US3630957A - Diagnostic agent - Google Patents

Diagnostic agent Download PDF

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Publication number
US3630957A
US3630957A US683129A US3630957DA US3630957A US 3630957 A US3630957 A US 3630957A US 683129 A US683129 A US 683129A US 3630957D A US3630957D A US 3630957DA US 3630957 A US3630957 A US 3630957A
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United States
Prior art keywords
film
diagnostic agent
water
polyvinyl
detection
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Expired - Lifetime
Application number
US683129A
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English (en)
Inventor
Hans-Georg Rey
Pieter Rieckmann
Hans Wielinger
Walter Rittersdorf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Diagnostics GmbH
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Boehringer Mannheim GmbH
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Classifications

    • 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
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • G01N33/521—Single-layer analytical elements
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING 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
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING 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
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING 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
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/54—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving glucose or galactose
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/805—Test papers
    • 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
    • Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
    • Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
    • Y10T436/143333—Saccharide [e.g., DNA, etc.]
    • Y10T436/144444—Glucose
    • 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
    • Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
    • Y10T436/145555—Hetero-N
    • Y10T436/146666—Bile pigment
    • 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
    • Y10T436/17—Nitrogen containing
    • Y10T436/171538—Urea or blood urea nitrogen
    • 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
    • Y10T436/17—Nitrogen containing
    • Y10T436/173076—Nitrite or nitrate

Definitions

  • the present invention relates to a new and improved diagnostic agent for use in the detection of chemical and biochemical components in biological fluids, and more particularly relates to test strips for use in the detection of chemical and biochemical components of biological fluids, a process of preparing such test strips and methods for using the same.
  • test papers with a semi-permeable film and/or membrane or to hydrophobe impregnated and dried papers.
  • these test papers can only be produced by multiple impregnations of filter papers which not only results in technical difliculties from the point of view of production, but also increases their cost considerably. Further, as with an increasing number of process steps, the possible number of production errors increases; either the reliability of the resultant test paper is reduced or additional intermediate controls are necessary, which are of course in and of themselves expensive.
  • a new and improved diagnostic agent i.e., test strip for use in detecting chemical and biochemical components present, for example, in biological fluids such as blood, urine, etc. and other fluids such as milk, etc.
  • a further object of the invention is to provide a new and improved diagnostic agent for use in detecting chemical and biochemical components present in biological fluids characterized by the extreme case with which they are produced and used, as well as by their reliability, i.e., accuracy and reproducibility of results.
  • Still another object of this invention is to provide a new and improved diagnostic agent for safely and reliably detecting single or multiple chemical and biochemical components in biological fluids.
  • diagnostic agents for the detection of biochemical and chemical components in biological fluids which are outstandingly useful and reliable and can be prepared in an economically feasible manner, are obtained by introducing the specific reagents and/or indicators necessary for a detection reaction into a solution or dispersion of the film-forming materials, i.e., the materials required for making the water-resistant films.
  • the film-forming mixture is applied either to a non-retaining substrate or to a substrate to which the film adheres firmly, and the coated or layered substrate is then dried.
  • the film can subsequently be removed, as for example by stripping, from the substrate, whereas in the second case, the substrate serves as a carrier for the film so that in this instance the film itself may be mechanically less stable and thinner.
  • the diagnostic agents according to the present invention for use in the detection of chemical or biochemical components in biological fluids comprises a waterresistant film in which the reagents for the detection reaction are substantially uniformly distributed, the film possibly being supported on a substrate.
  • film-forming agents there can be used those materials which are soluble in organic solvents or which can be dispersed in water, such as cellulose ethers, cellulose esters, cellulose acetate phthalate, polyvinyl esters, polyvinyl acetals, polyacrylic esters, polyacrylamide, polyamides and other film-forming, natural or synthetic polymers, as well as mixtures thereof.
  • cellulose ethers cellulose esters, cellulose acetate phthalate
  • polyvinyl esters polyvinyl acetals
  • polyacrylic esters polyacrylamide
  • polyamides polyamides and other film-forming, natural or synthetic polymers, as well as mixtures thereof.
  • Ethyl cellulose, acetyl cellulose, polyvinyl acetate, polyvinyl propionate, polyvinyl butyracetal and latex have proved to be especially useful.
  • synthetic resin foils As carriers or supports (substrates) for coating with the films, it is preferred to use synthetic resin foils but it is also possible to use, for example, glass, wood, paper, metal foils and other like materials.
  • the film-forming compositions can also contain any of the conventional fillers and adjuvants, such as for example chalk, titanium dioxide, silica gel, starch, talc, pearl white, metal soaps, cellulose powder and the like, as well as suitable thickening agents, emulsifiers, dispersion agents, plasticizers and the like. Pigments can also be included in the films and serve to render the same opaque.
  • the resultant films can be applied to a colored carrier material; in this manner, the reagent foils, in contradistinction to completely transparent foils, can be compared directly with color charts without porcelain tiles or the like being necessary.
  • composition of the reagents is, in principle, the same as in the case of the previously known diagnostic agents.
  • the presence of glucose can be detected with the use of a mixture of glucose oxidase, peroxidase, buffer and color-forming agent; for the detection of blood in urine, there can be used a mixture of peroxide and a color-forming agent and urobilinogen can be detected with p-dialkylamino-benzaldehyde and a strong acid.
  • test papers and indicator foils consist of the same material, namely, cellulose. Since the synthetic resin films according to the present invention can be made from the most varied materials, the most compatible and best suited material for each special purpose can be selected.
  • the materials used according to the present invention can be worked up much more easily with constant quality, are more homogeneous; and consequently are more dependable. Furthermore, We have found that not only the mechanical stability of the foils, but in addition the stability of the reagents is better than in the case of test papers. Even after the reaction has taken place with the body fluid being analyzed, the new test foils according to the present invention are considerably more stable than the previously used test papers so that the results obtained can, if desired, be evaluated at a later time or can even be checked after several days.
  • diagnostic agents according to the present invention for the detection of glucose in blood or urine can be enclosed with a patients examination report and can be filed away with the records relating to the findings in the patients file history.
  • the production of the new diagnostic agents according to the present invention takes place, in the simplest way, by the application of the film-forming solution or dispersion to a suitable substrate, followed by drying.
  • the film-forming solution or dispersion to a suitable substrate, followed by drying.
  • the resultant foil is cut at right angles to the direction of application, to thereby provide narrow strips suitable for simultaneously detecting a variety of components, i.e., there are obtained multi-test strips.
  • the synthetic resin films according to the present invention can be produced having any desired thickness and with any desired reagent concentration. Since the reagents also cannot be leached out or non-uniformly distributed by chromatographic effects, the fluid to be investigated can, if desired, be left to act upon the film for a comparatively long period of time, a stronger color reaction thereby being produced. Therefore, the new diagnostic agents according to the present invention can be used not only for the previously known test reactions but also for those which, because of the known disadvantages of test papers, have hitherto not been capable of being made up into the considerably simpler and easier used form of a test strip.
  • EXAMPLE 1 A reagent film for the detection of glucose in, for example, urine or whole blood, was prepared as follows: A mixture having the following composition was first prepared:
  • EXAMPLE 2 For the production of a reagent foil for use in the detection of glucose in, for example, urine or whole blood, there was first prepared a mixture having the following composition:
  • a 500a thick layer of the above mixture was applied onto a white polyvinyl chloride foil and the foil thereafter dried with warm air. There was obtained a water-insoluble film, the properties of which corresponded to those of the film described in Example 1.
  • a diagnostic agent for use in the detection of blood in urine was prepared as follows: A mixture having the following composition was prepared:
  • the above mixture was applied onto a polyvinyl chloride foil so as to provide a 500; thick layer and the thusly treated foil is then dried with warm air. There was obtained a water-insoluble film which, upon being immersed into blood-containing urine, provided a more or less strong color, corresponding to the concentration of blood in the urine specimen.
  • the mixture was then applied to a polyvinyl chloride foil so as to produce a 300,11. thick layer and the layered foil was then dried with warm air. There was obtained a water-insoluble film which, on being moistened with urobilinogen-containing urine, evidenced a more or less dark red color, depending upon the urobilinogen con centration.
  • EXAMPLE 6 For the production of a regagent film for use in the detection of glucose in, for example, urine or whole blood, there was first prepared a mixture having the following composition:
  • the mixture was then applied to a white polyvinyl chloride foil so as to provide a 300 thick layer of the mixture, and the thusly layered foil dried with warm air. There was obtained a water-insoluble film which on reaction with glucose, for example, in blood in a concentration within the range of 50-250 mg. percent evidenced a strong color.
  • EXAMPLE 7 90 g. of an aqueous dispersion of polyvinyl propionate (Propiofan), 1.3 g. of the sodium salt of a polymannuronic acid (Algipon), 70 ml. of a 0.5 M citrate or phosphate buffer having a pH value of 5.5, 2 g. of organic sodium sulfonate (Texapon P), 320 mg. glucose oxidase, 300 mg. peroxidase and 300 mg. 1-methoxy-4-hydroxynaphthalene in 20 ml. methanol were stirred together to form a homogeneous mixture. This mixture was then applied onto a foil to provide a layer thereof having a thickness of 300 2 and the layered foil dried.
  • Algipon polymannuronic acid
  • Texapon P organic sodium sulfonate
  • Propiofan, Algipon, and Texapon P are trademarks of BASF, Henkel and Dehydag respectively.
  • EXAMPLE 8 g. of polyvinyl propionate dispersion (Propiofan), 35 g. of a 1.85% solution of polymannuronic acid (Algipon) in 0.5 M phosphate buffer having a pH value of 5.5, 1 g. of organic sodium sulfonate (Texapon), 0.075 g. peroxidase, 0.15 g. glucose oxidase, 0.045 g. 3-amino-9-ethyl-carbazole and 0.25 g. o-tolidine dissolved in 6 ml. methanol, were stirred to form a homogeneous slurry. 0.50 ml.
  • a diagnostic agent for use in the detection of chemical and bio-chemical components in biological fluids comprising a homogeneous water-resistant film formed from a mixture of an aqueous dispersion of a natural or synthetic organic polymer and a color forming reagent capable of producing color in response to the presence of a chemical or bio-chemical component in a biological fluid, in which said color forming reagent is uniformly dispersed throughout the film.
  • a diagnostic agent according to claim 1 including a carrier support for said film.
  • a diagnostic agent according to claim 2 wherein said film is firmly attached to said carrier support to form an integral structure therewith.
  • a diagnostic agent according to claim 2 wherein said carrier support is a member selected from the group consisting of glass, paper, asbestos, wood, metal and synthetic resins inert to the biological fluid.
  • a diagnostic agent according to claim 1 wherein said water-resistant film is prepared on a basis of at least one polymer selected from the group consisting of polyvinyl esters, polyvinyl acetals, polyacrylic esters, polyacrylamides and polyamides.
  • a diagnostic agent according to claim 1 wherein said water-resistant film is prepared on a basis of at least one member selected from the group consisting of cellulose ethers and cellulose esters.
  • a diagnostic agent according to claim 6 wherein the said member is polyvinyl acetate, polyvinyl propionate or polyvinyl butyracetal.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises Polyvinyl propionate dispersion100.00 g. o-Vanillin-(vanilloyl)-hydrazone2.50 g. Glucose oxidase0.06 g.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises Ethyl cellulose-35.00 g. o-Vanillin-(vanilloyl) -hydrazone1.7 g. Glucose oxidase0.04 g.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises o-Tolidine-0.25 g.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises p-Dimethylamino-benzaldehyde-l .0 g. Orthophosphoric acid )20.0 g. Polyvinyl acetal20.0 g.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises a-Naphthylamine1.0 g. Sulfanilamide-2.5 g. Trichloroacetic acid3.0 g. Polyvinyl butyracetal20.0 g. Methanol-100.0 ml.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises Polyvinyl propionate dispersion45 .0 g. Phosphate buffer 0.4 M (pH 5.5)45.0 ml. Sodium alginate0.5 g.
  • said water-resistant film comprises g. of an aqueous dispersion of polyvinyl propionate, 1.3 g. of the sodium salt of a polymannuronic acid, 70 ml. of a 0.5 M citrate or phosphate buffer having a pH value of 5.5, 2 g. of organic sodium sulfonate, 320 mg. glucose oxidase, 300 mg. peroxidase and 300 mg. 1-methoxy-4-hydroxy-naphthalene in 20 ml. methanol, in dried form.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises 45 g. of a polyvinyl propionate dispersion, 35 g. of a 1.85% solution of polymannuronic acid in 0.5 M phosphate buffer having a pH value of 5.5, 1 g. of organic sodium sulfonate, 0.075 g. peroxidase, 0.15 g. glucose oxidase, 0.045 g. 3-amino-9- ethyl-carbazole and 0.25 g. o-tolidine dissolved in 6 ml. methanol, in dried form.
  • a diagnostic agent according to claim 1 wherein said water-resistant film comprises Polyisobutylene dispersion 22.50 Sodium alginate solution (1.85%) in 0.15 M
  • Method of detecting a chemical or biochemical component in a biological fluid which comprises contacting a diagnostic agent according to claim 1 with said fluid and comparing the color of said diagnostic agent with a standard.
  • a diagnostic agent for use in the detection of chemical and bio-chemical components in biological fluids comprising a homogeneous water-resistant film formed from a mixture of an aqueous dispersion of a natural or synthetic organic polymer selected from the group consistiing of cellulose ethers, cellulose esters cellulose acetate phthalate, polyvinyl esters, polyvinyl acetals, polyacrylic esters, polyacrylamide and polyamides, and a color forming reagent capable of producing color in response to the presence of a chemical or bio-chemical component in a biological fluid, in which the color forming reagent is uniformly dispersed throughout the film.
  • a natural or synthetic organic polymer selected from the group consistiing of cellulose ethers, cellulose esters cellulose acetate phthalate, polyvinyl esters, polyvinyl acetals, polyacrylic esters, polyacrylamide and polyamides, and a color forming reagent capable of producing color in response to the presence of a chemical or bio

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • General Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Food Science & Technology (AREA)
  • Cell Biology (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Sampling And Sample Adjustment (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
US683129A 1966-11-22 1967-11-15 Diagnostic agent Expired - Lifetime US3630957A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0089944 1966-11-22

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US683129A Expired - Lifetime US3630957A (en) 1966-11-22 1967-11-15 Diagnostic agent

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US (1) US3630957A (enExample)
JP (1) JPS4933800B1 (enExample)
AT (1) AT282832B (enExample)
BR (1) BR6794865D0 (enExample)
CH (1) CH480634A (enExample)
CY (1) CY789A (enExample)
DE (1) DE1598153C3 (enExample)
FI (1) FI48306C (enExample)
GB (1) GB1159627A (enExample)
GR (1) GR38283B (enExample)
NL (1) NL145048B (enExample)
SE (1) SE413439B (enExample)

Cited By (90)

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US4303753A (en) * 1980-03-20 1981-12-01 Miles Laboratories, Inc. Method and device for the semiquantitative determination of glucose in aqueous fluids
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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
US4966855A (en) * 1984-07-07 1990-10-30 Boehringer Mannheim Gmbh New redox indicators
US4994238A (en) * 1988-06-09 1991-02-19 Daffern George M Constant volume chemical analysis test device
US5055195A (en) * 1983-07-02 1991-10-08 Boehringer Mannheim Gmbh Erythrocyte-retention substrates
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
US5106581A (en) * 1991-05-30 1992-04-21 Industrial Test Systems, Inc. Test device for detection of molybdate, vanadate and ferric ions
US5106757A (en) * 1989-02-25 1992-04-21 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Process for the visualization of substance stains on layer chromatograms
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FI48306C (fi) 1974-08-12
CH480634A (de) 1969-10-31
DE1598153C3 (de) 1973-11-22
GB1159627A (en) 1969-07-30
DE1598153B2 (de) 1973-05-03
GR38283B (el) 1969-10-17
SE413439B (sv) 1980-05-27
NL145048B (nl) 1975-02-17
NL6715828A (enExample) 1968-05-24
AT282832B (de) 1970-07-10
FI48306B (enExample) 1974-04-30
CY789A (en) 1976-06-01
BR6794865D0 (pt) 1973-03-20
JPS4933800B1 (enExample) 1974-09-10
DE1598153A1 (de) 1970-04-23

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