FI75056B - FOERFARANDE FOER BEVISNING AV BIS- (2-CHLORETYL) -SULF ELLER BIS- (2-CHLORETYL) -IMIN. - Google Patents
FOERFARANDE FOER BEVISNING AV BIS- (2-CHLORETYL) -SULF ELLER BIS- (2-CHLORETYL) -IMIN. Download PDFInfo
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- FI75056B FI75056B FI852970A FI852970A FI75056B FI 75056 B FI75056 B FI 75056B FI 852970 A FI852970 A FI 852970A FI 852970 A FI852970 A FI 852970A FI 75056 B FI75056 B FI 75056B
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- Prior art keywords
- bis
- chloretyl
- dye
- chloroethyl
- bevisning
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- -1 2-CHLORETYL Chemical class 0.000 title description 3
- 239000000126 substance Substances 0.000 claims abstract description 10
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000003595 spectral effect Effects 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- GLVRJEJEXGVOMJ-UHFFFAOYSA-N neutral red base Chemical compound C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 GLVRJEJEXGVOMJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000002152 aqueous-organic solution Substances 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000003086 colorant Substances 0.000 abstract 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XKTMIJODWOEBKO-UHFFFAOYSA-M Guinee green B Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC=CC=2)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 XKTMIJODWOEBKO-UHFFFAOYSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/0004—Gaseous mixtures, e.g. polluted air
- G01N33/0009—General constructional details of gas analysers, e.g. portable test equipment
- G01N33/0027—General constructional details of gas analysers, e.g. portable test equipment concerning the detector
- G01N33/0036—General constructional details of gas analysers, e.g. portable test equipment concerning the detector specially adapted to detect a particular component
- G01N33/0047—Organic compounds
- G01N33/0049—Halogenated organic compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Biophysics (AREA)
- Combustion & Propulsion (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
1 750561 75056
Menetelmä bis-(2-kloorietyyli)-sulfidin tai bis-(2-kloori-etyyli)-imiinin osoittamiseksi - Förfarande för bevisning av bis-(2-kloretyl)-sulfid eller bis-(2-kloretyl)-iminMethod for the determination of bis- (2-chloroethyl) sulphide or bis- (2-chloroethyl) imine
Keksinnön kohteena on menetelmä bis-(3-kloorietyyli)-sulfidin tai bis-(2-kloorietyyli)-imiinin osoittamiseksi lisäämällä kemiallista reagenssia aineen pinnalle, jossa osoitettava aine luultavasti on ja toteamalla optisesti syntyvä säteily.The invention relates to a method for detecting bis- (3-chloroethyl) sulphide or bis- (2-chloroethyl) -imine by adding a chemical reagent to the surface of the substance in which the substance to be detected is probably present and by detecting the optical radiation generated.
Bis.(2-kloorietyyli)-sulfidi tai -imiini on LOST-niminen taisteluaine, jonka osoitus pinnasta suoritetaan tavallisesti indikaattoreilla, jotka on imeytetty paperiin tai pulveriin. Samoin LOST voidaan osoittaa kaasukromatografisesti pintakerroksen uuttamisen jälkeen. Sitä paitsi tunnetaan värireak-tioita, jotka tapahtuvat vesiliuoksessa tai orgaanisessa liuoksessa. Nämä reaktiot suoritetaan koeputkessa.Bis. (2-chloroethyl) sulfide or imine is a fighting agent called LOST, the detection of which on the surface is usually performed with indicators soaked in paper or powder. Likewise, LOST can be detected by gas chromatography after surface layer extraction. In addition, color reactions that take place in aqueous or organic solution are known. These reactions are performed in a test tube.
DE-patenttijulkaisusta 29 47 459 tunnetaan menetelmä, jolla voidaan saostamalla in situ osoittaa tietty, kiinteä fosfori-happoesteriryhmän sisältävä taisteluaine. Tämä yhdiste osoittaa indolia lisättäessä kemiallista lumiresenssia, joka voidaan osoittaa ilman kosketusta optisen detektorin avulla. Taistelu-aine LOST:11a ei kuitenkaan tapahdu tällaista reaktiota.DE-A-29 47 459 discloses a method by which a specific solid containing a phosphoric acid ester group can be detected by in situ precipitation. This compound shows an induction of chemical luminescence upon addition of indole, which can be detected without contact by means of an optical detector. However, the combatant LOST does not undergo such a reaction.
Oheisen keksinnön tarkoituksena on kehittää yksinkertaisesti toteutettava osoitusmenetelmä taistelukaasu LOST:lie.The object of the present invention is to develop a simple implementation method for combat gas LOST.
Osoitusmenetelmä suoritetaan keksinnön mukaisesti siten, että kemiallisena reagenssia käytetään fluoresoivaa trifenyyli-metiiniväriainetta, nimittäin väriainetta "Neutral Rot", "Guinea Griin B", "Lissamine Grun B" tai "Brilliant Blau R", joka muodostaa bis-(2-kloorietyyli)-sulfidin tai bir-(2-kloorietyyli )-imiinin kanssa additiotuotteen, joka on fluoresoiva väriaine toisella spektrialueella.The detection method according to the invention is carried out using a fluorescent triphenylmethine dye, namely "Neutral Rot", "Guinea Green B", "Lissamine Grun B" or "Brilliant Blau R", which forms bis- (2-chloroethyl) - as the chemical reagent. with sulfide or bir- (2-chloroethyl) imine to an adduct which is a fluorescent dye in the second spectral range.
2 75056 Nämä väriaineet levitetään edullisesti osoitettavan taiste-luaineen pinnalle vesipitoisena orgaanisena liuoksena tai orgaanisena liuoksena. Väriaineen määrä liuoksessa on 0,001 - 0,5 paino-%:n välillä, edullisesti 0,01 - 0,1 paino-%.27,556 These dyes are preferably applied to the surface of the target warfare agent as an aqueous organic solution or as an organic solution. The amount of dye in the solution is between 0.001 and 0.5% by weight, preferably between 0.01 and 0.1% by weight.
Keksinnön mukaisesti voidaan käyttää kaikkia väriaineita, joilla on reaktiivinen keskus, johon LOST tarttuu nukleo-fiilisesti tai elektrofiilisesti ja hajottaa väriaineen tai johon se sitoutuu adsorptiivisesti rakennemuutoksen aikana tai johon se liittyy yhdisteen muodostamisen kautta. Tällöin väriaineen oma fluoresenssi muuttuu.According to the invention, all dyes can be used which have a reactive center to which LOST adheres nucleophilically or electrophilically and degrades the dye or to which it binds adsorptively during structural change or to which it is associated through compound formation. This changes the dye's own fluorescence.
Aktivoimisaallon pituuden tulee olla edullisesti 300 - 400 nm:n välillä. Emissioaallonpituus on edullisesti 380 - 500 nm. Väriaineen liuottimeksi ovat erityisen sopivia vesi/alkoholi-, vesi/asetoni- tai vesi/dimetyyliformamidiseokset tai myös vedetön alkoholi, asetoni tai heksaani. Erityisesti trifenyyli-metiini-väriaineet ovat sopivia kemiallisiksi reagensseiksi.The activation wavelength should preferably be between 300 and 400 nm. The emission wavelength is preferably 380 to 500 nm. Particularly suitable diluent solvents are water / alcohol, water / acetone or water / dimethylformamide mixtures or also anhydrous alcohol, acetone or hexane. In particular, triphenylmethine dyes are suitable as chemical reagents.
Keksinnössä käytettyjen väriaineiden pääkomponentit ovat: "Neutral Rot"The main components of the dyes used in the invention are: "Neutral Rot"
Chemical Abstracts-nimi: N8,N8,3-trimetyyli-2,8-fenatsiini-diami inimonohydrokloridi "Guinea Griin B"Chemical Abstracts Name: N8, N8,3-trimethyl-2,8-phenazine diamine human monohydrochloride "Guinea Griin B"
Chemical Abstracts-nimi: N-etyyli-N-[4-[[4-[etyyli!(3-sulfo-nyyli)metyylilamino]fenyyli]fenyylimetyyli]-2,5-sykloheksa-dien-l-yylideeni]-3-sulfo-bentseenimetaaniaminiumhydroksidi, sisäsuola, natriumsuola "Lissamine Griin B"Chemical Abstracts Name: N-Ethyl-N- [4 - [[4- [ethyl (3-sulfonyl) methylamino] phenyl] phenylmethyl] -2,5-cyclohexadien-1-ylidene] -3- sulfo-benzenemethanamine hydroxide, inner salt, sodium salt "Lissamine Griin B"
Chemical Abstracts-nimi: N-[4-[[4-(dimetyyliamino)fenyyli]-(2-hydroksi-3,6-disulfo-l-naftalenyyli)metyleeni]-2,5-syklo-Chemical Abstracts Name: N- [4 - [[4- (dimethylamino) phenyl] - (2-hydroxy-3,6-disulfo-1-naphthalenyl) methylene] -2,5-cyclo-
IIII
3 75056 heksadien-1-yylideeni]-N-metyyli-metaaniaminiumhydroksidi, sisäsuola, mononatriumsuola "Brilliant Blau R"3,75056 hexadien-1-ylidene] -N-methyl-methanaminium hydroxide, inner salt, monosodium salt "Brilliant Blau R"
Chemical Abstracts-nimi: N-[4-[[4-[(4-etoksifenyyli)amino]-fenyyli]-[4-[etyyli[(3-sulfofenyyli)metyyli]amino]fenyyli]-metyyleeni]-2,5-sykloheksadien-l-ylideeni]-N-etyyli-3-sulfo-bentseenimetaaniaminiumhydroksidi, sisäsuola, mononatriumsuola.Chemical Abstracts Name: N- [4 - [[4 - [(4-ethoxyphenyl) amino] phenyl] - [4- [ethyl [(3-sulfophenyl) methyl] amino] phenyl] methylene] -2.5 -cyclohexadien-1-ylidene] -N-ethyl-3-sulfo-benzenemethanamine hydroxide, inner salt, monosodium salt.
Seuraavat esimerkit selventävät keksintöä tarkemmin:The following examples further illustrate the invention:
Esimerkki 1Example 1
Neutral Rot liuotetaan 10“3 paino-%:ksi liuokseksi etanoliin. Kun lisätään 5 μΐ sulfidi-LOST-taisteluainetta, saadaan additiotuote, joka aktivoitaessa 330 nm:n aallonpituisella valolla osoittaa 392 nm:ssa fluoresenssia, jonka suhteellinen intensiteetti on 1500.Neutral Rot is dissolved in a 10-3% w / w solution in ethanol. Addition of 5 μΐ of sulfide-LOST fighter gives an adduct which, when activated with light at 330 nm, shows fluorescence at 392 nm with a relative intensity of 1500.
Esimerkki 2Example 2
Esimerkin 1 mukainen menetelmä toistetaan. Väriaineena käytetään kuitenkin tällä kertaa Guinea Griin B:ta. Additiotuote osoittaa aktivoitaessa 320 nm:n aallonpituisella valolla 340 nm:ssa fluoresenssia, jonka suhteellinen intensiteetti on 11700.The procedure of Example 1 is repeated. However, this time Guinea Green B is used as the dye. The adduct shows fluorescence with a relative intensity of 11700 when activated by 320 nm light at 340 nm.
Esimerkki 3Example 3
Lissamine Griin B liuotetaan 10~3 paino-%:ksi liuokseksi 70 % vesi - 30 % etanoli-liuokseen. Kun lisätään 5 μιη LOST taisteluainetta, saadaan additiotuote, joka aktivoitaessa 340 nm:n aallonpituisella valolla osoittaa 470 nm:ssa fluoresenssia, jonka suhteellinen intensiteetti on 810.Lissamine Grin B is dissolved in a 10 ~ 3% by weight solution in a 70% water-30% ethanol solution. When 5 μιη LOST is added, an adduct is obtained which, when activated by 340 nm light, shows fluorescence at 470 nm with a relative intensity of 810.
Esimerkki 4 75 0 5 6 4Example 4 75 0 5 6 4
Brilliant Blau R liuotetaan 2 x 10”2 paino-%L:ksi liuokseksi 70 % vesi - 30 % etanoli-liuokseen. Additiotuote osoittaa aktivoitaessa 370 nm:n aallonpituisella valolla 455 nm:ssa fluoresenssia, jonka suhteellinen intensiteetti on 28100.Brilliant Blau R is dissolved in a 2 x 10 ”2 wt% L solution in a 70% water to 30% ethanol solution. The adduct shows fluorescence with a relative intensity of 28100 when activated by light at 370 nm at 455 nm.
Claims (2)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3344700 | 1983-12-10 | ||
| DE19833344700 DE3344700A1 (en) | 1983-12-10 | 1983-12-10 | METHOD FOR DETECTING BIS- (2-CHLORETHYL) -SULFIDE OR BIS- (2-CHLORETHYL) -IMINE |
| EP8400383 | 1984-12-01 | ||
| PCT/EP1984/000383 WO1985002679A1 (en) | 1983-12-10 | 1984-12-01 | Process for determining the presence of bis-(2-chlorethyl-sulphide) or bis-(2-chlorethyl-imine) |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI852970A0 FI852970A0 (en) | 1985-08-01 |
| FI852970L FI852970L (en) | 1985-08-01 |
| FI75056B true FI75056B (en) | 1987-12-31 |
| FI75056C FI75056C (en) | 1988-04-11 |
Family
ID=6216585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI852970A FI75056C (en) | 1983-12-10 | 1985-08-01 | FOERFARANDE FOER BEVISNING AV BIS- (2-CHLORETYL) -SULF ELLER BIS- (2-CHLORETYL) -IMIN. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0164379B1 (en) |
| JP (1) | JPS61500687A (en) |
| AT (1) | ATE37607T1 (en) |
| CA (1) | CA1231634A (en) |
| DE (1) | DE3344700A1 (en) |
| FI (1) | FI75056C (en) |
| NO (1) | NO164383C (en) |
| WO (1) | WO1985002679A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3803142A1 (en) * | 1988-02-03 | 1989-08-17 | Battelle Institut E V | METHOD FOR DETECTING A COMBAT SUBSTANCE |
| DE3844796C2 (en) * | 1988-02-03 | 1993-01-21 | Battelle-Institut E.V., 6000 Frankfurt, De | Chemical warfare agent detection with fluorescent reagent |
| GB9419659D0 (en) * | 1994-09-28 | 1994-11-16 | Secr Defence | Detection of sulphur containing compounds |
| US5591400A (en) * | 1994-10-31 | 1997-01-07 | Minnesota Mining And Manufacturing Company | Method for producing an ionic sensor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE722291C (en) * | 1933-09-28 | 1942-07-07 | Deutsches Reich Vertreten Durc | Process for the detection of splashes of adhesive warfare agents on the ground or on objects |
| CH184663A (en) * | 1935-08-07 | 1936-06-15 | Heinrich Dr Draeger Otto | Method for the detection of dichlorodiethyl sulfide. |
| 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 |
| US4083692A (en) * | 1970-06-04 | 1978-04-11 | The United States Of America As Represented By The Secretary Of The Army | Detection and estimation of microquantities of alkylating agents |
| JPS5621320A (en) * | 1979-07-28 | 1981-02-27 | Fujitsu Ltd | Manufacture of semiconductor device |
| DE2947459C2 (en) * | 1979-11-24 | 1983-06-23 | Battelle-Institut E.V., 6000 Frankfurt | Device for in-situ detection of toxic substances suspected in floor coverings |
-
1983
- 1983-12-10 DE DE19833344700 patent/DE3344700A1/en active Granted
-
1984
- 1984-11-28 CA CA000468798A patent/CA1231634A/en not_active Expired
- 1984-12-01 EP EP85900095A patent/EP0164379B1/en not_active Expired
- 1984-12-01 AT AT85900095T patent/ATE37607T1/en not_active IP Right Cessation
- 1984-12-01 JP JP60500190A patent/JPS61500687A/en active Pending
- 1984-12-01 WO PCT/EP1984/000383 patent/WO1985002679A1/en active IP Right Grant
-
1985
- 1985-08-01 FI FI852970A patent/FI75056C/en not_active IP Right Cessation
- 1985-08-06 NO NO85853093A patent/NO164383C/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0164379A1 (en) | 1985-12-18 |
| NO164383B (en) | 1990-06-18 |
| CA1231634A (en) | 1988-01-19 |
| FI75056C (en) | 1988-04-11 |
| FI852970A0 (en) | 1985-08-01 |
| NO853093L (en) | 1985-08-06 |
| NO164383C (en) | 1990-09-26 |
| ATE37607T1 (en) | 1988-10-15 |
| FI852970L (en) | 1985-08-01 |
| EP0164379B1 (en) | 1988-09-28 |
| JPS61500687A (en) | 1986-04-10 |
| DE3344700A1 (en) | 1985-06-20 |
| DE3344700C2 (en) | 1990-06-21 |
| WO1985002679A1 (en) | 1985-06-20 |
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