EP0968005B1 - Verwendung von isothiazolone zur reduzierung von emissionen von hcn - Google Patents

Verwendung von isothiazolone zur reduzierung von emissionen von hcn Download PDF

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Publication number
EP0968005B1
EP0968005B1 EP98900123A EP98900123A EP0968005B1 EP 0968005 B1 EP0968005 B1 EP 0968005B1 EP 98900123 A EP98900123 A EP 98900123A EP 98900123 A EP98900123 A EP 98900123A EP 0968005 B1 EP0968005 B1 EP 0968005B1
Authority
EP
European Patent Office
Prior art keywords
hcn
emission
octylisothiazolone
organothiocyanate
emissions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP98900123A
Other languages
English (en)
French (fr)
Other versions
EP0968005A2 (de
Inventor
Wolfgang Beilfuss
Ralf Gradtke
Herbert Mangold
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.)
Schuelke and Mayr GmbH
Air Liquide Sante International SA
Original Assignee
Schuelke and Mayr GmbH
Air Liquide Sante International SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schuelke and Mayr GmbH, Air Liquide Sante International SA filed Critical Schuelke and Mayr GmbH
Publication of EP0968005A2 publication Critical patent/EP0968005A2/de
Application granted granted Critical
Publication of EP0968005B1 publication Critical patent/EP0968005B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/26—Organic substances containing nitrogen or phosphorus
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/40—Inorganic substances
    • A62D2101/45—Inorganic substances containing nitrogen or phosphorus
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/40—Inorganic substances
    • A62D2101/47—Inorganic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen

Definitions

  • the invention relates to the use of special additives for reducing the emission of volatile compounds from compositions and products which comprise constituents which can form or release such volatile compounds.
  • the invention relates to the provision of additives for the reduction of emissions of HCN.
  • compounds such as HCN, amines such as NH 3 and CH 3 NH 2 or thio compounds such as H 2 S, for example.
  • a decrease in the release, in particular, of HCN is of interest, which can proceed in highly variable extents from, for example, cyanide or thiocyanate ions or compounds having cyanide or thiocyanate substituents or compositions comprising such compounds.
  • JP-A-63 209 798 discloses a deodoriser composition containing isothiazolone compounds for nitrate reducing bacteria by inhibiting the sulfur compounds emission or the ammonia emission.
  • JP-A-1 224 098 discloses a deodorising compound for sludge containing isothiazolone.
  • organothiocyanates which include aromatic and aliphatic organothiocyanates
  • HCN sources are potential HCN sources.
  • aliphatic and aromatic organothiocyanates are thiocyanate-substituted thiazoles, 3-thiocyanato-N-octylacrylamide and methylenebisthiocyanate (MBT). They frequently have a characteristic unpleasant odour and, under certain conditions, also release volatile compounds such as, for example, thio compounds and HCN.
  • the emission values in this case are, at least in the case of approved commercial products, within the permitted limit values (MAK values), but, in principle, can also lie above these. Emissions of this type and, in particular, elevated emissions, represent a potential hazard to persons handling or using the products containing these constituents.
  • the contents of the individual compounds in question in the surrounding atmosphere serve, for example, as measured parameter for the emission of a product, e.g., for the emission of HCN, the HCN content in the surrounding air serves as indicator, in which case this can be determined using an appropriate test tube (e.g. a Dräger tube: prussic acid 2/a (hydrogen cyanide) (CH 25701)).
  • an appropriate test tube e.g. a Dräger tube: prussic acid 2/a (hydrogen cyanide) (CH 25701)).
  • the object therefore underlying the invention is to reduce emissions of volatile compounds such as HCN, which are potentially hazardous or cause unpleasant odour, from compositions and products which comprise constituents which form such compounds which are potentially hazardous or cause unpleasant odour, and, in this regard, to provide low-emission compositions.
  • isothiazolone compounds such as N-octylisothiazolone and benzisothiazolone, are used as additive for the reduction of emissions of volatile compounds which are potentially hazardous or cause unpleasant odour from compositions which comprise constituents which form such compounds which are potentially hazardous or cause unpleasant odour.
  • Preferred embodiments are the subject-matter of the subclaims.
  • emissions which are potentially hazardous or have unpleasant odour may be greatly reduced or eliminated by addition of the abovementioned additive compounds.
  • the extent of the emission reduction may be set via the concentration of the additives.
  • MAK values legally prescribed limit values
  • a further reduction or elimination of such emissions can increase the safety margin until the MAK values are reached, whereas in the case of substances and compositions whose emission lies above this, a decrease or elimination of the emissions can lead to the corresponding commercial products being approved or being able to be put on the market.
  • the reduction can appear in advantages with respect to odour versus a comparison product which contains no additive according to the invention.
  • the advantage achieved is, for example, a reduction of the odour strength and/or a change of the odour note or type of odour.
  • test substances selected were firstly an aromatic thiocyanatothiazole or 3-thiocyanato-N-octylacrylamide and secondly aliphatic methylenebisthiocyanate (MBT).
  • Suitable emission-reducing additives according to the invention are, for example, the following isothiazolones and mixtures of the same: N-octylisothiazolone, 5-chloro-N-methylisothiazolone, N-methylisothiazolone, a mixture of 5-chloro-N-methylisothiazolone and N-methylisothiazolone, 1,2-benzisothiazolone, 5,6-dihydro-2-methyl-2H-cyclopent(d)isothiazol-3(4H)-one.
  • the preferred emission-reducing additive is N-octylisothiazolone.
  • the embodiments according to the invention prepared are preparations which comprise the emission-reducing additive, in particular an isothiazolone, which reduces the emission of the preparations and, inter alia, also acts as an HCN trap.
  • the invention makes it possible to reduce the release of HCN both in aqueous systems over a wide pH range, such as pH 1 to pH 12, e.g. by adding water-soluble isothiazolones, such as N-methylisothiazolone, benzisothiazolone or 5,6-dihydro-2-methyl-2H-cyclopent(d)isothiazol-3(4H)-one, and in lipophilic media, e.g. by adding N-octylisothiazolone.
  • water-soluble isothiazolones such as N-methylisothiazolone, benzisothiazolone or 5,6-dihydro-2-methyl-2H-cyclopent(d)isothiazol-3(4H)-one
  • lipophilic media e.g. by adding N-octylisothiazolone.
  • HCN emissions can be reduced from primarily liquid products (solutions, dispersions, preferably aqueous dispersions).
  • the action e.g. a biocidal action, ascribed to the treated compositions is not impaired by the emission-reducing additives.
  • the invention can be used, for example, in the area of solutions or dispersions for a fungicidal and algistatic finishing of materials and technical preservation.
  • Concrete areas of application and user products are, for example, preservatives, disinfectants, impregnating agents, paints, sizings and adhesives, primers, coatings, lubricants and plasters.
  • the emission-reducing additives according to the invention are used at least in a total amount of 0.01% by weight, preferably 0.01 to 10.0% by weight, in particular 0.1 to 7.5% by weight, and preferably 0.5 to 5.0% by weight, based on the composition.
  • the proportion of each of these additive components can be set according to the specific product requirements.
  • Aqueous dispersions which comprised 7.8% by weight of aromatic organothiocyanate (in the form of 26% by weight of a 30% strength dispersion), based on the weight of the dispersions, were admixed with various amounts of N-octylisothiazolone (45% strength solution) (0.5%, 1.0%, 2.0%, 3.0% or 5.0%, based on the weight of the dispersion) and were tested for compatibility and stability. The procedure and results of "HCN" measurements are reported below.
  • the Dräger test tube was used together with a pump. Both tips of the tube were broken off and one end of the tube was then inserted tightly into the pump.
  • the HCN content was tested by holding the other end of the tube in the air space over the surface of the respective sample in a 50 ml wide-neck sample vial which was filled with 50 g of the sample. The temperature was 23.5°C.
  • the sample vials had been sealed for 4 weeks.
  • the air was sucked through the tube. The measurement period was about 60 seconds for 5 strokes and correspondingly about 24 seconds for 2 strokes.
  • the result was then determined on the basis of the coloration (reaction of HCN with HgCl 2 and methyl red).
  • the measurement method corresponds to the Dräger instruction 234-257 of 1995.
  • Blank value (without additive, aromatic organothiocyanate-containing aqueous dispersions) ⁇ approx. 1.5 ppm.
  • N-octylisothiazolone 45% strength solution significantly decreases the HCN emission of aromatic-organothiocyanate-containing dispersions.
  • Aqueous dispersions were produced which comprised 7.8% by weight of aromatic organothiocyanate (in the form of 13% by weight of a 60% strength dispersion) based on the weight of the dispersions.
  • the dispersions were homogeneous and whitish-yellow (very high quality).
  • the dispersions were measured after storage at room temperature for 24 hours in a 250 ml wide-neck bottle which contained approximately 100 g of the respective sample: Zero value After 1 week at room temperature Blank: without additive >> 30 ppm > 30 ppm + 1% Kathon 893 approx. 25 ppm 8 ppm + 2% Kathon 893 approx. 10 ppm 5 ppm + 3% Kathon 893 approx. 5 ppm 2-3 ppm + 5% Kathon 893 approx. 2 ppm 2 ppm
  • the aromatic organothiocyanate content of the dispersions containing 0 or 1% N-octylisothiazolone (45% strength solution) was: without N-octylisothiazolone 7.1% with 1% N-octylisothiazolone 7.1%
  • N-octylisothiazolone significantly decreases the HCN emission of aromatic-organothiocyanate-containing dispersions.
  • the odour of such dispersions is improved in this case.
  • HCN emission in ppm measured using Dräger tubes at 22°C, measurement vessel 50 ml wide-neck bottle filled with 25 g of dispersion: HCN trap HCN after 48 h in ppm after 1 week ppm pH after 1 week Without addition > 30 20 4.5
  • B) 5,6-Dihydro-2-methyl-2H-cyclopent(d)isothiazol-3(4H)-one 0 0 4.1 Result The further additives studied lead to a reduction of the HCN emission, which reduction, in comparison with the isothiazolones, is somewhat lesser.
  • Preferred examples of these further additives lead to a comparatively high reduction (to ⁇ 20 ppm) of the HCN emission of aromatic-organothiocyanate-containing compositions.
  • N-octylisothiazolone to, for example, film preservatives based on compositions which contained aromatic organothiocyanate, led to optically clear, homogeneous solutions.
  • the HCN emission was significantly reduced.
  • the active compound content is virtually unchanged after storage at room temperature or +40°C for 1 month.
  • the 3-thiocyanato-N-octylacrylamide which was isolated in crystalline form is virtually insoluble in water ( ⁇ 0.01%) and dissolves at about 2.5 to 10% in glycols or glycol ethers.
  • the 2.5 to 10% strength solutions of 3-thiocyanato-N-octylacrylamide in glycols or glycol ethers emit HCN, that is to say approximately 30 ppm (1 stroke) after storage at room temperature for 1 week, whereas the crystalline material had an HCN emission of approximately 25 ppm at 5 strokes (Dräger tube, see above).
  • Solvent: HCN (1 stroke) 1,2-Propyl glycol approx. 2.5% completely soluble Dipropyl glycol 10% completely soluble > 40 Triethylene glycol 8% completely soluble approx.
  • a 5% strength aqueous dispersion of 3-thiocyanato-N-octylacrylamide is almost white, homogeneous and has an HCN emission of 13 ppm (5 strokes) (Dräger tube, see above).

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Business, Economics & Management (AREA)
  • Emergency Management (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (6)

  1. Verwendung von Isothiazolonverbindungen als Additiv zur Verminderung von Emissionen von HCN aus Zusammensetzungen, die Verbindungen enthalten, die Cyanid- oder Thiocyanationen oder -substituenten aufweisen, insbesondere Organothiocyanationen oder -substituenten.
  2. Verwendung nach Anspruch 1, dadurch gekennzeichnet, daß die Isothiazolonverbindungen unter N-Octylisothiazolon, 5-Chlor-N-methylisothiazolon, N-Methylisothiazolon, Mischung von 5-Chlor-N-methylisothiazolon und N-Methylisothiazolon, 1,2-Benzisothiazolon oder 5,6-Dihydro-2-methyl-2H-cyclopent(d)isothiazol-3(4H)on ausgewählt werden.
  3. Verwendung nach Anspruch 2, dadurch gekennzeichnet, daß als Isothiazolonverbindungen N-Octylisothiazolon verwendet wird.
  4. Verwendung von Isothiazolonverbindungen nach einem der Ansprüche 1 bis 3 als Additiv zur Verminderung von Emissionen von HCN aus flüssigen Zusammensetzungen, insbesondere aus Lösungen und Dispersionen, bevorzugt aus wäßrigen Dispersionen.
  5. Verwendung nach Anspruch 4, dadurch gekennzeichnet, daß die flüssige Zusammensetzung unter Reinigungsmitteln, Desinfektionsmitteln, Konservierungsmitteln, Schmiermitteln, Imprägniermitteln, Farben, Lacken und Putzen ausgewählt wird.
  6. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß die Isothiazololverbindungen bezogen auf die Zusammensetzung mindestens in einer Menge von 0,01 Gew.-%, bevorzugt 0,01 bis 10,0 Gew.-%, insbesondere 0,1 bis 7,5 Gew.-% und bevorzugt 0,5 bis 5,0 Gew.-% eingesetzt werden.
EP98900123A 1997-01-23 1998-01-16 Verwendung von isothiazolone zur reduzierung von emissionen von hcn Expired - Lifetime EP0968005B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19703711 1997-01-23
DE19703711A DE19703711C2 (de) 1997-01-23 1997-01-23 Verminderung von Emissionen von HCN durch Additive
PCT/IB1998/000063 WO1998032473A2 (en) 1997-01-23 1998-01-16 Reduction of emissions of volatile compounds by additives

Publications (2)

Publication Number Publication Date
EP0968005A2 EP0968005A2 (de) 2000-01-05
EP0968005B1 true EP0968005B1 (de) 2005-01-05

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EP98900123A Expired - Lifetime EP0968005B1 (de) 1997-01-23 1998-01-16 Verwendung von isothiazolone zur reduzierung von emissionen von hcn

Country Status (8)

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EP (1) EP0968005B1 (de)
JP (1) JP2001521411A (de)
AU (1) AU5336598A (de)
BR (1) BR9807087A (de)
CA (1) CA2278288A1 (de)
DE (2) DE19703711C2 (de)
ES (1) ES2235309T3 (de)
WO (1) WO1998032473A2 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5991401A (en) * 2000-08-18 2002-02-21 Procter & Gamble Company, The Reduction of odors from coating material
DE10340829A1 (de) * 2003-09-04 2005-04-07 Schülke & Mayr GmbH Salzarme oder salzfreie mikrobizide Zusammensetzung auf Basis von Isothiazolon-Derivaten und Pyriondisulfid
US20100189811A1 (en) * 2009-01-29 2010-07-29 Thor Gmbh Biocide compositions comprising 3-methylisothiazolin-3-one and a haloalkyl sulphone
ES2705088B2 (es) 2017-09-20 2020-03-30 Liderkit S L Nuevo gel-coat aditivado con particulas de dioxido de titanio y alumina
JP7415104B2 (ja) * 2019-06-03 2024-01-17 三井化学株式会社 ジヨードメタン化合物の水溶液の製造方法
WO2022246218A1 (en) * 2021-05-21 2022-11-24 Troy Technology Ii, Inc. Boosted ipbc for wet-state bacterial control

Family Cites Families (13)

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Publication number Priority date Publication date Assignee Title
US3996346A (en) * 1975-03-18 1976-12-07 Dominic Thomas Staffier Composition for reducing bodily odor and perspiration
LU81802A1 (fr) * 1978-10-20 1980-01-25 Metallurg Ct Voor Res Metallur Procede pour epurer les eaux residuaires
JPS63209798A (ja) * 1987-02-24 1988-08-31 Tokyo Met Gov Gesuidou Service Kk 汚泥消臭剤
JPH01204940A (ja) * 1988-02-12 1989-08-17 Asada Seifun Kk ポリプロピレン樹脂成型組成物
JPH01224098A (ja) * 1988-03-02 1989-09-07 Tokyo Met Gov Gesuidou Service Kk 脱水汚泥ケーキの消臭方法
JPH0683720B2 (ja) * 1990-06-19 1994-10-26 日本曹達株式会社 循環式トイレ処理剤
JPH05139918A (ja) * 1991-11-22 1993-06-08 Nikka Chem Co Ltd 抗菌防臭剤
JPH0623345A (ja) * 1992-07-09 1994-02-01 Hokko Chem Ind Co Ltd し尿用清浄剤
US5284649A (en) * 1992-09-29 1994-02-08 The Procter & Gamble Company Deodorant gel sticks containing 1-hydroxy pyridinethione active
US5415785A (en) * 1992-12-11 1995-05-16 Nalco Chemical Company Method for removing a cyanide contaminant from refinery waste water streams
JP3252239B2 (ja) * 1992-12-15 2002-02-04 コニカ株式会社 ハロゲン化銀写真感光材料の処理方法及び処理液
US5292776A (en) * 1993-03-26 1994-03-08 Betz Laboratories, Inc. Microbial inhibiting compositions and their use
JP2747880B2 (ja) * 1993-12-27 1998-05-06 株式会社工生研 脱水ケーキの消臭剤

Also Published As

Publication number Publication date
CA2278288A1 (en) 1998-07-30
DE19703711A1 (de) 1998-07-30
WO1998032473A3 (en) 1998-09-11
DE19703711C2 (de) 1999-07-01
WO1998032473A2 (en) 1998-07-30
ES2235309T3 (es) 2005-07-01
AU5336598A (en) 1998-08-18
JP2001521411A (ja) 2001-11-06
DE69828492D1 (de) 2005-02-10
EP0968005A2 (de) 2000-01-05
DE69828492T2 (de) 2005-12-15
BR9807087A (pt) 2000-04-18

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