CH467019A - Ready-to-use agent for combating harmful bacteria on textile materials - Google Patents

Ready-to-use agent for combating harmful bacteria on textile materials

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Publication number
CH467019A
CH467019A CH41767A CH41767A CH467019A CH 467019 A CH467019 A CH 467019A CH 41767 A CH41767 A CH 41767A CH 41767 A CH41767 A CH 41767A CH 467019 A CH467019 A CH 467019A
Authority
CH
Switzerland
Prior art keywords
ready
urea
textile materials
dichlorophenyl
harmful bacteria
Prior art date
Application number
CH41767A
Other languages
German (de)
Other versions
CH41767A4 (en
Inventor
Dieter Dr Duerr
Rudolf Dr Hitz Hans
Max Dr Duennenberger
Max Dr Schellenbaum
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Priority to CH41767A priority Critical patent/CH467019A/en
Priority to CA008,471A priority patent/CA961052A/en
Priority to US694121A priority patent/US3592932A/en
Priority to DE19681643848D priority patent/DE1643848B1/en
Priority to GB566/68A priority patent/GB1173872A/en
Priority to IT34071/68A priority patent/IT972013B/en
Priority to FR1575560D priority patent/FR1575560A/fr
Priority to SE00348/68A priority patent/SE332422B/xx
Priority to AT29268A priority patent/AT279058B/en
Priority to BE709240D priority patent/BE709240A/xx
Priority to NL6800445A priority patent/NL6800445A/xx
Priority to ES0349159A priority patent/ES349159A1/en
Publication of CH41767A4 publication Critical patent/CH41767A4/xx
Publication of CH467019A publication Critical patent/CH467019A/en
Priority to US00269686A priority patent/US3813437A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D203/00Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/20Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/34One oxygen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18Oxygen atoms
    • C07D263/20Oxygen atoms attached in position 2
    • C07D263/26Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/301,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/301,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/321,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/68Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/121,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/1251,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14Radicals substituted by nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

  

  
 



  Gebrauchsfertiges Mittel zur Bekämpfung von schädlichen Bakterien auf textilen Materialien
Gegenstand der Erfindung ist ein gebrauchsfertiges Mittel zur Bekämpfung schädlicher Bakterien auf textilen Materialien. Das Mittel enthält als Wirkstoff den   N-3 ,4-Dichlorphenyl-N'-2-äthylhexyl-( 1) - harnstoff    der Formel
EMI1.1     

Diese Verbindung kann durch Umsetzung von 2  ithyl-hexyl-(l)-amin    mit   3,4 - Dichlorphenylisocyanat    erhalten werden.



   Aus der belgischen Patentschrift Nr. 673 848 und der schweizerischen Auslegeschrift Nr. 16 314/64 sind N-3   ,4-Dichlorbenzyl-phenyl-harnstoffe    bekannt. In der südafrikanischen Patentschrift Nr. 66/2358 wird ein N-3   ,4-Dichlorphenyl-N'-n-octyl-( 1) - harnstoff    und im   Journal of the American Chemical Society , Bd. 79 (1957), Seite 1238, ein N-3   ,4-Dichlorphenyl-N'-tertiär-    octyl-harnstoff beschrieben. Alle diese bekannten Harnstoffderivate haben im Vergleich zum vorliegenden N-3   ,4-Dichlorphenyl-N'-2-äthylhexyl-( 1) - harnstoff    eine geringere Löslichkeit sowohl in polaren als auch unpolaren Lösungsmitteln, wodurch die Anwendung dieser bekannten Harnstoffe auf einen viel engeren Bereich eingeschränkt ist.



   Die gebrauchsfertigen Mittel zur Bekämpfung schädlicher Bakterien, welche den   N-3,4-Dichlorphenyl      N'-2-äthylhexyl-(l)-harnstoff    enthalten, können im übrigen in üblicher, an sich bekannter Weise hergestellt und angewendet werden. Besonders wertvoll an den neuen Mitteln ist das breite antibakterielle Wirkungsspektrum, das sich sowohl auf grampositive als auch gramnegative Bakterien erstreckt. Hierbei ist in anwendungstechnischer Hinsicht die Geruchlosigkeit und Farblosigkeit des N-3   ,4-Dichlorphenyl-N'-2-äthylhexyl    (l)-harnstoffes von besonderem Wert. Die Verwendung zum Schutze von textilen Substraten ist auf sehr breiter Basis möglich gegen den Befall durch zerstörende und pathogene Bakterien.

   Der   N-3 ,Dichlorphenyl-N'      2-äthylhexyl-(1)-harnstoff    eignet sich demnach sowohl als Konservierungsmittel wie auch als Desinfektionsmittel für Textilien und technische Produkte der Textilindustrie.



   Unter den technischen Produkten, welche mit Hilfe von N-3   ,4-Dichlorphenyl-N'-2-äthylhexyl-( 1) - harnstoff    konserviert werden können, seien die folgenden als Beispiele herausgegriffen:
Textilhilfsmittel bzw. Veredlungsmittel und Farbzubereitungen auf der Basis von organischen und anorganischen Farbstoffen bew. Pigmenten, auch solche, welche als Beimischungen Casein oder andere organische Verbindungen enthalten.



   Weiterhin kann   N - 3,4 -      4-Dichlorphenyl-N'-2-äthyl-    hexyl-(l)-harnstoff zur konservierenden und desinfizierenden Ausrüstung von Fasern und Textilien verwendet werden, wobei er auf natürliche und künstliche Fasern aufgebracht werden kann und dort eine dauerhatte Wirkung gegen   schädliche    (auch   pathogene)    Bakterien entfaltet. Der Zusatz kann dabei vor, gleichzeitig mit oder nach einer Behandlung dieser Textilien mit anderen Stoffen. z. B. Farb- oder Druckpasten, Appreturen usw., erfolgen.  



   Derart behandelte Textilien weisen auch einen Schutz gegen das Auftreten von Schweissgeruch, wie er durch Bakterien bedingt ist, auf.



   Ferner gelangt man durch Kombination von   N-3,4-      Dichlorphenyl-N'-2-äthylhexyl-(1)-harnstoff    mit waschbzw. oberflächenaktiven Stoffen zu Waschmitteln für textile Materialien mit ausgezeichneter antibakterieller Wirkung. Dieser Harnstoff kann z. B. in Seifen eingearbeitet, mit seifenfreien,   wasch- bzw.    oberflächenaktiven Stoffen oder mit Gemischen aus Seifen und seifenfreien waschaktiven Stoffen kombiniert werden, wobei in diesen Kombinationen seine antibakterielle Wirksamkeit in vollem Umfang erhalten bleibt.



   Der   N-3 ,4-Dichlorphenyl-N1-äthylhexyl-( 1)-harnstoff    kann auf zu schützende Textilmaterialien in verschiedenster Weise aufgebracht werden, zum Beispiel durch Imprägnieren oder Besprühen mit Lösungen oder Suspensionen, die die genannte Verbindung als Wirkstoff enthalten. Der Wirkstoffgehalt kann hierbei je nach Anwendungszweck zwischen 1 und 30 g   Wirksubstan    pro Liter Behandlungsflüssigkeit liegen. Meistens werden textile Materialien sowohl synthetischer oder natürlicher Herkunft durch einen Gehalt von 0,1 bis 3 % Wirkstoff ausreichend gegen   Bakterienbefail    geschützt. Der Wirkstoff kann zusammen mit anderen textilen Hilfsmitteln wie Appreturmitteln, Knitterfestausrüstungen usw. eingesetzt werden.



   Die Anwendungsformen können den üblichen Formulierungen von Schädlingsbekämpfungsmitteln entsprechen, beispielsweise können Mittel, die   N-3 ,4Di-      cholrphenyl-N'-2-äthylhexyl-( 1) -harnstoff    enthalten, gegebenenfalls auch noch Zusätze wie Trägerstoffe, Lösungsmittel,   Verdünnongs-,      Dispergier-,    Netz- oder Haftmittel usw. sowie andere Schädlingsbekämpfungsmittel, z. B. fungizide oder fungistatische Mittel, enthalten.



   Die in der nachfolgenden Herstellungsvorschrift und im Beispiel angegebenen Teile sind Gewichtsteile, die Prozente Gewichtsprozente, sofern nichts anderes angegeben.



      Herstellungsvorsch rijt   
37,6 Teile   3,4Dichlorphenylisocyanat    werden zu einer Lösung von 25,9 Teilen   2-Athyl-hexyl-(1)-amin    in 200   Volumteilen    Benzol gegeben. Durch Zugabe von 200   Volumteilen    Petroläther wird der entstandene N  3 ,4-Dichlorphenyl-N'-2-äthylhexyl-( 1)-harnstoff    der Formel (1) gefällt. Die Ausbeute beträgt ungefähr 57 Teile.



  Schmelzpunkt 65 bis   660 C.   



      Cl5H ON2Cl2    berechnet: N 8,83   Q    22,35 gefunden: N 8,70   C1    22,64
Antibakterielle Wirkung im Verdünnungstest
Eine   lSige    und eine 0,3   3% ige    Lösung der Wirkstoffe in Dimethylsulfoxyd werden in Röhrchen mit steriler Brain-Heart Infusion Broth gegeben und mit den Lösungen Verdünnungsreihen mit fortlaufender Verdünnung auf das Zehnfache angesetzt. Durch Kombination der beiden Reihen erhält man folgende kontinuierliche Verdünnungsreihe :
1000, 300, 100, 30, 10, 3 ppm usw.



   Die Lösungen werden mit dem Bakterium Staphylococcus aureus beimpft. Anschliessend wird während 48   Stunden    bei 370 C bebrütet (Bakteriostase).



   Nach, 24 Stunden Kulturdauer wird aus den Röhrchen eine Öse auf Glucose-Agarplatten ausgestrichen und während 24 Stunden bei 370 C bebrütet (Bakterizide).



   Nach den genannten Zeiten werden die Grenzkonzentrationswerte ermittelt.



   Bakteriostase 1 ppm
Bakterizide 1 ppm
Beispiel
Muster von 100 g   Baumwoll-Cretonne    werden mit einer   0,1 % eigen    Lösung des   N-3,4-Dichlorphenyl-N'-2-      äthylhexyl, (1)-harnstoffes    in Isopropanol bei 200 C am Foulard imprägniert und anschliessend mit einer 100   5    igen Flottenaufnahme abgequetscht.



   In gleicher Weise werden auch Muster von 100 g Wollcheviot behandelt
Die bei 30 bis 400 C getrockneten Gewebe enthalten   0, 1 %    Wirkstoff, bezogen auf ihr Eigengewicht.



   Zur Prüfung der Wirkung gegen Bakterien werden   Rondelle    von 10 mm Durchmesser der imprägnierten Gewebe (ungewässert und nach EMPA-Wässerung) auf Glucose-Agar-Platten gelegt, die mit Staphylococcus aureus vorbeimpft sind. Die Platten werden hierauf 24 Stunden bei 370 C bebrütet.   



  
 



  Ready-to-use agent for combating harmful bacteria on textile materials
The invention relates to a ready-to-use agent for combating harmful bacteria on textile materials. The agent contains N-3, 4-dichlorophenyl-N'-2-ethylhexyl- (1) - urea of the formula as active ingredient
EMI1.1

This compound can be obtained by reacting 2 ithyl-hexyl- (l) -amine with 3,4-dichlorophenyl isocyanate.



   N-3, 4-dichlorobenzyl-phenyl-ureas are known from Belgian patent specification No. 673 848 and Swiss patent application No. 16 314/64. In the South African patent specification No. 66/2358 an N-3, 4-dichlorophenyl-N'-n-octyl- (1) - urea and in the Journal of the American Chemical Society, Vol. 79 (1957), page 1238, an N-3, 4-dichlorophenyl-N'-tertiary octyl urea described. All these known urea derivatives have, compared to the present N-3, 4-dichlorophenyl-N'-2-ethylhexyl- (1) - urea, a lower solubility in both polar and non-polar solvents, whereby the use of these known ureas is much narrower Area is restricted.



   The ready-to-use agents for combating harmful bacteria, which contain N-3,4-dichlorophenyl N'-2-ethylhexyl- (1) -urea, can moreover be prepared and used in a conventional manner. What is particularly valuable about the new products is the broad spectrum of antibacterial activity, which extends to both gram-positive and gram-negative bacteria. From an application point of view, the odorlessness and colorlessness of the N-3,4-dichlorophenyl-N'-2-ethylhexyl (l) urea are of particular value. The use for protecting textile substrates is possible on a very broad basis against attack by destructive and pathogenic bacteria.

   The N-3, dichlorophenyl-N '2-ethylhexyl- (1) -urea is therefore suitable both as a preservative and as a disinfectant for textiles and technical products in the textile industry.



   Among the technical products that can be preserved with the help of N-3, 4-dichlorophenyl-N'-2-ethylhexyl- (1) - urea, the following are examples:
Textile auxiliaries or finishing agents and color preparations based on organic and inorganic dyes, particularly pigments, including those which contain casein or other organic compounds as admixtures.



   Furthermore, N - 3,4 - 4-dichlorophenyl-N'-2-ethyl-hexyl- (l) -urea can be used for preserving and disinfecting fibers and textiles, whereby it can be applied to natural and artificial fibers and there had a lasting effect against harmful (also pathogenic) bacteria. The addition can be made before, at the same time with or after treating these textiles with other substances. z. B. color or printing pastes, finishes, etc., take place.



   Textiles treated in this way also have protection against the occurrence of sweat odor, as is caused by bacteria.



   Furthermore, by combining N-3,4-dichlorophenyl-N'-2-ethylhexyl- (1) -urea with washing or. Surface-active substances for detergents for textile materials with excellent antibacterial properties. This urea can e.g. B. incorporated into soaps, combined with soap-free, detergent or surface-active substances or with mixtures of soaps and soap-free detergent substances, with its antibacterial effectiveness being fully retained in these combinations.



   The N-3, 4-dichlorophenyl-N1-ethylhexyl- (1) -urea can be applied to textile materials to be protected in a wide variety of ways, for example by impregnation or spraying with solutions or suspensions which contain the named compound as an active ingredient. The active ingredient content can be between 1 and 30 g of active ingredient per liter of treatment liquid, depending on the application. Textile materials of both synthetic and natural origin are mostly protected against bacterial contamination by a content of 0.1 to 3% active ingredient. The active ingredient can be used together with other textile aids such as finishing agents, anti-crease treatments, etc.



   The use forms can correspond to the customary formulations of pesticides, for example agents which contain N-3,4-dicholrphenyl-N'-2-ethylhexyl- (1) -urea, optionally also additives such as carriers, solvents, diluents, dispersants -, wetting or adhesive agents etc. as well as other pesticides, e.g. B. fungicidal or fungistatic agents contain.



   The parts given in the following manufacturing instructions and in the example are parts by weight and the percentages are percentages by weight, unless otherwise stated.



      Production proposal rijt
37.6 parts of 3,4-dichlorophenyl isocyanate are added to a solution of 25.9 parts of 2-ethylhexyl (1) amine in 200 parts by volume of benzene. By adding 200 parts by volume of petroleum ether, the resulting N 3, 4-dichlorophenyl-N'-2-ethylhexyl (1) urea of the formula (1) is precipitated. The yield is approximately 57 parts.



  Melting point 65 to 660 C.



      Cl5H ON2Cl2 calcd: N 8.83 Q 22.35 found: N 8.70 C1 22.64
Antibacterial effect in the dilution test
A liquid and a 0.3% solution of the active ingredients in dimethyl sulfoxide are placed in tubes with sterile Brain-Heart Infusion Broth and dilution series are made up to tenfold with the solutions. By combining the two series the following continuous dilution series is obtained:
1000, 300, 100, 30, 10, 3ppm etc.



   The solutions are inoculated with the bacterium Staphylococcus aureus. It is then incubated for 48 hours at 370 ° C. (bacteriostasis).



   After a culture time of 24 hours, a loop is streaked out of the tube on glucose agar plates and incubated for 24 hours at 370 ° C. (bactericides).



   After the specified times, the limit concentration values are determined.



   Bacteriostasis 1 ppm
Bactericidal 1 ppm
example
Samples of 100 g cotton cretonne are impregnated with a 0.1% proprietary solution of N-3,4-dichlorophenyl-N'-2-ethylhexyl, (1) -urea in isopropanol at 200 ° C. on a padder and then with a 100 5 igen liquor uptake squeezed.



   Samples of 100 g of wool cheviot are treated in the same way
The fabrics dried at 30 to 400 C contain 0.1% active ingredient, based on their own weight.



   To test the effect against bacteria, discs of 10 mm diameter of the impregnated tissue (not watered and after EMPA watering) are placed on glucose agar plates which have been inoculated with Staphylococcus aureus. The plates are then incubated at 370 ° C. for 24 hours.

 

Claims (1)

Beurteilt wird einerseits die um die Rondellen auftretende Hemmzone (HZ in mm) und anderseits das unter den Rondellen mikroskopisch feststellbare Wachstum (W S) : ungewässert gewässert Substrat (mit 0, 1% Wirkstoff- HZ W HZ W gehalt) (mm) (%) (mm) (%) Baumwolle 2 0 2 0 Wolle 1 0 0 0 PATENTANSPRUCH Gebrauchsfertiges Mittel zur Bekämpfung von schädlichen Bakterien auf textilen Materialien, enthaltend als Wirkstoff N-3 ,4-Dichlorphenyl-N'-2-äffiyl hexyl-(1)-harnstoff der Formel EMI2.1 On the one hand, the inhibition zone (HZ in mm) and on the other hand the growth (WS) that can be microscopically observed under the washers is assessed: non-watered watered substrate (with 0.1% active ingredient HZ W HZ W content) (mm) (%) (mm) (%) Cotton 2 0 2 0 Wool 1 0 0 0 PATENT CLAIM Ready-to-use agent for combating harmful bacteria on textile materials, containing as active ingredient N-3, 4-dichlorophenyl-N'-2-affiyl hexyl- (1) -urea of the formula EMI2.1
CH41767A 1967-01-12 1967-01-12 Ready-to-use agent for combating harmful bacteria on textile materials CH467019A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
CH41767A CH467019A (en) 1967-01-12 1967-01-12 Ready-to-use agent for combating harmful bacteria on textile materials
CA008,471A CA961052A (en) 1967-01-12 1967-12-27 N-2-ethylhexyl-n'-aryl ureas and preparation containing them
US694121A US3592932A (en) 1967-01-12 1967-12-28 N-2-ethylhexyl-n'-aryl ureas as antibacterial agents
DE19681643848D DE1643848B1 (en) 1967-01-12 1968-01-03 N-2-AEthylhexyl-N'-arylureas and their use as bactericides
GB566/68A GB1173872A (en) 1967-01-12 1968-01-04 N-2-Ethylhexyl-N'-Aryl Ureas and Preparations containing them
IT34071/68A IT972013B (en) 1967-01-12 1968-01-10 BACTERICIDES BASED ON UREA COMPOUNDS AND PROCEDURE FOR PRODUCING SUCH COMPOUNDS
FR1575560D FR1575560A (en) 1967-01-12 1968-01-10
SE00348/68A SE332422B (en) 1967-01-12 1968-01-11
AT29268A AT279058B (en) 1967-01-12 1968-01-11 Means to fight harmful bacteria
BE709240D BE709240A (en) 1967-01-12 1968-01-11
NL6800445A NL6800445A (en) 1967-01-12 1968-01-11
ES0349159A ES349159A1 (en) 1967-01-12 1968-01-11 Procedure for preparing agents to combat harmful bacteria. (Machine-translation by Google Translate, not legally binding)
US00269686A US3813437A (en) 1967-01-12 1972-07-07 N-2-ethylhexyl-n'-aryl ureas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH41767A CH467019A (en) 1967-01-12 1967-01-12 Ready-to-use agent for combating harmful bacteria on textile materials

Publications (2)

Publication Number Publication Date
CH41767A4 CH41767A4 (en) 1968-08-30
CH467019A true CH467019A (en) 1969-02-28

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Application Number Title Priority Date Filing Date
CH41767A CH467019A (en) 1967-01-12 1967-01-12 Ready-to-use agent for combating harmful bacteria on textile materials

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CH41767A4 (en) 1968-08-30

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