US3730702A - Biocidal unsymmetrical di-higher alkyl dimethyl ammonium compounds - Google Patents
Biocidal unsymmetrical di-higher alkyl dimethyl ammonium compounds Download PDFInfo
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- US3730702A US3730702A US00151583A US3730702DA US3730702A US 3730702 A US3730702 A US 3730702A US 00151583 A US00151583 A US 00151583A US 3730702D A US3730702D A US 3730702DA US 3730702 A US3730702 A US 3730702A
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- US
- United States
- Prior art keywords
- alkyls
- unsymmetrical
- higher alkyl
- dimethyl ammonium
- biocidal
- 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.)
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Classifications
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- 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
- R and R are either straight chain or predominantly straight chain but dissimilar alkyls, one of said alkyls having from 9 to 10 carbon atoms and the other having from 11 to 12 carbon atoms, at least one of the alkyls having an odd number of carbons, and the total sum of both alkyls being between and 21; and wherein X is a biocidally acceptable anion preferably derived from a halogen such as bromine or chlorine, or which may be methosulfate.
- This invention relates to the biocidal use of certain water-soluble unsymmetrical (ii-higher alkyl dimethyl ammonium salts.
- hard water is generally used to describe water having an appreciable amount of carbonates, bicarbonates, sulfates and chlorides of calcium and magnesium, and sometimes also of iron.
- hard water also includes the possible presence of alkaline earths and heavy metal ions in general.
- appreciable amoun is meant at least about 75 p.p.m. to about 500 p.p.m.
- Very hard water is that which contains over 1,000 p.p.m.
- R and R are either straight chain or predominantly straight chain but dissimilar alkyls, one of said alkyls having from 9 to 10 carbon atoms and the other having from 11 to 12 carbon atoms, at least one of the alkyls having an odd number of carbons, and the total sum of both alkyls being between 20 and 21; and wherein X is a biocidally acceptable anion preferably derived from a halogen such as bromine or chlorine. It is also possible to use methosulfate, although much less preferable since the results are not as effective and the compounds are somewhat more difficult to make.
- straight chain or predominantly straight chain alcohols such as may be obtained by the oxo-reaction of alpha-olefins.
- an oxo-derived alcohol containing about 20% by weight C12, C13, C14 and by weight C may be converted to a tertiary amine and quaternized.
- Decene-l may be converted to a C amine via the C oxo-alcohol.
- the biocides of the present invention are effective in very hard water in a concentration of the biocide of between about 100 to 1,000 p.p.m.
- the preferred and most effective range is about 200 to 400 p.p.m.
- the present compounds are all easily prepared in various manners.
- the following examples are illustrative of their preparation.
- EXAMPLE 3 In a similar manner to Examples 1 and 2, the corre sponding alkyl chlorides were substituted for the corresponding alkyl bromides in each instance, and the reactions were carried essentially to completion to yield nonyl dodecyl ammonium chloride in each instance.
- EXAMPLE 4 Using the same procedures as in Examples 1, 2 and 3, and using the same reaction conditions, the di-higher alkyl dimethyl ammonium bromides shown in Tables I and II hereinafter, as well as the corresponding chlorides, were prepared from the corresponding al-kyl dimethyl amines and alkyl bromides and chlorides.
- the aforesaid unsymmetrical quaternary ammonium compounds may also be prepared by a two-stage process whereby an unsymmetrical di-higher alkyl monomethyl amine is first prepared by the interaction of an alkyl halide such as chloride or bromide, and an alkyl monomethyl amnie. Then after liberating the tertiary amine, by treatment with a caustic, from its hydrohalide salt, the tertiary amine is quaternized by reaction with an alkylating agent. This is illustrated in Examples and 6 as follows:
- EXAMPLE 5 Equimolecular amounts of dodecyl monomethyl amine and nonyl bromide were mixed with an amount of 99% isopropanol equal to about the combined weight of the amine and the bromide. The mixture was then heated at about 90 C., under agitation and under reflux, at atomspheric pressure, for a period of hours until the reaction was essentially complete as indicated by argentometric titration of the bromide ion. The solution was then mixed with about twice its volume of water plus about 1 to 1.2 molecular equivalent of NaOH. The liberated tertiary amine (nonyl dodecyl monomethyl amine) was then separated in a separatory funnel, washed with water, and dried.
- EXAMPLE 6 The tertiary amine of Example 5 was quaternized by reaction with methyl chloride, in an agitated pressure vessel at about 90 C., in a medium of 99% isopropanol, along with about 3% of water and 0.5% of sodium bicarbonate as an acid acceptor. Methyl chloride was then passed into the vessel at such a rate as to maintain a pres sure of less than 30 p.s.i. in the reactor, the addition of the methyl chloride being continued until no further reaction occurred, as indicated by failure of the pressure to fall when the methyl chloride supply was cut off.
- the corresponding bromide was prepared in a similar manner by reacting the tertiary amine with methyl bromide at about 5055 C., at about atmospheric pressure.
- EXAMPLE 7 A process similar to Example 6 was used to obtain the corresponding methosulfatc, except that the reaction was conducted at about 60 C. and a stochiometric amount of dimethyl sulfate was used as the reactant.
- alkyl halide may then be employed as a quaternizing agent for the tertiary amines, or it may be reacted with either monomethyl amine or dimethyl amine to form the corresponding higher alkyl monomethyl amine or higher alkyl dimethyl amine. It It may thereafter be reacted according to the foregoing examples to yield the unsymmetrical di-higher alkyl dimethyl ammonium quaternary salts of this invention. This type of reaction is shown by the following example.
- EXAMPLE 8 The alochol derived by the oxo reaction from decene-l, which yields a mixture of n-undecanol and alpha-methyl decanol, was halogenated by reaction with hydrogen chloride to yield the undecyl chloride. This chloride was then reacted with dodecyl monomethyl amine in the manner de scribed in Example 5 to form undecyl dodecyl monomethyl amine. This was quaternized by reaction with methyl chloride in the same manner described in Example 6, to yield the unsymmetrical di-higher alkyl dimethyl ammonium salt.
- any desirable alcohol other than isopropanol may be used, or any other feasible solvent may be substituted.
- the organism used was Escherichia coli, the inoculum containing a concentration of the organism in the order of 100,000,000 per milliliter.
- the compound used was the bromide salt.
- the product of this invention may be used for the disinfection or sanitization of hard surfaces; for the sanitization of textile and other fabrics; as topical antiseptics; in water treatment; and for other bactericidal, fungicidal and algacidal purposes where quaternary ammonium compounds are compatible.
- the products When mixed with an equal amount of a non-ionic surfactant, such as alkyl phenol ethoxylate, the products retain a substantial proportion of their efiicacy. They also remain substantially potent in the presence of small amounts of anionic surfactants or the protein.
- a non-ionic surfactant such as alkyl phenol ethoxylate
- a method of disinfecting or sanitizing hard surfaces, fabrics, topical portions of the body, and water which comprises applying thereto a bactericidally, fungicidally or algacidally effective amount of a compound of the structure:
- R CH3 I R'/ OHa wherein R and R are straight chain or predominantly straight chain alkyls, one of said alkyls having 9 carbon atoms and the other of said alkyls having 11 carbon atoms, and X being a member of the group consisting of chloride, bromide and methosulfate.
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
R-N(+)(-R'')(-CH3)2 X(-)
WHEREIN R AND R'' ARE EITHER STRAIGHT CHAIN OR PREDOMINANTLY STRAIGHT CHAIN BUT DISMISSAL ALKYLS, ONE OF SAID ALKYLS HAVING FROM 9 TO 10 CARBON ATOMS AND THE OTHER HAVING FROM 11 TO 12 CARBON ATOMS, AT LEAST ONE OF THE ALKYLS HAVING AN ODD NUMBER OF CARBONS, AND THE TOTAL SUM OF BOTH ALKYLS BEING BETWEEN 20 AND 21, AND WHEREIN X IS BIOCIDALLY ACCEPTABLE ANION PREFERABLY DERIVED FROM A HALOGEN SUCH AS BROMINE OR CHLORINE, OR WHICH MAY BE METHOSULFATE.
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15158371A | 1971-06-09 | 1971-06-09 |
Publications (1)
Publication Number | Publication Date |
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US3730702A true US3730702A (en) | 1973-05-01 |
Family
ID=22539409
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00151583A Expired - Lifetime US3730702A (en) | 1971-06-09 | 1971-06-09 | Biocidal unsymmetrical di-higher alkyl dimethyl ammonium compounds |
Country Status (1)
Country | Link |
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US (1) | US3730702A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4720492A (en) * | 1981-01-19 | 1988-01-19 | Petrolite Corporation | Quaternary ammonium derivatives of 1,4-thiazine sulfonic acids |
US5100920A (en) * | 1985-03-18 | 1992-03-31 | Kao Corporation | Miticide |
US5332511A (en) * | 1993-06-25 | 1994-07-26 | Olin Corporation | Process of sanitizing swimming pools, spas and, hot tubs |
US5373025A (en) * | 1992-02-24 | 1994-12-13 | Olin Corporation | Sanitizer for swimming pools, spas, and hot tubs |
-
1971
- 1971-06-09 US US00151583A patent/US3730702A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4720492A (en) * | 1981-01-19 | 1988-01-19 | Petrolite Corporation | Quaternary ammonium derivatives of 1,4-thiazine sulfonic acids |
US5100920A (en) * | 1985-03-18 | 1992-03-31 | Kao Corporation | Miticide |
US5373025A (en) * | 1992-02-24 | 1994-12-13 | Olin Corporation | Sanitizer for swimming pools, spas, and hot tubs |
WO1994029266A1 (en) * | 1993-06-14 | 1994-12-22 | Olin Corporation | Sanitizer for swimming pools, spas, and hot tubs |
US5332511A (en) * | 1993-06-25 | 1994-07-26 | Olin Corporation | Process of sanitizing swimming pools, spas and, hot tubs |
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Legal Events
Date | Code | Title | Description |
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AS | Assignment |
Owner name: BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. 111 FOU Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004139/0941 Effective date: 19821222 Owner name: MILLMASTER ONYX GROUP, INC., A DE CORP. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:KEWANEE INDUSTRIES, INC.;REEL/FRAME:004139/0909 Effective date: 19830407 |
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AS | Assignment |
Owner name: STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A CORP. OF DE.;REEL/FRAME:004606/0309 Effective date: 19860815 Owner name: STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A CORP. OF DE.;REEL/FRAME:004606/0309 Effective date: 19860815 |