US3445306A - Solid propellant composition containing the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate - Google Patents
Solid propellant composition containing the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate Download PDFInfo
- Publication number
- US3445306A US3445306A US687393A US3445306DA US3445306A US 3445306 A US3445306 A US 3445306A US 687393 A US687393 A US 687393A US 3445306D A US3445306D A US 3445306DA US 3445306 A US3445306 A US 3445306A
- Authority
- US
- United States
- Prior art keywords
- nitrate
- propellant
- polyvinylene
- reaction product
- glycol nitrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title description 50
- 229910002651 NO3 Inorganic materials 0.000 title description 29
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 title description 28
- -1 polyvinylene Polymers 0.000 title description 27
- 229920001197 polyacetylene Polymers 0.000 title description 26
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title description 25
- 239000007795 chemical reaction product Substances 0.000 title description 7
- 239000004449 solid propellant Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 title description 3
- 239000003380 propellant Substances 0.000 description 26
- 239000000463 material Substances 0.000 description 15
- 230000008901 benefit Effects 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 230000006872 improvement Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 239000000020 Nitrocellulose Substances 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 229960003711 glyceryl trinitrate Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QUAMCNNWODGSJA-UHFFFAOYSA-N 1,1-dinitrooxybutyl nitrate Chemical compound CCCC(O[N+]([O-])=O)(O[N+]([O-])=O)O[N+]([O-])=O QUAMCNNWODGSJA-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- PZIMIYVOZBTARW-UHFFFAOYSA-N centralite Chemical compound C=1C=CC=CC=1N(CC)C(=O)N(CC)C1=CC=CC=C1 PZIMIYVOZBTARW-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- LYAGTVMJGHTIDH-UHFFFAOYSA-N diethylene glycol dinitrate Chemical compound [O-][N+](=O)OCCOCCO[N+]([O-])=O LYAGTVMJGHTIDH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical compound O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
-
- 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
Definitions
- This invention relates to an improved additive for use in a propellant. More particularly, this invention relates to additive for use in a propellant thereby producing increased stability coupled with enhanced physical and mechanical properties.
- polyvinylene glycol nitrate due to its inherent characteristics was thought to possess great potential as an additive for use in a propellant. It was also though to possess special advantages when utilized in a propellant designed for use in a gun or the motor of a rocket. These advantages are derived from the fact that polyvinylene glycol nitrate is polymeric in nature and possesses a relatively high amount of energy. Thus, it could be used to replace ammonium perchlorate, ammonium nitrate, or some of the explosive itself, such as HMX or RDX, with the advantage that it would not in any way degrade the energy level of the propellant but would, in fact, improve the mechanical properties of the final product.
- polyvinylene glycol nitrate possesses the ability to colloid with nitro-type plasticizers such as nitroglycerine, butane trioltrinitrate and diethylene glycol dinitrate. Thus, it may be used to partially replace these expensive plasticizers without loss of energy to the system. Also, the volatility of double base propellants ordinarily possessing these types of plasticizers may be reduced by replacement of a portion of such nitro-type plasticizers.
- nitro-type plasticizers such as nitroglycerine, butane trioltrinitrate and diethylene glycol dinitrate.
- the subject invention answers the needs of the art as described above with special emphasis on improving the stability of polyvinylene glycol nitrate at temperatures usually encountered in the desert.
- Another object is to provide a modified form of polyvinylene glycol nitrate which may be utilized in propellant under a desert type environment.
- polyvinylene glycol nitrate may be effectively stabilized by reaction with an aromatic diisocyanate such as toluene diisocyanate.
- the polyvinylene glycol nitrate thus stabilized may be incorporated in a propellant for use at temperatures in excess of 60 C., such as that encountered in desert warfare, without any adverse effects to the propellant.
- this incorporation has been found to be accompanied by the inclusion of all the inherent advantages of the polyvinylene glycol nitrate itself.
- This improvement in stability is evidenced by an increase in thermal stability as shown by diiferential thermal analysis. This improvement is also accompanied by a reduction in sensitivity to impact.
- the modified form of polyvinylene glycol nitrate is less sensitive than nitroglycerine and comparable to nitrocellulose. Further, a 'visual observation of the burning rate of the modified form of polyvinylene glycol nitrate was demonstrated to advantage to be many times faster than a nitrocellulose fiber having a nitrogen content of 12.6 percent.
- Example I A specified amount of polyvinylene glycol nitrate was dissolved in acetone and between 5 and 15 percent of toluene diisocyanate was added. The specific amount of diisocyanate is dependent on the hydroxyl content of the nitrated polymer. For instance, about 10 percent of diisocyanate was added, when the hydroxyl content of the nitrate polymer was about 1 percent. The resulting solution was stirred from 1 to 4 hours and then poured in a large volume of water producing a precipitate. The latter solid was filtered from the solution, washed with water and dried in a vacuum oven. The resulting solid material was then tested as hereafter described.
- Example II As an alternate procedure, the polyvinylene glycol nitrate is slurried in an inert solvent such as heptane and the same proportion of diisocyanate utilized in Example I is added to the solution. The slurry is stirredfrom 1 to 4 hours and then filtered to remove the precipitate. After drying, the precipitate was utilized in the tests which follow.
- an inert solvent such as heptane
- the test is carried out by heating a 5 gm. sample, under vacuum at specified temperatures, and measuring the evolution of gas. The latter is a measurement of the degradation of a compound when exposed to a particular temperature for a particular length of time.
- polyvinylene glycol nitrate possesses relatively greater instability than that of the reaction 'roduct of this material and toluene diisocyanate as videnced by the greater loss in weight at a relatively lower emperature for the initial heating period.
- the material of this invention may be used to replace solid crystalline oxidizer in both double and triple base lropellants as indicated previously. If this were done, the esulting propellant would be more homogeneous due to he colloiding action of such material with the nitroplasicizers.
- the material of this invention may be partially or wholly substituted for other ingredients of a conventional propellant. It was found that this substitution was not accompanied with any loss of energy of the propellant itself. In fact, the propellant compositions themselves after substitution were assured of increased stability and in some cases a greater amount of energy.
- the aromatic diisocyanate which may be used to advantage in this invention includes phenylene-l-4-diisocyanate; p,p -biphenylene diisocyanate; p,p -diphenyl methane diisocyanate.
- a solid propellant for use at temperatures inexcess of 60 C., said propellant containing nitrocellulose and nitrate esters, the improvement of a high energy additive consisting of the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate.
- a solid propellant for use at temperatures in excess of 60 C. said propellant containing nitrocellulose, nitrate esters and nitroquanidine, the improvement of a high energy additive consisting of polyvinylene glycol nitrate and an aromatic diisocyanate.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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)
- Polyurethanes Or Polyureas (AREA)
Description
SOLID PROPELLANT COMPOSITION CONTAINING THE REACTION PRODUCT F POLYVINYL- ENE GLYCOL NITRATE AND AN AROMATIC DHSOCYANATE Daniel R. Satriana, Verona, N.J., assignor to the United States of America as represented by the Secretary of the Arm No rawing. Filed Dec. 1, 1967, Ser. No. 687,393
Int. Cl. C06b /00, 19/04 US. Cl. 14996 6 Claims ABSTRACT OF THE DISCLOSURE An improved high energy additive for use in a propellant subjected to a desert type environment consisting of the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate.
This invention relates to an improved additive for use in a propellant. More particularly, this invention relates to additive for use in a propellant thereby producing increased stability coupled with enhanced physical and mechanical properties.
Sometime in the past, polyvinylene glycol nitrate due to its inherent characteristics was thought to possess great potential as an additive for use in a propellant. It was also though to possess special advantages when utilized in a propellant designed for use in a gun or the motor of a rocket. These advantages are derived from the fact that polyvinylene glycol nitrate is polymeric in nature and possesses a relatively high amount of energy. Thus, it could be used to replace ammonium perchlorate, ammonium nitrate, or some of the explosive itself, such as HMX or RDX, with the advantage that it would not in any way degrade the energy level of the propellant but would, in fact, improve the mechanical properties of the final product. Further, it was found that polyvinylene glycol nitrate possesses the ability to colloid with nitro-type plasticizers such as nitroglycerine, butane trioltrinitrate and diethylene glycol dinitrate. Thus, it may be used to partially replace these expensive plasticizers without loss of energy to the system. Also, the volatility of double base propellants ordinarily possessing these types of plasticizers may be reduced by replacement of a portion of such nitro-type plasticizers.
However, conventional warfare under a desert type environment dictates that a propellant possess stability at temperatures in excess of 60 C. But to dismay, it was found that propellants, having polyvinylene glycol nitrate incorporated therein, did not possess the stability desired due to the low softening point and other inherent characteristics of such nitrate compound. It was also found that such polymer decomposed under the conditions desired affecting the ballistic characteristics of the round and rendering firing unreproducible from round to round.
The subject invention answers the needs of the art as described above with special emphasis on improving the stability of polyvinylene glycol nitrate at temperatures usually encountered in the desert.
It is, therefore, an object of this invention to provide a stable form of polyvinylene glycol nitrate for use in propellants.
Another object is to provide a modified form of polyvinylene glycol nitrate which may be utilized in propellant under a desert type environment.
Other objects and many of the attendant advantages of this invention will be readily appreciated as the same becomes better understood by reference to the following detailed description.
3,4453% Patented May 20, 1969 We have discovered that polyvinylene glycol nitrate may be effectively stabilized by reaction with an aromatic diisocyanate such as toluene diisocyanate. The polyvinylene glycol nitrate thus stabilized may be incorporated in a propellant for use at temperatures in excess of 60 C., such as that encountered in desert warfare, without any adverse effects to the propellant. In fact, this incorporation has been found to be accompanied by the inclusion of all the inherent advantages of the polyvinylene glycol nitrate itself. This improvement in stability is evidenced by an increase in thermal stability as shown by diiferential thermal analysis. This improvement is also accompanied by a reduction in sensitivity to impact. It has been found to advantage that the modified form of polyvinylene glycol nitrate is less sensitive than nitroglycerine and comparable to nitrocellulose. Further, a 'visual observation of the burning rate of the modified form of polyvinylene glycol nitrate was demonstrated to advantage to be many times faster than a nitrocellulose fiber having a nitrogen content of 12.6 percent.
The following are examples of the preparation of the material of this invention.
Example I A specified amount of polyvinylene glycol nitrate was dissolved in acetone and between 5 and 15 percent of toluene diisocyanate was added. The specific amount of diisocyanate is dependent on the hydroxyl content of the nitrated polymer. For instance, about 10 percent of diisocyanate was added, when the hydroxyl content of the nitrate polymer was about 1 percent. The resulting solution was stirred from 1 to 4 hours and then poured in a large volume of water producing a precipitate. The latter solid was filtered from the solution, washed with water and dried in a vacuum oven. The resulting solid material was then tested as hereafter described.
Example II As an alternate procedure, the polyvinylene glycol nitrate is slurried in an inert solvent such as heptane and the same proportion of diisocyanate utilized in Example I is added to the solution. The slurry is stirredfrom 1 to 4 hours and then filtered to remove the precipitate. After drying, the precipitate was utilized in the tests which follow.
The following are the results obtained with a vacuum stability test which measures thermal stability of a particular compound. The test is carried out by heating a 5 gm. sample, under vacuum at specified temperatures, and measuring the evolution of gas. The latter is a measurement of the degradation of a compound when exposed to a particular temperature for a particular length of time.
TABLE I Vaccum Stability Test Thermal Stability Temp., C. A B
60 11 r1115. (16 hrs.) 1.22 11115. (40 hrs.). 4.37 mls. (40 hrs.). 11 mls. (40 hrs.).
1 Polyvinylene glycol nitrate. 2 Reaction product of the above and toluene diisocyanate.
xhibits complete instability. This is quite an improvement nd is evidence of the fact that the modified material of 1is invention may be incorporated into a propellant which my be utilized in a desert environment without exhibiting ny instability due to temperature. Table II, which fol- )ws, illustrates the loss of weight achieved by an 0.6 ample when heated for a specified time at a specified emperature. This evidence indicates the degree of intability of the material under study at each of the temeratures specified.
TABLE IL-HEAT TEST Loss in Weight 2nd 48 hrs. 100 hrs.
1st 48 hrs.
No Explosion. 60. 7% 4.9% Do.
No Explosion.
Do. Do.
1 Polyvinylene glycol dinitrate (material under study).
2 Reaction product of polyvinylene glycol nitrate and toluene diis0- Ianate.
As indicated above, polyvinylene glycol nitrate possesses relatively greater instability than that of the reaction 'roduct of this material and toluene diisocyanate as videnced by the greater loss in weight at a relatively lower emperature for the initial heating period.
Another indication of the stability of the material of his invention is the impact sensitivity of the material. Vhen a 2 kilogram weight was dropped from a 3-inch leight on top of a sample of the material of this invenion, it did not explode. However, when polyvinylene lycol nitrate was subjected to the same test, it detonated. t was found that a 4-inch height was required before he reaction product, a polyvinylene glycol nitrate and an romatic diisocyanate, which is the material of this inention, was exploded under otherwise identical testing onditions. This is substantial evidence of the improvement achieved in the stability of the polymer by the conept of this invention.
The physical strength of both polyvinylene glycol nitrate nd the material of this invention was tested as follows. )ne inch strips of each of the above materials were preared and tested in an Instrom Tensile Tester utilizing onventional procedures. It was found that the tensile trength of the nitrate polymer was 8,700 p.s.i. while the ensile strength of the material of this invention was found 0 be 11,500 p.s.i. This is a good indication of improvement in physical strength of the polymer under study.
The material of this invention may be used to replace solid crystalline oxidizer in both double and triple base lropellants as indicated previously. If this were done, the esulting propellant would be more homogeneous due to he colloiding action of such material with the nitroplasicizers. The following are examples of the substitutions pecified, to the advantage of the propellant.
A, percent 1 litrocellulose 28. 0 litroglycerin 22. 5 litroguanidine 47. 7 ,thyl Centralite g B, percent 0, percent 1 Conventional propellant. 2 Retaction product of polyvinylene glycol nitrate and toluene diisocyana e.
As indicated above, the material of this invention may be partially or wholly substituted for other ingredients of a conventional propellant. It was found that this substitution was not accompanied with any loss of energy of the propellant itself. In fact, the propellant compositions themselves after substitution were assured of increased stability and in some cases a greater amount of energy.
The aromatic diisocyanate which may be used to advantage in this invention includes phenylene-l-4-diisocyanate; p,p -biphenylene diisocyanate; p,p -diphenyl methane diisocyanate.
Obviously, many modifications and variations of the present invention are possible in light of the above teachings. It is, therefore, to be understood that within the scope of the appended claims, the invention may be practiced otherwise than as specifically described.
I claim:
1. In a solid propellant for use at temperatures inexcess of 60 C., said propellant containing nitrocellulose and nitrate esters, the improvement of a high energy additive consisting of the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate.
2. The propellant of claim 1 wherein said aromatic diisocyanate is toluene diisocyanate.
3. The propellant of claim 1 wherein said diisocyanate is present in an amount between 5 and 15 percent by weight of said additive.
4. In a solid propellant for use at temperatures in excess of 60 C., said propellant containing nitrocellulose, nitrate esters and nitroquanidine, the improvement of a high energy additive consisting of polyvinylene glycol nitrate and an aromatic diisocyanate.
5. The propellant of claim 4 wherein said aromatic diisocyanate is toluene diisocyanate.
6. The propellant of claim 4 wherein said diisocyanate is present in an amount between 5 and 15 percent by weight of said additive.
References Cited UNITED STATES PATENTS 3,249,631 5/1966 Sofier 14988 X BENJAMIN R. PADGETT, Primary Examiner.
S. J. LECHE-RT, Assistant Examiner.
U.S. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68739367A | 1967-12-01 | 1967-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3445306A true US3445306A (en) | 1969-05-20 |
Family
ID=24760277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US687393A Expired - Lifetime US3445306A (en) | 1967-12-01 | 1967-12-01 | Solid propellant composition containing the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3445306A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954667A (en) * | 1970-07-01 | 1976-05-04 | The United States Of America As Represented By The Secretary Of The Army | Combustion catalyst for propellants |
| US4052943A (en) * | 1976-09-16 | 1977-10-11 | The United States Of America As Represented By The Secretary Of The Navy | Coating composition and method for improving propellant tear strength |
| US4082584A (en) * | 1971-02-11 | 1978-04-04 | The United States Of America As Represented By The Secretary Of The Army | Ballistic modifier |
| US4298411A (en) * | 1969-07-14 | 1981-11-03 | Hercules Incorporated | Crosslinked smokeless propellants |
| US4555277A (en) * | 1985-01-29 | 1985-11-26 | The United States Of America As Represented By The Unites States Department Of Energy | Extrusion cast explosive |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3249631A (en) * | 1956-08-10 | 1966-05-03 | Louis M Soffer | Nitrate ester of polyvinylene glycol |
-
1967
- 1967-12-01 US US687393A patent/US3445306A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3249631A (en) * | 1956-08-10 | 1966-05-03 | Louis M Soffer | Nitrate ester of polyvinylene glycol |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4298411A (en) * | 1969-07-14 | 1981-11-03 | Hercules Incorporated | Crosslinked smokeless propellants |
| US3954667A (en) * | 1970-07-01 | 1976-05-04 | The United States Of America As Represented By The Secretary Of The Army | Combustion catalyst for propellants |
| US4082584A (en) * | 1971-02-11 | 1978-04-04 | The United States Of America As Represented By The Secretary Of The Army | Ballistic modifier |
| US4052943A (en) * | 1976-09-16 | 1977-10-11 | The United States Of America As Represented By The Secretary Of The Navy | Coating composition and method for improving propellant tear strength |
| US4555277A (en) * | 1985-01-29 | 1985-11-26 | The United States Of America As Represented By The Unites States Department Of Energy | Extrusion cast explosive |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5468313A (en) | Plastisol explosive | |
| DE69220200T2 (en) | Chlorine-free rocket fuel | |
| US3245849A (en) | Solid propellant compositions containing polyurethane resins of low cure temperature | |
| DE4026465C2 (en) | Solid fuels with a binder of non-crystalline polyester / inert plasticizer | |
| US4216039A (en) | Smokeless propellant compositions having polyester or polybutadiene binder system crosslinked with nitrocellulose | |
| US3354010A (en) | Flexible explosive containing rdx and/or rmx and process therefor | |
| US20140261928A1 (en) | Desensitisation of energetic materials | |
| US3756874A (en) | Temperature resistant propellants containing cyclotetramethylenetetranitramine | |
| US4165247A (en) | Polyurethane solid propellant binder | |
| US3445306A (en) | Solid propellant composition containing the reaction product of polyvinylene glycol nitrate and an aromatic diisocyanate | |
| US3447980A (en) | Castable explosive containing tnt and a reaction product of a diisocyanate and 1,4-butyleneoxide polyglycol | |
| US3489623A (en) | Process of gelling tmetn nitrocellulose explosives using nitroparaffin solvents and tmetn nitrocellulose explosive gels | |
| US4659402A (en) | Cross-linked double base propellant having improved low temperature mechanical properties | |
| US3726729A (en) | Solid propellant compositions having a nitrocellulose-hydroxyl-terminated polybutadiene binder and method of preparing the same | |
| US3923564A (en) | Double base propellant with thorium containing ballistic modifier | |
| US3400025A (en) | Flexible explosive comprising rdx, hmx or petn and mixed plasticizer | |
| US3102834A (en) | Composition comprising nitrocellulose, nitroglycerin and oxides of lead or copper | |
| US3943017A (en) | Explosive composition comprising HMX, RDX, or PETN and a high viscosity nitrocellulose binder plasticized with TMETN | |
| US3354172A (en) | Triaminoguanidinium 5-aminotetrazo-late and its preparation | |
| US5798481A (en) | High energy TNAZ, nitrocellulose gun propellant | |
| US3140207A (en) | Pyrotechnic composition | |
| US3103458A (en) | Process for making nitrocellulose pro- | |
| US2982638A (en) | Nitrocellulose propellants containing lead salts of aliphatic acids | |
| US3896865A (en) | Propellant with polymer containing nitramine moieties as binder | |
| US3767489A (en) | Nitrasol propellant |