US2696430A - Stabilizers for nitro-cellulose mixtures - Google Patents
Stabilizers for nitro-cellulose mixtures Download PDFInfo
- Publication number
- US2696430A US2696430A US159872A US15987250A US2696430A US 2696430 A US2696430 A US 2696430A US 159872 A US159872 A US 159872A US 15987250 A US15987250 A US 15987250A US 2696430 A US2696430 A US 2696430A
- Authority
- US
- United States
- Prior art keywords
- nitro
- nitroaniline
- stabilizers
- ethyl
- methyl
- 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
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- 239000000020 Nitrocellulose Substances 0.000 title claims description 15
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 title claims description 15
- 229920001220 nitrocellulos Polymers 0.000 title claims description 15
- 239000003381 stabilizer Substances 0.000 title claims description 12
- 229940079938 nitrocellulose Drugs 0.000 title description 9
- 239000000203 mixture Substances 0.000 title description 4
- 229960003711 glyceryl trinitrate Drugs 0.000 claims description 3
- 239000000843 powder Substances 0.000 description 15
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 12
- 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 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 4
- XBNNLAWQCMDISJ-UHFFFAOYSA-N n-ethyl-4-nitroaniline Chemical compound CCNC1=CC=C([N+]([O-])=O)C=C1 XBNNLAWQCMDISJ-UHFFFAOYSA-N 0.000 description 4
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 3
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 241000736839 Chara Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- ZVSJFPOKRSIYSH-UHFFFAOYSA-N n-butyl-3-nitroaniline Chemical compound CCCCNC1=CC=CC([N+]([O-])=O)=C1 ZVSJFPOKRSIYSH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- 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
- C06B25/18—Compositions containing a nitrated organic compound the compound being nitrocellulose present as 10% or more by weight of the total composition
- C06B25/20—Compositions containing a nitrated organic compound the compound being nitrocellulose present as 10% or more by weight of the total composition with a non-explosive or a non-explosive or a non-thermic component
Definitions
- the present method of stabilizing single base powders is by adding diphenylamine, and in double base powders by adding centralite.
- a disadvantage of using diphenylamine as a stabilizer is that it reacts with oxygen of the air and also with oxides of nitrogen to form black or dark colored dyes of unproved structures. It further reacts with nitrogen dioxide and nitric acid to form nitrogen monoxide gas. Centralite also reacts with nitrogen tetroxide to form nitrogen monoxide. Since it is the function of a stabilizer to remove these undesirable products, these materials are not as eflective in removing oxides of nitrogen as the chemicals herein disclosed.
- N-alkyl-nitroanilines which contain an alkyl group such as methyl, ethyl, isopropyl, etc., and contain a nitro group in the three or four positions on the benzene ring, when mixed in a nitro-cellulose powder, either single or double base, lead to a powder possessing superior stability.
- N-methyl-4-nitroaniline, N-ethyl-4-nitroaniline, N- is1opropyl-3-nitroaniline, N-butyl-3-nitroaniline are examp es.
- An important object of the present invention is the substitution of from one-half to one percent (up to five percent) of N-ethyl-4-nitroaniline or N-methyl-4-nitroaniline or mixtures thereof in place of diphenylamine in single base nitro-cellulose powders and in place of ethyl centralite in double base nitrocellulose powders.
- a further object of the invention is to produce a superior powder of improved stability which does not become discolored by oxidation impurities.
- a still further object of the invention is to make the aniline nitrogen sufficiently neutral by the nitro group in N-alkyl-4-nitroanilines, so that it would be compatible with nitroesters and still be a strong absorbent of highly oxidized nitrogen atoms, such as nitric acid and nitrogen tetroxide.
- Still a further object of the invention is to prepare a eutectic mixture of N-ethyl-4-nitroaniline and N-methyl- The control dropped an average of 30 poises for this period.
- N- alkyl mononitroanilines possess excellent stabilizing prop erties for single base powder. They efiiciently absorb nitrogen dioxide reducing little or none of it. They further do not aifect the viscosity of cellulose nitrate solution as much as diphenylamine. In the heat test which shows the time in minutes to decolorize methyl violet paper, they compare favorably with diphenylamine.
- Double base powders were prepared by dissolving 60 percent cellulose nitrate (13.47% N), 39 percent nitroglycerine and 1 percent stabilizer in acetone and evaporating oif the acetone at room temperature. The products were extended through a micro-press and placed in a vacuum oven for 7 days at 45 C. The comparative results are shown as follows:
- h invention described here nnay he manuia tq a d s b or o the GQ ernmww t e -niteds ate Amerce f r gove nmenta pun s; wi hout he: Paym t of ny w a s the eon arft erefq st b iz e mn isin an I l a ky troan line .Q n re han' pe ent b b l in com nati n withon qf the g o 9 96 919.
- the combination of a nitrocellulose powder and a s a ilize ther i 9 materiah leqt d t am er up consisting of N-ethyl-4-nitroan i1ine and H l ⁇ I -methyL-4 nitroaniline of not more than 5 percent by bulk.
- a stabilizer for nitrocellulose powders comprising a mixture of"N'-ethyl-4-nitroaniline and N-methyl-4-nitroanilineof-not more than 5 percentfiby bulhiucorporate'd into a nitrocellulose powder with improved plasticizing qualities.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
United States Patent Ofi 2,696,430 Patented Dec. 7, 1954 ice STABILIZERS FOR NITRO-CELLULOSE MIXTURES John A. Gallaghan, Indian Head, Md., and Irving Pincus, State College, Pa., assignors to the United States of America as represented by the Secretary of the Navy No Drawing. Application May 3, 1950, Serial No. 159,872
7 Claims. (Cl. 525) (Granted under Title 35 U. S. Code (1952), see. 266) 4-nitroaniline, incorporating them into powders, to lower the melting point, and to improve the plasticizing qualities of these compounds.
Other objects of the invention will appear in and be apparent from the specification.
In the preparation of experimental powders for possible stabilizers, several tests are useful to eliminate all but the most promising for addition to the nitrocellulose. The results of these tests for certain of the compounds screened are tabulated for comparison. Samples used in the 134.5 C. heat test are formed by mechanically extruding 12.6 percent pyrocotton with one-half /2) percent stabilizer, using ether and alcohol as a solvent. The product is allowed to stand one day in air and is then placed in a vacuum oven for eight (8) hours at 40 C. A standard 134.5 heat test and a 5 hour test are run on the sample. The nitrogen dioxide absorption and viscosity tests are conventional laboratory procedures for these purposes.
Screening tests for stabilizers N 02 Absorption at 25 0., Pressure in Heat Test Mercury Viscosity at 134.5 5 hour Change 1 Methyl Test, 10 1 10 (poises) Violet hrs. 1mm] seconds min. min. Final (mm') Diphenylamine 72 32 22 20 1. 5 Ethyl-Oentralite 72 63 48 37 34 g0 82 6 7 86 N -Methyl-4-nitro anilme 72 0 0 0 58 103 5 60 105 N-ethyl-4-n1tro aniline 72 7 1 0 5 1 Viscosity change at 0. for five days using an ethyl Cellosolve solution of cellulose nitrate The present method of stabilizing single base powders is by adding diphenylamine, and in double base powders by adding centralite. A disadvantage of using diphenylamine as a stabilizer is that it reacts with oxygen of the air and also with oxides of nitrogen to form black or dark colored dyes of unproved structures. It further reacts with nitrogen dioxide and nitric acid to form nitrogen monoxide gas. Centralite also reacts with nitrogen tetroxide to form nitrogen monoxide. Since it is the function of a stabilizer to remove these undesirable products, these materials are not as eflective in removing oxides of nitrogen as the chemicals herein disclosed.
The N-alkyl-nitroanilines which contain an alkyl group such as methyl, ethyl, isopropyl, etc., and contain a nitro group in the three or four positions on the benzene ring, when mixed in a nitro-cellulose powder, either single or double base, lead to a powder possessing superior stability. N-methyl-4-nitroaniline, N-ethyl-4-nitroaniline, N- is1opropyl-3-nitroaniline, N-butyl-3-nitroaniline are examp es.
An important object of the present invention is the substitution of from one-half to one percent (up to five percent) of N-ethyl-4-nitroaniline or N-methyl-4-nitroaniline or mixtures thereof in place of diphenylamine in single base nitro-cellulose powders and in place of ethyl centralite in double base nitrocellulose powders.
A further object of the invention is to produce a superior powder of improved stability which does not become discolored by oxidation impurities.
A still further object of the invention is to make the aniline nitrogen sufficiently neutral by the nitro group in N-alkyl-4-nitroanilines, so that it would be compatible with nitroesters and still be a strong absorbent of highly oxidized nitrogen atoms, such as nitric acid and nitrogen tetroxide.
Still a further object of the invention is to prepare a eutectic mixture of N-ethyl-4-nitroaniline and N-methyl- The control dropped an average of 30 poises for this period.
The results of the screening tests indicate that the N- alkyl mononitroanilines possess excellent stabilizing prop erties for single base powder. They efiiciently absorb nitrogen dioxide reducing little or none of it. They further do not aifect the viscosity of cellulose nitrate solution as much as diphenylamine. In the heat test which shows the time in minutes to decolorize methyl violet paper, they compare favorably with diphenylamine.
Double base powders were prepared by dissolving 60 percent cellulose nitrate (13.47% N), 39 percent nitroglycerine and 1 percent stabilizer in acetone and evaporating oif the acetone at room temperature. The products were extended through a micro-press and placed in a vacuum oven for 7 days at 45 C. The comparative results are shown as follows:
H120 t 610 C.
- eat es aeuum Stabfluer (Average) Stability Minutes Test Ethyl Centralite (Control).. 65 8. 32
N-Methyl-4-nitroanlline- 90 8. 37
N -Ethyl-4-nitroaniline 8. 45
third more effective than ethyl-centralite in the heat test and-areabout the sameintheNaQuum-tests, "andtheresiqub q ba e; pow ers is. thus Pre en ed .apnar nt y has improved and superior chara lemfliw, roduc ngia e er es lt than the ngredients-n w. cqrnmen y kno and used as stabilizers.
h invention described here nnay he manuia tq a d s b or o the GQ ernmww t e -niteds ate Amerce f r gove nmenta pun s; wi hout he: Paym t of ny w a s the eon arft erefq st b iz e mn isin an I l a ky troan line .Q n re han' pe ent b b l in com nati n withon qf the g o 9 96 919. ni re e'a d qellules nitrat tm ce in 1 h co hinat enz fi trocellul s .n wde am a k l- -nirroaml ae con itut a t b i er the or- 3. The combination of a nitrocellulose powder and a s a ilize ther i 9 materiah leqt d t am er up consisting of N-ethyl-4-nitroan i1ine and H l\I -methyL-4 nitroaniline of not more than 5 percent by bulk.
4. The combination of cellulose nitrate nitroglycerine powder and not more than five percent by. bulkpf N1 methyl-4-nitroaniline constituting a stabilizer'therefor;
5. A stabilizer for nitrocellulose powders comprising a mixture of"N'-ethyl-4-nitroaniline and N-methyl-4-nitroanilineof-not more than 5 percentfiby bulhiucorporate'd into a nitrocellulose powder with improved plasticizing qualities.
References Cited in the file or this patent .SIATESPATEN S Number. Name I Date 875.922 mes. a 7. 9 8 875,923 Holmes Jan. 7, 1908 1,329,212 Spelling et a1. Ian. 27, 1920 2,261,630 Regestein Nov. 4, 1941 2,323,948 Von-'Bramenet a1 July 13, 1943 2,378,594 Swan et a1. June 19, 1945 2,381,015 Von Bramenet a1 Aug. 7,1945 2,383,361 Basset a1. Aug..'21, 1945 F R N PATEN S.
Number Country Date 12,746 Great Britain of 1912 'DavisJohn' Wiley and Sons, 1943, N. Y., vol. II, pp. 269
and 307-312.
Claims (1)
1. A STABILIZER COMPRISING AN N-ALKYL-NITROANILINE OF NOT MORE THAN 5 PERCENT BY BULK IN COMBINATION WITH ONE OF THE GROUP OF CELLULOSE NITRATE AND CELLULOSE NITRATE NITROGLYCERINE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US159872A US2696430A (en) | 1950-05-03 | 1950-05-03 | Stabilizers for nitro-cellulose mixtures |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US159872A US2696430A (en) | 1950-05-03 | 1950-05-03 | Stabilizers for nitro-cellulose mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2696430A true US2696430A (en) | 1954-12-07 |
Family
ID=22574444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US159872A Expired - Lifetime US2696430A (en) | 1950-05-03 | 1950-05-03 | Stabilizers for nitro-cellulose mixtures |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2696430A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3000721A (en) * | 1960-06-13 | 1961-09-19 | Donker Hendrik Jean Louis | Method of manufacturing progressive burning molded nitrocellulose gun powder |
| US20090314289A1 (en) * | 2008-01-28 | 2009-12-24 | Fine David H | Conversion of Nitrogen Dioxide (NO2) to Nitric Oxide (NO) |
| US11202880B2 (en) | 2004-08-18 | 2021-12-21 | Vero Biotech LLC | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11554241B2 (en) | 2004-08-18 | 2023-01-17 | Vero Biotech Inc. | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11744978B2 (en) | 2008-08-21 | 2023-09-05 | Vero Biotech Inc. | Systems and devices for generating nitric oxide |
| US11925764B2 (en) | 2009-06-22 | 2024-03-12 | Vero Biotech Inc. | Nitric oxide therapies |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US875922A (en) * | 1907-05-20 | 1908-01-07 | Du Pont Powder Co | Stabilized nitrated starch. |
| US875923A (en) * | 1907-05-20 | 1908-01-07 | Du Pont Powder Co | Stabilized nitrated starch. |
| GB191212746A (en) * | 1912-05-30 | 1913-09-01 | Frederic Lewis Nathan | Improvements in and relating to Explosives. |
| US1329212A (en) * | 1918-06-22 | 1920-01-27 | Trojan Powder Co | Method of manufacturing nitrostarch explosives |
| US2261630A (en) * | 1938-12-07 | 1941-11-04 | Du Pont | Propellent powder |
| US2323948A (en) * | 1940-11-06 | 1943-07-13 | Eastman Kodak Co | Process for preparing phenylenediamine derivatives |
| US2378594A (en) * | 1942-11-19 | 1945-06-19 | Eastman Kodak Co | Stabilizing of nitrocellulose |
| US2381015A (en) * | 1943-07-07 | 1945-08-07 | Eastman Kodak Co | Process for preparing phenylene-diamine derivatives |
| US2383361A (en) * | 1943-05-05 | 1945-08-21 | Dow Chemical Co | Stabilizing cellulose ethers |
-
1950
- 1950-05-03 US US159872A patent/US2696430A/en not_active Expired - Lifetime
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US875922A (en) * | 1907-05-20 | 1908-01-07 | Du Pont Powder Co | Stabilized nitrated starch. |
| US875923A (en) * | 1907-05-20 | 1908-01-07 | Du Pont Powder Co | Stabilized nitrated starch. |
| GB191212746A (en) * | 1912-05-30 | 1913-09-01 | Frederic Lewis Nathan | Improvements in and relating to Explosives. |
| US1329212A (en) * | 1918-06-22 | 1920-01-27 | Trojan Powder Co | Method of manufacturing nitrostarch explosives |
| US2261630A (en) * | 1938-12-07 | 1941-11-04 | Du Pont | Propellent powder |
| US2323948A (en) * | 1940-11-06 | 1943-07-13 | Eastman Kodak Co | Process for preparing phenylenediamine derivatives |
| US2378594A (en) * | 1942-11-19 | 1945-06-19 | Eastman Kodak Co | Stabilizing of nitrocellulose |
| US2383361A (en) * | 1943-05-05 | 1945-08-21 | Dow Chemical Co | Stabilizing cellulose ethers |
| US2381015A (en) * | 1943-07-07 | 1945-08-07 | Eastman Kodak Co | Process for preparing phenylene-diamine derivatives |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3000721A (en) * | 1960-06-13 | 1961-09-19 | Donker Hendrik Jean Louis | Method of manufacturing progressive burning molded nitrocellulose gun powder |
| US11383059B2 (en) | 2004-08-18 | 2022-07-12 | Vero Biotech Inc. | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11202880B2 (en) | 2004-08-18 | 2021-12-21 | Vero Biotech LLC | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11554241B2 (en) | 2004-08-18 | 2023-01-17 | Vero Biotech Inc. | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11291793B2 (en) | 2004-08-18 | 2022-04-05 | Vero Biotech Inc. | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11312626B2 (en) * | 2008-01-28 | 2022-04-26 | Vero Biotech Inc. | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US9701538B2 (en) | 2008-01-28 | 2017-07-11 | Geno Llc | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US8741222B2 (en) | 2008-01-28 | 2014-06-03 | Geno Llc | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US7914743B2 (en) * | 2008-01-28 | 2011-03-29 | Geno Llc | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US20090314289A1 (en) * | 2008-01-28 | 2009-12-24 | Fine David H | Conversion of Nitrogen Dioxide (NO2) to Nitric Oxide (NO) |
| US8609026B2 (en) | 2008-01-28 | 2013-12-17 | Geno Llc | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11884541B2 (en) | 2008-01-28 | 2024-01-30 | Vero Biotech Inc. | Conversion of nitrogen dioxide (NO2) to nitric oxide (NO) |
| US11744978B2 (en) | 2008-08-21 | 2023-09-05 | Vero Biotech Inc. | Systems and devices for generating nitric oxide |
| US12171948B2 (en) | 2008-08-21 | 2024-12-24 | Vero Biotech Inc. | Systems and devices for generating nitric oxide |
| US11925764B2 (en) | 2009-06-22 | 2024-03-12 | Vero Biotech Inc. | Nitric oxide therapies |
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