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.

Patents

  1. Advanced Patent Search
Publication numberUS3484523 A
Publication typeGrant
Publication dateDec 16, 1969
Filing dateDec 27, 1966
Priority dateDec 27, 1966
Publication numberUS 3484523 A, US 3484523A, US-A-3484523, US3484523 A, US3484523A
InventorsFindlan John C, Sorrentino Ralph P, Wakeman Reginald L
Original AssigneeMillmaster Onyx Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Quaternary ammonium-tertiary amine oxide compositions
US 3484523 A
Abstract  available in
Images(2)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

United States Patent 3,484,523 QUATERNARY AMMONlUM-TERTIARY AMINE OXIDE COMPOSITIONS John C. Findlan, Chappaqua, and Ralph P. Sorrentino,

Elmhurst, N.Y., and Reginald L. Wakeman, Philadelphia, Pa., assignors to Millmaster Onyx Corporation, New York, N.Y., a corporation of New York N 0 Drawing. Continuation-impart of application Ser. No. 500,282, Oct. 21, 1965. This application Dec. 27, 1966, Ser. No. 604,598 The portion of the term of the patent subsequent to Jan. 3, 1984, has been disclaimed Int. Cl. A61k 27/00; C11d 1/62 U.S. Cl. 424-448 3 Claims ABSTRACT OF THE DISCLOSURE A composition for both cleaning and degerming human skin and similar organic tissue, consistlng of at least one tertiary amine oxide of the formula:

wherein R is a member of the group consisting of alkyl and alkenyl having 8 to 20 carbon atoms, and 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.

where 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. If desired, R and R" may jointly constitute the CH 'CH O-CH CH radical, i.e. the above formula is:

While all of these amine oxides have detersive power, those containing fourteen carbon atoms, or less, are also good foaming agents whereas those possessing 16 carbon atoms, or more, are poor foaming agents.

As suitable quaternary ammonium compounds utilizable in the compositions of this invention, there may be employed 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. Typical examples of these 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, alkyl pyridinium chlorides, alkyl isoquinolinium chlorides and bromides alkyl lower-alkyl pyrrolidinium chlorides, alkyl lower-alkyl morpholinium chlorides in all of which the alkyl group may have from 8 to 22 carbon atoms and the lower-alkyl group may have from 1 to 4 carbon atoms and alkyl phenoxyethoxyethyl dimethylbenzyl ammonium chloride in which the alkyl radical may be iso-octyl or nonyl and in which the benzyl radical may, if desired, be substituted by a methyl radical. Various other analogs of these quaternaries may also be employed such, for example, as cetyl dimethyl ethyl ammonium bromide or oleyl dimethyl ethyl ammonium bromide. Instead of the foregoing chlorides, there may also be employed the corresponding bromides, methosulfates, ethosulfates or other water-soluble analogs. Mixtures of two or more of the foregoing quaternary ammonium compounds may also be employed. In particular, it is preferred to employ a mixture of 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.

It is preferred to use 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. The aforesaid products are sold by Onyx Chemical Company under the previously mentioned trademark designations.

The 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.

The aforementioned application Serial No. 500,282, and its abandoned parent application Serial No. 339,307,

filed January 21, 1964, indicated that a proportion of about 50:1 to about 5:1 of the disclosed amine oxide relative to the disclosed quarternary ammonium compounds could be utilized for the disclosed purposes. It has, however, now been unexpectedly discovered that thisproportion can be as low as 0.5 :1 and still be compatible with the anionic surface active agents as well as providing very effective microbiocidal action.

The following example illustrate the present invention, but are not to be considered limitative thereof except as claimed:

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.

In parts by weight 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,

wherein the first alkyl has a distribution of 60% C14, 30% Om, 5% C11, and 5% C15, and the second alkyl has a distribution of 50% C12,

30% C14, 17% C16, and 3% C13 2. 0 1. 0 2. O 1. O Acetylated lanolin 0. 5 0.5 0.5 0. 5 Hydroxyethyl cellulose.-. 0. 5 0.5 0. 5 0. 5

r 93.9 94. 9 95. 25 90. 1 Ratio, amine oxide to quaternary 1:1 2:1 0. 5: 1 4. 8: 1

EXAMPLE 2 A series of detergent-sanitizer-softener compositions were prepared in the same manner as in Example 1. These compositions are identified as follows as Comp. E, Comp. F, and Comp. G:

In parts by weight Composition E F 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 wherein R is a member of the group consisting of alkyl and alkenyl having 8 to 20 carbon atoms, and wherein R and R" are selected from the group consisting of methyl, ethyl, propyl, isopropyl, hydroxyalkyl, hydroxylalkoxyalkyl, hydroxyalkyl olyalkoxyalkyl, and morpholine containing R, R" and N as members, the alkyl of the hydroxyalkyl compounds being lower alkyl, and (2) 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 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.

2. The germicidal agent of claim 1 in admixture with an softeningly effective amount of a fabric softener.

3. 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:

wherein R is a member of the group consisting of alkyl and alkenyl having 8 to 20 carbon atoms, and wherein 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, and (2) 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.

References Cited UNITED STATES PATENTS 3,296,145 1/1967 Findlan et al 16730 FRANK CACCIAPAGLIA, IR., Primary Examiner V. D. TURNER, Assistant Examiner US. Cl. X.R.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3296145 *Oct 21, 1965Jan 3, 1967Millmaster Onyx CorpQuaternary ammonium-tertiary amine oxide compositions
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4062976 *Dec 18, 1975Dec 13, 1977Michaels Edwin BAntimicrobial compositions employing certain substituted alanines and certain t-amine oxides
US4075350 *Dec 18, 1975Feb 21, 1978Michaels Edwin BAcyl-n-betaine
US4107328 *May 26, 1977Aug 15, 1978Michaels Edwin BAntimicrobial compositions and methods for utilizing the same employing mixtures of amines
US4145436 *Nov 7, 1977Mar 20, 1979Michaels Edwin BAntimicrobial compositions and method for using same
US4179504 *Oct 14, 1977Dec 18, 1979Block Drug Company, Inc.Alkyl amine oxide toxicants
US4183952 *Dec 18, 1975Jan 15, 1980Michaels Edwin BAntimicrobial compositions
US4333921 *Oct 2, 1980Jun 8, 1982American Cyanamid CompanyHair cleansing conditioner with lathering action
US4597975 *Oct 11, 1983Jul 1, 1986Woodward Fred EIodine surface active compositions
US5476615 *May 20, 1994Dec 19, 1995Lonza Inc.Low foam sanitizers
US5486315 *May 20, 1994Jan 23, 1996Lonza Inc.Low foam branched alkyldimethylamine oxides
US5679633 *Oct 17, 1995Oct 21, 1997Lonza Inc.Low foam branched alkyldimethylamine oxides
US5833741 *Jan 16, 1997Nov 10, 1998Lonza Inc.Mixture of alkyl amine oxide, alkyl acetoacetate, quaternary ammonium compound and microbiocides
US6172029Feb 24, 1999Jan 9, 2001Showa Water Industries Co., Ltd.Containing amine oxide
US6268326Jan 10, 2000Jul 31, 2001Showa Water Industries Co., Ltd.Bactericides and cleaning agents for eradicating Legionella bacteria
US6340384May 24, 2000Jan 22, 2002Lonza Inc.Copper/amine oxide wood preservatives
US6375727May 24, 2000Apr 23, 2002Lonza Inc.Improved phase and color stability and corrosion resistance, able to form compositions containing phosphonic acid compounds as iron stain inhibitors at higher ph; particularly iodopropynyl butyl carbamate
US6448279May 24, 2000Sep 10, 2002Lonza Inc.Preserving and/or waterproofing wood; improved leach resistance; single solution; low volatility
US6485790Oct 5, 2001Nov 26, 2002Lonza Inc.Methods for enhancing penetration of wood preservatives
US6508869Jun 29, 2001Jan 21, 2003Lonza Inc.Wood protectant comprising a boron compound biocide and an amine oxide preservative/waterproofing agent and an article produced from said protected wood
US6527981May 24, 2000Mar 4, 2003Lonza Inc.A fungicide enhancing effective amount of one or more amine oxides and a fungiciadal effective amount of one or more 1,2,4- triazoles or benzimidazoles
US6572788May 24, 2001Jun 3, 2003Lonza, Inc.Amine oxide wood preservatives
DE2844157A1 *Oct 10, 1978Apr 19, 1979Block Drug CoMittel zur vertilgung von ektoparasiten und/oder zur abtoetung von deren eiern
DE10138456A1 *Aug 4, 2001Feb 13, 2003Bode Chemie Gmbh & CoAlkoholische Gele
EP0081801A2 *Dec 7, 1982Jun 22, 1983Kao CorporationLiquid detergent composition
Classifications
U.S. Classification514/231.2, 514/643, 514/307, 514/408, 514/642, 514/358
International ClassificationC11D3/48, C11D1/75
Cooperative ClassificationC11D3/48, C11D1/75
European ClassificationC11D3/48, C11D1/75
Legal Events
DateCodeEventDescription
Sep 2, 1986AS02Assignment of assignor's interest
Owner name: MILLMASTER ONYX GROUP, INC., A CORP. OF DE.
Effective date: 19860815
Owner name: STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE
Sep 2, 1986ASAssignment
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
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A CORP. OF DE.;REEL/FRAME:004606/0309
Jun 9, 1983ASAssignment
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