Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.


  1. Advanced Patent Search
Publication numberUS2459062 A
Publication typeGrant
Publication dateJan 11, 1949
Filing dateFeb 8, 1944
Priority dateFeb 8, 1944
Publication numberUS 2459062 A, US 2459062A, US-A-2459062, US2459062 A, US2459062A
InventorsCook Elmer W, Moss Philip H
Original AssigneeAmerican Cyanamid Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Quaternary ammonium compounds
US 2459062 A
Abstract  available in
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

Patented Jan. 11, 1949 UNITED STATES PATENT OFFICE QUATERNARY AMMONIUM COMPOUNDS Elmer W. Cook, New York, N. Y., and Philip B. Moss, Greenwich, Conn., assignors to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application February 8, 1944,

Serial No. 521,588

Claims. 1

The present invention is concerned with the production of new organic ammonium compounds which are adapted for various uses, more particularly as germicidal agents, wetting agents, and softening agents for textiles and the like.

These compounds are of the quaternary ammonium type which conform to the general formula The new products are in part crystalline, in-

part thickly liquid, viscous substances which in general dissolve readily in water and form stable aqueous solutions. In view of their dispersing and disinfecting properties, they exert a remarkable action as wetting and emulsifying agents and also as antiseptics. They are practically odorless and relatively non-toxic to man.

Representative compounds which fall within the scope of this invention are:

( CIHI 09H;

These quaternary ammonium salts may be prepared by treating a tertiary amine of the formulain whichR, R1 and R2 represent the molecular groups above referred to, with an alkylating agent such as an alkyl halide, dialkyl sulfate, aralkyl chloride, etc. Thus, -for example, 'ymyri'stamidopropyldimethylamine treated with benzyl chloride produces the ammonium salt, '1 myrlstamidopropyldimethylbenzylammonium chloride according to the reaction Reactions which may be involved in the preparation of the tertiary amine may be outlined as follows:

CH:=CHCN As an alternative method for step (3), the acid chloride,

Ri E-Cl may be used in place of the acid.

The invention is further illustrated by the following examples, the parts being by weight unless otherwise stated.

Example 1 Into 545 parts of a 25% aqueous solution of dimethyl amine, cooled with ice and water, there were added from a dropping funnel 170 parts of acrylonltrile. The rate of addition of the nitrile was controlled so that the temperature in the reaction vessel remained below 20 C. After the cold reaction mixture had stood for one hour, it

.vacuum distilled. 204.5 parts of N,N-dimethylpropylenediamine were collected, B. P. 134 C. at atmospheric pressure.

38 parts of myristyl chloride were added dropwise to a solution of 15.5 parts of N,N-dimethylpropylenediamine in 160 parts of benzene. After one hour of stirring, the benzene solution was washed with aqueous sodium hydroxide. The benzene layer was then washed once with water and the solvent removed by vacuum distillation. The residue was distilled at 208-215" C./1-2 mm, giving a solid distillate of y-myristamidopropyldimethylamine.

A solution of 6.2 parts of Y-myristamidopropyldimethylamine and 8.4 parts of benzyl chloride in 30 parts of benzene was refluxed during a period of four hours. The benzene was removed under vacuum, giving a light-colored, amorphous semi-solid at room temperature, which melts at about 54 C. to a clear, straw-colored liquid. This quaternary ammonium salt, 'y-myristamidopropyldimethylbenzylammonium chloride, is soluble in most organic solvents and forms a clear 25% solution in water.

This compound is an a excellent germicidal agent. It has been found effective against Staphylococcus aureus in a dilution of one part in 25,000 at 37 C. during a test of five minutes. The phenol coefficient of the compound is in the range of 277 to 333.

This product is also particularly suitable as a wetting agent for cotton fabrics.

Example II A mixture consisting of 30 parts of benzene. 8.1 parts of y-capyrylamidopropyldimethyiamine and 5 parts of benzyl chloride was heated at reflux temperature for six hours. After removing the benzene, the -caprylamidopropyldimethylbenzylammonium chloride was obtained as a viscous syrup.

Example II! Two parts of benzyl chloride were gradually added to a solution of 4.5 parts of 'y-palmitamidopropyldimethylamine dissolved in 30 parts of benzene. The resulting solution was refluxed for about four hours. The benzene was removed by vacuum distillation, leaving the quaternary ammonium salt, 1-palmitamidopropyidimethylbenzylammonium chloride, as an opaque solid, readily soluble in water. This product is an effective germicide, and also a good softening and wetting agent for textile fabrics.

Example IV A solution of 6.9 parts of y-lauramidopropyl.

dimethylamine and 4.5 parts of benzyl chloride in parts of benzene was refluxed during a period of four hours. After removing the solvent, the 'y-lauramidopropyldimethylbenzylammonium chloride was obtained as a colorless viscous mass, soluble in water. This product is a good germicide, and may be advantageously used for various disinfecting purposes.

Other quaternary ammonium salts can be prepared according to the procedure followed in the above examples, such as the 'y-myristamidopropyldimethyl a-naphthylmethylammonium chloride, 'y-oleamidopropyldimethylbenzylammonium chloride, -lauramidopropyldiethylmethylammonium bromide, 'y-stearamidopropyldimethylbenzylammonium chloride and 'y-myristamidopropyldimethylailyiammonium bromide.

The y-steararnidopropyldimethylbenzylammonium chloride is an excellent softening agent for rayon and cotton fibers, and acts as a permanent re-wetting agent on fabrics.

While the invention has been described with particular reference to specific embodiments, it is to be understood that it is not to be limited thereto but is to be construed broadly and restricted solely by the scope of the appended claims.

We claim:

l. A germicidal composition containing as an effective germicidal agent the quaternary ammonium compound of the following formula 2. A germicidal composition containing as an eifective germicidal agent the quaternary ammonium compound of the following formula CH; CH:

3. A germicidal composition containing as an effective germicidal agent a compound of the formula OH; CH: R.CO.NH.CHQCHIOHJIf-CHIR1 CH: CH;

in wnich R. is an alkyl radical of 11-13 carbon atoms inclusive and Hal is a halogen.

5. A germicidal composition comprisinz, as an effective germicidal agent, an aqueous solution of a compound of the formula H2O CH:

11.0 O.NH.C HaQHiCHnI-C H 5 in which R is an alkyl radical of 11-13 carbon atoms.


REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PA'I'ENTS Number" Name Date 1,860,563 Wayne May 31, 1932 1,737,458 ,Hartmann et al. Nov. 26, 1939 20 2,262,741 De Groote Nov. 11, 1941 2,345,570 Bley Apr. 4, 1944 2,362,760 Maxwell Nov. 14, 1944

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US1737458 *Jul 19, 1928Nov 26, 1929Chem Ind BaselQuaternary ammonium compound and process of making same
US1860563 *May 21, 1931May 31, 1932Wayne Truman BMethod of resolving petroleum emulsions
US2262741 *Oct 11, 1940Nov 11, 1941Petrolite CorpComposition of matter and process for preventing water-in-oil type emulsions resulting from acidization of calcareous oil-bearing strata
US2345570 *Oct 7, 1938Apr 4, 1944North American Rayon CorpCoagulating bath containing cationactive inhibitors
US2362760 *Jan 12, 1943Nov 14, 1944Shell DevInsecticidal compositions
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2589674 *May 24, 1947Mar 18, 1952American Cyanamid CoAliphatic amido propyl quaternary ammonium salts
US2644003 *Feb 2, 1951Jun 30, 1953Geigy Ag J RQuaternary ammonium compounds and their manufacture
US2737509 *Nov 19, 1953Mar 6, 1956Jelling MurrayCarboxylic acid salts of n-dialkylaminoalkylamides
US2785092 *Aug 2, 1954Mar 12, 1957Ciba LtdCondensation product and textile material softened therewith
US2862009 *Feb 24, 1955Nov 25, 1958Ciba LtdNew water soluble quaternary ammonium salts
US2950253 *Jul 27, 1954Aug 23, 1960Bohme Fettchemie GmbhMethods of washing textile fabrics
US3060185 *Apr 17, 1959Oct 23, 1962Ciba Geigy CorpHydroxamic acid esters of alkanolamines
US3082227 *Sep 27, 1961Mar 19, 1963American Cyanamid CoMethod of preparing a quaternary ammonium compound
US3145137 *May 12, 1961Aug 18, 1964Monsanto CoAlkanoylamidoalkyleneamines and their quaternary ammonium salts as fungicides
US3260671 *Nov 23, 1962Jul 12, 1966Emery Industries IncAmide oxidation inhibitor for lubricants
US3270039 *Apr 10, 1963Aug 30, 1966Henkel & Cie GmbhAddition compounds of surface active sulfuric acid semiester salts and sulfobetainesand the production thereof
US3390158 *Nov 30, 1964Jun 25, 1968Spofa Vereinigte Pharma WerkeAromatic quaternary ammonium salts with disinfectant activity
US3410880 *Oct 30, 1963Nov 12, 1968Procter & GambleN-trialkylammonium imides of higher fatty acids
US3492324 *Sep 7, 1966Jan 27, 1970I C I Organics IncQuaternary salts of tertiary amines
US4012398 *Sep 16, 1975Mar 15, 1977Van Dyk & Company, IncorporatedQuaternary halides of mink oil amides
US4168302 *Mar 30, 1978Sep 18, 1979The Richardson CompanyHair conditioning compositions containing a non-irritating cationic surfactant
US4185098 *Apr 13, 1977Jan 22, 1980Hoechst AktiengesellschaftDisinfectant
US4228042 *Jun 26, 1978Oct 14, 1980The Procter & Gamble CompanyBiodegradable cationic surface-active agents containing ester or amide and polyalkoxy group
US4239660 *Dec 13, 1978Dec 16, 1980The Procter & Gamble CompanyDetergent composition comprising a hydrolyzable cationic surfactant and specific alkalinity source
US4965362 *Jul 6, 1989Oct 23, 1990Franz MergerJoint preparation of 3-dialkylaminopropionitriles, bis-(2-cyanoethyl) ether and, if desired, ethylene-cyanohydrin
US5783604 *Dec 10, 1996Jul 21, 1998Garcia Nunez; Maria RosaliaGermicidal compositions containing iodine compounds
US8691899 *Oct 9, 2007Apr 8, 2014Ethicon, Inc.Antimicrobial polymer compositions and the use thereof
US20090092648 *Oct 9, 2007Apr 9, 2009Ethicon, Inc.Antimicrobial polymer compositions and the use thereof
CN101100432BJul 4, 2006Aug 4, 2010中国人民解放军军事医学科学院毒物药物研究所Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride
CN101820931BSep 29, 2008Apr 2, 2014伊西康公司Antimicrobial polymer compositions and the use thereof
CN102869354A *Feb 15, 2011Jan 9, 2013梅根医药股份有限公司Pharmaceutical comprising myramistin
CN102869354B *Feb 15, 2011Dec 16, 2015梅根医药股份有限公司包含肉豆蔻酰氨基丙基二甲基苄基氯化铵的药物制剂
DE1031270B *Jul 7, 1952Jun 4, 1958American Cyanamid CoVerfahren zum Antistatischmachen von Gebilden aus Vinylharzen
DE102008039254A1 *Aug 20, 2008Feb 25, 2010Megainpharm GmbhMedicament, useful e.g. for treating infectious- and purulent inflammatory diseases of e.g. eyes, comprises benzyl-dimethyl-(3-(myristoylamino)-propyl)-ammonium chloride, dimethyl-(3-(myristoylamino)-propyl)-amine oxide and solvent
EP0327379A2 *Feb 3, 1989Aug 9, 1989CRODA INTERNATIONAL plcHumectants
WO1993002042A1 *Jul 16, 1992Feb 4, 1993Eastman Kodak CompanyAmide-containing quaternary ammonium salts
WO2004108125A1 *Jun 3, 2004Dec 16, 2004Megainpharm GmbhCoronavirus inactivating agent
WO2007075101A1 *Dec 28, 2005Jul 5, 2007Obschestvo S Organichennoi Otvetstvennostyu Naucho-Proizvodstvennaya Firma 'flobi'Method for determining concentration of c26h47cin2o in an aqueous medium
WO2011100994A1Feb 19, 2010Aug 25, 2011Megainpharm GmbhPharmaceutical comprising myramistin
WO2011101113A1Feb 15, 2011Aug 25, 2011Megainpharm GmbhPharmaceutical comprising myramistin
U.S. Classification514/625, 530/221, 554/52
International ClassificationC07C255/24
Cooperative ClassificationC07C255/24
European ClassificationC07C255/24