WO1993021766A1 - Ammonium quaternaire et son procede de preparation - Google Patents

Ammonium quaternaire et son procede de preparation Download PDF

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Publication number
WO1993021766A1
WO1993021766A1 PCT/US1993/003268 US9303268W WO9321766A1 WO 1993021766 A1 WO1993021766 A1 WO 1993021766A1 US 9303268 W US9303268 W US 9303268W WO 9321766 A1 WO9321766 A1 WO 9321766A1
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WO
WIPO (PCT)
Prior art keywords
water
mixture
quaternary ammonium
carbons
methyl
Prior art date
Application number
PCT/US1993/003268
Other languages
English (en)
Inventor
James E. Borland
E. Frederick Perkins, Jr.
Joe D. Sauer
Kim R. Smith
Original Assignee
Ethyl Corporation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ethyl Corporation filed Critical Ethyl Corporation
Publication of WO1993021766A1 publication Critical patent/WO1993021766A1/fr

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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
    • A01N33/12—Quaternary ammonium compounds

Definitions

  • This invention relates to quaternary ammonium haUde-containing compositions having an increased ability to wet hydrophobic surfaces.
  • Quaternary ammonium compounds such as N-alkyl-tyN-dmiethyl-N-berizylarnmo- nium chlorides (ADBAC) are water-soluble antimicrobial agents which are frequently used in dilute aqueous solution to clean germ-laden surfaces, such as hospital floors. These biocides are very effective in killing gram-positive bacteria; but the bacteria having more hydrophobic cell walls, including gram-negative bacteria and — to an even greater extent —the acid-fast bacteria (e.g., mycobacterium tuberculosis), are resistant to attack by such hydrophilic substances, which cannot wet the hydrophobic cell walls adequately. Thus, it would be desirable to improve the ability of the quats to wet hydrophobic surfaces.
  • ADBAC N-alkyl-tyN-dmiethyl-N-berizylarnmo- nium chlorides
  • compositions thus formed are mixtures of: (A) 1-99% by weight of a water-soluble quaternary ammonium compound corresponding to one of the formulas RR' 2 R"N + X " and R 2 (CH 3 ) 2 N + X " wherein R is an alkyl group containing 8-24 carbons, R' is methyl or -(CH 2 CH 2 0) n H in which n is 1-20, R" is methyl, benzyl, or alkylbenzyl, and X is chloro or bromo and
  • a water-insoluble compound selected from fatty alcohols and amides, dialkylmethylbenzylammonium chlorides and bromides, and dialkylmethyl ⁇ amine oxides containing alkyl groups of 8-24 carbons.
  • compositions may be prepared by mixing preformed quats with the water- insoluble compounds or by synthesizing the quats in the presence of the water-insoluble compounds.
  • the quaternary ammonium compounds improved by the practice of the invention are the water-soluble quats which, although known to have antimicrobial activity, have previously been found to be deficient in killing bacteria which are resistant to attack by hydrophilic substances.
  • they may be chlorides or bromides, although they are more commonly chlorides; and they contain one or two alkyl groups of 8-24 carbons as well as one or two methyl, hydroxyefhyl, or efhoxylated hydroxyethyl groups contributed by the amines from which they are prepared and the methyl, benzyl, or alkylbenzyl residue of the quaternization agent used in their syntheses.
  • any alkylbenzyl group in these compounds is a lower alkyl group, usually methyl or ethyl.
  • these quats are the N-octyl-, N-nonyl-, N-decyl-, N-dodecyl-, N- tridecyl-, N-tetradecyl-, N-pentadecyl-, N-hexadecyl-, N-octadecyl-, N-eicosyl-, N-doco- syl-, and N-tetracosyl-N,N,N-trimethylammonium chlorides and bromides; the corresponding N-ai ⁇ l-N,N-di-2-hydroxyemyl-N-methylammonium halides; the cor ⁇ espondmgN-alkyl-N,N-di(ethoxylatedhydroxyethyl)-N-methylammomuinhalides wherein the ethoxylated hydroxyethyl groups correspond to the formula (CH 2 CH 2 0) r ⁇ H in which
  • quats may be coirjmercially-available compounds prepared by conventional quaternizations of the appropriate tert-amines corresponding to one of the formulas RR' 2 N and R 2 (CH 3 )N, wherein R and R' are as defined above, with the appropriate quaternizing agent corresponding to the formula R"X, wherein R" and X are as defined above.
  • the quats are compounds prepared by reacting these appropriate tert-amines and quaternizing agents by a novel technique in which the solvent, instead of being one of the solvents normally used for the reaction (e.g., water or a lower alkanol, such as ethanol or isopropanol), is one of the water-insoluble compounds which it is desired to have in admixture with the quat to improve its ability to wet hydrophobic surfaces.
  • the solvent instead of being one of the solvents normally used for the reaction (e.g., water or a lower alkanol, such as ethanol or isopropanol), is one of the water-insoluble compounds which it is desired to have in admixture with the quat to improve its ability to wet hydrophobic surfaces.
  • the quaterni- zation is conducted by conventional techniques except for the use of the different solvent.
  • the reaction may be effected under ambient conditions; or elevated temperatures and/or elevated pressures may be used to speed the reaction. Most commonly, the process is conducted at a temperature in the range of 20-100 ° C with or without added pressure.
  • the solvent employed in the process of the invention may be any of the fatty alcohols and amides, dialkylmethylbenzylammonium chlorides and bromides, and dialkylmemylamine oxides mentioned above and described more fully below.
  • the fatty alcohols are apt to be preferred.
  • the solvent is employed in a solvent amount, and an advantage of its use is that it permits the quat/water-insoluble compound product to be formed as a flakeable solid rather than as a liquid solution when the higher molecular weight starting materials are utilized.
  • Fatty alcohols utilizable in the practice of the invention are the alkanols containing 8-24 carbons, such as octanol, decanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, octadecanol, eicosanol, docosanol, tetracosanol, and mixtures of any two or more thereof. Those containing 12-16 carbons are apt to be preferred.
  • the water-insoluble compound is a fatty amide, it may be any amide — cyclic or acyclic in structure — containing an alkyl group of 8-24 carbons.
  • Such amides include, e.g., unsubstituted amides of fatty acids, alkylamides and alkanolamides of such acids (especially the superamides, i.e., alkanolamides of the type obtained by reacting a fatty acid with an a&anolan ⁇ ine in equimolar proportions), and N-alkyllac- tams.
  • the preferred fatty amides are superamidesprepared from ethanolamine and a fatty acid containing 10-20 carbons, most preferably cocodiethanolsuperamide; and N-alkylcaprolactams wherein the alkyl group contains 10-20 carbons, most preferably N-dodecylcaprolactam.
  • diallcyjjTiethylbenzylammonium chlorides and bromides and the dialkyl- memylamine oxides which can be used are those in which the alkyl groups contain 8-24 carbons.
  • Particularly preferred compounds of these types are N,N-didecyl-N- memyl-N-ben2ylammonium chloride and N,N-didec l-N-memylamine oxide.
  • the bromide corresponding to the chloride as well as the corresponding chlorides, bromides, and oxides in which at least one the decyl groups is replaced with another alkyl group containing 8-24 carbons (e.g., octyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl, or tetracosyl) are also utilizable.
  • compositions of the invention may have water-soluble quat/water- insoluble compound weight ratios anywhere in the range of 1/99 to 99/1, those containing the smaller amounts of water-insoluble compound are less capable of wetting hydrophobic surfaces, while those containing the larger amounts of water-insoluble compound naturally contain less of the antimicrobial agent.
  • the water-soluble quat/water-insoluble compound weight ratio is preferably OJ-10/1, more preferably 1-5/1. Particularly good results have been achieved when the weight ratio is about 2/1.
  • the water-soluble quat/water-insoluble compound mixtures of the invention will eventually be diluted with water and optionally also a chelating agent, such as emylenediaminetetraacetic acid or diethylenetriaminepentaacetic acid, to form aqueous compositions containing up to 250 ppm of chelating agent and 500-1000 ppm of the water-soluble quat — the same concentration found in conventional aqueous quat solutions used for cleaning germ-laden surfaces.
  • a chelating agent such as emylenediaminetetraacetic acid or diethylenetriaminepentaacetic acid
  • the mixtures prepared in solid form may also be used in combination with talc or other mild abrasive to form a scouring powder.
  • compositions of the invention have the advantage of being able to wet hydrophobic surfaces more readily than the water-soluble quats alone and frequently have the added advantage of providing better solubilization of those surfaces. These advantages should make them more effective in killing microbes, such as mycobacterium tuberculosis, which have cell walls containing so much lipid that they are resistant to attack by hydrophilic quats, such as ADBAC.
  • the product is a yellow-white solid having the alcohol mixture in admixture with a mixture of N-dodecyl-, N-tetradecyl-, and N-hexadecyl-N,N-dimethyl-N-benzylammonium chlorides.
  • SP solubilization parameter
  • ADBAC a mixture of N-dodecyl-, N-tetradecyl-, and N-hexade yl-N,N-dimethyl- N-benzylammonium chlorides
  • the use of the water-insoluble compound togetherwith the water-insoluble quat ordinarily increases the surface area of hydrophobic surface wetted immediately, invariable increases the surface area wetted after five minutes, and usually also increases the solubility parameter.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne un composé d'ammonium quaternaire soluble dans l'eau correspondant à la formule RR'2R'N?+X- ou R¿2(CH3)2N+X-, dans laquelle R est un groupe alkyle contenant de 8 à 24 atomes de carbone, R' représente méthyle ou -(CH¿2?CH2O)nH où n représente 1-20, R' méthyle, benzyle ou benzyle d'alkyle, et X représente chloro ou bromo. Ledit composé est utilisé en mélange avec au moins un composé insoluble dans l'eau sélectionné parmi des alcools et des amides gras, des chlorures et des bromures de dialkylméthylbenzylammonium, et des oxydes de dialkylméthylamine contenant des groupes alkyle de 8 à 24 atomes de carbone, afin d'augmenter la capacité dudit composé quaternaire soluble dans l'eau de s'imbiber dans les surfaces hydrophobes lorsqu'il est utilisé, par exemple, dans des solutions biocides aqueuses. Ledit composé quaternaire soluble dans l'eau utilisé peut être un matériau disponible ou un produit synthétisé dans le composant insoluble dans l'eau tel qu'un solvant.
PCT/US1993/003268 1992-04-27 1993-04-06 Ammonium quaternaire et son procede de preparation WO1993021766A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US87478792A 1992-04-27 1992-04-27
US07/874,787 1992-04-27

Publications (1)

Publication Number Publication Date
WO1993021766A1 true WO1993021766A1 (fr) 1993-11-11

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2731585A1 (fr) * 1995-03-13 1996-09-20 Stepan Co Procedes et compositions pour la desinfection des surfaces comportant des bacteries responsables de la tuberculose
WO1997022246A1 (fr) * 1995-12-20 1997-06-26 Nigel Paul Maynard Solubilisation de biocides dans des solvants anhydres de type 'onium'
WO1998035933A1 (fr) * 1997-02-14 1998-08-20 Timoleon Venetsianos Nouvelle composition chimique polydynamique a applications multiples et procede de preparation de cette composition
WO2008057773A2 (fr) * 2006-10-27 2008-05-15 3M Innovative Properties Company Compositions antimicrobiennes

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1045186A (fr) * 1951-11-16 1953-11-24 Consortium De Prod Chim Et De Perfectionnements aux procédés de dissolution des sels d'ammenium quaternaires dans les huiles minérales
US2666010A (en) * 1950-09-05 1954-01-12 California Research Corp Quaternary ammonium germicidal compositions
GB718050A (en) * 1951-04-05 1954-11-10 Miles Lab Improvements in or relating to compositions having germicidal, fungicidal and anesthetic properties
US3296145A (en) * 1965-10-21 1967-01-03 Millmaster Onyx Corp Quaternary ammonium-tertiary amine oxide compositions
GB1220947A (en) * 1966-07-18 1971-01-27 Baird Chemical Ind Inc Germicidal compositions
EP0068399A1 (fr) * 1981-06-27 1983-01-05 Hoechst Aktiengesellschaft Concentrés liquides d'agents désinfectants
WO1992014362A1 (fr) * 1991-02-21 1992-09-03 Bio-Lab, Inc. Biocides d'ammonium quaternaire c14 non cristallisants

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2666010A (en) * 1950-09-05 1954-01-12 California Research Corp Quaternary ammonium germicidal compositions
GB718050A (en) * 1951-04-05 1954-11-10 Miles Lab Improvements in or relating to compositions having germicidal, fungicidal and anesthetic properties
FR1045186A (fr) * 1951-11-16 1953-11-24 Consortium De Prod Chim Et De Perfectionnements aux procédés de dissolution des sels d'ammenium quaternaires dans les huiles minérales
US3296145A (en) * 1965-10-21 1967-01-03 Millmaster Onyx Corp Quaternary ammonium-tertiary amine oxide compositions
GB1220947A (en) * 1966-07-18 1971-01-27 Baird Chemical Ind Inc Germicidal compositions
EP0068399A1 (fr) * 1981-06-27 1983-01-05 Hoechst Aktiengesellschaft Concentrés liquides d'agents désinfectants
WO1992014362A1 (fr) * 1991-02-21 1992-09-03 Bio-Lab, Inc. Biocides d'ammonium quaternaire c14 non cristallisants

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
MANUFACTURING CHEMIST. (INCL. MANUFACTURING PERFUMER) vol. 27, no. 8, August 1956, LONDON GB pages 305 - 309 C.D.MOORE ET AL. 'Germicides Based on Surface-Active Agents' *
MANUFACTURING CHEMIST. (INCL. MANUFACTURING PERFUMER) vol. 29, no. 1, January 1958, LONDON GB pages 194 - 198 C.D.MOORE ET AL. 'Germicides Based on Surface-Active Agents' *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2731585A1 (fr) * 1995-03-13 1996-09-20 Stepan Co Procedes et compositions pour la desinfection des surfaces comportant des bacteries responsables de la tuberculose
WO1997022246A1 (fr) * 1995-12-20 1997-06-26 Nigel Paul Maynard Solubilisation de biocides dans des solvants anhydres de type 'onium'
WO1998035933A1 (fr) * 1997-02-14 1998-08-20 Timoleon Venetsianos Nouvelle composition chimique polydynamique a applications multiples et procede de preparation de cette composition
WO2008057773A2 (fr) * 2006-10-27 2008-05-15 3M Innovative Properties Company Compositions antimicrobiennes
WO2008057773A3 (fr) * 2006-10-27 2009-03-26 3M Innovative Properties Co Compositions antimicrobiennes
JP2010508287A (ja) * 2006-10-27 2010-03-18 スリーエム イノベイティブ プロパティズ カンパニー 抗菌剤組成物
AU2007317622B2 (en) * 2006-10-27 2010-12-16 3M Innovative Properties Company Antimicrobial compositions
US8338491B2 (en) 2006-10-27 2012-12-25 3M Innovative Properties Company Antimicrobial compositions
JP2013126998A (ja) * 2006-10-27 2013-06-27 Three M Innovative Properties Co 抗菌剤組成物
US8569384B2 (en) 2006-10-27 2013-10-29 3M Innovative Properties Company Antimicrobial compositions

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