EP0991783B1 - Use of a composition containing 2-mercaptopyridine-N-oxide - Google Patents

Use of a composition containing 2-mercaptopyridine-N-oxide Download PDF

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Publication number
EP0991783B1
EP0991783B1 EP98930776A EP98930776A EP0991783B1 EP 0991783 B1 EP0991783 B1 EP 0991783B1 EP 98930776 A EP98930776 A EP 98930776A EP 98930776 A EP98930776 A EP 98930776A EP 0991783 B1 EP0991783 B1 EP 0991783B1
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EP
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Prior art keywords
salts
oxide
leather
mercapto
pyridine
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Expired - Lifetime
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EP98930776A
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German (de)
French (fr)
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EP0991783A1 (en
Inventor
Otto Exner
Heinz-Joachim Rother
Martin Kugler
Hartmut Rehbein
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Bayer Chemicals AG
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Lanxess Deutschland GmbH
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Publication of EP0991783A1 publication Critical patent/EP0991783A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C1/00—Chemical treatment prior to tanning
    • C14C1/02—Curing raw hides

Definitions

  • the present application relates to the use of a composition comprising 2-mercapto-pyridine-N-oxide and / or its salts, and / or its metal complexes and the active compounds o-phenylphenol and p-chloro-meta-cresol and / or their ammonium, Alkali and alkaline earth salts and / or mixtures of these salts for the preservation of animal skins and leather.
  • the subject of the application is therefore the use of a composition comprising 2-mercapto-pyridine-N-oxide and / or its salts and / or metal complexes and the active compounds o-phenylphenol and p-chloro-meta-cresol and / or their ammonium, alkali and alkaline earth salts and / or mixtures of these salts in the preservation of animal skins and leather.
  • Preferred 2-mercapto-pyridine N-oxide salts and metal complexes are the sodium, potassium salts and copper and zinc complexes.
  • compositions containing CMK and 2-mercapto-pyridine-N-oxide-Na salt and OPP and their use according to the invention are preferred.
  • the mixing ratios of 2-mercapto-pyridine-N-oxide is generally 1 part by weight to 5 to 200, preferably 10 to 100, in particular 12 to 50, parts by weight of the further active compound mixture.
  • the ratio of the phenolic compounds with each other can be widely varied and is easily determined by conventional experiments.
  • the ratio is preferably 1: 1 to 1: 5.
  • the abovementioned active ingredient or the mixtures of the active ingredients are generally used in the form of formulations.
  • the application concentration is preferably 0.1 to 1% of active compound mixture based on the hides or leather to be protected.
  • the resulting in the formulation agents containing the active ingredient mixture is preferably 10 to 50%.
  • the agents generally contain from 10 to 30% of alkali metal and / or alkaline earth metal hydroxides; 1 to 20% of ionic and / or nonionic emulsifiers; 5 to 30% organic solvents such as in particular glycols, ketones, glycol ethers, alcohols such as ethanol, methanol, 1,2-propanediol, n-propanol, 2-propanol and 0-0.5% flavorings and fragrances. The rest to 100% is water.
  • the active substance mixtures and the products which can be prepared therefrom are used according to the generally customary application methods in leather production for the protection of animal hides against attack and damage by microorganisms. It is of particular interest that representatives of the species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum and Trichoderma viride, Penicillium species such as P. citrinum or P. glaucum, Paecilomyces variotii, Cladosporium species such as Mucor species such as Mucor mucedo Rhizopus species such as Rhizopus oryzae, Rhizopus rouxii are completely and permanently suppressed.
  • Agar plates are contaminated with conidia of the species Aspergillus niger, Aspergillus repens, Penicillium glaucum, Trichoderma viride and Hormoconis resinae. Then treated with Mixture I, II and Mixture III wet chrome leather (wet blue) are applied and incubated for 28 days at 95% relative humidity and 20 to 30 ° C.
  • Mixture I Mixture II (Invention) 30 parts by weight of p-chloro-m-cresol 30 parts by weight of p-chloro-m-cresol 13 parts by weight of o-phenylphenol 13 parts by weight of o-phenylphenol 1.2 parts by weight of 2-mercapto-pyridine N-oxide - Na salt
  • Mixture III 37 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine-N-oxide Na salt

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

The present application relates to the use of 2-mercapto-pyridine N-oxide and/or its alkali metal and alkaline earth metal salts and its metal complexes for the preservation of animal skins and leather.

Description

Die vorliegende Anmeldung betrifft die Verwendung einer Zusammensetzung enthaltend 2-Mercapto-pyridin-N-oxid und/oder seine Salze, und/oder seine Metallkomplexe und die Wirkstoffe o-Phenylphenol und p-Chlor-meta-kresol und/oder deren Ammonium-, Alkali- und Erdalkalisalze und/oder Gemische dieser Salze zur Konservierung von tierischen Häuten und Leder.The present application relates to the use of a composition comprising 2-mercapto-pyridine-N-oxide and / or its salts, and / or its metal complexes and the active compounds o-phenylphenol and p-chloro-meta-cresol and / or their ammonium, Alkali and alkaline earth salts and / or mixtures of these salts for the preservation of animal skins and leather.

2-Mercapto-pyridin-N-oxid sowie seine Verwendung als Konservierungsmittel für Kosmetika ist bekannt ( Microbicides for the Protecting of Materials, Paulus; 1993 Chepron & Hall, S. 294-300 ).2-Mercapto-pyridine-N-oxide and its use as a preservative for cosmetics is known ( Microbicides for the Protecting of Materials, Paul; 1993 Chepron & Hall, pp. 294-300 ).

Es wurde nun überraschenderweise gefunden, daß 2-Mercapto-pyridin-N-oxid, seine Salz und Metallkomplexe in Kombination mit den Wirkstoffen o-Phenylphenol (OPP) und p-Chlor-meta-kresol (CMK) einen ausgezeichneten und dauerhaften Schutz der tierischen Häute und Leder vor mikrobiellen Befall während der Herstellung und deren Lagerung ermöglicht.It has now surprisingly been found that 2-mercapto-pyridine-N-oxide, its salt and metal complexes in combination with the active ingredients o-phenylphenol (OPP) and p-chloro-meta-cresol (CMK) excellent and permanent protection of animal Hides and leather against microbial infestation during manufacture and storage.

Gegenstand der Anmeldung ist daher die Verwendung einer Zusammensetzung enthaltend 2-Mercapto-pyridin-N-oxid und/oder seiner Salze und/oder Metallkomplexe und die Wirkstoffe o-Phenylphenol und p-Chlor-meta-kresol und/oder deren Ammonium-, Alkali- und Erdalkalisalze und/oder Gemische dieser Salze bei der Konservierung von tierischen Häuten und Leder.The subject of the application is therefore the use of a composition comprising 2-mercapto-pyridine-N-oxide and / or its salts and / or metal complexes and the active compounds o-phenylphenol and p-chloro-meta-cresol and / or their ammonium, alkali and alkaline earth salts and / or mixtures of these salts in the preservation of animal skins and leather.

Diese Kombination zeigt hervorragende und sich synergistisch ergänzende Eigenschaften.This combination shows excellent and synergistically complementary properties.

Bevorzugte 2-Mercapto-pyridin-N-oxid-Salze und Metallkomplexe, sind die Natrium-, Kaliumsalze sowie Kupfer- und Zinkkomplexe.Preferred 2-mercapto-pyridine N-oxide salts and metal complexes are the sodium, potassium salts and copper and zinc complexes.

Insbesondere werden Zusammensetzungen enthaltend CMK und 2-Mercapto-pyridin-N-oxid - Na-Salz und OPP und deren erfindungsgemäße Verwendung bevorzugt.In particular, compositions containing CMK and 2-mercapto-pyridine-N-oxide-Na salt and OPP and their use according to the invention are preferred.

Die Mischungsverhältnisse von 2-Mercapto-pyridin-N-oxid beträgt im allgemeinen 1 Gew.-Teil zu 5 bis 200, vorzugsweise 10 bis 100, insbesondere 12 bis 50, Gew.-Teile der weiteren Wirkstoffmischung.The mixing ratios of 2-mercapto-pyridine-N-oxide is generally 1 part by weight to 5 to 200, preferably 10 to 100, in particular 12 to 50, parts by weight of the further active compound mixture.

Das Verhältnis der phenolischen Verbindungen untereinander kann breit variiert werden und ist durch übliche Versuche leicht bestimmbar. Bei einer Mischung von z.B. OPP und CMK liegt das Verhältnis vorzugsweise bei 1:1 bis 1: 5.The ratio of the phenolic compounds with each other can be widely varied and is easily determined by conventional experiments. In a mixture of e.g. OPP and CMK, the ratio is preferably 1: 1 to 1: 5.

Der obengenannte Wirkstoff bzw. die Mischungen der Wirkstoffe werden im allgemeinen in Form von Formulierungen eingesetzt. Dabei beträgt die Anwendungskonzentration vorzugsweise 0,1 bis 1 % Wirkstoffmischung bezogen auf die zu schützenden Häute bzw. Leder.The abovementioned active ingredient or the mixtures of the active ingredients are generally used in the form of formulations. The application concentration is preferably 0.1 to 1% of active compound mixture based on the hides or leather to be protected.

Die bei der Formulierung entstehenden Mittel enthalten die Wirkstoffmischung vorzugsweise zu 10 bis 50 %. Als weitere Bestandteile enthalten im allgemeinen die Mittel 10 bis 30 % Alkali- und/oder Erdalkalihydroxide; 1 bis 20 % ionische und/oder nicht- ionische Emulgatoren; 5 bis 30 % organische Lösemittel wie insbesondere Glykole, Ketone, Glykolether, Alkohole wie Ethanol, Methanol, 1,2-Propandiol, n-Propanol, 2-Propanol sowie 0-0,5 % Aroma- und Duftstoffe. Der Rest zu 100 % ist Wasser.The resulting in the formulation agents containing the active ingredient mixture is preferably 10 to 50%. As further constituents, the agents generally contain from 10 to 30% of alkali metal and / or alkaline earth metal hydroxides; 1 to 20% of ionic and / or nonionic emulsifiers; 5 to 30% organic solvents such as in particular glycols, ketones, glycol ethers, alcohols such as ethanol, methanol, 1,2-propanediol, n-propanol, 2-propanol and 0-0.5% flavorings and fragrances. The rest to 100% is water.

Die Wirkstoffmischungen und die daraus herstellbaren Mittel werden erfindungsgemäß nach allgemein üblichen Anwendungsmethoden bei der Lederherstellung zum Schutz von tierischen Häuten gegen Angriff und Beschädigung durch Mikroorganismen verwendet. Dabei ist von besonderem Interesse, daß Vertreter der Species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum und Trichoderma viride, Penicillium-Arten wie P. citrinum oder P. glaucum, Paecilomyces variotii, Cladosporium-Arten wie Mucor-Arten wie Mucor mucedo, Rhizopus-Arten wie Rhizopus oryzae, Rhizopus rouxii vollständig und dauerhaft unterdrückt werden.According to the invention, the active substance mixtures and the products which can be prepared therefrom are used according to the generally customary application methods in leather production for the protection of animal hides against attack and damage by microorganisms. It is of particular interest that representatives of the species Aspergillus niger, Aspergillus repens, Hormoconis resinae, Penicillium glaucum and Trichoderma viride, Penicillium species such as P. citrinum or P. glaucum, Paecilomyces variotii, Cladosporium species such as Mucor species such as Mucor mucedo Rhizopus species such as Rhizopus oryzae, Rhizopus rouxii are completely and permanently suppressed.

Die nachfolgenden Beispiele dienen zur Erläuterung der Erfindung und sind nicht auf diese beschränkt.The following examples serve to illustrate the invention and are not limited to these.

Beispiel 1example 1

Agarplatten werden mit Konidien der Species Aspergillus niger, Aspergillus repens, Penicillium glaucum, Trichoderma viride und Hormoconis resinae kontaminiert. Anschließend werden mit Mischung I, II und Mischung III behandelte feuchte Chromleder (wet blue) aufgelegt und 28 Tage bei 95 % relativer Luftfeuchtigkeit und 20 bis 30°C inkubiert. Mischung I Mischung II
(Erfindungsgemäß) 30 Gew.-Teile p-Chlor-m-kresol 30 Gew.-Teile p-Chlor-m-kresol 13 Gew.-Teile o-Phenylphenol 13 Gew.-Teile o-Phenylphenol 1,2 Gew.-Teile 2-Mercapto-pyridin- N-oxid - Na-Salz Mischung III 37 Gew.-Teile p-Chlor-m-kresol 1,2 Gew.-Teile 2-Mercapto-pyridin-N-oxid - Na-Salz Agar plates are contaminated with conidia of the species Aspergillus niger, Aspergillus repens, Penicillium glaucum, Trichoderma viride and Hormoconis resinae. Then treated with Mixture I, II and Mixture III wet chrome leather (wet blue) are applied and incubated for 28 days at 95% relative humidity and 20 to 30 ° C. Mixture I Mixture II
(Invention) 30 parts by weight of p-chloro-m-cresol 30 parts by weight of p-chloro-m-cresol 13 parts by weight of o-phenylphenol 13 parts by weight of o-phenylphenol 1.2 parts by weight of 2-mercapto-pyridine N-oxide - Na salt Mixture III 37 parts by weight of p-chloro-m-cresol 1.2 parts by weight of 2-mercapto-pyridine-N-oxide Na salt

Die mit der Mischung I konservierten wet blues zeigen schon nach 10 Tagen Inkubationszeit Schimmelwachstum auf den Prüfkörpern. Im Fall von Mischung II und III wird nach 28 Tagen Inkubationszeit kein Befall festgestellt.The wet blues preserved with the mixture I show mold growth on the test specimens after just 10 days of incubation. In the case of mixture II and III no infestation is observed after 28 days of incubation.

Beispiel 2Example 2 Formulierung I (Erfindungsgemäß)Formulation I (Inventive)

  • 27 Gew.-Teile p-Chlor-m-kresol27 parts by weight of p-chloro-m-cresol
  • 12 Gew.-Teile o-Phenylphenol12 parts by weight of o-phenylphenol
  • 1,2 Gew.-Teile 2-Mercapto-pyridin-N-oxid - Na-Salz1.2 parts by weight of 2-mercapto-pyridine-N-oxide-Na salt
  • 12 Gew.-Teile NaOH12 parts by weight NaOH
  • 14,2 Gew.-Teile 1,2-Propandiol14.2 parts by weight of 1,2-propanediol
  • Rest zu 100 Gew.-Teile WasserBalance to 100 parts by weight of water
Formulierung IIFormulation II

  • 37 Gew.-Teile p-Chlor-m-kresol37 parts by weight of p-chloro-m-cresol
  • 1,2 Gew.-Teile 2-Mercapto-pyridin-N-oxid - Na-Salz1.2 parts by weight of 2-mercapto-pyridine-N-oxide-Na salt
  • 10,5 Gew.-Teile NaOH10.5 parts by weight NaOH
  • 14 Gew.-Teile 1,2-Propandiol14 parts by weight of 1,2-propanediol
  • Rest zu 100 Gew.-Teile WasserBalance to 100 parts by weight of water
Formulierung IIIFormulation III

  • 30 Gew.-Teile p-Chlor-m-kresol30 parts by weight of p-chloro-m-cresol
  • 1,2 Gew.-Teile 2-Mercapto-pyridin-N-oxid - Na-Salz1.2 parts by weight of 2-mercapto-pyridine-N-oxide-Na salt
  • 8,5 Gew.-Teile NaOH8.5 parts by weight NaOH
  • 14 Gew.-Teile 1,2-Propandiol14 parts by weight of 1,2-propanediol
  • Rest zu 100 Gew.-Teile Wasser.Balance to 100 parts by weight of water.

Claims (6)

  1. Use of a composition containing 2-mercapto-pyridine N-oxide and/or its salts and/or its metal complexes and the active ingredients o-phenylphenol and p-chloro-meta-cresol and/or ammonium, alkali metal and alkaline earth metal salts thereof and/or mixtures of said salts for the preservation of animal skins and leather.
  2. Process for the protection of animal skins and leather from microbial attack, characterized in that a composition containing 2-mercapto-pyridine N-oxide and/or its salts and/or its metal complexes and the active ingredients o-phenylphenol and p-chloro-meta-cresol and/or ammonium, alkali metal and alkaline earth metal salts thereof and/or mixtures of said salts is added to animal skins or leather or allowed to act on animal skins or leather.
  3. Composition containing 2-mercapto-pyridine N-oxide and/or its salts and/or its metal complexes and the active ingredients o-phenylphenol and p-chloro-meta-cresol and/or ammonium, alkali metal and alkaline earth metal salts thereof and/or mixtures of said salts.
  4. Composition according to Claim 3, characterized in that alkali metal hydroxides and/or alkaline earth metal hydroxides, ionic and/or nonionic emulsifiers, solvents and optionally aromas and fragrances are present.
  5. Use of compositions according to at least one of Claims 3 and 4 in the and for the processing of animal skins.
  6. Animal skins, leather and products which are obtained or used in leather production, containing 2-mercapto-pyridine N-oxide and/or its salts and/or its metal complexes and the active ingredients o-phenylphenol and p-chloro-meta-cresol and/or ammonium, alkali metal and alkaline earth metal salts thereof and/or mixtures of said salts.
EP98930776A 1997-06-13 1998-06-02 Use of a composition containing 2-mercaptopyridine-N-oxide Expired - Lifetime EP0991783B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19725017 1997-06-13
DE19725017A DE19725017A1 (en) 1997-06-13 1997-06-13 Use of 2-mercapto-pyridine-N-oxide
PCT/EP1998/003260 WO1998056959A1 (en) 1997-06-13 1998-06-02 Use of 2-mercapto-pyridine-n-oxide

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EP0991783A1 EP0991783A1 (en) 2000-04-12
EP0991783B1 true EP0991783B1 (en) 2010-03-03

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EP98930776A Expired - Lifetime EP0991783B1 (en) 1997-06-13 1998-06-02 Use of a composition containing 2-mercaptopyridine-N-oxide

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US (1) US6479521B2 (en)
EP (1) EP0991783B1 (en)
JP (1) JP2002504166A (en)
KR (1) KR100524094B1 (en)
CN (1) CN1218051C (en)
AT (1) ATE459731T1 (en)
AU (1) AU735238B2 (en)
BR (1) BR9810518A (en)
CA (2) CA2293555C (en)
CZ (1) CZ299251B6 (en)
DE (2) DE19725017A1 (en)
DK (1) DK0991783T3 (en)
ES (1) ES2340228T3 (en)
ID (1) ID23533A (en)
MX (1) MXPA99011362A (en)
NO (1) NO996130D0 (en)
NZ (1) NZ501646A (en)
PL (1) PL194833B1 (en)
PT (1) PT991783E (en)
TR (1) TR199902951T2 (en)
WO (1) WO1998056959A1 (en)

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AUPP060597A0 (en) * 1997-11-27 1998-01-08 Novapharm Research (Australia) Pty Ltd Improved biocide and biocidal cloth
DE10046265A1 (en) 2000-09-19 2002-03-28 Bayer Ag Synergistic mixtures protecting animal hides or leather against microbial attack comprise phenols and fungicides such as mercaptobenzothiazole or chlorthalonil
JP4538982B2 (en) * 2001-04-26 2010-09-08 ぺんてる株式会社 Aqueous pigment composition
US7893047B2 (en) * 2006-03-03 2011-02-22 Arch Chemicals, Inc. Biocide composition comprising pyrithione and pyrrole derivatives
DE102006045066B4 (en) * 2006-09-21 2010-07-01 Schülke & Mayr GmbH Microbicidal preparation based on 1,2-benzisothiazolin-3-one with an aromatic alcohol content
DE102008038709A1 (en) 2008-08-12 2010-02-18 Lanxess Deutschland Gmbh Liquid preparations of phenolic drugs
EP2570502A1 (en) 2011-09-13 2013-03-20 LANXESS Deutschland GmbH Liquid preparations for fungicidal protection of substrates containing collagen fibres
EP2777396A1 (en) 2013-03-12 2014-09-17 LANXESS Deutschland GmbH Preparations for fungicidal protection of substrates containing collagen fibre
CN105454250B (en) * 2014-09-10 2018-01-30 浙江新农化工股份有限公司 The composition of 2 mercaptobenzothiazole zincs and mitochondrial cytochrome enzyme inhibitor series bactericidal agent
CN105454249B (en) * 2014-09-10 2018-03-02 浙江新农化工股份有限公司 Bactericidal composition and its preparation and application containing 2 mercaptobenzothiazole zincs

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GB2230190A (en) * 1989-03-28 1990-10-17 Ici Plc Compositions containing an isothiazolin(thi)one derivative and a 2-mercaptopyridine-1-oxide derivative
DE4122654A1 (en) * 1991-07-09 1993-01-14 Bayer Ag Microbicidal compsns. for protection of technical materials including wood - contain synergistic mixt. of phenolic cpd. and pyrithione deriv,
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GB2230190A (en) * 1989-03-28 1990-10-17 Ici Plc Compositions containing an isothiazolin(thi)one derivative and a 2-mercaptopyridine-1-oxide derivative
US5464622A (en) * 1990-11-27 1995-11-07 Rohm And Haas Company Antimicrobial compositions comprising iodopropargyl butylcarbamate and 2-mercaptopyridine n-oxide and method of controlling microbes
DE4122654A1 (en) * 1991-07-09 1993-01-14 Bayer Ag Microbicidal compsns. for protection of technical materials including wood - contain synergistic mixt. of phenolic cpd. and pyrithione deriv,

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PT991783E (en) 2010-04-27
AU8109098A (en) 1998-12-30
PL194833B1 (en) 2007-07-31
NO996130L (en) 1999-12-10
TR199902951T2 (en) 2000-08-21
DK0991783T3 (en) 2010-06-14
ES2340228T3 (en) 2010-05-31
DE19725017A1 (en) 1998-12-17
US6479521B2 (en) 2002-11-12
ID23533A (en) 2000-04-27
KR100524094B1 (en) 2005-10-26
US20020147227A1 (en) 2002-10-10
NO996130D0 (en) 1999-12-10
NZ501646A (en) 2001-09-28
CA2293555C (en) 2007-05-15
AU735238B2 (en) 2001-07-05
CZ9904457A3 (en) 2001-06-13
DE59814438D1 (en) 2010-04-15
KR20010013214A (en) 2001-02-26
MXPA99011362A (en) 2004-09-01
PL337159A1 (en) 2000-07-31
CA2661724C (en) 2013-05-28
JP2002504166A (en) 2002-02-05
CA2661724A1 (en) 1998-12-17
CN1260840A (en) 2000-07-19
CZ299251B6 (en) 2008-05-28
ATE459731T1 (en) 2010-03-15
BR9810518A (en) 2000-09-19
CN1218051C (en) 2005-09-07
WO1998056959A1 (en) 1998-12-17
EP0991783A1 (en) 2000-04-12
CA2293555A1 (en) 1998-12-17

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