US3484523A - Quaternary ammonium-tertiary amine oxide compositions - Google Patents
Quaternary ammonium-tertiary amine oxide compositions Download PDFInfo
- Publication number
- US3484523A US3484523A US604598A US3484523DA US3484523A US 3484523 A US3484523 A US 3484523A US 604598 A US604598 A US 604598A US 3484523D A US3484523D A US 3484523DA US 3484523 A US3484523 A US 3484523A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- quaternary ammonium
- amine oxide
- tertiary amine
- carbon atoms
- 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.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/75—Amino oxides
Definitions
- R is a member of the group consisting of alkyl and alkenyl having 8 to 20 carbon atoms
- R and R" are selected from the group consisting of lower alkyl, hydroxy lower alkyl and individual valences of heterocyclic radicals such as morpholine, and at least one germicidal quaternary ammonium compound having a phenol co eflicient of at least 100 with respect to Staphylococcus aureus and Salmonella typhosa at 20 C., the amine oxide and quaternary compounds being respectively present in a proportion of between less than 5:1 to about 0.5: 1, by weight.
- R contains from 8 to 20 carbon atoms and may, if desired, be unsaturated in nature, where R and R" may be methyl, ethyl, propyl, isopropyl, hydroxyethyl, hydroxyethoxyethyl or hydroxyethyl polyethoxyethyl radicals and wherein the oxygen is linked to nitrogen by means of a semi-polar bond.
- R and R" may jointly constitute the CH 'CH O-CH CH radical, i.e. the above formula is:
- any water-soluble quaternary ammonium salt having a long alkyl radical containing from 8 to 22 carbon atoms attached either directly to the nitrogen atom or through an intermediate benzyl or phenoxy ethyl radical and having a phenol coefficient of at least with respect to the Staphylococcus aureus and Salmonella typhosa at 20 C. when determined by the standard method given in the Oificial Method of Analysis of the Association of Oflicial Agricultural Chemists, Ninth Edition (1960), page 63 et seq.
- quaternary ammonium compounds are alkyl trimethyl ammonium chlorides, alkyl-benzyl trimethyl ammonium chlorides, alkyl dimethyl benzyl ammonium chlorides, alkyl dimethyl menaphthyl ammonium chlorides, alkyl dimethyl substituted benzyl ammonium chlorides in which the benzyl radical is substituted with one or more side chains containing from 1 to 5 carbon atoms such, for example, as methyl, dimethyl, ethyl, isopropyl, ter-butyl, n-amyl, isoamyl, tetramethyl, trimethyl and the like in which the carbon atoms may all be in the same or different side chains or in which the benzyl radical may be substituted by .an alkylene group such as tetrahydro menaphthyl or in which the benzyl radical bears one, two or more halogen atoms such as chlorine or bromine, alky
- alkyl dimethyl benzyl ammonium chloride in which the alkyl radical blend contains at least 50% myristyl, together with alkyl dimethyl ethyl-benzyl ammonium chloride in which the alkyl radical blend is predominantly (at least 50%) C this blend being employed in approximately 1:1 ratio, by Weight.
- the quaternary ammonium compounds which have phenol coefficients of more than 500 against Staphylococcus aureus such, for example, are ETC-824, an alkyl dimethyl benzyl ammonium chloride in IS C14, C15, C12 and C18; Tetrosan 3,4 D, an alkyl dimethyl dichlorobenzyl ammonium chloride in which alkyl is 50% C 30% C 17% C and 8% C BTC471 and ETC-927, which are, respectively, alkyl dimethyl ethyl-benzyl and alkyl dimethyl dimethylbenzyl ammonium chlorides in which the alkyl distribution is the same as in Tetrosan 3,4 D; lauryl dimethyl menaphthyl or tetrahydromenaphthyl ammonium chloride; lauryl isoquinolinium bromide and the like; or mixtures thereof.
- ETC-824 an alkyl dimethyl benzyl ammonium chloride in IS C14,
- compositions of this invention are preferably prepared as liquids for convenient use as a surgical or other degerming scrub soap. However, if desired, they may be thickened by certain additives into a gel or a paste or to be molded into a bar by methods well known to the art; or they. may be prepared as a powder, as, for example, as an adduct with urea, by mixing the composition with crystalline urea in sufiicient amounts to produce a free-flowing powder.
- EXAMPLE 1 A series of surgical scrub compositions were prepared containing the following listed components in the individually listed parts by weight. There were four compositions listed as Comp. A, Comp. B, Comp. C, and Comp. D. Each composition was prepared by mixing under ambient conditions, and was adjusted to a pH of 6.0, to give a non-irritating surgical scrub having satisfactory slip and emollient properties.
- Composition A B C D Lauryl dimethlamine oxide, 30% 2.0 2. 1.0 9 Stearyl dimethlyamine oxide, 30% 1. 1 1. 1 0.75 2. 0 50% aqueous solution of quaternary ammonium germieide blend of equal parts of alkyl dimethyl benzyl ammonium chloride and alkyl dimethyl ethylbenzyl ammonium chloride,
- first alkyl has a distribution of 60% C14, 30% Om, 5% C11, and 5% C15
- second alkyl has a distribution of 50% C12
- Composition E Sodium tripolyphosphate Sodium metasilicate- Sodium bicarbonate.
- Optical brightener (Uvitex SIA-Ciba)- 50% aqueous solution of quaternary ammonium germicide blend of equal parts of alkyl dimethyl benzyl ammonium chloride and alkyl dimethyl ethylbenzyl ammonium chloride, wherein the first alkyl has a distribution of 60% C14, 30% C 5% C12, and 5% C18, and the second alkyl has a glistgibution 01 50% C12, 30% C14, 17% C15, and
- a is 50% aqueous solution of a mixture of 3 parts of 75% active di-(hydrogenated tallow), dimethyl ammonium methosulfate, and 75% active stearyl dimethyl benzyl ammonium chloride (softener for fabrics and the like) Stearyl dimethylamine oxide, 30% Ratio, amine oxide to quaternary germicide Killing dilutions were run on the preceding compositions by the method given in Official Methods of Analysis of the Association of Ofiicial Agricultural Chemists, Ninth Edition (1960), page 63 et seq., using as test organisms both Sta hylococcus aureus and Salmonella
- R is a member of the group consisting of alkyl and alkenyl having 8 to 20 carbon atoms
- R and R" are selected from the group consisting of methyl, ethyl, propyl, isopropyl, hydroxyalkyl, hydroxylalkoxyalkyl, hydroxyalkyl
- the germicidal agent of claim 1 in admixture with an softeningly effective amount of a fabric softener.
- a method of simultaneously cleaning and sterilizing human tissue which comprises applying to said tissue a composition consisting essentially of (1) at least one tertiary amine oxide of the formula:
- R is a member of the group consisting of alkyl and alkenyl having 8 to 20 carbon atoms
- R and R" are selected from the group consisting of methyl, ethyl, propyl, isopropyl, hydroxyalkyl, hydroxyalkoxyalkyl, hydroxyalkyl polyalkoxyalkyl, and morpholine containing R and R" and N as members, the alkyl of the hydroxyalkyl compounds being lower alkyl
- at least one germicidal quaternary ammonium compOund having at least one long chain alkyl group of 8 to 22 carbon atoms attached to the quaternary nitrogen and having a phenol coeflicient of at least 100 with respect to Staphylococcus aureus and Salmonella typhosa at 20 C., the amine oxide and quaternary ammonium compound being respectively present in the proportion of 4.8:1 to about 0.5: 1, by weight.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60459866A | 1966-12-27 | 1966-12-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3484523A true US3484523A (en) | 1969-12-16 |
Family
ID=24420268
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US604598A Expired - Lifetime US3484523A (en) | 1966-12-27 | 1966-12-27 | Quaternary ammonium-tertiary amine oxide compositions |
Country Status (1)
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US (1) | US3484523A (en) |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4062976A (en) * | 1975-12-18 | 1977-12-13 | Michaels Edwin B | Antimicrobial compositions employing certain substituted alanines and certain t-amine oxides |
US4075350A (en) * | 1975-12-18 | 1978-02-21 | Michaels Edwin B | Antimicrobial compositions employing certain betaines and certain amine oxides |
US4107328A (en) * | 1975-12-18 | 1978-08-15 | Michaels Edwin B | Antimicrobial compositions and methods for utilizing the same employing mixtures of amines |
US4145436A (en) * | 1977-11-07 | 1979-03-20 | Michaels Edwin B | Antimicrobial compositions and method for using same |
DE2844157A1 (en) * | 1977-10-14 | 1979-04-19 | Block Drug Co | MEANS FOR DISTRIBUTING EECTOPARASITES AND / OR KILLING THEIR EGGS |
FR2406439A1 (en) * | 1975-04-02 | 1979-05-18 | Michaels Edwin | Antimicrobial compsn. contg. acyl-betaine and amine oxide - giving long term control of body odour |
US4183952A (en) * | 1975-12-18 | 1980-01-15 | Michaels Edwin B | Antimicrobial compositions |
US4333921A (en) * | 1980-10-02 | 1982-06-08 | American Cyanamid Company | Hair cleansing conditioner with lathering action |
EP0081801A2 (en) * | 1981-12-14 | 1983-06-22 | Kao Corporation | Liquid detergent composition |
US4597975A (en) * | 1981-11-06 | 1986-07-01 | Woodward Fred E | Iodine surface active compositions |
US5476615A (en) * | 1994-05-20 | 1995-12-19 | Lonza Inc. | Low foam sanitizers |
US5486315A (en) * | 1994-05-20 | 1996-01-23 | Lonza Inc. | Low foam branched alkyldimethylamine oxides |
US5833741A (en) * | 1997-01-16 | 1998-11-10 | Lonza Inc. | Waterproofing and preservative compositons for wood |
GB2334677A (en) * | 1998-02-25 | 1999-09-01 | Showa Water Ind Co Ltd | Antimicrobial agents containing an amine oxide |
US6340384B1 (en) | 1999-05-24 | 2002-01-22 | Lonza Inc. | Copper/amine oxide wood preservatives |
US6375727B1 (en) | 1999-05-24 | 2002-04-23 | Lonza Inc. | Amine oxide/iodine containing blends for wood preservation |
US6448279B1 (en) | 1999-05-24 | 2002-09-10 | Lonza Inc. | Isothiazolone/amine oxide wood preservatives |
US6485790B2 (en) | 1999-04-08 | 2002-11-26 | Lonza Inc. | Methods for enhancing penetration of wood preservatives |
US6508869B2 (en) | 2000-06-30 | 2003-01-21 | Lonza Inc. | Boron compound/amine oxide compositions |
DE10138456A1 (en) * | 2001-08-04 | 2003-02-13 | Bode Chemie Gmbh & Co | Alcoholic gels |
US6527981B1 (en) | 1999-05-24 | 2003-03-04 | Lonza Inc. | Azole/amine oxide preservatives |
US6572788B2 (en) | 2000-05-24 | 2003-06-03 | Lonza, Inc. | Amine oxide wood preservatives |
US20060257282A1 (en) * | 2005-05-12 | 2006-11-16 | Tony Buhr | Large-scale decontamination of biological microbes using amine oxides at acidic pH |
WO2015091163A1 (en) * | 2013-12-16 | 2015-06-25 | Henkel Ag & Co. Kgaa | Disinfectant composition with excellent foam profile |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3296145A (en) * | 1965-10-21 | 1967-01-03 | Millmaster Onyx Corp | Quaternary ammonium-tertiary amine oxide compositions |
-
1966
- 1966-12-27 US US604598A patent/US3484523A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3296145A (en) * | 1965-10-21 | 1967-01-03 | Millmaster Onyx Corp | Quaternary ammonium-tertiary amine oxide compositions |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2406439A1 (en) * | 1975-04-02 | 1979-05-18 | Michaels Edwin | Antimicrobial compsn. contg. acyl-betaine and amine oxide - giving long term control of body odour |
US4062976A (en) * | 1975-12-18 | 1977-12-13 | Michaels Edwin B | Antimicrobial compositions employing certain substituted alanines and certain t-amine oxides |
US4075350A (en) * | 1975-12-18 | 1978-02-21 | Michaels Edwin B | Antimicrobial compositions employing certain betaines and certain amine oxides |
US4107328A (en) * | 1975-12-18 | 1978-08-15 | Michaels Edwin B | Antimicrobial compositions and methods for utilizing the same employing mixtures of amines |
US4183952A (en) * | 1975-12-18 | 1980-01-15 | Michaels Edwin B | Antimicrobial compositions |
DE2844157A1 (en) * | 1977-10-14 | 1979-04-19 | Block Drug Co | MEANS FOR DISTRIBUTING EECTOPARASITES AND / OR KILLING THEIR EGGS |
US4179504A (en) * | 1977-10-14 | 1979-12-18 | Block Drug Company, Inc. | Alkyl amine oxide toxicants |
US4145436A (en) * | 1977-11-07 | 1979-03-20 | Michaels Edwin B | Antimicrobial compositions and method for using same |
US4333921A (en) * | 1980-10-02 | 1982-06-08 | American Cyanamid Company | Hair cleansing conditioner with lathering action |
US4597975A (en) * | 1981-11-06 | 1986-07-01 | Woodward Fred E | Iodine surface active compositions |
EP0081801A2 (en) * | 1981-12-14 | 1983-06-22 | Kao Corporation | Liquid detergent composition |
EP0081801A3 (en) * | 1981-12-14 | 1984-10-17 | Kao Corporation | Liquid detergent composition |
US5679633A (en) * | 1994-05-20 | 1997-10-21 | Lonza Inc. | Low foam branched alkyldimethylamine oxides |
US5486315A (en) * | 1994-05-20 | 1996-01-23 | Lonza Inc. | Low foam branched alkyldimethylamine oxides |
US5476615A (en) * | 1994-05-20 | 1995-12-19 | Lonza Inc. | Low foam sanitizers |
US5833741A (en) * | 1997-01-16 | 1998-11-10 | Lonza Inc. | Waterproofing and preservative compositons for wood |
GB2334677A (en) * | 1998-02-25 | 1999-09-01 | Showa Water Ind Co Ltd | Antimicrobial agents containing an amine oxide |
GB2334677B (en) * | 1998-02-25 | 2000-01-26 | Showa Water Ind Co Ltd | Bactericides and cleaning agents containing the same |
US6172029B1 (en) | 1998-02-25 | 2001-01-09 | Showa Water Industries Co., Ltd. | Bactericides and cleaning agents containing the same |
US6268326B1 (en) | 1998-02-25 | 2001-07-31 | Showa Water Industries Co., Ltd. | Bactericides and cleaning agents for eradicating Legionella bacteria |
US6485790B2 (en) | 1999-04-08 | 2002-11-26 | Lonza Inc. | Methods for enhancing penetration of wood preservatives |
US6375727B1 (en) | 1999-05-24 | 2002-04-23 | Lonza Inc. | Amine oxide/iodine containing blends for wood preservation |
US6448279B1 (en) | 1999-05-24 | 2002-09-10 | Lonza Inc. | Isothiazolone/amine oxide wood preservatives |
US6340384B1 (en) | 1999-05-24 | 2002-01-22 | Lonza Inc. | Copper/amine oxide wood preservatives |
US6527981B1 (en) | 1999-05-24 | 2003-03-04 | Lonza Inc. | Azole/amine oxide preservatives |
US6572788B2 (en) | 2000-05-24 | 2003-06-03 | Lonza, Inc. | Amine oxide wood preservatives |
US6508869B2 (en) | 2000-06-30 | 2003-01-21 | Lonza Inc. | Boron compound/amine oxide compositions |
DE10138456A1 (en) * | 2001-08-04 | 2003-02-13 | Bode Chemie Gmbh & Co | Alcoholic gels |
US20060257282A1 (en) * | 2005-05-12 | 2006-11-16 | Tony Buhr | Large-scale decontamination of biological microbes using amine oxides at acidic pH |
WO2015091163A1 (en) * | 2013-12-16 | 2015-06-25 | Henkel Ag & Co. Kgaa | Disinfectant composition with excellent foam profile |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
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 |
|
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 |