US2926072A - Detection of g agents - Google Patents
Detection of g agents Download PDFInfo
- Publication number
- US2926072A US2926072A US804550A US80455059A US2926072A US 2926072 A US2926072 A US 2926072A US 804550 A US804550 A US 804550A US 80455059 A US80455059 A US 80455059A US 2926072 A US2926072 A US 2926072A
- Authority
- US
- United States
- Prior art keywords
- cyanide
- agents
- oxime
- bis
- compound selected
- 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
- 238000001514 detection method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000012530 fluid Substances 0.000 claims description 6
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 claims description 3
- PJVJTCIRVMBVIA-UHFFFAOYSA-N [dimethylamino(ethoxy)phosphoryl]formonitrile Chemical compound CCOP(=O)(C#N)N(C)C PJVJTCIRVMBVIA-UHFFFAOYSA-N 0.000 claims description 3
- 229940075610 mercuric cyanide Drugs 0.000 claims description 3
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 claims description 3
- 229940098221 silver cyanide Drugs 0.000 claims description 3
- DYAHQFWOVKZOOW-UHFFFAOYSA-N Sarin Chemical compound CC(C)OP(C)(F)=O DYAHQFWOVKZOOW-UHFFFAOYSA-N 0.000 claims description 2
- GRXKLBBBQUKJJZ-UHFFFAOYSA-N Soman Chemical compound CC(C)(C)C(C)OP(C)(F)=O GRXKLBBBQUKJJZ-UHFFFAOYSA-N 0.000 claims description 2
- SNTRKUOVAPUGAY-UHFFFAOYSA-N cyclosarin Chemical compound CP(F)(=O)OC1CCCCC1 SNTRKUOVAPUGAY-UHFFFAOYSA-N 0.000 claims description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
- TYWAOIBYSDORAH-UHFFFAOYSA-N 1,2-bis(4-aminophenyl)ethane-1,2-dione Chemical compound C1=CC(N)=CC=C1C(=O)C(=O)C1=CC=C(N)C=C1 TYWAOIBYSDORAH-UHFFFAOYSA-N 0.000 claims 1
- CIRXMHIWCRIQJE-UHFFFAOYSA-N CN(C)C1=CC=CC=C1C(=NO)C1=CC=CC=C1 Chemical compound CN(C)C1=CC=CC=C1C(=NO)C1=CC=CC=C1 CIRXMHIWCRIQJE-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 14
- 150000002923 oximes Chemical class 0.000 description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- -1 4-dimethylamino-4'-nitrobenzophenone oxime Chemical compound 0.000 description 2
- NQEKWUWNYBWHGF-UHFFFAOYSA-N N-[[4,4-bis(diethylamino)cyclohexa-1,5-dien-1-yl]-phenylmethylidene]hydroxylamine Chemical compound C(C)N(C1(CC=C(C(C2=CC=CC=C2)=NO)C=C1)N(CC)CC)CC NQEKWUWNYBWHGF-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- RHVSVZXFVMCNAT-UHFFFAOYSA-N n-[bis[4-(dimethylamino)phenyl]methylidene]hydroxylamine Chemical compound C1=CC(N(C)C)=CC=C1C(=NO)C1=CC=C(N(C)C)C=C1 RHVSVZXFVMCNAT-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- OLBYFEGTUWWPTR-SQFISAMPSA-N (2z)-2-hydroxyimino-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=N/O)/C(=O)C1=CC=CC=C1 OLBYFEGTUWWPTR-SQFISAMPSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- ICZWVCDXVPRBMM-UHFFFAOYSA-N OP(F)=O Chemical class OP(F)=O ICZWVCDXVPRBMM-UHFFFAOYSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- PJVJTCIRVMBVIA-JTQLQIEISA-N [dimethylamino(ethoxy)phosphoryl]formonitrile Chemical compound CCO[P@@](=O)(C#N)N(C)C PJVJTCIRVMBVIA-JTQLQIEISA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- NHMJUOSYSOOPDM-UHFFFAOYSA-N cadmium cyanide Chemical compound [Cd+2].N#[C-].N#[C-] NHMJUOSYSOOPDM-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 239000002575 chemical warfare agent Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- FQUZOEORODDIIM-UHFFFAOYSA-N cyanophosphonamidic acid Chemical compound NP(O)(=O)C#N FQUZOEORODDIIM-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MDSZMADSQRPHQY-UHFFFAOYSA-N n-[bis[4-(diethylamino)phenyl]methylidene]hydroxylamine Chemical compound C1=CC(N(CC)CC)=CC=C1C(=NO)C1=CC=C(N(CC)CC)C=C1 MDSZMADSQRPHQY-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/16—Phosphorus containing
- Y10T436/163333—Organic [e.g., chemical warfare agents, insecticides, etc.]
Definitions
- the preferred activating agents are metallic ya Grandview Heights, and Robert H. Poitier, Columbus, o i y i e being preferred-
- Other cyanides that Ohio, assignors, by direct and mesne assignments, to have been used successfully are mercuric cyanide, potasflle United States Of America as represented y the siurn cyanide, silver cyanide and cadmium cyanide.
- the Secretary of the y oxime and cyanide may be mixed in the dry state in about No Drawing Application April 6, 1959 equal proportions and exposed to air suspected of con- Serial 804,550 taming vapors of the G agents.
- Table I shows the characteristic color produced by dif- 3 Claimsferent combinations of oxime, cyanide and G agent in spot tests using the liquid G agent and on exposure to
- the invention described herein may be manufactured very dilute concentrations of vapors, 44 gamma (microand used by or for the Government of the United States grams) per liter of air.
- This invention is directed to the detection of' toxic chemical warfare agents of the class known as G agents.
- Important members of this class are GB or sarin (isopropyl methylphosphonofiuoridate), GA or tabun (ethyl dimethylphosphoroamidocyanidate), GD (pinacolyl methylphosphonofluoridate), and GF (cyclohexyl methylphosphonofluoridate.
- Our method consists in contacting a fluid suspected of containing the agent with oximes of certain aromatic ketones containing at least one paradialkylamine substituent.
- These reagents show several important characteristics as detecting agents. When used alone, some of them show a color change with GA, but not with the other G agents listed above. With certain additives, however, they respond to the other agents as well. Thus, they may be used to distinguish between the phosphoroamidocyanidate, GA, and the phosphonofluoridates GB, GD and GF. Others give color reactions only in the presence of the additives, even with GA.
- the compounds which we find most effective, and which give the reaction with GA in the absence of additives, are the oximes of Michlers ketone and its ethyl homologue, i.e., 4,4'-bis(dimethylamino) benzophenone oxime, which we designate MMK-O, and 4,4-bis (di- The oximes of 4-dimethylaminobenzaldehyde and 4- dimethylaminoacetophenone did not give a sufiiciently positive color change to be satisfactory for our purposes.
- the remaining compounds listed in the table are satisfactory, EMK-O and MMK-O being preferred, and EMK-O being presently regarded as the best.
- the sensitivity of colorimetric detectors for chemical warfare agents is commonly expressed in terms of CT value, i.e., the product of the concentration (C) of the agent in the air expressed in gamma (micrograms) per liter of air multiplied by the time (T) in minutes to produce the change in color.
- CT value i.e., the product of the concentration (C) of the agent in the air expressed in gamma (micrograms) per liter of air multiplied by the time (T) in minutes to produce the change in color.
- CT value for the blend of EMK-O with sodium cyanide was less than 1 gamma minute per liter, which is a very low value, indicating very high sensitivity.
- the oxime detecting compositions may be utilized in the form of crayons.
- a typical crayon formulation is:
- Component Percent Blane fixe (barium sulfate).
- NIK-O Sodium Cyanide the mark on a wall, for instance, is extremely sensitive, having a CT value for GB of less than 1 gamma minute per liter.
- a method for the detection of the presence in a fluid of a compound selected from the class consisting of ethyl dirnethylphosphoroamidocyanidate, isopropyl methylphosphonofiuoridate, pinacolyl methylphosphonofiuoridate and cyclohexyl rnethylphosphonofiuoridate which comprises contacting said fluid with a compound selected from the class consisting of 4,4'-bis (dimethylamino) benzophenone oxime, 4,4'-bis (diethylamino) benzophenone oxime, 4-dimethylamino-4'-nitrobenzophenone oxime and 4,4-tetramethyl diaminobenzil monoxime in admixture with a compound selected from the class consisting of sodium cyanide, potassium cyanide, mercuric cyanide and silver cyanide.
- a method for detecting the presence of ethyl dimethylphosphoroamidocyanidate in a fluid which comprises contacting said fiuid with a compound selected from the class consisting of 4,4-bis (dimethylamino) benzophenone oxime and 4,4-bis (diethylamino) benzophenone oxime.
- a crayon for use in the detection of G agents comprising a compressed stick consisting essentially of a mixture of about 80 percent blanc fixe, 10 percent sodium cyanide and 10 percent 4,4-bis (diethylamino) benzophenone oxime.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Description
DETECTION OF G AGENTS ethylamino) benzophenone oxime, which we designate 2,926,072 Patented Feb. 23, 1960 "ice EMK-O, respectively. Of these EMK-O appears to be the most sensitive and constitutes our presently preferred species.
David N. Kramer, Stevenson, Md., and Richard D. Morin, 5 The preferred activating agents are metallic ya Grandview Heights, and Robert H. Poitier, Columbus, o i y i e being preferred- Other cyanides that Ohio, assignors, by direct and mesne assignments, to have been used successfully are mercuric cyanide, potasflle United States Of America as represented y the siurn cyanide, silver cyanide and cadmium cyanide. The Secretary of the y oxime and cyanide may be mixed in the dry state in about No Drawing Application April 6, 1959 equal proportions and exposed to air suspected of con- Serial 804,550 taming vapors of the G agents.
Table I shows the characteristic color produced by dif- 3 Claimsferent combinations of oxime, cyanide and G agent in spot tests using the liquid G agent and on exposure to The invention described herein may be manufactured very dilute concentrations of vapors, 44 gamma (microand used by or for the Government of the United States grams) per liter of air.
Table I Oxlme Cyanide G Color Spot Test Color Dilute Vapors Agent red. 110x18. orange or red. pink in one second, orange .za aaa reddish orange.
MMK'O red orange igg orange. 4-Dimethylamlno-benzaldoxlme Slightly 4-Dlmethylamlno-acetophenone oxlme 4-Dimethylamino-benzophenone oxlme 4,4'-Tetramethyldlan1ino benzil monoxime kDimethylamino-4-nitro-benzophenone oxime of America for governmental purposes without the payment to us of any royalty thereon.
This invention is directed to the detection of' toxic chemical warfare agents of the class known as G agents. Important members of this class are GB or sarin (isopropyl methylphosphonofiuoridate), GA or tabun (ethyl dimethylphosphoroamidocyanidate), GD (pinacolyl methylphosphonofluoridate), and GF (cyclohexyl methylphosphonofluoridate.
Our method consists in contacting a fluid suspected of containing the agent with oximes of certain aromatic ketones containing at least one paradialkylamine substituent. These reagents show several important characteristics as detecting agents. When used alone, some of them show a color change with GA, but not with the other G agents listed above. With certain additives, however, they respond to the other agents as well. Thus, they may be used to distinguish between the phosphoroamidocyanidate, GA, and the phosphonofluoridates GB, GD and GF. Others give color reactions only in the presence of the additives, even with GA.
The compounds which we find most effective, and which give the reaction with GA in the absence of additives, are the oximes of Michlers ketone and its ethyl homologue, i.e., 4,4'-bis(dimethylamino) benzophenone oxime, which we designate MMK-O, and 4,4-bis (di- The oximes of 4-dimethylaminobenzaldehyde and 4- dimethylaminoacetophenone did not give a sufiiciently positive color change to be satisfactory for our purposes. The remaining compounds listed in the table are satisfactory, EMK-O and MMK-O being preferred, and EMK-O being presently regarded as the best.
The sensitivity of colorimetric detectors for chemical warfare agents is commonly expressed in terms of CT value, i.e., the product of the concentration (C) of the agent in the air expressed in gamma (micrograms) per liter of air multiplied by the time (T) in minutes to produce the change in color. The CT value for the blend of EMK-O with sodium cyanide was less than 1 gamma minute per liter, which is a very low value, indicating very high sensitivity.
The oxime detecting compositions may be utilized in the form of crayons. A typical crayon formulation is:
Component Percent Blane fixe (barium sulfate). NIK-O Sodium Cyanide the mark on a wall, for instance, is extremely sensitive, having a CT value for GB of less than 1 gamma minute per liter.
We claim:
1. A method for the detection of the presence in a fluid of a compound selected from the class consisting of ethyl dirnethylphosphoroamidocyanidate, isopropyl methylphosphonofiuoridate, pinacolyl methylphosphonofiuoridate and cyclohexyl rnethylphosphonofiuoridate, which comprises contacting said fluid with a compound selected from the class consisting of 4,4'-bis (dimethylamino) benzophenone oxime, 4,4'-bis (diethylamino) benzophenone oxime, 4-dimethylamino-4'-nitrobenzophenone oxime and 4,4-tetramethyl diaminobenzil monoxime in admixture with a compound selected from the class consisting of sodium cyanide, potassium cyanide, mercuric cyanide and silver cyanide.
2. A method for detecting the presence of ethyl dimethylphosphoroamidocyanidate in a fluid which comprises contacting said fiuid with a compound selected from the class consisting of 4,4-bis (dimethylamino) benzophenone oxime and 4,4-bis (diethylamino) benzophenone oxime.
3. A crayon for use in the detection of G agents comprising a compressed stick consisting essentially of a mixture of about 80 percent blanc fixe, 10 percent sodium cyanide and 10 percent 4,4-bis (diethylamino) benzophenone oxime.
References Cited in the file of this patent Young et al.: Anal. Chem. 30; 1236-39 (1958). Cherry et 21.: Anal. Chem. 30, 1239-47 (1958).
Claims (1)
1. A METHOD FOR THE DETECTION OF THE PRESENCE IN A FLUID OF A COMPOUND SELECTED FROM THE CLASS CONSISTING OF ETHYL DIMETHYLPHOSPHOROAMIDOCYANIDATE, ISOPROPYL METHYLPHOSPHONOFLUORIDATE, PINACOLYL METHYLPHOSPHONOFLUORIDATE AND CYCLOHEXYL METHYLPHOSPHONOFLUORIDATE, WHICH COMPRISES CONTACTING SAID FLUID WILTH A COMPOUND SELECTED FROM THE CLASS CONSISTING OF 4,4''-BIS (DIMETHYLAMINO) BENZOPHENONE OXIME, 4,4''-BIS (DIETHYLAMINO) BENZOPHENONE OXIME, 4-DIMETHYLAMINO-4''-NITROBENZOPHENONE OXIME AND 4,4''-TETRAMETTHYL DIAMINOBENZIL MONOXINE IN ADMIXTURE WITH A COMPOUND SELECTED FROM THE CLASS CONSISTING OF SODIUM CYANIDE, POTASSIUM CYANIDE, MERCURIC CYANIDE AND SILVER CYANIDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US804550A US2926072A (en) | 1959-04-06 | 1959-04-06 | Detection of g agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US804550A US2926072A (en) | 1959-04-06 | 1959-04-06 | Detection of g agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2926072A true US2926072A (en) | 1960-02-23 |
Family
ID=25189239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US804550A Expired - Lifetime US2926072A (en) | 1959-04-06 | 1959-04-06 | Detection of g agents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2926072A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275534A (en) * | 1963-03-19 | 1966-09-27 | Jr Paul L Cannon | Bioelectric method for the detection of anticholinester-ases |
| US3515644A (en) * | 1967-04-10 | 1970-06-02 | Us Army | Reversed enzymatic detection method for anticholinesterases |
| US3844905A (en) * | 1972-05-24 | 1974-10-29 | Us Army | Testing a toxic agent alarm with a nontoxic simulant |
| US3877874A (en) * | 1969-10-17 | 1975-04-15 | Us Army | Method for detection and droplet measurement of S-(2-diisopropylaminoethyl)O-ethyl methylphosphonothioate chemical warfare agent with 1,3,5 trinitrobenzene |
| US3910763A (en) * | 1969-10-03 | 1975-10-07 | Us Army | Method of detecting organophosphorus agents using 1-phenyl-1,2,3-butanetrione-2-oxime and cyanide indicating composition |
| US3960759A (en) * | 1965-11-24 | 1976-06-01 | The United States Of America As Represented By The Secretary Of The Navy | Liquid vesicant differentiating paint |
| US4225316A (en) * | 1961-11-28 | 1980-09-30 | The United States Of America As Represented By The Secretary Of The Navy | Chemical agent detection method and apparatus |
| US20100130757A1 (en) * | 2004-12-16 | 2010-05-27 | University Of Wyoming | Compositions and methods for detecting nerve agents |
| RU2562990C2 (en) * | 2013-12-17 | 2015-09-10 | Открытое акционерное общество "Государственный научно-исследовательский химико-аналитический институт" (ОАО "ГосНИИхиманалит") | Indicator paint for detecting unsymmetrical dimethylhydrazine |
-
1959
- 1959-04-06 US US804550A patent/US2926072A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4225316A (en) * | 1961-11-28 | 1980-09-30 | The United States Of America As Represented By The Secretary Of The Navy | Chemical agent detection method and apparatus |
| US3275534A (en) * | 1963-03-19 | 1966-09-27 | Jr Paul L Cannon | Bioelectric method for the detection of anticholinester-ases |
| US3960759A (en) * | 1965-11-24 | 1976-06-01 | The United States Of America As Represented By The Secretary Of The Navy | Liquid vesicant differentiating paint |
| US3515644A (en) * | 1967-04-10 | 1970-06-02 | Us Army | Reversed enzymatic detection method for anticholinesterases |
| US3910763A (en) * | 1969-10-03 | 1975-10-07 | Us Army | Method of detecting organophosphorus agents using 1-phenyl-1,2,3-butanetrione-2-oxime and cyanide indicating composition |
| US3877874A (en) * | 1969-10-17 | 1975-04-15 | Us Army | Method for detection and droplet measurement of S-(2-diisopropylaminoethyl)O-ethyl methylphosphonothioate chemical warfare agent with 1,3,5 trinitrobenzene |
| US3844905A (en) * | 1972-05-24 | 1974-10-29 | Us Army | Testing a toxic agent alarm with a nontoxic simulant |
| US20100130757A1 (en) * | 2004-12-16 | 2010-05-27 | University Of Wyoming | Compositions and methods for detecting nerve agents |
| US7951607B2 (en) * | 2004-12-16 | 2011-05-31 | University Of Wyoming | Compositions and methods for detecting nerve agents |
| RU2562990C2 (en) * | 2013-12-17 | 2015-09-10 | Открытое акционерное общество "Государственный научно-исследовательский химико-аналитический институт" (ОАО "ГосНИИхиманалит") | Indicator paint for detecting unsymmetrical dimethylhydrazine |
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