CH372871A - Process for protecting textiles against fungal attack and rotting - Google Patents
Process for protecting textiles against fungal attack and rottingInfo
- Publication number
- CH372871A CH372871A CH7704559A CH7704559A CH372871A CH 372871 A CH372871 A CH 372871A CH 7704559 A CH7704559 A CH 7704559A CH 7704559 A CH7704559 A CH 7704559A CH 372871 A CH372871 A CH 372871A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- rotting
- fungal attack
- against fungal
- ones
- Prior art date
Links
- 230000002538 fungal effect Effects 0.000 title claims description 9
- 239000004753 textile Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 9
- OWYZMSKLLKTUGB-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3h-1,3-benzoxazol-2-one Chemical compound ClC1=C(Cl)C(Cl)=C2OC(=O)NC2=C1Cl OWYZMSKLLKTUGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000012459 cleaning agent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- 241000228143 Penicillium Species 0.000 description 2
- 241001123663 Penicillium expansum Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical class NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
- DEUSSOTUEGORRC-UHFFFAOYSA-N 4,5,7-trichloro-3h-1,3-benzoxazol-2-one Chemical compound ClC1=CC(Cl)=C2OC(=O)NC2=C1Cl DEUSSOTUEGORRC-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241001515917 Chaetomium globosum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000322338 Loeseliastrum Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000122123 Penicillium italicum Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 241000192023 Sarcina Species 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 241001279364 Stachybotrys chartarum Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000129 anionic group Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019351 sodium silicates Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/343—Heterocyclic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/38—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zum Schützen von Textilien gegen Pilzbefall und Verrottung Die vorliegende Erfindung betrifft ein Verfahren zum Schützen von Textilien gegen Pilzbefall und Verrottung.
Es sind aus der schweizerischen Patentschrift Nr.337359 di- oder trihalogenierte 2,3-Dihydro- benzoxazol-2-one bekannt, welche gegen Fungi und Bakterien wirksam sind.
Es wurde nun gefunden, @dass man Textilien gegen Pilzbefall und Verrottung dauerhaft schützen kann, wenn man dazu tetrahalogenierte 2,3-D.ihydro- benzoxazol-2-one der Formel
EMI0001.0020
worin X1, X2, X3 und X4 Halogenatome bedeuten, verwendet,
welche gegenüber den in der schweize rischen Patentschrift Nr.337359beschriebenen di- oder trihalagenierten 2,3-Dihydrobenzoxazol-2-onen eine grössere Wirksamkeit ,gegen Fungi und Bakte rien aufweisen.
Als erfindungsgemäss zu verwendende Wirksub stanzen kommen am Benzolring in 4,5,6,7-Stellung tetrahalogan-substituierte 2,3-Dihydro-benzoxazol-2- one und die tautomeren 2-Hydroxy-benzoxazole bzw. deren Salze, insbesondere die Alkalimetallsalze oder auch die Ammoniumsalze, in Betracht.
Die erfindungsgemäss zur Verwendung gelangen den ringhalogenierten 2,3-Dihydro-benzoxazol-2-one erhält man beispielsweise aus ringhalogenierten 2-Aminophenolen bei der Umsetzung mit Phosgen. Gegebenenfalls kann man Halogen auch erst nach träglich in 2,3-Dihydro-benzoxazol-2-one einführen, beispielsweise in 2,
3-Dihydro-#benzoxazol-2-one mit freier 6-Stellung. Sie stellen im allgemeinen farblose bis schwach gelblich gefärbte Körper dar, die in heissem Wasser eine meist geringe Löslichkeit auf weisen.
Viel leichter löslich sind die Alkalimetallsalze, beispielsweise die Lithium-, Natrium- und Kalium- salze, ebenso ,die Magnesium- oder Calciums,alze, fer ner die Ammoniumsalze starker anorganischer oder organischer Stickstoffbasen. Die erfindungsgemäss zu verwendenden halogenierten 2,3-Dihydro-benzoxazol- 2-one lassen :
sich dank dieser Löslichkeitseigenschaf- ten und wegen ihrer verhältnismässig guten Stabilität gegen Alkalien Textilbehandlungsflotten einverleiben, insbesondere oberflächenaktiven Waschflotten, die neben synthetischen waschaktiven Substanzen und/ oder neben Seifen im herkömmlichen Sinn ,auch ge bräuchliche Füllstoffe, wie Natriumcarbonat,
Na triumsilicate und Alkali-mono- und -polyphosphate, sowie weitere in Waschmitteln übliche Ingredienzien enthalten können. Man kann sie solchen Wasch- und Reinigungsmitteln, wie auch der Seife, direkt zu mischen und erhält mit den so zusammengesetzten Reinigungsmitteln Waschflotten,
welche das damit behandelte Material vor Pilzbefall und Pilzschäden schützen. Die ;genügende Löslichkeit der Wirksub- stanzen in organischen Lösungsmitteln, wie sie in der sogenannten Trockenreinigung Verwendung finden, erlaubt ihre Anwendung in solchen aus aliphatischen oder aromatischen,
gegebenenfalls chlorierten Kohlen wasserstoffen bestehenden und meist auch öllösliche Kalisalze von anionaktiven Netz- und Reinigungs mitteln enthaltenden Trockenreinigungsmitteln.
Als Wirkstoffe werden beispielsweise. das 4,5,6,7- Tetrachlor - 2,3 - dihydro - benzoxazol - 2 - an und das 6-Brom-4, 5,7-trichlor- <B>2,3</B> -dihydro@benzoxazol- 2 -on verwendet. Bevorzugt wird seiner leichten Zugänglich- keit wegen das 4,5,6,7-Tetrachlor-2,3-dihydrobenz- oxazol-2-on.
Das Aufbringen der fungiziden Wirkstoffe auf das zu schützende organische Textilmaterial geschieht meist durch Besprühen oder durch Imprägnieren mit organischen wässrigen .oder wässrig-alkalischen Lösun gen der Wirkstoffe oder mit Wasch-, Reinigungs- oder Spülflotten,
welche Wirkstoffe gelöst oder disper- giert enthalten. Gehalte von 0,5 bis 10 g Wirk substanz im Liter Behandlungsflotte ,genügen im all gemeinen für einen wirksamen Schutz des behandelten Materials. Gegebenenfalls kann die Waschfestigkeit des Fungiziden Mittels auf dem behandelten Material durch Nachbehandlung mit Schwermetall abgebenden Mitteln noch erhöht werden.
Als Schwermetall ab gebende Mittel können beispielsweise Kupfersalz ver- wendet werden.
Im folgenden Beispiel bedeuten Teile, sofern nichts anderes ausdrücklich vermerkt ist, Gewichts teile. Die Temperaturen sind in Celsiusgraden ange geben. Gewichtsteile verhalten sich zu Volumteilen wie g zu cm3.
<I>Beispiel</I> Man löst 20 Teile 4,5,6,7-Tetrachlor-2,3-dihydro- benzoxazol-2-on unter Zusatz von 10 Teilen 30o/aiger Natronlau @ge in 400 Volumteilen Äthylenglykol-mono- methyläther und stellt mit dieser Stammlösung unter Verdünnung mit Wasser eine Behandlungsflotte her, welche 0,5g Wirksubstanz im Liter enthält.
Mit dieser Behandlungsflotte wird Baumwollkaliko 30 Minuten bei 40 im Flottenverhältnis 1 : 10 behan- delt, auf 72 % Gewichtszunahme abgeschleudert und kalt getrocknet.
Das so behandelte Material ist gegen Stockfleckenbildung und Verrottung geschützt, wie folgende Prüfungen zeigen: <I>a)</I> Stockfleckentest Kreisförmige Gewebeausschnitte von 9 cm Durch messer werden in Petrischalen einem Agarnährboden aufgelegt und mit der Suspension einer Sporen- mischung von Penicillium expansum, Stachybotrys atra und Aspexgillus niger,
welche 40000 Keime im cm3 enthält, beimpft. Die geschlossenen Petrischalen werden 10 Tage bei 281 bebrütet und dann die Anzahl der Pilzkolonien ausgezählt.
<I>b)</I> Verrottungstest Kreisförmige Gewebeausschnitte von 3,8 cm Durchmesser werden in Petrischalen auf einen Agar- nährboden aufgelegt, welcher mit 0,5 cm3 einer Spo- rensuspension von Chaetomium globosum beimpft ist, welche ungefähr<B>700000</B> Keime pro cm3 enthält.
Man bebrütet 10 Tage bei 281, unterbricht dann die Keimentwicklung mit einer alkoholischen Thymol- lösung, spült die Stoffabschnitte und trocknet sie. Dann wird im Durchstossapparat nach R. Bu.rgess (Micro@organismus and Textileis: The Journal of Applie,d Bacteriology 17, 241 (1954)] auf Durch stossfestigkeit geprüft.
Beim Verrottungstest wird der Durchschnittswert von 10 Proben benützt. Die Festigkeit wird in 11/o der ursprünglichen Gewebefestigkeit angegeben. Es wur den folgende Resultate erhalten:
EMI0002.0121
Gehalt <SEP> der <SEP> Stockfleckentest
<tb> Verrottungstest
<tb> Substanz <SEP> Behandlungsflotte <SEP> Anzahl <SEP> Pilzkolonien
<tb> Durchstossfestigkeit
<tb> g/Liter <SEP> Pen. <SEP> exp. <SEP> I <SEP> Stach. <SEP> a. <SEP> I <SEP> Asp. <SEP> n.
<tb> nach <SEP> Beispiel <SEP> 1 <SEP> 0,5 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> <B>9311/o</B>
<tb> Blindversuch <SEP> 0 <SEP> 00 <SEP> 00 <SEP> 00 <SEP> <B>0"/o</B> <I>Vergleichsversuch</I> Vergleich der Wirksamkeit bei Bakterien und Fungi von den Wirksubstanzen I 4,5,7-Trichlor-2,3-dihydrobenzoxazol-2-on und 1I 4,5,6,7-Tetrachlor-2,3-dihydro-benzoxazol- 2-on.
<I>Versuchsanordnung</I> Die Prüfungen werden im Prinzip nach der von John M. Leonard und Virginia L. Brackford in Fungus-Inhibitive Properties of Bromo-Acetamides, Journal of Bacteriology, 57 p.
339, March 1949 be schriebenen Methode durchgeführt, indem der Wirk- stoff in abgestuften Konzentrationen dem Nährboden zugesetzt wird.
Für jeden zu prüfenden Organismus wird der geeignete Nährboden nämlich für: Staphylo- cocous aureus SG 511, Bacillus mesentiericus Sarcina spec., Staphylococcus aureus (Geigy), Penicillium italicum, Fusarium oxysporum,
Candida albicans, Penicillium expansum, gewählt.
Der Wirkstoff wird in Äthylenglykohnonome@thyl- äther - im Verhältnis von 1 Teil Wirkstoff zu 20 Tei len Lösungsmittel - vorgelöst und in der Konzentra tionsabstufung 300 ppm, 100 ppm, 30 ppm, 10 ppm, 3 ppm,
1 ppm dem flüssigen Nähragar zugesetzt. Die Nährböden werden in Platten gegossen und nach dem Erkalten der Platten die angeführten Bakterien und die Pilze aufgeimpft. Die Bebrütung erfolgt bei den Bakterien während 48 Stunden bei 37 C, bei den Pilzen 5 Tage bei 28 C;
daraufhin wird registriert, bei welchen Mindestkonzentrationen der einzelnem Wirkstoffe kein Wachstum der Organismen erfolgt ist. Die in den Tabellen 1 und 2 angeführten Zahlen geben die Mindestkonzentration in ppm an,
bei wel cher kein Wachstum der betreffenden Mikroorga- nismen mehr erfolgt.
EMI0003.0016
<I>Tabelle <SEP> 1</I>
<tb> <I>Wirkungsgrenze <SEP> gegen <SEP> verschiedene <SEP> Bakterien</I>
<tb> Staphylococcus <SEP> Bacillus <SEP> Stäphylococcus
<tb> Substanz <SEP> Sarina <SEP> spec.
<tb> aureus <SEP> SG <SEP> 511 <SEP> mesentiericus <SEP> aureus <SEP> (Geigy)
<tb> I <SEP> 30 <SEP> 10 <SEP> 30 <SEP> 30
<tb> II <SEP> 3 <SEP> 3 <SEP> 3 <SEP> 3
<tb> <I>Tabelle <SEP> 2</I>
<tb> <I>Wirkungsgrenze <SEP> gegen <SEP> verschiedene <SEP> Fungi</I>
<tb> Penicillium <SEP> Penicillium <SEP> Fusarium <SEP> Candida
<tb> S <SEP> tanz <SEP> ubs <SEP> expansum
<tb> italicum <SEP> oxysporium
<tb> albicans
<tb> I <SEP> 10 <SEP> 30 <SEP> 30 <SEP> 30
<tb> 1I <SEP> 3 <SEP> 10 <SEP> 10 <SEP> 10
Method for protecting textiles against fungal attack and rotting The present invention relates to a method for protecting textiles against fungal attack and rotting.
There are known from Swiss Patent No. 337359 di- or trihalogenated 2,3-dihydrobenzoxazol-2-ones which are effective against fungi and bacteria.
It has now been found that textiles can be permanently protected against fungal attack and rotting by adding tetrahalogenated 2,3-dihydrobenzoxazol-2-ones of the formula
EMI0001.0020
wherein X1, X2, X3 and X4 are halogen atoms, used,
which, compared to the di- or trihalogenated 2,3-dihydrobenzoxazol-2-ones described in Swiss patent specification No. 337359, are more effective against fungi and bacteria.
As active substances to be used according to the invention come on the benzene ring in the 4,5,6,7-position tetrahalo-substituted 2,3-dihydro-benzoxazol-2-ones and the tautomeric 2-hydroxy-benzoxazoles or their salts, in particular the alkali metal salts or also the ammonium salts.
The ring-halogenated 2,3-dihydro-benzoxazol-2-ones used according to the invention are obtained, for example, from ring-halogenated 2-aminophenols in the reaction with phosgene. If necessary, halogen can also be introduced into 2,3-dihydro-benzoxazol-2-ones afterwards, for example in 2,
3-Dihydro- #benzoxazol-2-ones with free 6-position. They are generally colorless to pale yellowish colored bodies which are mostly poor in solubility in hot water.
The alkali metal salts, for example the lithium, sodium and potassium salts, as well as the magnesium or calcium salts, and also the ammonium salts of strong inorganic or organic nitrogen bases, are much more readily soluble. The halogenated 2,3-dihydro-benzoxazol-2-ones to be used according to the invention leave:
Thanks to these solubility properties and because of their relatively good stability against alkalis, textile treatment liquors are incorporated, in particular surface-active washing liquors which, in addition to synthetic detergent substances and / or in addition to soaps in the conventional sense, also include common fillers such as sodium carbonate,
Sodium silicates and alkali mono- and polyphosphates, as well as other ingredients common in detergents, may contain. They can be mixed directly with such detergents and cleaning agents, as well as the soap, and with the cleaning agents composed in this way, washing liquors are obtained.
which protect the material treated with it from fungal attack and fungal damage. The sufficient solubility of the active substances in organic solvents, such as those used in so-called dry cleaning, allows their use in those made from aliphatic or aromatic,
optionally chlorinated hydrocarbons and mostly also oil-soluble potassium salts of anionic wetting agents and cleaning agents containing dry cleaning agents.
The active ingredients are, for example. the 4,5,6,7-tetrachloro-2,3-dihydro-benzoxazole-2-an and the 6-bromo-4,5,7-trichloro-2,3-dihydro @ benzoxazole - 2 -on used. 4,5,6,7-tetrachloro-2,3-dihydrobenzoxazol-2-one is preferred because of its easy accessibility.
The fungicidal active ingredients are usually applied to the organic textile material to be protected by spraying or impregnating with organic aqueous or aqueous-alkaline solutions of the active ingredients or with washing, cleaning or rinsing liquors,
which active ingredients contain dissolved or dispersed. Contents of 0.5 to 10 g of active substance per liter of treatment liquor are generally sufficient for effective protection of the treated material. If necessary, the resistance to washing of the fungicidal agent on the treated material can be increased by post-treatment with agents that release heavy metals.
Copper salt, for example, can be used as a heavy metal releasing agent.
In the following example, unless expressly stated otherwise, parts mean parts by weight. The temperatures are given in degrees Celsius. Parts by weight relate to parts by volume as g to cm3.
<I> Example </I> 20 parts of 4,5,6,7-tetrachloro-2,3-dihydrobenzoxazol-2-one are dissolved with the addition of 10 parts of 30% sodium hydroxide solution in 400 parts by volume of mono-ethylene glycol - methyl ether and uses this stock solution by diluting it with water to produce a treatment liquor which contains 0.5g of active substance per liter.
With this treatment liquor, cotton calico is treated for 30 minutes at 40 in a liquor ratio 1:10, spun off to 72% weight gain and dried cold.
The material treated in this way is protected against mold staining and rotting, as the following tests show: <I> a) </I> Mold stain test Circular tissue sections 9 cm in diameter are placed on an agar medium in Petri dishes and mixed with the suspension of a spore mixture of Penicillium expansum , Stachybotrys atra and Aspexgillus niger,
which contains 40,000 germs per cm3. The closed Petri dishes are incubated for 10 days at 281 and then the number of fungal colonies is counted.
<I> b) </I> Decomposition test Circular tissue sections 3.8 cm in diameter are placed in Petri dishes on an agar medium which is inoculated with 0.5 cm 3 of a spore suspension of Chaetomium globosum, which is approximately 700,000 </B> Contains germs per cm3.
Incubate for 10 days at 281, then interrupt the development of germs with an alcoholic thymol solution, rinse the fabric sections and dry them. The puncture resistance is then tested in the puncture apparatus according to R. Bu.rgess (Micro @ organism and Textileis: The Journal of Applie, d Bacteriology 17, 241 (1954)].
The rotting test uses the average value of 10 samples. The strength is given in 11 / o of the original fabric strength. The following results were obtained:
EMI0002.0121
Salary <SEP> the <SEP> mold stain test
<tb> Rot test
<tb> substance <SEP> treatment liquor <SEP> number <SEP> fungal colonies
<tb> puncture resistance
<tb> g / liter <SEP> pen. <SEP> exp. <SEP> I <SEP> Stach. <SEP> a. <SEP> I <SEP> Asp. <SEP> n.
<tb> according to <SEP> example <SEP> 1 <SEP> 0.5 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> <B> 9311 / o </B>
<tb> Blind test <SEP> 0 <SEP> 00 <SEP> 00 <SEP> 00 <SEP> <B> 0 "/ o </B> <I> Comparative test </I> Comparison of the effectiveness in bacteria and fungi from the active substances I 4,5,7-trichloro-2,3-dihydrobenzoxazol-2-one and 1I 4,5,6,7-tetrachloro-2,3-dihydro-benzoxazol-2-one.
<I> Test arrangement </I> The tests are carried out in principle according to that of John M. Leonard and Virginia L. Brackford in Fungus-Inhibitive Properties of Bromo-Acetamides, Journal of Bacteriology, 57 p.
339, March 1949, by adding the active ingredient to the nutrient medium in graduated concentrations.
For each organism to be tested, the suitable culture medium is namely for: Staphylococous aureus SG 511, Bacillus mesentiericus Sarcina spec., Staphylococcus aureus (Geigy), Penicillium italicum, Fusarium oxysporum,
Candida albicans, Penicillium expansum, were chosen.
The active ingredient is pre-dissolved in Äthylenglykohnonome @ ethyl ether - in a ratio of 1 part active ingredient to 20 parts solvent - and in the concentration graduation 300 ppm, 100 ppm, 30 ppm, 10 ppm, 3 ppm,
1 ppm added to the liquid nutrient agar. The culture media are poured into plates and after the plates have cooled down, the bacteria and fungi are inoculated. The bacteria are incubated for 48 hours at 37 C, for the fungi for 5 days at 28 C;
it is then recorded at which minimum concentrations of the individual active ingredients no growth of the organisms occurred. The figures given in Tables 1 and 2 indicate the minimum concentration in ppm,
at which there is no longer any growth of the microorganisms concerned.
EMI0003.0016
<I> Table <SEP> 1 </I>
<tb> <I> Limit of effectiveness <SEP> against <SEP> various <SEP> bacteria </I>
<tb> Staphylococcus <SEP> Bacillus <SEP> Stäphylococcus
<tb> substance <SEP> Sarina <SEP> spec.
<tb> aureus <SEP> SG <SEP> 511 <SEP> mesentiericus <SEP> aureus <SEP> (Geigy)
<tb> I <SEP> 30 <SEP> 10 <SEP> 30 <SEP> 30
<tb> II <SEP> 3 <SEP> 3 <SEP> 3 <SEP> 3
<tb> <I> Table <SEP> 2 </I>
<tb> <I> Limit of effectiveness <SEP> against <SEP> various <SEP> fungi </I>
<tb> Penicillium <SEP> Penicillium <SEP> Fusarium <SEP> Candida
<tb> S <SEP> dance <SEP> ubs <SEP> expansum
<tb> italicum <SEP> oxysporium
<tb> albicans
<tb> I <SEP> 10 <SEP> 30 <SEP> 30 <SEP> 30
<tb> 1I <SEP> 3 <SEP> 10 <SEP> 10 <SEP> 10
Claims (1)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL254931D NL254931A (en) | 1955-07-20 | ||
| NL95172D NL95172C (en) | 1955-07-20 | ||
| NL120102D NL120102C (en) | 1955-07-20 | ||
| BE594099D BE594099A (en) | 1955-07-20 | ||
| NL209088D NL209088A (en) | 1955-07-20 | ||
| BE549699D BE549699A (en) | 1955-07-20 | ||
| CH337359D CH337359A (en) | 1955-07-20 | 1955-07-20 | Method for combating fungi and for protecting organic materials and objects from fungal attack |
| GB22364/56A GB830902A (en) | 1955-07-20 | 1956-07-19 | Improvements relating to fungicidal compositions and their use |
| FR1156972D FR1156972A (en) | 1955-07-20 | 1956-07-19 | Fungicidal agents and their industrial applications |
| DEG20127A DE1023627B (en) | 1955-07-20 | 1956-07-19 | Fungicides |
| US756515A US2922794A (en) | 1955-07-20 | 1958-08-22 | 5, 6-dichlorobenzoxazolinone-2 and 5, 6-dichlorobenzothiazolinone-2 |
| CH7704559A CH372871A (en) | 1959-10-01 | 1959-10-01 | Process for protecting textiles against fungal attack and rotting |
| FR835946A FR78656E (en) | 1955-07-20 | 1960-08-16 | Fungicidal agents and their industrial applications |
| DEG30305A DE1147007B (en) | 1955-07-20 | 1960-08-16 | Fungicides |
| US49818A US3190797A (en) | 1955-07-20 | 1960-08-16 | Biocidal agents |
| GB28320/60A GB956571A (en) | 1955-07-20 | 1960-08-16 | Improvements relating to fungicidal compositions and their use |
| MY196186A MY6100086A (en) | 1955-07-20 | 1961-12-31 | Improvements relating to fungicidal compositions and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7704559A CH372871A (en) | 1959-10-01 | 1959-10-01 | Process for protecting textiles against fungal attack and rotting |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CH7704559A4 CH7704559A4 (en) | 1963-07-15 |
| CH372871A true CH372871A (en) | 1963-12-14 |
Family
ID=4535353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7704559A CH372871A (en) | 1955-07-20 | 1959-10-01 | Process for protecting textiles against fungal attack and rotting |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH372871A (en) |
-
1959
- 1959-10-01 CH CH7704559A patent/CH372871A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH7704559A4 (en) | 1963-07-15 |
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