DE1107215B - Process for the production of biocidal guanidine compounds - Google Patents
Process for the production of biocidal guanidine compoundsInfo
- Publication number
- DE1107215B DE1107215B DEG27328A DEG0027328A DE1107215B DE 1107215 B DE1107215 B DE 1107215B DE G27328 A DEG27328 A DE G27328A DE G0027328 A DEG0027328 A DE G0027328A DE 1107215 B DE1107215 B DE 1107215B
- Authority
- DE
- Germany
- Prior art keywords
- biocidal
- carbon atoms
- parts
- hydrochloride
- dodecyl
- 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
- 230000003115 biocidal effect Effects 0.000 title claims description 11
- 150000002357 guanidines Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- -1 tetradecyl radical Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KRYWEAYKLGCRRH-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]azanium;chloride Chemical compound Cl.CSC(N)=N KRYWEAYKLGCRRH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- QCENGKPIBJNODL-UHFFFAOYSA-N n'-dodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCN QCENGKPIBJNODL-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YZPMGCUOUVFLJC-UHFFFAOYSA-N n'-decylethane-1,2-diamine Chemical compound CCCCCCCCCCNCCN YZPMGCUOUVFLJC-UHFFFAOYSA-N 0.000 description 2
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 2
- QIBKKTQVKFEWCH-UHFFFAOYSA-N n'-tetradecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCNCCN QIBKKTQVKFEWCH-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000005654 1,2-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([*:1])C1([H])[H] 0.000 description 1
- 125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 241000304886 Bacilli Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- JPXSVVYXEDEUIB-UHFFFAOYSA-N C(CCCCCCCCCCC)NC1C(CCC1)N Chemical compound C(CCCCCCCCCCC)NC1C(CCC1)N JPXSVVYXEDEUIB-UHFFFAOYSA-N 0.000 description 1
- GSVHTYBZRGIBSA-UHFFFAOYSA-N C(CCCCCCCCCCC)NC1C(CCCC1)N Chemical compound C(CCCCCCCCCCC)NC1C(CCCC1)N GSVHTYBZRGIBSA-UHFFFAOYSA-N 0.000 description 1
- QQLIZKQQMZGCCA-UHFFFAOYSA-N Cl.C(CCCCCCCCCCC)NCCNC(=N)N Chemical compound Cl.C(CCCCCCCCCCC)NCCNC(=N)N QQLIZKQQMZGCCA-UHFFFAOYSA-N 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 241000588724 Escherichia coli 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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 241000192023 Sarcina Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- GTRLQRHWPXEBLF-UHFFFAOYSA-N benzyl carbamimidothioate Chemical compound NC(=N)SCC1=CC=CC=C1 GTRLQRHWPXEBLF-UHFFFAOYSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- LFXAECSQJSRSTP-UHFFFAOYSA-N hydron;methyl carbamimidothioate;iodide Chemical compound I.CSC(N)=N LFXAECSQJSRSTP-UHFFFAOYSA-N 0.000 description 1
- WAEDMQMDOHQPFL-UHFFFAOYSA-N n,n-bis(2-chloroethyl)propan-2-amine Chemical compound ClCCN(C(C)C)CCCl WAEDMQMDOHQPFL-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XSSNABKEYXKKMK-UHFFFAOYSA-N s-isopropyl-isothiourea Chemical compound CC(C)SC(N)=N XSSNABKEYXKKMK-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von bio eiden Guanidinverbindungen Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von biociden Guanidinverbindungen der allgemeinen Formel In dieser bedeutet A einen durch 6c,goder a,y-Kohlenstoffatome mit den Stickstoffatomen verbundenen aliphatischen oder einen durch os,ß-Kohlenstoffatome verbundenen cycloaliphatischen Rest und R eine lipophile Gruppe von 10 bis 16 Kohlenstoffatomen oder eine einen solchen Rest enthaltende araliphatische Gruppe.Process for the production of biocidal guanidine compounds The present invention relates to a process for the production of biocidal guanidine compounds of the general formula In this, A denotes an aliphatic radical connected to the nitrogen atoms by 6c, g or a, y carbon atoms or a cycloaliphatic radical connected by os, β carbon atoms and R denotes a lipophilic group of 10 to 16 carbon atoms or an araliphatic group containing such a radical.
In der allgemeinen Formel bedeutet R vorzugsweise einen Dodecyl- oder Tetradecylrest oder einen eine solche Gruppe enthaltenden araliphatischen Rest, z.B. einen (4'-Dodecyl)-benzylrest. Erfindungsgemäße Verbindungen, welche diese Reste enthalten, sind besonders wirksame Biocide. In the general formula, R preferably denotes a dodecyl or tetradecyl radical or an araliphatic radical containing such a group, e.g. a (4'-dodecyl) benzyl radical. Compounds according to the invention which these Containing residues are particularly effective biocides.
Die neuen Guanidinverbindungen erhält man, wenn man bei Raumtemperatur 1 Mol N-substituierte Diaminoverbindung der allgemeinen Formel R-NH-A-NH2 und 1 Mol Salz aus einem S-substituierten Isothioharnstoff und einer starken Säure, wie z. B. ein Hydrohalogenid, umsetzt. Zweckmäßig läßt man die Umsetzung in einem organischen Lösungsmittel, z. B. The new guanidine compounds are obtained if one is at room temperature 1 mol of N-substituted diamino compound of the general formula R-NH-A-NH2 and 1 Mole salt of an S-substituted isothiourea and a strong acid, such as z. B. a hydrohalide, converts. The reaction is expediently left in an organic Solvents, e.g. B.
Methylalkohol, vor sich gehen, wobei man die Lösung gegen Ende der Reaktion bis auf etwa 80' C erwärmt, um das abgespaltene Mercaptan auszutreiben.Methyl alcohol, going on, taking the solution towards the end of the Reaction heated up to about 80 ° C. in order to drive off the split off mercaptan.
Durch Zugabe äquivalenter Mengen starker Alkalien, z. B. Natrium- oder Kaliumalkoholat, zum so entstandenen Salz, z. B. dem Hydrochlorid der Guanidinverbindung, erhält man die freie Base. Es ist jedoch von Vorteil, die Guanidinverbindungen in Form ihrer Salze, z. B. in Form ihrer Hydrochloride, aufzubewahren und zu verwenden. By adding equivalent amounts of strong alkalis, e.g. B. Sodium or potassium alcoholate, to the resulting salt, e.g. B. the hydrochloride of the guanidine compound, the free base is obtained. However, it is advantageous to use the guanidine compounds in Form of their salts, e.g. B. in the form of their hydrochloride to store and use.
Als Beispiele für A in den Formeln kommen folgende Reste in Frage: Alkylenreste, wie 1,2-Äthylen-, 1,2-Propylen-, 1,2oder 2,3-Butylen-, 1,3-Propylen-2-Methyl-l,3-propylen- und Cycloalkylenreste, wie 1,2-Cyclopentylen- oder 1,2-Cyclohexylenreste, und deren homologe Derivate. The following radicals are possible examples of A in the formulas: Alkylene radicals, such as 1,2-ethylene, 1,2-propylene, 1,2 or 2,3-butylene, 1,3-propylene-2-methyl-1,3-propylene and cycloalkylene groups such as 1,2-cyclopentylene or 1,2-cyclohexylene groups and their homologous derivatives.
Als Beispiele von Diaminoverbindungen, welche erfindungsgemäß verwendbar sind, seien folgende genannt: N-Decyl-1,2-diaminoäthan, N-Dodecyl-1 ,2-diaminoäthan, N-Tetradecyl-1,2-diaminoäthan, N-(4'-Dodecyl)-benzyl- 1 ,2-diaminoäthan, N-Dodecyl- 1 ,3-di- aminopropan, N-Dodecyl-1,2-diaminocyclohexan und N-Dodecyl-1,2-diaminocyclopentan. As examples of diamino compounds which can be used according to the invention are, the following may be mentioned: N-decyl-1,2-diaminoethane, N-dodecyl-1,2-diaminoethane, N-tetradecyl-1,2-diaminoethane, N- (4'-dodecyl) -benzyl- 1,2-diaminoethane, N-dodecyl- 1, 3-di- aminopropane, N-dodecyl-1,2-diaminocyclohexane and N-dodecyl-1,2-diaminocyclopentane.
Als Beispiele von substituierten Isothiahamstoffen kommen folgende in Frage: Niedere S-Alkyl-isothioharnstoffe, wie z. B. S-Methyl-, S-Athyl-, S-Propyl-oder S-Isopropyl-isothioharnstoff oder S-Aralkylisothioharnstoffe, wie z. B. S-Benzyl-isothioharnstoff. The following are examples of substituted isothiaureas in question: lower S-alkyl isothioureas, such as B. S-methyl, S-ethyl, S-propyl or S-isopropyl-isothiourea or S-aralkylisothioureas, such as e.g. B. S-benzyl isothiourea.
Die erfindungsgemäß herstellbaren Guanidinverbindungen sind farblose bis schwach gefärbte, kristalline bis wachsartige, lichtbeständige Substanzen, die in Form ihrer Salze mit Säuren wasserlöslich sind. Die Verbindungen sind wertvolIe biocide Mittel, die sich durch große Wirkungsbreite und gute baktericide Wirkung auszeichnen. Sie sind auch algicid wirksam. The guanidine compounds which can be prepared according to the invention are colorless to slightly colored, crystalline to waxy, lightfast substances that are water-soluble in the form of their salts with acids. The connections are valuable biocidal means, which are characterized by a wide range of effects and a good bactericidal effect distinguish. They are also algicidally effective.
Die Mittel können für sich allein, in Lösung oder in Mischung mit anderen biociden Stoffen sowie mit inerten Träger- oder Füllstoffen, Salbengrundlagen, Cremes usw. gebraucht werden. Sie finden Verwendung in den verschiedensten Applikationsgebieten. So sind sie z.B. in der Human- und Veterinärmedizin gut brauchbare, desinfizierende und antiseptische Mittel, da sie gute bis sehr gute Wirksamkeit gegen Staphylokokken, Coli-, Typhus-, Paratyphus- und Enteritisbazillen zeigen. Dank der guten Wasserlöslichkeit ihrer Salze mit Säuren können die neuen Verbindungen mit Vorteil auch zur desinfizierenden und antiseptischen Ausrüstung von Textilien, beispielsweise Wolldecken oder Bettwäsche, verwendet werden. Textilgewebe, welches mit einer 1- bis 20i0igen wäßrigen Lösung von erfindungsgemäßen Verbindungen behandelt wird, ist nach dem Trocknen nicht nur keimfrei, sondern es zeigt auch eine gewisse Dauerwirkung in bakteriostatischer Hinsicht. So behandelte Textilien weisen nach längerer Lagerung oder Belichtung keine Vergilbungserscheinungen auf. Die erfindungsgemäßen Produkte können auchin organischen Lösungsmitteln zur Trockenreinigung von Textilien verwendet werden.The funds can be used on their own, in solution or in a mixture with other biocidal substances as well as inert carriers or fillers, ointment bases, Creams etc. are needed. They are used in a wide variety of application areas. For example, they are useful and disinfectant in human and veterinary medicine and antiseptic agents, as they have good to very good effectiveness against staphylococci, Show coli, typhoid, paratyphoid and enteritis bacilli. Thanks to the good solubility in water Their salts with acids can also be used with advantage to disinfect the new compounds and antiseptic finishing of textiles, for example wool blankets or Bed linen, to be used. Textile fabric, which with a 1- to 20i0igen aqueous Solution treated by compounds according to the invention is after drying not only germ-free, but it also shows a certain permanent bacteriostatic effect Respect. Textiles treated in this way show signs of prolonged storage or exposure no signs of yellowing. The products according to the invention can also be used in organic solvents can be used for dry cleaning of textiles.
Ferner können sie zur Raumdesinfektion dienen, wobei man sie vorteilhaft in Form von Sprays und Aerosolen anwendet. Sie können auch zur Desinfektion von Geräten und Einrichtungsgegenständen im Haushalt oder in Lebensmittel- und Fermentationsbetrieben dienen. Schließlich sei als weiteres Anwendungsgebiet die Kosmetik genannt, wo man die Mittel z. B. in Salben und Cremes verwendet.They can also be used to disinfect rooms, whereby they are advantageous in the form of sprays and aerosols. You can also use it to disinfect Appliances and furnishings in the household or in food and fermentation plants to serve. Finally, cosmetics should be mentioned as a further area of application, where one can the means z. B. used in ointments and creams.
Gegenüber ähnlichen Verbindungen, wie z. B. den aus der britischen Patentschrift 785 937 bekannten Biguaniden, zeigen vergleichbare erfindungsgemäß erhältliche Verbindungen eine bessere fungistatische und baktericide Wirkung. Compared to similar compounds such. B. the one from the British Patent 785,937 known biguanides show comparable according to the invention available compounds have a better fungistatic and bactericidal effect.
Nähere Einzelheiten sind aus den folgenden Beispielen ersichtlich. In diesen Beispielen sind die Teile als Gewichtsteile verstanden. Gewichtsteile verhalten sich zu Volumteilen wie Kilogramm zu Liter. Further details can be found in the following examples. In these examples, the parts are understood to be parts by weight. Parts by weight relate to parts of volume like kilograms to liters.
Beispiel 1 ß-Decylaminoäthylguanidin-hydrochlorid In die kalte Lösung von 40 Teilen N-Decyl-l,2-diaminoäthan in 100 Volumteilen Methylalkohol werden 25,3 Teile S-Methylisothioharnstoff-hydrochlorid eingetragen. Die Mischung wird zunächst 90 Minuten bei Raumtemperatur gerührt und anschließend 4 Stunden am Rückfluß gekocht. Unter Abspaltung von Methylmercaptan bildet sich das ß-Decylaminoäthylguanidinhydrochlorid. Dieses wird als weißes Kristallpulver vom Zersetzungspunkt 111° C erhalten, wenn man den Methylalkohol am Vakuum entfernt und den Rückstand aus Äthylacetat umkristallisiert. Das Produkt zeigt sehr gute biocide Wirkung. So ist es beispielsweise gegen folgende Bakterien wirksam: Staphylokokken, wie Staphylococcus aureus spez., Escherichia coli, Bacillus mesenticus und Sarcina spez. Es kann darum als wirksamer Bestandteil in Desinfektionsmitteln verwendet werden, beispielsweise in Salben, Tinkturen, als Zusatz zu Reinigungsmitteln und in antiseptischen Verbandsmaterialien.example 1 ß-decylaminoethylguanidine hydrochloride 25.3 parts of S-methylisothiourea hydrochloride are added to the cold solution of 40 parts of N-decyl-1,2-diaminoethane in 100 parts by volume of methyl alcohol. The mixture is first stirred for 90 minutes at room temperature and then refluxed for 4 hours. The β-decylaminoethylguanidine hydrochloride is formed with the elimination of methyl mercaptan. This is obtained as a white crystal powder with a decomposition point of 111 ° C. if the methyl alcohol is removed in vacuo and the residue is recrystallized from ethyl acetate. The product shows a very good biocidal effect. For example, it is effective against the following bacteria: Staphylococci, such as Staphylococcus aureus spec., Escherichia coli, Bacillus mesenticus and Sarcina spec. It can therefore be used as an active ingredient in disinfectants, for example in ointments, tinctures, as an additive to cleaning agents and in antiseptic dressings.
Beispiel 2 ß-Dodecylaminoäthylguanidin-hydrojodid Die Mischung von 45,6 Teilen N-Dodecyl-1,2-di aminoäthan, 43,6 Teilen S-Methyl-isothioharnstoff hydrojodid und 150 Volumteilen Methylalkohol wird 1 Stunde bei Raumtemperatur gerührt und dann 5 Stunden am Rückfluß gekocht. Die Lösung wird nun triert, und anschließend wird der Methylalkohol des Filtrates am Vakuum entfernt. Der aus Äthylacetat umkristallisierte Rückstand ist das ß-Dodecylaminoäthylguanidin-hydrojodid. Es stellt ein farbloses Kristallpulver vom Schmelzpunkt 103 bis 104"C dar, besitzt ähnliche - biocide Eigenschaften wie das im Beispiel 1 beschriebene Guanidinderivat und kann zu denselben Zwecken wie jenes verwendet werden.Example 2 ß-Dodecylaminoethylguanidine hydroiodide The mixture of 45.6 parts of N-dodecyl-1,2-di aminoethane, 43.6 parts of S-methyl isothiourea hydroiodide and 150 parts by volume of methyl alcohol is stirred for 1 hour at room temperature and then refluxed for 5 hours . The solution is now triturated, and then the methyl alcohol of the filtrate is removed in vacuo. The residue recrystallized from ethyl acetate is β-dodecylaminoethylguanidine hydroiodide. It is a colorless crystal powder with a melting point of 103 to 104 "C, has biocidal properties similar to the guanidine derivative described in Example 1 and can be used for the same purposes as that.
Beispiel 3 ß-Tetradecylaminoäthylguanidin-hydrochlorid Die Lösung von 51,2 Teilen N-Tetradecyl-1,2-diaminoäthan und 25,3 Teilen S-Methyl-isothioharnstoffhydrochlorid in 100 Volumteilen Methylalkohol wird zuerst 2 Stunden bei Raumtemperatur und anschließend 5 Stunden beim Siedepunkt des Lösungsmittels gerührt. Die Reaktionslösung wird zwecks Reinigung filtriert und der Methylalkohol am Vakuum abdestilliert.Example 3 ß-Tetradecylaminoethylguanidine hydrochloride The solution of 51.2 parts of N-tetradecyl-1,2-diaminoethane and 25.3 parts of S-methyl-isothiourea hydrochloride in 100 parts by volume of methyl alcohol is stirred first for 2 hours at room temperature and then for 5 hours at the boiling point of the solvent . The reaction solution is filtered for the purpose of purification and the methyl alcohol is distilled off in vacuo.
Der Rückstand, welcher zur Hauptsache aus ß.Tetradecylaniinoäthylguanidin-hydrochlorid besteht, wird aus Äthylacetat umkristallisiert. Das ß-Tetradecylaminoäthylguanidin-hydrochlorid stellt ein farbloses kristallines Pulver vom Zersetzungspunkt 130°C dar. Es zeigt ähnliche biocide Eigenschaften wie das im Beispiel 1 beschriebene Guanidinderivat und kann zu denselben Zwecken verwendet werden. The residue, which mainly consists of ß.Tetradecylaniinoäthylguanidin hydrochloride consists, is recrystallized from ethyl acetate. The ß-tetradecylaminoethylguanidine hydrochloride represents a colorless crystalline powder with a decomposition point of 130 ° C. It shows Similar biocidal properties to the guanidine derivative described in Example 1 and can be used for the same purposes.
Beispiel 4 y-Dodecylaminopropylguanidin-hydrochlorid 48,4 Teile N-Dodecyl- 1,3- diaminopropan und 25,3 Teile S-Methylisothioharnstoff-hydrochlorid werden in 100 Volumteilen Methylalkohol gelöst. Diese Lösung wird 11/2 Stunden bei Raumtemperatur verrührt.Example 4 γ-Dodecylaminopropylguanidine hydrochloride 48.4 parts of N-dodecyl-1,3-diaminopropane and 25.3 parts of S-methylisothiourea hydrochloride are dissolved in 100 parts by volume of methyl alcohol. This solution is stirred for 11/2 hours at room temperature.
Dann wird sie 5 Stunden unter Rückfluß gekocht. Beim Erkalten kristallisiert das y-Dodecylaminopropylguanidin-hydrochlorid aus. Es wird abfiltriert und aus einem Gemisch von Äthylalkohol und Äthylacetat umkristallisiert. Es stellt ein wasserlösliches, farbloses Pulver vom Schmelzpunkt 137 bis 138"C dar, zeigt ähnliche biocide Eigenschaften wie das im Beispiel 1 beschriebene Guanidinderivat und kann zu denselben Zwecken verwendet werden.Then it is refluxed for 5 hours. Crystallizes on cooling the y-dodecylaminopropylguanidine hydrochloride. It is filtered off and from one Recrystallized mixture of ethyl alcohol and ethyl acetate. It represents a water-soluble, colorless powder with a melting point of 137 to 138 "C, shows similar biocidal properties as the guanidine derivative described in Example 1 and can be used for the same purposes be used.
Beispiel 5 ß-Dodecylaminoäthylguanidin-hydrochlorid Zur Lösung von 45,6 Teilen N-Dodecyl-1,2-diaminoäthan in 80 Volumteilen Methanol werden bei 20 bis 25"C 25,3 Teile S-Methylisothioharnstoff-hydrochlorid gegeben. Die Lösung wird 1 Stunde bei Raumtemperatur und 5 Stunden unter Rückfluß gerührt. Dann wird der Methylalkohol am Vakuum abdestilliert. Der Rückstand wird aus Äthylacetat umkristallisiert, wobei das ß-Dodecylaminoäthylguanidin-hydrochlorid in wasserlöslichen, farblosen Kristallen erhalten wird, die bei 115"C unter Zersetzung schmelzen. Der Stoff zeigt ähnliche biocide Eigenschaften wie das im Beispiel 1 beschriebene Produkt und kann zu denselben Zwecken verwendet werden.Example 5 ß-Dodecylaminoethylguanidine hydrochloride 25.3 parts of S-methylisothiourea hydrochloride are added to the solution of 45.6 parts of N-dodecyl-1,2-diaminoethane in 80 parts by volume of methanol. The solution is added for 1 hour at room temperature and stirred for 5 hours under reflux. The methyl alcohol is then distilled off in vacuo. The residue is recrystallized from ethyl acetate, the β-dodecylaminoethylguanidine hydrochloride being obtained in water-soluble, colorless crystals which melt at 115 ° C. with decomposition. The substance shows similar biocidal properties as the product described in Example 1 and can be used for the same purposes.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1107215X | 1958-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1107215B true DE1107215B (en) | 1961-05-25 |
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ID=4557841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG27328A Pending DE1107215B (en) | 1958-06-20 | 1959-06-19 | Process for the production of biocidal guanidine compounds |
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| Country | Link |
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| DE (1) | DE1107215B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1196640B (en) * | 1961-11-18 | 1965-07-15 | Dehydag Gmbh | Process for the production of biocidal urea or urethane compounds |
| US3201459A (en) * | 1961-11-23 | 1965-08-17 | Farmaceutici Italia | Guanidine |
| US3291829A (en) * | 1961-03-02 | 1966-12-13 | Ciba Geigy Corp | Alkyl guanidines |
| DE102009029010A1 (en) | 2009-08-31 | 2011-03-03 | Evonik Goldschmidt Gmbh | Antimicrobial ether guanidines |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689249A (en) * | 1952-07-10 | 1954-09-14 | Rohm & Haas | Dialkyl-2-iminoimidazolidines and their salts |
| GB785937A (en) * | 1955-02-10 | 1957-11-06 | Ici Ltd | Biguanides |
-
1959
- 1959-06-19 DE DEG27328A patent/DE1107215B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689249A (en) * | 1952-07-10 | 1954-09-14 | Rohm & Haas | Dialkyl-2-iminoimidazolidines and their salts |
| GB785937A (en) * | 1955-02-10 | 1957-11-06 | Ici Ltd | Biguanides |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3291829A (en) * | 1961-03-02 | 1966-12-13 | Ciba Geigy Corp | Alkyl guanidines |
| DE1196640B (en) * | 1961-11-18 | 1965-07-15 | Dehydag Gmbh | Process for the production of biocidal urea or urethane compounds |
| US3201459A (en) * | 1961-11-23 | 1965-08-17 | Farmaceutici Italia | Guanidine |
| DE102009029010A1 (en) | 2009-08-31 | 2011-03-03 | Evonik Goldschmidt Gmbh | Antimicrobial ether guanidines |
| WO2011023465A2 (en) | 2009-08-31 | 2011-03-03 | Evonik Goldschmidt Gmbh | Antimicrobial ether guanidines |
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