US2113606A - Quaternary ammonium compounds - Google Patents

Quaternary ammonium compounds Download PDF

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US2113606A
US2113606A US2210635A US2113606A US 2113606 A US2113606 A US 2113606A US 2210635 A US2210635 A US 2210635A US 2113606 A US2113606 A US 2113606A
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Taub Ludwig
Leuchs Friedrich
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ALBA PHARMACEUTICAL Co IN
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ALBA PHARMACEUTICAL Co IN
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/40Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton

Description

Patented Ap 12, 1938 UNITED STATES PATENT OFFICE Elberfeld, Germany,

assignors, by mesne assignments, to Alba Pharmaceutical Company, Inc., New York, N. Y., a corporation of New York N Drawing.

18 Claim.

This invention relates to the manufacture of quaternary ammonium compounds which display bactericidal and fungicidal properties.

U. S. Letters Patent No. 2,108,765, issued February 15, 1938 (application Serial No. 719,592, filed April 7, 1934), refers to quaternary ammonium compounds containing at least one higher molecular aliphatic hydrocarbon radical attached to the nitrogen atom, which compounds are characterized by their bactericidal and fungicidal properties.

In further development of the said invention we have now found that among the ammonium compounds particularly also the formerly not described polyammonium compounds which contain at least one higher molecular aliphatic hydrocarbon radical attached to a quaternary nitrogen atom display considerable bactericidal and fungicidal properties, particularly with regard to disinfecting and preserving media for various purposes, for instance, as a mouth-wash, for disinfecting hands, dental protheses and the like,

animal material, such as meat, skins, blood, glands 3 or other organs, for disinfecting table utensils, store-vessels, medical instruments, bandages, laundry, floors, walls, etc.

The higher aliphatic hydrocarbon radical which is present in the new compounds at least once preferably contains from 8 to 18 carbon atoms. Sometimes it is advantageous that the said radical is present in the form of that mixture which results when manufacturing the new polyammonium compounds by means of those higher alkylamines or alkylhalides which are obtained in the known manner from the mixture of fatty acids obtained by saponification of natural fats and resins, such as coconut oil, palm-oil and colophony. The other radicals may be saturated or unsaturated 40 alkyl groups or aralkyl groups, such as methyl,

ethyl, propyl, isopropyl, butyl, allyl, crotyl, benzyl, phenylethyl and the like.

The new polyammonium compounds specified are preferably used in the form of their salts with acids, such as the hydrohalic acids, sulfuric and suifonic acids, for instance, alkyland aryl-sulfonic acids, such as methane, ethane, benzene or toluene suifonic acids, furthermore nitric and phosphoric acids or carboxylic acids, such as 50 and the like. These salts as well as the free ammonium bases in general readily dissolve in water and alcohols.

The substances specified kill coll-bacteria and 55 staphylococci within a short time in concentra- No. 22,106. In Germany May 24,

antiseptic action. Therefore they can be used as formic, acetic, lactic, citric, tartaric, benzoicjacid Application May 1'7, 1935, Serial tions between about 1:1000 and 1:100000, and hinder the growthof the said bacteria in still lower concentrations.

The polyammonium compounds of the above specified kind may be used in substance as well as in solution or emulsion, eventually also in admixture with one another or with other active or inert substances, such as powders, ointmentbases, creams and the like.

The new polyammonium compounds containing at least one higher molecular aliphatic hydrocarbon radical are prepared for instance by causing aliphatic compounds containing at least two reactive substituents to react with tertiary amines. In this case at least one of the reagents must contain a higher aliphatic hydrocarbon radical. The aliphatic compounds above specified con taining at least two reactive substituents are preferably the esters of polyvalent alcohols, for instance, with halogen 'hydracids or aromatic suifonic acids.

On the other hand, also tertiary polyamines in which one or more nitrogen atoms may be nuclearly bound as is the case with tertiary piperazines, may be caused to react with reactive esters of alcohols, for instance alkyl halides or alkyl esters of suifonic acids. again required that at least one of the reagents contains a higher aliphatic hydrocarbon radical. The transformation of the tertiary polyamines into quaternary ammonium compounds may be carried out in several stages.

The new polyammonium compounds containing higher molecular aliphatic hydrocarbon radicals may likewise be obtained by reacting upon a tertiary amine with a quaternary ammonium compound containing a hydrocarbon radical with a reactive substituent. Also in this case one of the reagents must contain a higher aliphatic hydrocarbon radical. It is, for instance, possible to. cause a trialkylammoniumalkyl halide to react upon a tertiary amine containing a higher aliphatic hydrocarbon radical. A higher aliphatic hydrocarbon radical may also be contained in the quaternary trialkylammoniumalkyl halide or also in both reagents.

The polyammonium compounds thus obtainable may contain substituents, such as hydroxyl groups, sulfhydrylgroups and further, for instance, halogen atoms. The aliphatic radicals, in particular the higher aliphatic radicals, may likewise contain ether-like bound oxygen atoms or sulfur atoms.

It is understood that when using in the specification and in the appended claims the term In this case it is higher molecular aliphatic radical this term is intended to include also the said substitution products and the radicals which contain etherlike bound oxygen or sulfur atoms.

The invention is further'illustrated by the following examples without being restricted thereto:

Example 1.-,-116 parts by weight of tetramethyi-ethylenediamine are heated with 498 parts by weight of dodecylbromide to 100 C. for several hours. After cooling the viscous sirupformed, which after prolonged standing solidifies to crystals, is dissolved in 9 times its weight of distilled water. In this manner a 10% aqueous solution of tetra-methyl-didodecyl-ethylenediammonium bromide is obtained.

The same compound is also obtained by causing methyl bromide to react upon symmetrical dimethyldidodecyl-ethylene-diamine in molecular quantities (2 mols of methyl bromide +1 mol. of dimethyldidodecyl-ethylenediamine) in a closed vessel at about 100 C.

The above described tetramethyl-didodecylethylene-diammonium bromide may be transformed into the corresponding thiocyanate, nitrate or cyanide by reacting thereupon with 2 mols of potassium thiocyanate, silver nitrate or sodium cyanide. The free base may be obtained by treating the aqueous solution of the bromide with the calculated quantity of freshly precipitated silver hydroxide. After separating the silver bromide formed the base may be obtained by evaporating the solution.

Example 2.-116 parts by weight of tetramethyl-ethylenediamine are triturated with 469 parts by weight of dodecyloxymethyl chloride. After the reaction temperature has fallen the tetramethyl-diidodecyloxymethyl-ethylene-diammonium chloride formed is recrystallized from benzene. It forms a crystalline powder of indefinite melting point, which is soluble in water and forms strongly foaming solutions.

Example 3.501 parts by weight of dodecylthiomethyl chloride are added to 116 parts by weight of tetramethyl-ethy1enediamine. The

mixture is heated for several hours on the water bath. After cooling the reaction product is triturated and washed with cold benzene. The tetramethyl-di-dodecylthiomethyl-ethylenediammonium chloride thus obtained forms a yellowish white powder and yields strongly foaming solutions when dissolved in water.

Example 4.-284 parts by weight of tetrabutylethylenediamine are triturated with 469 parts by weight of do-decyloxymethyl chloride. The mixture is then treated in accordance with the directions given in Example 2. The tetrabutyl-di-dodecyloxymethyl-ethylenediammonium chloride thus obtained forms a viscous sirup which is soluble in water.

Example 5.--146 parts by weight of N-tetramethyl- -hydroxy-propy1enediamine are treated with 498 parts by weight of dodecyl bromide and heated for 12 hours on the water bath. The tetramethyl,-- didodecyl fl-hYdl'OILV-DIODYIGIlB-diammonium bromide is thus obtained in the form of a colorless viscous sirup which is soluble in water to a clear solution and the concentrated solution of which forms a highly viscous-liquid.

The same compound is obtained by heating 426 parts by weight of dimethyldodecylamine with 218 parts by weight of glycerine-dibromhydrin at a temperature of -90 C.

Example 6.590 parts by weight of dimethyloleylamine are heated with 281 parts by weight of tribromhydrin in a closed vessel for 12 hours viscous solution of tetramethyl-dioleyl-fl-bromopropylenediammonium bromide is obtained.

Example 7.146 parts by weight of tetramethyl-e-hydroxy-propylenediamine are heated with 557 parts by weight of p-hydroxy- -dodecyloxy-propyl chloride for 12 hours to C. The viscous sirup thus formed is dissolved in 19 times its weight of distilled water. In this manner a 5% solution of tetramethyl-di-(dodecyloxy-p-hydroxy-propyl) -p-hydroxy propylene diammonium chloride is formed.

Example 8.454 parts by weight of symmetrical dimethyl-di-dodecyl-p-hydroxypropylenediamine are heated with 253 parts by weight of benzyl chloride for 10 hours to 100 C. The dimethyl-dibenzyl-di-dodecylsp-hydromropylenediammonium chloride obtained forms a yellowish brown viscous sirup the aqueous solution of which foams strongly.

Example 9.--229 parts by weight of methyl-bisdiethyl-aminoethyl-amine of the formula are stirred with 619 parts by weight of decyloxymethyl chloride. After cooling the bis-(diethyldecyloxymethyl-c h l o r o a m m o n i u m-ethyl) methyl-decyloxymethyl-ammonium chloride of the formula (Rica): CH;

r -c,m }n cmo.cuim

nucwoen, 01 or forms a. yellowish viscous mass which is readily soluble in water.

Example 10.-424 parts by weight of symmet rical dimethyl-di-dodecylethylenediamine are heated with 341 parts by weight of benzylthiomethyl chloride for 3 hours to 80 C. After cooling the resin-like reaction product is dissolved in 9 times its quantity of distilled water. A clear solution of dimethyl-di-dodecyl-dibenzylthiomethyl-ethylenediammonium chloride is thus obtained.

Example 11.- parts by weight of diethylamino-ethylchlorideare heated with 171 parts by weight of benzyl bromide for 4 hours to 70-80 C. 213 parts by weight of dimethyl dodecylamine are added and the mixture is again heated for 6 hours to 90-100 C. After cooling the reaction product is dissolved in four times the quantity by weight of distilled water. In this manner a 20% solution of a-(dimethyl-dodecyl-chloroammonium) B (diethyl benzyl brornoammonium) ethane is obtained.

Example 12.594 parts by weight of dimethyloctadecylamine are dissolved in 1000 parts by weight of dry benzene. The mixture is treated with an ice cold solution of 127 parts by weight of symmetrical dichloracetone in 1000 parts by weight of dry benzene. After the reaction is complete the benzene is distilled off in vacuo and the tetramethyl-dioctadecyl-p-oxopropylene-diammonium chloride formed is dissolved in nine times the quantity by weight of distilled water. Example 13.-114 parts by weight of N.N-dimethylpiperazine are triturated with 558 parts by weight of dodecyloxymethyl bromide. After the reaction temperature has fallen the mixture is dissolved in distilled water. A clear solution of dimethyl-di-dodecyloxy-methyl-piperazinium dibromide is thus obtained.

Example 14.-342 parts by weight of symmetrical dimethyl-dioctyl p hydroxypropylenediamine (prepared by reacting upon 2 mols of methyloctylamine with 1 mol. of glycerine-dibromohydrln) are heated with 242 parts by weight oi. allylbromide in a closed vessel at 90-100" C. during several hours. After the mixture is cold the reaction product is dissolved in nine times its quantity of distilled water. A'10% solution of dimethyl-diallyl-dioctyl-p-hydroxypropylene diammonium bromide is thus obtained.

Example 15.-l84 parts by weight of N-diethylamino-ethyl-piperidine are heated with 442 parts by weight of decylbromide at 100 C. for 10 hours. After the mixture is cold the reaction product is dissolved in four times its quantity of water. A 20% solution of the N- (dimethyl-decyl-bromammoniumethyl) -decyl-piperidinium bromide 01' the is thus obtained.

Example 16.-424 parts by weight of symmetrical dimethyl didodecyl ethylenediamine are heated with 252 parts by weight of dimethylsulfate at C. for 6 hours. The symmetrical tetramethyl-didodecyl-ethylenediammonium-dimethosulfate is thus obtained.

Example 17.100 parts by weight of tetramethyl-methylenediamine are heated with 498 parts by weight of dodecylbromide for 6 hours in a closed vessel to C. .Thus the tetramethyl-didodecyl-methylenediammoniumbromideis obtained which is readily soluble in water and. alcohol.

When using instead of the tetramethyl-methylenediamine 158 parts by weight of tetramethylpentamethylenediamine the tetramethyl-dldodecyl-pentamethylene-diammonium bromide is obtained. It is likewise readily soluble in water and alcohol.

We claim:-

1. Quaternary polyammonium compounds containing, attached to a quaternary nitrogen atomwhich is connected with. another quaternary nitrogen atom by a lower aliphatic radical, at least one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, and containing upon each quaternary nitrogen atom an anion selected from the group consisting of the hydroxyl anion and the anions of mineral and carboxylic acids, the excess valences of the nitrogen atoms being satisfied by radicals selected from the group consisting of alkyl, alkenyl and aralkyl radicals.

2. Quaternary polyammonium compounds containing, attached to each of the quaternary nitrogen atoms which are connected by a lower aliphatic radical, one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, and containing upon each quaternary nitrogen atom an anion selected from the group consisting of the hydroxyl anion and the anions of mineral and carboxylic acids, the excess valences of the nitrogen atoms being satisfied by radicals selected from the group consisting of alkyl, alkenyl and aralkyl radicals.

3. Quaternary diammonium compounds containing, attached to a quaternary nitrogen atom which is connected with the other quaternary 111- trogen atom by a lower aliphatic radical, at least one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, and containing upon each quaternary nitrogen atom an anion selected from the group consisting of the hydroxyl anion and the anions oi mineral and carboxylic acids, the excess valences of the nitrogen atoms being satisfled by radicals selected from the group consisting of alkyl, alkenyl and aralkyl radicals.

4. Quaternary diammonium compounds containing, attached to each of the quaternary nitrogen atoms which are connected by a lower allphatic radical, one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, and containing upon each quaternary nitrogen atom an anion selected from the group consisting of the hydroxyl anion and the anions of mineral and carboxylic acids, the excess valences of the nitrogen atoms being satisfied by radicals selected from the group consisting of alkyl, alkenyl and aralkyl radicals.

5. Quaternary polyammonium compounds containing, attached to a quaternary nitrogen atom which is connected with another quaternary nitrogen atom by a lower aliphatic radical, at least one hydrocarbon radical from 8 to 18 carbon atoms, and containing upon each quaternary nitrogen atom an anion of a mineral acid, the excess valences of the nitrogen atoms being satisfled by radicals selected from the group consisting oi. alkyl, alkenyl and aralkyl radicals.

6. Quaternary diammonium compounds containing, attached to a quaternary nitrogen atom which is connected with the other quaternary nitrogen atom by a lower aliphatic radical, at least one aliphatic hydrocarbon radical from 8 to 18' carbon atoms, and containing upon each quaternary nitrogen atom an anion of a mineral acid, the excess valences of the nitrogen atoms being satisfied by radicals selected from the group consisting 01' alkyl, alkenyl and aralkyl radicals.

7. N.N.N.Nf-tetramethyl-N.N'-didodecyl-p-hydroxy-propylene-diammo'nium halides.

8. N.N.N'.N'-tetramethyl-N.N'-didodecyl-fl-hydroxy-propylenediammonium bromide.

9. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by a lower aliphatic radical one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, two lower alkyl groups and an anion selected from the group consisting of the hydroxyl anion and the anions of mineral and carboxylic acids.

10. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by a lower aliphatic radical one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, two lower alkyl groups phatic radical of 2 to 3 carbon atoms one ali-.

phatic hydrocarbon radical from 8 to 18 carbon atoms, two lower alkyl groups and an anion of a mineral acid.

13. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by a lower aliphatic radical of two to three carbon atoms one aliphatic hydrocarbon radical from 8 to 18 carbon atoms, two lower alkyl and an anion o! a hydrohalic acid.

14. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by a lower aliphatic radical of 2 to 3 carbon atoms one dodecyl radical, two lower alkyl groups and an anion selected from the group consisting of the hydroxyl anion and the anions of mineral and carboxylic acids. 1

15. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by a lower aliphatic radical of 2 to 3 carbon atoms one dodecyl radical, two lower alkyl groups and an anion of a hydrohalic acid.

16. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by the p-hydroxypropylene radical one dodecyl radical, two lower alkyl groups and an anion seiected 1rom the group consisting of the hydroxyl anion and the anions of mineral and carboxylic acids.

1'7. Quaternary diammonium compounds containing attached to each of the quaternary nitrogen atoms which are connected by the fi-hydroxypropylene radical one dodecyl radical, two lower alkyl groups and an anion of a hydrohalic acid.

18. It" .N.N.N' tetramethyl N.N' didodecyl hydroxypropylene-diammonium compounds containing attached to each nitrogen atom an anion selected from the group consisting of the hydroxyi anion and the anions of mineral and carboxylic acids.

LUDWIG TAUB.

FRIEDRICH LEUCHS.

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2487707A (en) * 1943-07-30 1949-11-08 Ciba Pharmaceutical Products Beta-(5.7-dichloroquinolyl-(8)-oxy)-ethyl]-dimethyl-dodecyl ammonium bromide
US2520275A (en) * 1946-12-28 1950-08-29 Onyx Oil & Chemical Company Aromatic diquaternary ammonium compounds
US2523177A (en) * 1948-09-01 1950-09-19 Standard Oil Dev Co Ethylene diamine condensation products and parasiticidal compositions containing them
US2566535A (en) * 1949-01-27 1951-09-04 Sterling Drug Inc Quaternary ammonium salts of tertiary-aminoalkyl substituted phenylacetonitriles
US2654785A (en) * 1949-02-15 1953-10-06 Ciba Pharm Prod Inc Quaternated aza-pentane amines
US2807910A (en) * 1952-10-09 1957-10-01 Gen Mills Inc Soil conditioning with polyquaternary ammonium compounds
US2941004A (en) * 1955-05-19 1960-06-14 Pfizer & Co C 1, 5-bis-dimethylamino-3-pentanol diethobromide
US2951751A (en) * 1958-07-30 1960-09-06 Exxon Research Engineering Co Hydrocarbon oils having improved electrical properties
US3068235A (en) * 1960-01-05 1962-12-11 U S Vitamin And Pharmaceutical Quaternary ammonium salts of omega-(n-methyl-2,6-dimethylanilino) alkyl halides
US3507690A (en) * 1967-05-24 1970-04-21 Procter & Gamble Softening process for a cellulosic textile fabric and the softened fabric
JPS4852712A (en) * 1971-10-29 1973-07-24
US3925556A (en) * 1971-09-30 1975-12-09 Colgate Palmolive Co Anti microbial compositions containing unsymmetrical oligoquaternary ammonium compounds
US3983079A (en) * 1973-09-04 1976-09-28 The Procter & Gamble Company Dishwashing composition
US4166073A (en) * 1968-03-27 1979-08-28 Colgate Palmolive Company Unsymmetrical oligoquaternary ammonium compounds
WO2004035523A1 (en) * 2002-10-16 2004-04-29 Neopharm, Inc. Cationic cardiolipin analogs and use thereof
US20050181037A1 (en) * 2002-05-24 2005-08-18 Neopharm, Inc. Cardiolipin compositions their methods of preparation and use
US20050277611A1 (en) * 2002-10-16 2005-12-15 Neopharm, Inc. Cationic cardiolipin analoges and its use thereof
US20060078560A1 (en) * 2003-06-23 2006-04-13 Neopharm, Inc. Method of inducing apoptosis and inhibiting cardiolipin synthesis

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2487707A (en) * 1943-07-30 1949-11-08 Ciba Pharmaceutical Products Beta-(5.7-dichloroquinolyl-(8)-oxy)-ethyl]-dimethyl-dodecyl ammonium bromide
US2520275A (en) * 1946-12-28 1950-08-29 Onyx Oil & Chemical Company Aromatic diquaternary ammonium compounds
US2523177A (en) * 1948-09-01 1950-09-19 Standard Oil Dev Co Ethylene diamine condensation products and parasiticidal compositions containing them
US2566535A (en) * 1949-01-27 1951-09-04 Sterling Drug Inc Quaternary ammonium salts of tertiary-aminoalkyl substituted phenylacetonitriles
US2654785A (en) * 1949-02-15 1953-10-06 Ciba Pharm Prod Inc Quaternated aza-pentane amines
US2807910A (en) * 1952-10-09 1957-10-01 Gen Mills Inc Soil conditioning with polyquaternary ammonium compounds
US2941004A (en) * 1955-05-19 1960-06-14 Pfizer & Co C 1, 5-bis-dimethylamino-3-pentanol diethobromide
US2951751A (en) * 1958-07-30 1960-09-06 Exxon Research Engineering Co Hydrocarbon oils having improved electrical properties
US3068235A (en) * 1960-01-05 1962-12-11 U S Vitamin And Pharmaceutical Quaternary ammonium salts of omega-(n-methyl-2,6-dimethylanilino) alkyl halides
US3507690A (en) * 1967-05-24 1970-04-21 Procter & Gamble Softening process for a cellulosic textile fabric and the softened fabric
US4166073A (en) * 1968-03-27 1979-08-28 Colgate Palmolive Company Unsymmetrical oligoquaternary ammonium compounds
US3925556A (en) * 1971-09-30 1975-12-09 Colgate Palmolive Co Anti microbial compositions containing unsymmetrical oligoquaternary ammonium compounds
JPS5238008B2 (en) * 1971-10-29 1977-09-27
JPS4852712A (en) * 1971-10-29 1973-07-24
US3983079A (en) * 1973-09-04 1976-09-28 The Procter & Gamble Company Dishwashing composition
US20050181037A1 (en) * 2002-05-24 2005-08-18 Neopharm, Inc. Cardiolipin compositions their methods of preparation and use
US20050266068A1 (en) * 2002-05-24 2005-12-01 Neopharm, Inc. Cardiolipin molecules and methods of synthesis
WO2004035523A1 (en) * 2002-10-16 2004-04-29 Neopharm, Inc. Cationic cardiolipin analogs and use thereof
US20050277611A1 (en) * 2002-10-16 2005-12-15 Neopharm, Inc. Cationic cardiolipin analoges and its use thereof
US20060078560A1 (en) * 2003-06-23 2006-04-13 Neopharm, Inc. Method of inducing apoptosis and inhibiting cardiolipin synthesis

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