DE1090382B - Bactericidal agent - Google Patents
Bactericidal agentInfo
- Publication number
- DE1090382B DE1090382B DEM38781A DEM0038781A DE1090382B DE 1090382 B DE1090382 B DE 1090382B DE M38781 A DEM38781 A DE M38781A DE M0038781 A DEM0038781 A DE M0038781A DE 1090382 B DE1090382 B DE 1090382B
- Authority
- DE
- Germany
- Prior art keywords
- diphenylamine
- hydroxy
- bactericidal
- bactericidal agent
- bacteria
- 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.)
- Pending
Links
- 239000003899 bactericide agent Substances 0.000 title claims description 9
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000945 filler Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 241000894006 Bacteria Species 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000645 desinfectant Substances 0.000 description 5
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 241000295644 Staphylococcaceae Species 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YRUPBAWWCPVHFT-UHFFFAOYSA-N 4-(4-hydroxyanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C(O)C=C1 YRUPBAWWCPVHFT-UHFFFAOYSA-N 0.000 description 2
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229960002242 chlorocresol Drugs 0.000 description 2
- 229960005443 chloroxylenol Drugs 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 229940044949 eucalyptus oil Drugs 0.000 description 2
- 239000010642 eucalyptus oil Substances 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JSQGOXTYKZBABW-UHFFFAOYSA-N 3-(3-hydroxyanilino)phenol Chemical compound OC1=CC=CC(NC=2C=C(O)C=CC=2)=C1 JSQGOXTYKZBABW-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241000304886 Bacilli Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241001112696 Clostridia Species 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Description
Der Erfindung liegt die Aufgabe zugrunde, ein baktericides Mittel zu entwickeln, welches bei breitem antibakteriellem, Wirkungsspektrum gute keimabtötende Eigenschaften aufweist. Es wurde gefunden, daß p-Hydroxy-diphenylamin diese Eigenschaften besitzt. Diese Tatsache war überraschend, da die meisten phenoh'schen Verbindungen, die heute als Desinfektionsmittel benutzt werden, diese Eigenschaften nur in geringem Umfang zeigen, insbesondere tritt bei diesen Verbindungen eine starke Reduzierung der keimabtötenden Wirkung im eiweißhaltigen Milieu ein.The invention is based on the object of developing a bactericidal agent which, with a broad spectrum of antibacterial activity, has good germicidal properties Has properties. It has been found that p-hydroxy-diphenylamine has these properties. This fact was surprising since most of the phenolic compounds are used today as disinfectants are used to show these properties only to a small extent, especially occurs with these compounds a strong reduction in the germicidal effect in the protein-containing environment.
Gegenstand der Erfindung ist dementsprechend ein baktericides Mittel mit einem Gehalt an p-Hydroxydiphenylamin der FormelThe invention accordingly relates to a bactericidal agent containing p-hydroxydiphenylamine the formula
HO-HO-
-NH--NH-
neben üblichen Träger- und Füllstoffen.in addition to the usual carriers and fillers.
p-Hydroxy-diphenylamin kann auch in Kombination mit anderen bekannten baktericiden Mitteln angewendet werden, z. B. in Mischung mit 2,2'-Methylen-bis-3,4,6-trichlorphenol, Kresolen, Xylenolen, Estern der p-Hydroxybenzoesäure oder Invertseifen.p-Hydroxy-diphenylamine can also be used in combination with other known bactericidal agents be e.g. B. in a mixture with 2,2'-methylene-bis-3,4,6-trichlorophenol, cresols, xylenols, esters of p-hydroxybenzoic acid or invert soaps.
p-Hydroxy-diphenylamin kann z. B. hergestellt werden durch Kondensation von Hydrochinon mit Anilin, gegebenenfalls in Anwesenheit von Calciumchlorid, sowie bei erhöhter Temperatur und unter erhöhtem Druck (Journal of the Chemical Society, London, 1927, S. 2856;· Berichte der Deutschen Chemischen Gesellschaft, Bd. 16 [1883], S. 2786; Bd. 17 [1884], S. 2431).p-Hydroxy-diphenylamine can e.g. B. be prepared by condensation of hydroquinone with aniline, optionally in the presence of calcium chloride, as well as at elevated temperature and pressure (Journal of the Chemical Society, London, 1927, p. 2856; · Reports of the German Chemical Society, Vol. 16 [1883], P. 2786; Vol. 17 [1884], p. 2431).
Die Verbindung läßt sich zu allen für baktericide Mittel üblichen Anwendungsformen verarbeiten. Man kann sie z. B. verwenden in alkoholischer Lösung, als Streupulver in Verbindung mit inerten Füllstoffen oder als Pastille, z. B. mit Stärkemehl verpreßt, als Emulsion mit einem der üblichen Netzmittel oder als Lösung, die aus den üblichen Aerosol-Sprühdosen versprüht werden kann.The compound can be processed into all application forms customary for bactericidal agents. You can z. B. use in alcoholic solution, as a powder in connection with inert fillers or as a lozenge, z. B. pressed with starch, as an emulsion with one of the usual wetting agents or as a solution that consists of the conventional aerosol spray cans can be sprayed.
p-Hydroxy-diphenylamin zeigt gegenüber Bakterien einen etwa zehnmal größeren Abtötungseffekt in 10°/0iger Serumlösung als die bekannten chlorkresol- und/oder chlorxylenolhaltigen Desinfektionsmittel. Selbst die bei starken Verdünnungen noch auftretende baktericide Wirkung des 2,2'-Methylen-bis-3,4,6-trichlorphenols gegen pyogene Kokken wird vom p-Hydroxy-diphenylamin erreicht und zum Teil sogar noch übertroffen. Bei der Prüfung der desinfizierenden Wirkung (Abtötung von an glatten bzw. rauhen Oberflächen angetrockneten Keimen) zeigte sich, daß durch 1- bis 0,50/0ige Lösungen nicht nur vegetative Keimformen, sondern auch resistente Sporenformen von Bazillen und Chlostridien nach relativ kurzer Einwirkungszeit sicher abgetötet werden.p-hydroxy-diphenylamine shows to bacteria an approximately ten times larger killing effect at 10 ° / 0 hydrochloric serum solution than the known chlorkresol- and / or chlorxylenolhaltigen disinfectant. Even the bactericidal effect of 2,2'-methylene-bis-3,4,6-trichlorophenol against pyogenic cocci, which still occurs at high dilutions, is achieved and in some cases even exceeded by p-hydroxydiphenylamine. In examining the disinfecting effect (killing on smooth and porous surfaces dried bacteria) showed that by 1- to 0.5 0/0 by weight solutions not only seed vegetative forms but also resistant spore forming bacilli and clostridia after a relatively short Exposure time can be safely killed.
Durch den bei Desinfektionsmittehi üblichen Zusatz von Netzmitteln kann die Wirkung verstärkt werden.The effect can be increased by adding wetting agents, which is customary with disinfectants.
Anmelder:Applicant:
E. Merck Aktiengesellschaft,
Darmstadt, Frankfurter Str. 250E. Merck Aktiengesellschaft,
Darmstadt, Frankfurter Str. 250
Dr. Ernst Jacobi und Dr. Dietrich Erdmann, Darmstadt, sind als Erfinder genannt wordenDr. Ernst Jacobi and Dr. Dietrich Erdmann, Darmstadt, have been named as the inventor
22
Der in den üblichen Anwendungskonzentrationen geringe Eigengeruch und -geschmack des p-Hydroxydiphenylamins sowie die Tatsache, daß sich die SubstanzThe low inherent odor and taste of p-hydroxydiphenylamine in the usual use concentrations as well as the fact that the substance
ao in wasserfreiem Milieu nur gering verfärbt, erlaubt ihre Verwendung als Desinfektionsmittel sowohl im schwach alkalischen als auch im schwach sauren Bereich.ao only slightly discolored in an anhydrous environment, allows its use as a disinfectant both in the weak alkaline as well as weakly acidic range.
Im »erschwerten« Suspensionsversuch (Zusatz von 10 °/0 Serum) bei einer Temperatur von 25° C werden bei einer Konzentration von 1:2 000 durch das p-Hydroxy-diphenylamin CoIi- und Pyocyaneusbakterien nach spätestens 30minutiger Einwirkungszeit abgetötet. Zur Erreichung des gleichen baktericiden Effektes muß Phenol, Chlorkresol oder Chlorxylenol in einer Konzentration von 1: 200 angewendet werden.In "difficult" suspension test (Addition of 10 ° / 0 serum) at a temperature of 25 ° C at a concentration of 1: 2000 killed by the p-hydroxy-diphenylamine and CoII Pyocyaneusbakterien 30minutiger latest after exposure. To achieve the same bactericidal effect, phenol, chlorocresol or chloroxylenol must be used in a concentration of 1: 200.
In Verdünnung von 1:10 000 wirkt p-Hydroxy-diphenylamin unter gleichen Versuchsbedingungen gegenüber CoIi- und Pyocyaneusbakterien sowie pyogenen Staphylokokken wesentlich stärker als Phenol oder Chlorkresol oder Chlorxylenol bei einer Konzentration von 1:1 000 wirken.In a dilution of 1:10 000 p-Hydroxydiphenylamine works under the same test conditions against Coli and Pyocyaneus bacteria as well as pyogenic Staphylococci much stronger than phenol or chlorocresol or chloroxylenol at one concentration of 1: 1 000 work.
Dem p-Hydroxy-diphenylamin konstitutionell nahestehende Verbindungen sind in der deutschen Patentschrift 554 817 beschrieben. Die dort genannten Verbindüngen sind, soweit sie hergestellt werden konnten, weniger stark bakterizid wirksam als p-Hydroxy-diphenylamin. So tötet p-Hydroxy-diphenylamin CoH- und Pyocyaneusbakterien sowie Staphylokokken und Streptokokken, in einer Konzentration von 1:1000 angewendet, innerhalb von 10 Minuten ab. Bis-(4-hydroxyphenyl)-amin (vgl. deutsche Patentschrift 554 817) benötigt dagegen, wenn es in derselben Konzentration angewendet wird, zur Abtötung von CoIi- und Pyocyaneusbakterien sowie von Staphylokokken 2 Stunden und von Streptokokken 6 Stunden. Bis-(3-hydroxyphenyl)-amin (vgl. deutsche Patentschrift 554 817) benötigt, ebenfalls in einer Konzentration von 1 :1000 angewendet, zum Abtöten von Colibakterien 4 Stunden, von Pyocyaneusbakterien und Staphylokokken 6 Stunden und vonCompounds which are constitutionally related to p-hydroxy-diphenylamine are described in the German patent 554 817. The connections named there are, as far as they could be established, less bactericidal than p-hydroxy-diphenylamine. So p-hydroxy-diphenylamine kills CoH and Pyocyaneus bacteria as well as staphylococci and streptococci, used in a concentration of 1: 1000, within 10 minutes. Bis (4-hydroxyphenyl) amine (cf. German Patent 554 817), on the other hand, requires when used in the same concentration, to kill Coli and Pyocyaneus bacteria as well as staphylococci 2 hours and streptococci 6 hours. Bis (3-hydroxyphenyl) amine (cf. German patent 554 817), also used in a concentration of 1: 1000, for Killing of coli bacteria 4 hours, of pyocyanic bacteria and staphylococci 6 hours and of
009 610/339009 610/339
Streptokokken 24 Stunden. Diese Vergleichsversuche wurden bei einer Temperatur von 22° C durchgeführt.Strep 24 hours. These comparative tests were carried out at a temperature of 22 ° C.
In der USA.-Patentschrift 2220981 wird unter anderem p-Hydroxy-diphenylamin-borat als fungizid wirksame Verbindung bezeichnet. Dieser Patentschrift ist indessen nicht zu entnehmen, daß das freie p-Hydroxy-diphenylamin eine stark bakterizid wirkende Verbindung ist.In U.S. Pat. No. 2220981, among other things p-Hydroxy-diphenylamine-borate referred to as a fungicidally active compound. This patent is meanwhile it cannot be seen that the free p-hydroxy-diphenylamine is a strong bactericidal compound.
Mit der Erfindung wird dementsprechend ein neues baktericides Mittel offenbart, das in seiner Wirkungsbreite und seiner Wirkungsintensität den besten bisher bekannten baktericiden Mitteln überlegen ist und das sich nach einfachen Methoden herstellen läßt.The invention accordingly discloses a new bactericidal agent which, in its breadth of action and its intensity of action is superior to the best bactericidal agents known to date and that itself can be produced by simple methods.
1. Bakterieide Lösung.
Eine Mischung von1. Bacterial solution.
A mix of
25 Teilen p-Hydroxy-diphenylamin,25 parts of p-hydroxy-diphenylamine,
10 Teilen Butylacetat,10 parts of butyl acetate,
10 Teilen Dimethylformamid,10 parts of dimethylformamide,
10 Teilen Äthylenglykolmonoäthyläther,10 parts of ethylene glycol monoethyl ether,
35 Teilen Xylol,35 parts xylene,
5 Teilen Wasser,5 parts of water,
5 Teilen Diäthanolaminaralkylsulfonat5 parts of diethanol amine aralkyl sulfonate
wird in 10- bis 30%iger wäßriger Lösung als Desinfektionsmittel angewendet.is used as a disinfectant in 10 to 30% aqueous solution applied.
2. Baktericider Puder.2. Bactericidal powder.
50 kg Talkum werden mit50 kg of talc are added
1,5 kg p-Hydroxy-diphenylamin mit Hilfe von Aceton imprägniert und mit1.5 kg of p-hydroxy-diphenylamine impregnated with the help of acetone and with
1,5 kg Zinkstearat und
47 kg Talkum vermischt.1.5 kg zinc stearate and
47 kg of talc mixed.
Das Präparat, das auch noch parfümiert und mit hautpflegenden Zusätzen versehen werden kann, ist als baktericider Puder anwendbar.The preparation, which can also be perfumed and provided with skin-care additives, is as bactericidal powder applicable.
3. Bakterieide Tablette.3. Bacterial both tablet.
0,5 kg p-Hydroxy-diphenylamin,0.5 kg p-hydroxy-diphenylamine,
0,5 kg Polyvinylpyrrolidon,0.5 kg polyvinylpyrrolidone,
1,0 kg Ascorbinsäure,1.0 kg ascorbic acid,
2,0 kg Sorbit,2.0 kg sorbitol,
2,0 kg Eukalyptusöl,2.0 kg eucalyptus oil,
2,0 kg Ammoniumchlorid,
25,0 kg Harnstoff,
47,0 kg Lactose
werden mit Äthanol granuliert und in noch schwach2.0 kg ammonium chloride,
25.0 kg urea,
47.0 kg of lactose
are granulated with ethanol and in still weak
äthanolfeuchtem Zustand zu Tabletten verpreßt, die sowohl zum Lutschen als auch zum Gurgeln verwendbar sind.In the ethanol-moist state, compressed into tablets, which can be used both for sucking and for gargling are.
4. Bakterieide Sprühlösung.4. Bacteria and spray solution.
2 g p-Hydroxy-diphenylamin,2 g p-hydroxy-diphenylamine,
1 g Conifernenöl,1 g conifer oil,
2 g Polypropylenglykol,
80 g Isopropanol,2 g polypropylene glycol,
80 g isopropanol,
80 g Methylenchlorid,80 g methylene chloride,
80 g Dichlordifluormethan,80 g dichlorodifluoromethane,
20 g Trichlorfluormethan20 g trichlorofluoromethane
werden in eine Aerosoldose gefüllt und ergeben einen baktericiden Spray.are filled into an aerosol can and make a bactericidal spray.
5. Bakterieide Tablette.5. Bacterial both tablet.
0,25 kg p-Hydroxy-diphenylamin,
0,25 kg Bis-(4-hydroxyphenyl)-amin,
1,0 kg Ascorbinsäure,
2,0 kg Sorbit,0.25 kg p-hydroxy-diphenylamine,
0.25 kg bis (4-hydroxyphenyl) amine,
1.0 kg ascorbic acid,
2.0 kg sorbitol,
2,0 kg Eukalyptusöl,
2,0 kg Ammoniumchlorid,
25,0 kg Harnstoff und
47,0 kg Lactose2.0 kg eucalyptus oil,
2.0 kg ammonium chloride,
25.0 kg urea and
47.0 kg of lactose
werden mit Äthanol granuliert und in noch schwach ■ äthanolfeuchtem Zustand zu Tabletten verpreßt, die sowohl zum Lutschen als auch zum Gurgeln verwendet werden können.are granulated with ethanol and pressed into tablets while still slightly moist with ethanol Can be used for both sucking and gargling.
Claims (2)
Deutsche Patentschrift Nr. 554 817;
USA.-Patentschrift Nr, 2 220 981.Considered publications:
German Patent No. 554 817;
U.S. Patent No. 2,220,981.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM38781A DE1090382B (en) | 1958-08-30 | 1958-08-30 | Bactericidal agent |
| GB2316959A GB901419A (en) | 1958-08-30 | 1959-07-06 | Bactericidal agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM38781A DE1090382B (en) | 1958-08-30 | 1958-08-30 | Bactericidal agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1090382B true DE1090382B (en) | 1960-10-06 |
Family
ID=7303200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM38781A Pending DE1090382B (en) | 1958-08-30 | 1958-08-30 | Bactericidal agent |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1090382B (en) |
| GB (1) | GB901419A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE554817C (en) * | 1930-05-10 | 1932-07-14 | I G Farbenindustrie Akt Ges | Procedure for disinfection and preservation |
| US2220981A (en) * | 1938-10-14 | 1940-11-12 | Us Rubber Co | Fungicide |
-
1958
- 1958-08-30 DE DEM38781A patent/DE1090382B/en active Pending
-
1959
- 1959-07-06 GB GB2316959A patent/GB901419A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE554817C (en) * | 1930-05-10 | 1932-07-14 | I G Farbenindustrie Akt Ges | Procedure for disinfection and preservation |
| US2220981A (en) * | 1938-10-14 | 1940-11-12 | Us Rubber Co | Fungicide |
Also Published As
| Publication number | Publication date |
|---|---|
| GB901419A (en) | 1962-07-18 |
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