US3853466A - Diagnostic composition for the detection of urobilinogens - Google Patents

Diagnostic composition for the detection of urobilinogens Download PDF

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Publication number
US3853466A
US3853466A US00262923A US26292372A US3853466A US 3853466 A US3853466 A US 3853466A US 00262923 A US00262923 A US 00262923A US 26292372 A US26292372 A US 26292372A US 3853466 A US3853466 A US 3853466A
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US
United States
Prior art keywords
diagnostic agent
diazonium
acid
urobilinogen
benzene
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Expired - Lifetime
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US00262923A
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English (en)
Inventor
W Rittersdorf
P Rieckmann
D Berger
H Rey
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Roche Diagnostics GmbH
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Boehringer Mannheim GmbH
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    • 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
    • G01N33/72—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood pigments, e.g. haemoglobin, bilirubin or other porphyrins; involving occult blood
    • 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
    • Y10S436/00—Chemistry: analytical and immunological testing
    • Y10S436/903—Diazo reactions
    • 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

Definitions

  • ABSTRACT Diagnostic agent for the detection of urobilinogens, optionally in the presence of bilirubin, in body fluids which agent comprises at least one stable benzene diazonium salt wherein the phenyl radical may be polysubstituted and contains in the Q; or p-position at least one polyatomic electron donor group with at least one mesomeric electron pair, the sum of the Hammett sigma values for all the substituents not exceeding the value of +0.4.
  • the present invention provides a diagnostic agent for the detection of urobilinogen in body fluids which comprises a solid or liquid acid and at least one stable, optionally polysubstituted benzene diazonium salt, the phenyl radical of which contains in the 0 or pposition at least one polyatomic electron donor group with at least one mesomeric electron pair; especially when the sum of the Hammett sigma values of all substituents does not exceed the value of +0.4.
  • Electron donor groups are, according to the present invention, groups which contain oxygen, sulfur or nitrogen connected directly to the phenyl radical.
  • Oxygen-containing groups include; for example, hydroxyl, alkoxy, aralkoxy and aryloxy radicals.
  • sulfurcontaining groups there can only be considered alkylthio and arylthio radicals, because free mercapto groups cannot, as a rule, be used due to their sensitivity to oxidation.
  • nitrogen-containing groups there may be mentioned, for example, acylamino (i.e.
  • alkanoylamino arylamino and aryl-alkylamino radicals
  • unsubstituted amino groups and alkylamino groups are, because of their basicity under the conditions of the reaction, usually protonized and then no longer possess a mesomeric electron pair.
  • the electron donor groups will not contain more than 18, preferably eight, carbon atoms.
  • benzene-diazonium salts of the general formula:
  • R and R which may be the same or different are polyatomic electron donor groups containing at least one mesomeric electron pair, whereby one of the symbols R and R can also be a hydrogen or halogen'atom or a lower alkyl radical (of, e.g., up to 10 carbon atoms), and the symbols R and R which may be the same or different, are hydrogen atoms or groups which do not sterically hinder the diazo coupling with urobilinogen, the sum of the Hammett sigma values of all the substituents R R R and R not exceeding +0.4.
  • R is a hydroxyl group or a lower alkylthio or lower alkoxy radical and R is a hydroxyl group or an alkoxy, phenoxy, aralkoxy, alkylthio, phenylthio, phenylalkylamino or optionally substituted phenylamino or acylamino radical, whereby one of the symbols R and R can also be a hydrogen or halogen atom or a methyl radical and R and R which may be the same or different, are hydrogen or halogen atoms or hydroxyl groups or alkoxy, phenoxy, alkylthio, phenylthio, phenyl-alkylamino, optionally substituted phenylamino, acyl-(i.e., alkanoyl) amino, alkyl, sulfo or carboxyl radicals and X is a halide ion or
  • the benzene diazonium salts used according to the present invention react with urobilinogen almost instantaneously and give very specific red to blue colored materials which are especially well suited for the detection of very low concentrations of urobilinogen. Furthermore, the compounds used according to the present invention have the great advantage that the color reaction is not disturbed by urea.
  • the previously known test papers are colored yellow due to the urea present in the urine, depending upon the concentration, which can make the detection of small amounts of urobilinogen very difficult.
  • the color reaction according to the present invention is not influenced by those substances which frequently occur in urine and which, as is known, usually have a disturbing effect on the Ehrlich test; these substances include, in particular, the aromatic amines which, as medicaments (sulfonamides, sulfonyl-ureas and the like), are frequently excreted in the urine.
  • these aromatic amines which, as medicaments (sulfonamides, sulfonyl-ureas and the like), are frequently excreted in the urine.
  • the presence of these aromatic amines in urine previously gave rise to yellow or orange color reactions which cannot only mask but also simulate the color brought about by urobilinogen.
  • diazonium salts such as diazosulfanilic acid, p-nitrobenzene diazonium salts and dichlorobenzene diazonium salts, have admittedly already been used for a comparatively long time. However, as is to be expected, these do not give a useful color reaction with urobilinogen.
  • the compounds used according to the present invention permit the specific detection of urobilinogen in the presence of bilirubin.
  • a red color can indicate the presence of urobilinogen and a later developing blue coloration the presence of bilirubin.
  • the test first becomes red and, subsequently, increasingly violet. ln exceptional cases, the color reactions develop simultaneously but this does not influence the test result.
  • reaction with bilirubin is to be suppressed, this can be achieved by using a diazonium salt of relatively low electrophilic character and allowing the reaction to take place in the presence of a cationic wetting agent.
  • the optionally polysubstituted benzene diazonium salts used according to the present invention are preferably employed for the production of test papers.
  • the compounds are applied to an absorbent carrier with a solid acid and possibly with additional materials, for example stabilizers and wetting agents.
  • the compounds (I) are also suitable for the production of test film strips according to German Patent Specification No. l,598, l 53 and for the detection of urobilinogen in solutions.
  • an absorbent carrier preferably filter paper
  • a solution which contains, per 100 ml., 0.05- g., preferably 0. 1-] g., of the diazonium salt, as well as 2-30 g., preferably 5-20 g., of a solid inorganic or organic acid and possibly at least one wetting agent and/or at least one stabilizer.
  • solvents for the impregnation solutions it is especially preferred to use water or readily volatile organic solvents which do not react with diazonium salts, which are, in particular, lower alcohols, ethyl acetate and acetonitrile.
  • the previously prepared diazonium salt can be added to the solution or the salt can be produced in known manner in the solution by diazotization of an appropriate aromatic amine.
  • salts which possess a stabilizing anion include, in particular, the sulfate, tetrafluoborate, tetrachlorozincate, hexachloroantimonate and aryl-sulfonate ions.
  • solid inorganic and organic acids there can be used, for example, orthophosphoric acid, metaphosphoric acid, sulfosalicyclic acid or oxalic acid, or acidic salts, for example, potassium bisulfate, as well as adducts of Lewis acids and Lewis bases provided that they have a suitably acidic reaction.
  • the commercially available metaphosphoric acid has proved to be especially useful which contains about 50-60 percent of its sodium salt since we have found that this gives especially stable test papers.
  • metaphosphoric acid and oxalic acid have the advantage that they give test reagents which only react slowly with bilirubin. Generally, it is preferred to use an acid which has a p value of less than 3.0.
  • the stabilizing additives which are preferably used, are well known in diazo chemistry; such additives include, for example, sodium fluoborate, sodium aryl sulfonate, magnesium sulfate and sodium metaphosphate.
  • anionic wetting agents especially sulfates and sulfonates, bring about an increased sensitivity and a slight bathochromic color displacement in the case of the detection of urobilinogen.
  • anionic wetting agents which can be used include sodium lauryl sulfate and sodium p-dodecyl-benzene sulfonate.
  • cationic wetting agents for example, lauryl pyridinium chloride.
  • Non-ionic wetting agents for example, polyoxyethylene triglyceride, generally only influence the wettability of the test papers.
  • the wetting agents can be added to the impregnation solution in amounts of about O.l3 g., preferably of 0.31 g., per ml.
  • the individual components of the formulations can also be applied successively when the solubilities thereof require this or when special effects are to be achieved.
  • it can be advantageous first to apply the diazonium salt and the stabilizer and thereafter to impregnate with the acid.
  • the absorbent carrier After the absorbent carrier has been impregnated, it is dried at the lowest possible temperature in order not to damage the diazonium salt.
  • filter paper is especially preferred but there can also be used fleeces and felts of acid-resistant synthetic resins, for example of polypropylene and polyesters.
  • the absorbent carriers provided with the reagents are preferably cut up into small squares and sealed on to synthetic resin films or sealed between two synthetic resin films or between a synthetic resin film and a finemeshed material.
  • test papers represent a preferred embodiment of the present invention and are the most elegant diagnostic agent for the component materials of body fluids, it is, of course, also possible, to use the diazonium salts according to the present invention for the detection of urobilinogen in the liquid phase.
  • an organic solvent for example, chloroform.
  • the new diagnostic agents are dipped into the solution to be investigated and the color change read off after a short period of time.
  • the diazonium salts and the corresponding amines used according to the present invention are generally known.
  • the Hammett sigma values are, as is known, measurement values for the electron attracting or electron repelling effect of substituents (in the first case, positive sigma values are obtained and in the latter case, negative values).
  • the sigma values are additive, the sign before the sum indicating whether, compared with hydrogen, the electron atracting or electron repelling effect preponderates.
  • the limiting value according to the present invention thus means that the action of the electron repelling substituents may be reduced by electron attracting substituents only up to a sigma value of +0.4.
  • a benzene diazonium salt with a hydroxyl group in the p-position can contain one or more electron attracting groups with a total sigma value of up to +0.83
  • a henzene diazonium salt which is substituted with an omethoxy or p-acetamino radical can only contain electron attracting groups up to a total sigma value of +0.4.
  • test paper Upon dipping into urine, the test paper gave, after about 5-l0 seconds, the following color reactions:
  • urobilinogen-free urine no coloration urine with normal urobilinogen content; pink discharge with Increased urobllinogen content: carmine red
  • test papers which contained 0.3 g.. of one of the following diazonium salts: 2-methoxybenzene diazonium fluoborate;
  • test paper (a) so obtained were subsequently impregnated with solutions each containing 0.4 g. of polyoxyethylene triglyceride (b), dodecylbenzene sulfonic acid sodium salt (c) and lauryl-pyridinium chloride (d) in 100 ml. methylene chloride and dried in a current of warm air.
  • the test papers gave, with urobilinogen-containing urine, after about 5-10 seconds, the following reactions:
  • dodecylbenzene sulfonic acid sodium salt 0.4 1 g.
  • test paper reacted with urobilinogen-containing urine with a Carmine-red color.
  • Polyester fleece was impregnated with solutions of the following composition and dried at 40C.:
  • dodecylbenzene sulfonic acid sodium salt in methylene chloride sodium lauryl sulfate in chloroform-methanol; dodecane sulfonic acid sodium salt in chloroformmethanol; dioctyl sodium sulfosuccinate in methylene chloride.
  • test paper reacted with urobilinogen-containing urine to give a brick red color.
  • EXAMPLE 9 5.0 ml. of urobilinogen-containing urine were mixed with 2.0 ml. of a solution of 2% by weight 2,4- dimethoxybenzene diazonium fluoborate in 2N hydrochloric acid. After 2 minutes, the solution was mixed with 5.0 ml. chloroform and vigorously shaken up. Thereafter, a part of the chloroform phase was placed in a cuvette and the extinction measured at 495 nm. By comparison of the extinction with that of a standard, the precise urobilinogen content of the urine could be determined.
  • Diagnostic agent for the detection of urobilinogen in body fluids which agent comprises an acid and at least one stable benzene diazonium salt wherein the phenyl radical contains at least one polyatomic electron donor group substituent with at least one mesomeric electron pair, in the or p-position and wherein the phenyl ring may contain additional substituents, the sum of the Hammett sigma values for all the substituents not exceeding the value of +0.4.
  • said benzene diazonium salt is of the formula Ilia 1'11 R2NEN X in which X is a stabilizing anion, R and R which may be the same or different, are polyatomic electron donor groups containing at least one mesomeric electron pair, or are hydrogen, halogen, or lower alkyl, provided one of R and R is a polyatomic electron donor group, and R and R.,, which may be the same or different, are hydrogen or groups which do not sterically hinder diazo coupling with urobilinogen, the sum of the Hammett sigma vlues of all the substituents R R R and R not exceeding +0.4.
  • R is hydroxy or lower alkoxy, phenoxy, lower aralkoxy, lower alkylthio, phenylthio, lower phenylalkylamino, phenylamino or 'lower alkanoylamino.
  • R and R are, individually, hydrogen, halogen, hydroxy, lower alkoxy, phenoxy, lower alkylthio, phenylthio, phenyl-lower alkylamino, lower alkyl, sulfo, or carboxyl.
  • X- is a halide or the anion of an oxygen acid or the anion of a Lewis acid coordinatively saturated with a hydrogen halide.
  • X- is a chloride, sulfate, tetrafluoborate, tetrachlorozincate, hexachloroantimonate, arylsulfonate or carboxylic acid ion.
  • Diagnostic agent as claimed in claim 10 wherein the acid is orthophosphoric acid, metaphosphoric acid, sulfosalicyclic acid, oxalic acid or an acid salt.
  • Diagnostic agent as claimed in claim 11 in the form of an absorbent carrier which has been impreg nated with a solution of a solid acid and at least one of said diazonium salts.
  • Diagnostic agent as claimed in claim 12 additionally comprising a wetting agent.
  • Diagnostic agent as claimed in claim 12 additionally comprising a stabilizing agent for the diazonium salt.
  • Method for the detection of urobilinogen optionally together with bilirubin comprises contacting the test substance with a diagnostic agent as claimed in claim 1.
  • said benzene-diazonium salt is at least one of 4- methoxybenzene diazonium fluoborate, 4- ethoxybenzene-diazonium-fluoborate, 4- acetoamidobenzene diazonium fluoborate or 3-chloro- 4-methoxybenzene diazonium toluene sulfonate.
  • benzene-diazonium salt is 4-methoxybenzene diazonium fluoborate, 4-ethoxybenzene-diazonium-fluoborate, 4-acetoamidobenzene diazonium fluoborate or 3-chloro-4-methoxybenzene diazonium toluene sulfonate.
  • Diagnostic agent as claimed in claim 2 in the form of an absorbent carrier which has been impregnated with a solution of the acid and at least one of said benzene-diazonium salts.
  • Diagnostic agent as claimed in claim 3 in the form of an absorbent carrier which has been impregnated with a solution of the acid and at least one of said benzene-diazonium salts.
  • Diagnostic agent as claimed in claim 4 in the form of an absorbent carrier which has been impregnated with a solution of the acid and at least one of said benzene-diazonium salts.
  • Diagnostic agent as claimed in claim 5 in the form of an absorbent carrier which has been impregnated with a solution of the acid and at least one of said bendiazo- -zene-diazonium salts.
  • Diagnostic agent as claimed in claim 6 in the form of an absorbent carrier which has been impregnated with a solution of the acid and at least one of said benzene-diazonium salts.
  • Diagnostic agent as claimed in claim 7 in the form of an absorbent carrier which has been impregnated with a solution of the acid and at least one of said benzene-diazonium salts.
  • Method for the detection of urobilinogen optionally together with bilirubin comprises contacting the test substance with a diagnostic agent as claimed in claim 5.
  • Method for the detection of urobilinogen optionally together with bilirubin which method comprises contacting the test substance with a diagnostic agent as claimed in claim 6.
  • Method for the detection of urobilinogen optionally together with bilirubin which method comprises contacting the test substance with a diagnostic agent as claimed in claim 7.

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US00262923A 1971-06-19 1972-06-14 Diagnostic composition for the detection of urobilinogens Expired - Lifetime US3853466A (en)

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DE2130559A DE2130559C3 (de) 1971-06-19 1971-06-19 Diagnostisches Mittel zum Nach weis von Urobihnogen

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JP (1) JPS5741693B1 (enrdf_load_stackoverflow)
AT (2) AT322116B (enrdf_load_stackoverflow)
CA (1) CA959389A (enrdf_load_stackoverflow)
CH (1) CH564774A5 (enrdf_load_stackoverflow)
DD (1) DD98763A5 (enrdf_load_stackoverflow)
DE (1) DE2130559C3 (enrdf_load_stackoverflow)
DK (1) DK143147C (enrdf_load_stackoverflow)
ES (1) ES403875A1 (enrdf_load_stackoverflow)
FI (1) FI53508C (enrdf_load_stackoverflow)
FR (1) FR2158791A1 (enrdf_load_stackoverflow)
GB (1) GB1343247A (enrdf_load_stackoverflow)
HU (1) HU162948B (enrdf_load_stackoverflow)
IT (1) IT956664B (enrdf_load_stackoverflow)
NL (1) NL170773C (enrdf_load_stackoverflow)
SE (1) SE394328B (enrdf_load_stackoverflow)
SU (1) SU535914A3 (enrdf_load_stackoverflow)
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989462A (en) * 1975-05-14 1976-11-02 Riedel-De Haen Aktiengesellschaft Test composition for detecting urobilinogen
US4158546A (en) * 1978-07-24 1979-06-19 Miles Laboratories, Inc. Composition, test device and method for determining the presence of urobilinogen in a test sample
US4246133A (en) * 1979-06-22 1981-01-20 Sherwood Medical Industries Inc. Stabilized diazotized sulfanilic acid solutions
US4260579A (en) * 1979-05-10 1981-04-07 Miles Laboratories, Inc. Device and method for simulating bilirubin in urine
US4311483A (en) * 1979-06-18 1982-01-19 Beckman Instruments, Inc. Kinetic method for directly determining total bilirubin
US4405718A (en) * 1981-07-20 1983-09-20 Miles Laboratories, Inc. Method and composition for urobilinogen control standard
US4468467A (en) * 1982-02-01 1984-08-28 Eastman Kodak Company Diazonium salt for bilirubin assay
EP0197439A3 (en) * 1985-03-29 1987-03-25 Kyowa Medex Co. Ltd. Method for the determination of bilirubin
WO1988009496A1 (en) * 1987-05-29 1988-12-01 Drug Screening Systems, Inc. Cannabinoid detection system
US5541115A (en) * 1988-06-09 1996-07-30 Abbott Laboratories Method and device employing covalently immobilized colored dyes
US5736408A (en) * 1994-11-23 1998-04-07 Carter; Jesse M. Method for the detection of urobilinogen in urine on an automated analyzer
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
US9551920B2 (en) 2009-06-12 2017-01-24 Draper, Inc. Tensioned projection screen assembly
US9612517B2 (en) * 2006-08-28 2017-04-04 Draper Inc. Tensioned projection screen

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT347600B (de) 1974-11-11 1979-01-10 Wellcome Found Testeinrichtungen
DE2839931A1 (de) * 1978-09-14 1980-03-27 Behringwerke Ag Diagnostisches mittel zum nachweis von urobilinogen
JPH0270495U (enrdf_load_stackoverflow) * 1988-11-17 1990-05-29

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US2854317A (en) * 1950-08-08 1958-09-30 Miles Lab Method and composition for testing bilirubin in urine
US3511607A (en) * 1967-10-06 1970-05-12 Smithkline Corp Laboratory reagent for assay of total bilirubin
US3585001A (en) * 1969-02-17 1971-06-15 Miles Lab Stabilized test device and process for detecting couplable compounds
US3585004A (en) * 1969-03-21 1971-06-15 Miles Lab Test composition and device for detecting couplable compounds
US3630680A (en) * 1967-10-26 1971-12-28 Boehringer Mannheim Gmbh Diagnostic agents for the detection of urobilinogen materials in body fluids
US3652222A (en) * 1969-04-07 1972-03-28 American Monitor Corp Bilirubin assay

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US2854317A (en) * 1950-08-08 1958-09-30 Miles Lab Method and composition for testing bilirubin in urine
US3511607A (en) * 1967-10-06 1970-05-12 Smithkline Corp Laboratory reagent for assay of total bilirubin
US3630680A (en) * 1967-10-26 1971-12-28 Boehringer Mannheim Gmbh Diagnostic agents for the detection of urobilinogen materials in body fluids
US3585001A (en) * 1969-02-17 1971-06-15 Miles Lab Stabilized test device and process for detecting couplable compounds
US3585004A (en) * 1969-03-21 1971-06-15 Miles Lab Test composition and device for detecting couplable compounds
US3652222A (en) * 1969-04-07 1972-03-28 American Monitor Corp Bilirubin assay

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Edward S. West et al., Textbook of Biochemistry, 4th Edition, 516-517, Macmillan Co., New York, 1967. *
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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989462A (en) * 1975-05-14 1976-11-02 Riedel-De Haen Aktiengesellschaft Test composition for detecting urobilinogen
US4158546A (en) * 1978-07-24 1979-06-19 Miles Laboratories, Inc. Composition, test device and method for determining the presence of urobilinogen in a test sample
US4260579A (en) * 1979-05-10 1981-04-07 Miles Laboratories, Inc. Device and method for simulating bilirubin in urine
US4311483A (en) * 1979-06-18 1982-01-19 Beckman Instruments, Inc. Kinetic method for directly determining total bilirubin
US4246133A (en) * 1979-06-22 1981-01-20 Sherwood Medical Industries Inc. Stabilized diazotized sulfanilic acid solutions
US4405718A (en) * 1981-07-20 1983-09-20 Miles Laboratories, Inc. Method and composition for urobilinogen control standard
US4468467A (en) * 1982-02-01 1984-08-28 Eastman Kodak Company Diazonium salt for bilirubin assay
EP0197439A3 (en) * 1985-03-29 1987-03-25 Kyowa Medex Co. Ltd. Method for the determination of bilirubin
WO1988009496A1 (en) * 1987-05-29 1988-12-01 Drug Screening Systems, Inc. Cannabinoid detection system
US5541115A (en) * 1988-06-09 1996-07-30 Abbott Laboratories Method and device employing covalently immobilized colored dyes
US5736408A (en) * 1994-11-23 1998-04-07 Carter; Jesse M. Method for the detection of urobilinogen in urine on an automated analyzer
US9612517B2 (en) * 2006-08-28 2017-04-04 Draper Inc. Tensioned projection screen
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
US9551920B2 (en) 2009-06-12 2017-01-24 Draper, Inc. Tensioned projection screen assembly
US10018901B2 (en) 2009-06-12 2018-07-10 Draper, Inc. Tensioned projection screen assembly

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SU535914A3 (ru) 1976-11-15
AT322116B (de) 1975-05-12
FI53508B (enrdf_load_stackoverflow) 1978-01-31
SE394328B (sv) 1977-06-20
NL170773C (nl) 1982-12-16
CA959389A (en) 1974-12-17
ES403875A1 (es) 1975-05-16
FI53508C (fi) 1978-05-10
JPS5741693B1 (enrdf_load_stackoverflow) 1982-09-04
DK143147B (da) 1981-06-29
DE2130559A1 (de) 1972-12-21
NL7208232A (enrdf_load_stackoverflow) 1972-12-21
FR2158791A1 (enrdf_load_stackoverflow) 1973-06-15
CH564774A5 (enrdf_load_stackoverflow) 1975-07-31
AU4354072A (en) 1973-07-12
DK143147C (da) 1981-11-09
DE2130559C3 (de) 1973-11-22
DD98763A5 (enrdf_load_stackoverflow) 1973-07-05
IT956664B (it) 1973-10-10
GB1343247A (en) 1974-01-10
ZA724152B (en) 1973-04-25
DE2130559B2 (de) 1973-04-26
HU162948B (enrdf_load_stackoverflow) 1973-05-28
AT317441B (de) 1974-08-26

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