US3853471A - Diagnostic composition for the detection of peroxidatively active substances in body fluids - Google Patents

Diagnostic composition for the detection of peroxidatively active substances in body fluids Download PDF

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Publication number
US3853471A
US3853471A US00376249A US37624973A US3853471A US 3853471 A US3853471 A US 3853471A US 00376249 A US00376249 A US 00376249A US 37624973 A US37624973 A US 37624973A US 3853471 A US3853471 A US 3853471A
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Prior art keywords
test strip
formula
acid amide
test
dimethylamino
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Expired - Lifetime
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US00376249A
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W Rittersdorf
H Rey
P Rieckmann
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Roche Diagnostics GmbH
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Boehringer Mannheim GmbH
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C12Q1/28Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S436/00Chemistry: analytical and immunological testing
    • Y10S436/904Oxidation - reduction indicators

Definitions

  • ABSTRACT Test strips are provided for detecting even small amounts of blood or other peroxidatively active substances in body fluids; the strips comprising a carrier containing a hydroperoxide, at least one chromogen and, as a stabilizer, at least one phosphoric or phosphonic acid amide of the formula wherein R is a dimethylamino, alkoxy, aryloxy, alkyl, aryl or N-morpholine radical; and R and R which may be the same or different, are
  • hemorrhages in the stomach, intestines and urinary tract.
  • Such hemorrhages are caused, for example, by tumors, ulcers or inflammations of the organs in question.
  • free hemoglobin can also occur in the urine and plasma due to the influence of certain hemolytic toxins.
  • Blood and hemoglobin are peroxidate-active, i.e., they liberate oxygen from hydroperoxides and transfer it to certain acceptors. Other peroxidate-active substances also occur in leukocytes and bacteria. The detection of these substances is important for the diagnosis of diseases and infections of the kidneys and urinary tract.
  • Myoglobin which is also peroxidateactive, is found, for example, in the urine after a cardiac infarct. Blood occurs especially frequently in the urine when calculi are present in the bladder or kidneys.
  • the peroxidate-activity is especially suitable for a sensitive detection of all of these substances.
  • the oxygen liberated from a hydroperoxide can be transferred to a chromogen which is oxidized to a colored material and thus indicates the presence of the peroxidateactive substance.
  • This reaction has already been used for quite a long time in medicinal and forensic analysis, especially for the detection of blood. It is usually carried out in test tubes or by spot tests, hydrogen peroxide usually being used as the hydroperoxide (oxidation agent).
  • chromogen there is preferably used benzidine, o-tolidine or leuco malachite green.
  • tests of this type have also been developed in various ways for the detection of blood in body fluids.
  • Rapid tests are usually absorbent carriers, preferably papers, which have been impregnated with all of the reagents necessary for the detection reaction and, after simply dipping into the body fluid to be tested, show a color reaction.
  • Test papers of this type are described, for example, in U.S. Pat. Nos. 3,012,976 and 3,092,464.
  • organic hydroperoxides for example cumol hydroperoxide or p-menthane hydroperoxide.
  • the invention comprises test strips having hydroperoxides applied thereto together with at least one phosphoric or phosphonic acid amide of the general formula wherein R, is a dimethylamino, alkoxy, aryloxy, alkyl, aryl or N-morpholine radical and R and R which may be the same or different, are dimethylamino or N- morpholine radicals.
  • the alkoxy or alkyl radicals R preferably contain up to 10 carbon atoms.
  • the aryl or aryloxy radicals can be, for example, phenyl or naphthyl radicals which are optionally substituted by halogen atoms or lower alkyl or alkoxy radicals.
  • test papers according to the present invention can be produced by dissolving a hydroperoxide in a solvent, preferably in a water-alcohol mixture, together with an-amide of general formula (I) and optionally together with a buffer and a wetting agent and impregnating filter paper with this solution followed by drying.
  • a solvent preferably in a water-alcohol mixture
  • an-amide of general formula (I) optionally together with a buffer and a wetting agent
  • filter paper can be continuously impregnated and dried without difficulty.
  • the present invention provides a test strip for the detection of peroxidate-active substances in body fluids, comprising a carrier containing a hydroperoxide, at least one chromogen and a compound of general formula (I), as stabilizer.
  • test strips according to the present invention are most surprising since substances, the action of which, as stabilizers for hydrogen peroxide, is known, for example, urea, mannitol, acetanilide and the like, here show no stabilizing action whatsoever.
  • the compounds of general formula (I) are preferably used in a ratio of at least one mole per mole hydroperoxide group, a two to fourfold excess having proved to be especially useful.
  • hydroperoxides there can be used the common representatives when they are not too volatile, for example, tert.-butyl hydroperoxide.
  • the solid compounds 2,5-dimethylhexane-2,S-dihydroperoxide, tetraline hydroperoxide and diisopropyl-benzene dihydroperoxide have proved to be especially useful but liquid compounds, such as diisopropyl-benzene-hydroperoxide, cumol hydroperoxide, p-menthane hydroperoxide and pinane hydroperoxide can also be used.
  • the hydroperoxides can be used in amounts of 0.5- g., preferably of l-3 g., per 100 ml. of impregnation solution
  • Further components of the test papers according to the present invention include chromogens, buffers, wetting agents, thickening agents and possibly activators.
  • chromogens there can be used all those which can easily be oxidized to give deep-colored compounds. These include, in particular, benzidine and its homologues, especially o-tolidine. Furthermore, the heterocyclic azines according to German Pat. No. l,648,840 have also proved to be useful.
  • the chromogens can be used in amounts of from 0.05-5 g., preferably of 0.2-1 .0 g., per 100 ml. impregnation solution.
  • buffers there can be used, for example, citrate, phosphate, phthalate or succinate buffers, the pH value and capacity thereof being selected in such a manner that, after dipping the test strip into the body fluid, there is obtained a pH value of 4-7 and preferably of 5-6.
  • a complex former for example sodium metaphosphate or ethylene-diamine tetraacetic acid, falsely positive reaction which can be caused by traces of metals thereby being avoided.
  • test papers can tend to bleed due to the relatively large amounts of water-soluble substances present therein, it can be desirable to add to the formulation thickening agents, for example methyl cellulose and especially of gelatine, in amounts of about 0.5-5 g. per 100 ml.
  • thickening agents for example methyl cellulose and especially of gelatine
  • activators can also be added. These include, for example, quinoline and derivatives thereof according to German Pat. No. 1,242,905.
  • wetting agents there are preferably used longchain organic sulfates or sulfonates, for example sodium dodecylbenzene sulfonate, dioctyl sodium sulfosuccinate or sodium lauryl sulfate, which, as is known, stabilize radical cations, such as oxidized o-tolidine.
  • longchain organic sulfates or sulfonates for example sodium dodecylbenzene sulfonate, dioctyl sodium sulfosuccinate or sodium lauryl sulfate, which, as is known, stabilize radical cations, such as oxidized o-tolidine.
  • absorbent carriers for example filter paper, cellulose or synthetic fiber fleeces, which are impregnated with solutions of the reagents in readily volatile solvents.
  • the impregnation is preferably carried out in two steps. First, impregnation is carried out with a solution which contains an amide of general formula (I), as well as a hydroperoxide, a wetting agent, a buffer and possibly a thickening agent. Thereafter, impregnation is carried out with a solution of the indicator and possibly of the activator..When using hydrophobic monohydroperoxides, it is advisable to apply the buffer and the hydroperoxide to the carrier in separate impregnation steps.
  • reagents for the production of water-stable films, all the reagents, together with a stabilizer of general formula (I), are introduced into a solution or dispersion of a filmforming substance, for example, a polyvinyl ester or polyamide and mixed homogeneously. The mixture is then applied in a thin layer to a substrate, for example a synthetic resin carrier, and dried.
  • a filmforming substance for example, a polyvinyl ester or polyamide
  • test strips according to the present invention are, after drying, cut up into strips and preferably sealed between a synthetic resin film and a fine-mesh material in the manner described in German Pat. No. 2,1 18,455.
  • dioctyl sodium sulphosuccinate 200 g. ethylenediaminc-tetraacetic acid, l0 g. disodium salt 2,5-dimethyl-hexane-2,5dihydro- 160 g. peroxide phosphoric acid trimorpholide 1270 g. citrate buffer (1.2 molar, pH 5.25) 3.5 liters ethanol 3.0 liters distilled water ad 10.0 liters
  • the solution is placed into a trough which is provided with deflection rollers. Thereafter, a filter paper strip is drawn continuously at a speed of about 2 meters/minute through the solution and dried in a drying canal with a length of 15 meters in a current of air with a temperature of 40C.
  • the paper pre-treated in this manner is further impregnated in the same manner with a 0.3% solution of o-tolidine in toluene which contains 0.2% quinine as activator.
  • test papers which, instead of phosphoric acid trimorpholide, contain equimolar amounts of the following amides: phosphoric acid dimethylamide dimorpholide, phosphoric acid ethyl ester dimorpholide and ethane phosphonic acid dimorpholide.
  • test papers thus obtained were characterized by an outstanding stability and do not become discolored.
  • test papers which, instead of benzene phosphonic acid dimorpholide, contain equimolar amounts of the following amides: benzene phosphonic acid bis-(dimethylamide) or phosphoric acid phenyl ester dimorpholide.
  • Test strip for the detection of peroxidatively active substances in body fluids, comprising a carrier containing a hydroperoxide, at least one chromogen and, as a stabilizer, at least one phosphoric or phosphonic acid amide of the formula wherein I R, is dimethylamino, alkoxy, aryloxy, alkyl, aryl or N-morpholino and contains not more than carbon atoms; R and R are individually selected from dimethylamino and N-morpholino. 2. Test strip as claimed in claim 1, wherein R, in the formula is dimethylamino.
  • Test strip as claimed in claim 1 wherein the carrier is a water-stable film containing the reagents.
  • Test strip as claimed in claim 1 wherein there is at least one mole of said acid amide per mole of hydroperoxide.
  • Test strip as claimed in claim 1 also containing at least one of a complex former, a thickening agent, an activator and a wetting agent.
  • Method of detecting a peroxidatively active substance in a body fluid comprises contacting a test sample with a test strip as claimed in claim 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Analytical Chemistry (AREA)
  • Biotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
US00376249A 1972-07-18 1973-07-03 Diagnostic composition for the detection of peroxidatively active substances in body fluids Expired - Lifetime US3853471A (en)

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Application Number Priority Date Filing Date Title
DE2235127A DE2235127C2 (de) 1972-07-18 1972-07-18 Diagnostisches Mittel zum Nachweis von Blut und anderen peroxidatisch wirksamen Substanzen in Körperflüssigkeiten

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JP (1) JPS583679B2 (en:Method)
DE (1) DE2235127C2 (en:Method)
FR (1) FR2198644A5 (en:Method)
GB (1) GB1390899A (en:Method)

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917452A (en) * 1973-12-20 1975-11-04 Boehringer Mannheim Gmbh Diagnostic agent for the detection of peroxidatively active substances
DE2460903A1 (de) 1974-12-21 1976-06-24 Boehringer Mannheim Gmbh Verwendung von 3,3',5,5'-tetraalkylbenzidinen als oxidationsindikatoren in schnelltesten
US3966414A (en) * 1974-01-16 1976-06-29 Bio-Medical Sciences, Inc. Time temperature indicators
US4063894A (en) * 1975-11-21 1977-12-20 Shionogi & Co., Ltd. Test strip for the detection of occult blood in excreta
US4071317A (en) * 1977-03-14 1978-01-31 Miles Laboratories, Inc. Test composition and device for determining peroxidatively active substances and process for preparing same
US4071321A (en) * 1977-03-14 1978-01-31 Miles Laboratories, Inc. Test composition and device for determining peroxidatively active substances
US4071318A (en) * 1977-03-14 1978-01-31 Miles Laboratories, Inc. Test composition and device for determining peroxidatively active substances
DE2803955A1 (de) * 1977-03-14 1978-09-21 Miles Lab Pruefmittel und verfahren zur bestimmung peroxidativ wirksamer substanzen
US4161507A (en) * 1977-06-23 1979-07-17 Behringwerke Aktiengesellschaft Stabilized diagnostic test strip for the detection of urobilinogen
US4175923A (en) * 1978-06-26 1979-11-27 Friend William G Method and apparatus for occult blood testing in the home
EP0029917A1 (en) * 1979-11-13 1981-06-10 Miles Laboratories, Inc. Indicator composition and test device containing amine oxide
US4329317A (en) * 1981-01-29 1982-05-11 Smithkline Instruments, Inc. Method of stabilizing a specimen slide for occult blood testing
US4372746A (en) * 1980-07-04 1983-02-08 Behringwerke Aktiengesellschaft Agent for detecting peroxidatively active substances and the use of a polyvinylmethylacylamide in such an agent
US4382064A (en) * 1981-01-29 1983-05-03 Smithkline Instruments, Inc. Specimen slide for occult blood testing
EP0130520A1 (en) * 1983-06-29 1985-01-09 Miles Laboratories, Inc. Stabilized test composition, device and method for the determination of peroxidatively active substances
WO1985002018A1 (en) * 1983-11-04 1985-05-09 Immuno Concepts, Inc. Stabilization of indicators for detecting enzyme activity
DE2462952C2 (en:Method) * 1974-12-21 1987-10-01 Boehringer Mannheim Gmbh, 6800 Mannheim, De
US4755472A (en) * 1986-01-16 1988-07-05 Miles Inc. Stable composition for the determination of peroxidatively active substances
US4956300A (en) * 1982-01-05 1990-09-11 Helena Laboratories Corporation Aid for determining the presence of occult blood, method of making the aid, and method of using the aid
US5081040A (en) * 1987-06-29 1992-01-14 Helena Laboratories Corporation Composition and kit for testing for occult blood in human and animal excretions, fluids, or tissue matrixes
US5089420A (en) * 1990-01-30 1992-02-18 Miles Inc. Composition, device and method of assaying for a peroxidatively active substance utilizing amine borate compounds
US5196167A (en) * 1989-04-04 1993-03-23 Helena Laboratories Corporation Fecal occult blood test product with positive and negative controls
US5217874A (en) * 1989-04-04 1993-06-08 Helena Laboratories Corporation Fecal occult blood test product with positive and negative controls
US5273888A (en) * 1984-01-16 1993-12-28 Helena Laboratories Corporation Chemical test kit and method for determining the presence of blood in a specimen and for verifying the effectiveness of the chemicals
US5369013A (en) * 1987-06-22 1994-11-29 Yissum Research Development Company Of The Hebrew University Of Jerusalem Method, reagent mixture and kit for determining the presence of bacterial or somatic cells in urine
EP0697481A2 (en) 1994-07-23 1996-02-21 Ciba-Geigy Ag Aqueous textile treatment compositions containing an ultra-violet absorbing agent
US5702913A (en) * 1983-12-21 1997-12-30 Helena Laboratories Corporation Chromgen-reagent test system
US5827677A (en) * 1996-02-01 1998-10-27 Universal Lavel Method and device for specifically detecting myoglobin using a non-discriminating peroxidase sensitive assay
WO1999004755A1 (en) * 1997-07-23 1999-02-04 Lemmerman, Pranee Tongue wash
US20060131241A1 (en) * 2002-08-30 2006-06-22 Johnsondiversey, Inc. Phosphonamide and phosphonamide blend compositions and method to treat water
US7846383B2 (en) 2006-12-15 2010-12-07 Kimberly-Clark Worldwide, Inc. Lateral flow assay device and absorbent article containing same
US8012761B2 (en) 2006-12-14 2011-09-06 Kimberly-Clark Worldwide, Inc. Detection of formaldehyde in urine samples

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2436598C2 (de) * 1974-07-30 1983-04-07 Boehringer Mannheim Gmbh, 6800 Mannheim Stabiler Teststreifen zum Nachweis von Inhaltsstoffen in Flüssigkeiten
CS175782B1 (en:Method) * 1974-10-16 1977-05-31
CS176664B1 (en:Method) * 1975-02-14 1977-06-30
JPS6139779A (ja) * 1984-07-31 1986-02-25 Sony Corp 同期信号発生装置
JPS61290872A (ja) * 1985-06-19 1986-12-20 Canon Inc 映像信号再生装置
JPS6271975U (en:Method) * 1985-10-23 1987-05-08
US5318894A (en) * 1990-01-30 1994-06-07 Miles Inc. Composition, device and method of assaying for peroxidatively active substances

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3252762A (en) * 1961-05-04 1966-05-24 Miles Lab Stabilized occult blood diagnostic
US3290117A (en) * 1963-06-24 1966-12-06 Miles Lab Occult blood diagnostic composition with color enhancing agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3252762A (en) * 1961-05-04 1966-05-24 Miles Lab Stabilized occult blood diagnostic
US3290117A (en) * 1963-06-24 1966-12-06 Miles Lab Occult blood diagnostic composition with color enhancing agent

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917452A (en) * 1973-12-20 1975-11-04 Boehringer Mannheim Gmbh Diagnostic agent for the detection of peroxidatively active substances
US3966414A (en) * 1974-01-16 1976-06-29 Bio-Medical Sciences, Inc. Time temperature indicators
DE2460903A1 (de) 1974-12-21 1976-06-24 Boehringer Mannheim Gmbh Verwendung von 3,3',5,5'-tetraalkylbenzidinen als oxidationsindikatoren in schnelltesten
DE2462952C2 (en:Method) * 1974-12-21 1987-10-01 Boehringer Mannheim Gmbh, 6800 Mannheim, De
US4063894A (en) * 1975-11-21 1977-12-20 Shionogi & Co., Ltd. Test strip for the detection of occult blood in excreta
US4071317A (en) * 1977-03-14 1978-01-31 Miles Laboratories, Inc. Test composition and device for determining peroxidatively active substances and process for preparing same
US4071321A (en) * 1977-03-14 1978-01-31 Miles Laboratories, Inc. Test composition and device for determining peroxidatively active substances
US4071318A (en) * 1977-03-14 1978-01-31 Miles Laboratories, Inc. Test composition and device for determining peroxidatively active substances
DE2803955A1 (de) * 1977-03-14 1978-09-21 Miles Lab Pruefmittel und verfahren zur bestimmung peroxidativ wirksamer substanzen
US4161507A (en) * 1977-06-23 1979-07-17 Behringwerke Aktiengesellschaft Stabilized diagnostic test strip for the detection of urobilinogen
US4175923A (en) * 1978-06-26 1979-11-27 Friend William G Method and apparatus for occult blood testing in the home
EP0029917A1 (en) * 1979-11-13 1981-06-10 Miles Laboratories, Inc. Indicator composition and test device containing amine oxide
US4372746A (en) * 1980-07-04 1983-02-08 Behringwerke Aktiengesellschaft Agent for detecting peroxidatively active substances and the use of a polyvinylmethylacylamide in such an agent
US4329317A (en) * 1981-01-29 1982-05-11 Smithkline Instruments, Inc. Method of stabilizing a specimen slide for occult blood testing
US4382064A (en) * 1981-01-29 1983-05-03 Smithkline Instruments, Inc. Specimen slide for occult blood testing
US4956300A (en) * 1982-01-05 1990-09-11 Helena Laboratories Corporation Aid for determining the presence of occult blood, method of making the aid, and method of using the aid
EP0130520A1 (en) * 1983-06-29 1985-01-09 Miles Laboratories, Inc. Stabilized test composition, device and method for the determination of peroxidatively active substances
US4615972A (en) * 1983-11-04 1986-10-07 Immuno Concepts, Inc. Stabilization of indicators for detecting enzyme activity
WO1985002018A1 (en) * 1983-11-04 1985-05-09 Immuno Concepts, Inc. Stabilization of indicators for detecting enzyme activity
AU570522B2 (en) * 1983-11-04 1988-03-17 Immuno Concepts Inc. Stabilization of indicators for detecting enzyme activity
US5702913A (en) * 1983-12-21 1997-12-30 Helena Laboratories Corporation Chromgen-reagent test system
US5273888A (en) * 1984-01-16 1993-12-28 Helena Laboratories Corporation Chemical test kit and method for determining the presence of blood in a specimen and for verifying the effectiveness of the chemicals
US4755472A (en) * 1986-01-16 1988-07-05 Miles Inc. Stable composition for the determination of peroxidatively active substances
US5369013A (en) * 1987-06-22 1994-11-29 Yissum Research Development Company Of The Hebrew University Of Jerusalem Method, reagent mixture and kit for determining the presence of bacterial or somatic cells in urine
US5081040A (en) * 1987-06-29 1992-01-14 Helena Laboratories Corporation Composition and kit for testing for occult blood in human and animal excretions, fluids, or tissue matrixes
US5196167A (en) * 1989-04-04 1993-03-23 Helena Laboratories Corporation Fecal occult blood test product with positive and negative controls
US5217874A (en) * 1989-04-04 1993-06-08 Helena Laboratories Corporation Fecal occult blood test product with positive and negative controls
US5089420A (en) * 1990-01-30 1992-02-18 Miles Inc. Composition, device and method of assaying for a peroxidatively active substance utilizing amine borate compounds
EP0697481A2 (en) 1994-07-23 1996-02-21 Ciba-Geigy Ag Aqueous textile treatment compositions containing an ultra-violet absorbing agent
US5827677A (en) * 1996-02-01 1998-10-27 Universal Lavel Method and device for specifically detecting myoglobin using a non-discriminating peroxidase sensitive assay
WO1999004755A1 (en) * 1997-07-23 1999-02-04 Lemmerman, Pranee Tongue wash
US20060131241A1 (en) * 2002-08-30 2006-06-22 Johnsondiversey, Inc. Phosphonamide and phosphonamide blend compositions and method to treat water
US7077976B2 (en) * 2002-08-30 2006-07-18 Johnsondiversey, Inc. Phosphonamide and phosphonamide blend compositions to treat water
US8012761B2 (en) 2006-12-14 2011-09-06 Kimberly-Clark Worldwide, Inc. Detection of formaldehyde in urine samples
US7846383B2 (en) 2006-12-15 2010-12-07 Kimberly-Clark Worldwide, Inc. Lateral flow assay device and absorbent article containing same

Also Published As

Publication number Publication date
GB1390899A (en) 1975-04-16
FR2198644A5 (en:Method) 1974-03-29
DE2235127C2 (de) 1974-08-08
JPS583679B2 (ja) 1983-01-22
DE2235127A1 (en:Method) 1974-01-10
DE2235127B1 (de) 1974-01-10
JPS4954093A (en:Method) 1974-05-25

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