P-DEND 846 2.5 1.0 39 10.3 31
(X443-62)
PGA 1480 2.5 1.0 19 10.5 86
(S1011-35)
______________________________________
*77° F., 1.0 in/in/min
Claims (2)
1. A method for preparing poly(diethylene glycol-4,7-dinitrazadecane-dioate) comprising:
(i) completing a Michael addition of ethylene dinitramine to methyl acrylate to yield dimethyl-4,7-dinitrazadecane-dioate (DMDND);
(ii) reacting under vacuum, said DMDND with an excess ratio amount of diethylene glycol to said DMDND at an elevated temperature of about 85° C. while employing a catalyst of p-toluenesulfonic acid to form diethylene glycol-4,7-dinitrazadecane-dioate in mother liquid, said vacuum effecting removal of methanol as generated during said reacting;
(iii) continuing said reacting for about 18 hours under vacuum and thereafter initiating and completing a high vacuum distillation process to remove excess diethylene glycol from mother liquid containing said diethylene glycol-4,7-dinitrazadecane-dioate;
(iv) heating said mother liquid remaining after said distillation of excess diethylene glycol under high vacuum at about 80° C. to achieve polymerization of said diethylene glycol-4,7-dinitrazadecane-dioate to form poly(diethylene glycol-4,7-dinitrazadecane-dioate) (P-DEND); and,
(v) purifying said P-DEND by passing it through a silica gel column using methylene chloride as solvent to yield pure P-DEND having a molecular weight ranging from about 1500 to about 2000.
2. The method of claim 1 for preparing poly(diethylene glycol-4,7-dinitrazadecane-dioate) wherein said excess ratio of said diethylene glycol to said DMDND is about 15:1.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/008,511 USH365H (en) | 1987-01-29 | 1987-01-29 | New energetic polymer, P-DEND |
| CA000553707A CA1320612C (en) | 1987-01-29 | 1987-12-07 | Energetic polymer, p-dend |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/008,511 USH365H (en) | 1987-01-29 | 1987-01-29 | New energetic polymer, P-DEND |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH365H true USH365H (en) | 1987-11-03 |
Family
ID=21732012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/008,511 Abandoned USH365H (en) | 1987-01-29 | 1987-01-29 | New energetic polymer, P-DEND |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | USH365H (en) |
| CA (1) | CA1320612C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0501956A4 (en) * | 1988-11-14 | 1992-12-09 | Olin Corporation | Nitramine-containing homopolymers and copolymers and a process for the preparation thereof |
-
1987
- 1987-01-29 US US07/008,511 patent/USH365H/en not_active Abandoned
- 1987-12-07 CA CA000553707A patent/CA1320612C/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Hackh's Chemical Dictionary, Fourth Edition, (Copyright 1969), p. 428. |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0501956A4 (en) * | 1988-11-14 | 1992-12-09 | Olin Corporation | Nitramine-containing homopolymers and copolymers and a process for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1320612C (en) | 1993-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| AS | Assignment |
Owner name: UNITED STATES OF AMERICA, AS REPRESENTED BY THE SE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST. SUBJECT TO LICENSE RECITED;ASSIGNOR:CHI, MINN-SHONG;REEL/FRAME:004757/0024 Effective date: 19870112 |