US3928605A - Phenylantimony bis(2-pyridinethiol-1-oxide in antibacterial and antifungal compositions - Google Patents

Abstract

Phenylantimony bis(2-pyridinethiol 1-oxide) in antibacterial and antifungal compositions.

Description

United States Patent Curry [45] Dec. 23, 1975 PHENYLANTIMONY [56] References Cited BIS(2-PYRIDINETHIOL-1-OXIDE IN UNITED STATES PATENTS ANTIBACTERIAL AND ANTIFUNGAL 1 3,027,371 3/l962 Starts 260/270 COMPOSITIONS 3,027,372 3/1962 Starts 260/270 75 Inventor; John Downing Curry, oxford, Ohio 3,236,733 2/1966 Karsten et a1 424/245 3,287,210 11/1966 Lubrlck 424/245 [73] Assignee: The Procter & Gamble Com any, 3,321,480 5/1967 Schroder et al. 260/270 Cincinnati, Ohio 3,636,213 l/l972 Gerstein et a1. 424/245 3,723,435 3/l973 Furia et a1 260/270 R [22] plied: June 27, 1974 3,787,417 1/1974 Kaufman 260/270 R {21] Appl. No.: 483,596 1 Primary Examiner-A bert T. Meyers Related Apphcauon a Assistant Examiner-Vera C. Clarke Division of Set. N0. 293,633, Sept. 29, 1972, Pat. Attorney Agent or Firm. Ge -ge Richard 3,833,565 C. Witte; Ronald L. Hemingway [52] US. Cl. 424/245; 252/106; 252/107;

260/270 A; 424/DIG. 4; 424/10 [57] ABSTRACT [51] Int. Cl. A61K 31/44 Phenylantimony bis(2-pyridinethiol l-oxide) in anti- [58] Field Of Search 424/245, DIG. 4; bacterial and antifungal compositions.

8 Claims, No Drawings PHENYLANTIMONY BIS( Z-PYRIDINETHIOL-l-OXIDE IN ANTIBACTERIAL AND ANTIFUNGAL COMPOSITIONS CROSS-REFERENCE TO RELATED APPLICATION This application is a divisional application of my copending application Ser. No. 293,633, filed Sept. 29, 1972, John Downing Currey, entitled PHENYLAN- TIMONY BIS (Z-PYRIDINETI-IIOL l-OXIDE, now US. Pat. No. 3,833,565, issued Sept. 3, 1974.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a new compound, phenylantimony bis(2-pyridinethiol l-oxide), which can be formed by the reaction of a phenylantimony dihalide and an alkali metal 2-pyridinethiol l-oxide salt in a suitable solvent such as dimethylforrnamide. This invention also relates to the use of this compound, which is highly effective against a broad spectrum of bacteria as well as yeast and fungal species, especially when used on the skin, where the compound is fairly substantive, and to compositions, including detergent compositions, containing said compound.

2. Prior Art My US. Pat. No. 3,753,990, issued Aug. 21, 1973, teaches phenylbismuth bis(2pyridinethiol l-oxide) and its antibacterial and antifungal activities; Schroder et al.s US. Pat. No. 3,321,480 teaches triphenyl tin Z-pyridinethiol l-oxide.

SUMMARY OF THE INVENTION Phenylantimony bis(2-pyridinethiol l-oxide) formula:

Compositions containing phenylantimony bis(2- pyn'dinethiol l-oxide) have excellent broad-sprectrum antibacterial and antifungal action.

Phenylantimony bis( 2-pyridinethiol l-oxide), hereinafter referred to as PADP, is a stable white powder having a melting point of about 2046C.

Phenylantimony bis(2-pyridinethiol l-oxide) has been shown to exhibit antibacterial and antifungal effectiveness against, e.g., Gram-positive organisms such as: Staphylococcus aureus, Sarcina lutea, and Streptococcus pyogenes; Gram-negative organisms such as: Escherichia coli and Pseudomonas aeruginosa; and Fungi (including yeasts and dermatophytes) such as: Aspergillus niger, Mycrosporum gypseum, and Candida albicans.

Because of the extremely broad antibacterial and antifungal effectiveness of PADP, it is desirably used as a component of surgical scrub products, bar soaps, shampoos, first aid sprays, foot powder, first aid creams, toilet bowl cleaners, hard surface cleaners, detergents, paints, cosmetics, burn dressings, wood preservatives, mildewcides, germicides, fungicides, medicines, packing preservatives, etc. In extremely small amounts e.g., 100 ppm., the PADP will inhibit has the the growth of a broad variety of organisms. When the PADP is incorporated in larger amounts, the compositions can be used to destroy organisms, as required. For example, in medicine, both for humans and veterinary medicine, the PADP can be used topically to treat a variety of diseases and/or organisms including dandruff and fungus (e.g., athlete s foot). Compositions containing PADP can be used to treat tissue either to prevent infections or to cure infections.

PADP is substantive to cellulose. Thus, it can be used on bandages, diapers, and sanitary napkins to prevent infections, diaper rash, odor, etc. PADP can also be used as a slimicide and preservative for paper and wood.

PREPARATION OF PI-IENYLANTIMONY BIS( 2-PYRIDINETHIOL l-OXIDE) Reactions to form phenylantimony bis(2-pyridinethiol l-oxide) include the reaction of sodium, potassium, ammonium, or lithium Z-pyridinethiol I-oxide or any other salt containing a loosely held cation with a phenylantimony dihalide (e.g., a chloride, bromide, or iodide).

COMPOSITIONS CONTAINING PI-IENYLANTIMONY BIS( Z-PYRIDINETHIOL l-OXIDE) Phenylantimony bis (Z-pyridinethiol l-oxide) can be used in aqueous and/or non-aqueous solvents to provide antibacterial action. Preferably, the compositions will contain from about 0.2% to about 3% phenylantimony bis(2-pyridinethiol l-oxide), most preferably from about I% to about 2-%. Desirable compositions are those containing soap and non-soap synthetic detergent compounds. Preferably, the synthetic detergent compounds are cationic, amphoteric, or nonionic.

The term soap as used herein is meant to designate alkali metal soaps such as the sodium and potassium salts of the higher fatty acids of naturally occuring plant or animal esters, e.g., palm oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, whale and fish oils, grease and lard and mixtures thereof. Sodium and potassium soaps can be made by direct saponification of the fats and oils or by. the neutralization of the fatty acids which are prepared in a separate manufacturing process. Examples of suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C -C Particularly useful are the sodium and potassium salts and the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.

Anionic synthetic detergents which can be used with the antibacterial, antifungal, and antiyeast compound of the present invention can be broadly defined'asthe watersoluble salts, including the alkali metal, ammonium and substituted ammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals.

Important examples of the synthetic detergents which can be used with the compound of the present invention are the following: alkali metal (e.g., sodium and potassium), ammonium and substituted ammonium (e.g., lower alkyl ammonium) salts of the following: alkyl sulfates, especially those obtained by sulfating the higher alcohols produced by reducing the glycerides of tallow or coconut oil; random paraffin sulfonates, in which the alkyl group contains from about 8 to about 22 carbon atoms, prepared by treating random paraffin hydrocarbons in sulfur dioxide and chlorine in the presence of light followed by treating with a base; branched or linear alkyl benzene sulfonates, in which the alkyl group contains from about 8 to about 18 carbon atoms, preferably from about to about 14 carbon atoms, especially those of the types described in US. Pat. Nos. 2,220,099, and 2,477,383; sodium alkyl glyceryl ether sulfonates, especially those ethers of the higher alcohols derived from tallow and coconut oil; coconut oil fatty acid monoglyceride sulfates and sulfonates; sulfuric acid esters of the reaction product of one mole of a higher fatty alcohol (e.g., tallow or coconut alcohols) and from about 1 to about 6, preferably about 3 moles of ethylene oxide; alkyl phenol ethylene oxide ether sulfates with about 4 units of ethylene oxide per molecule and in which the alkyl radicals contain about 9 carbon atoms; the reaction product of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, fatty acids are derived from coconut oil; fatty acid amides of methyl taurine in which the fatty acids, for example, are derived from coconut oil; sulfonated olefins of US. Pat. No. 3,332,880; and others known in the art, a number being specifically set forth in US. Pat. Nos. 2,486,921, 2,486,922 and 2,396,278.

The nonionic synthetic detergents which can be used with the antibacterial compound of the present invention may be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound which may be aliphatic or alkyl-aromatic in nature. The length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elemerits.

For example, a well-known class of nonionic synthetic detergents is made available on the market under the trade name of Pluronic. The compounds are fonned by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol. The hydrophobic portion of the molecule which, of course, exhibits water insolu-' Other suitable nonionic synthetic detergents include:

I l; The polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to 10 to 60 moles of ethylene oxide per mole of alkyl phenol. The alkyl substituent in such compounds may be derived from polymerized propylene, diisobutylene, octane, or nonane, for example.

2. Those derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine products which may be varied in composition depending upon the balance between the hydrophobic and hydrophilic containing from about 40% to about polyoxythylene by weight and having a molecular weight of from about 5,000 to about 11,000 resulting from the reaction of ethylene oxide groups with a hydrophobic base constituted by the reaction product of ethylene diamine and excess propylene oxide, said base having a molecular weight of the order of 2,500 to 3,000, are satisfactory.

3. The condensation product of aliphatic alcohols having 'from 8 to 18 carbon atoms, in either straight chain or branched chain configuration, with ethylene oxide, e.g., a coconut alcohol ethylene oxide condensate having from 10 to 30 moles of ethylene oxide per mole of coconut alcohol, the coconut alcohol fraction having from 10 to 14 carbon atoms.

4. Long chain tertiary amine oxides corresponding to the following general formula,

wherein R. contains an alkyl, alkenyl or monohydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties, and from 0 to 1 glyceryl moiety, and R: and R contain from 1 to about 3 carbon atoms and from 0 to about 1 hydroxy group, e.g., methyl, ethyl, propyl, hydroxy ethyl, or hydroxy propyl radicals. The arrow in the formula is a convention representation of a semi-polar bond. Examples of amine oxides suitable for use in this invention include dimethyldodecylamine oxide, oleyldi(2-hydroxyethyl)amine oxide, dimethyloctylamine oxide, dimethyldecylamine oxide, dimethyltetradecylamine oxide, 3,6,9-trioxaheptadecyldiethylamine oxide, di(2-hydroxyethyl)-tetradecylamine oxide, 2-dodecoxyethyldimethylamine oxide, 3-dodecoxy-2-hydroxypropyldi(3-hydroxypropyl) amine oxide, dimethylhexadecylamine oxide.

5. Long chain tertiary phosphine oxides corresponding to the following general formula RR RP 0. wherein R contains an alkyl, alkenyl or monohydroalkyl radical ranging from 8 to 18 carbon atoms in chain length from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety and R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms. The arrow in the formula is a conventional representation of a semi-polar bond. Examples of suitable phosphine oxides are: dodecyldimethylphosphine oxide, tetradecyldimethylphosphine oxide, tetradecylmethylethylphosphine oxide, 3,6,9-trioxaoctadecyldimethylphosphine oxide, cetyldimethylphospine oxide, 3-dodecoxy-2-hydroxypropyldi( 2-hydroxyethyl phosphine oxide,

stearyldimethylphosphine oxide,

cetylethylpropylphosphine oxide,

oleyldiethylphosphine oxide, dodecyldiethylphosphine oxide, tetradecyldiethylphosphine oxide, dodecyldipropylphosphine oxide, dodecyldi(hydroxymethyl)phosphine oxide, dodecyldi( 2-hydroxyethyl )phosphine oxide, tetradecylmethyl-2-hydroxypropylphosphine oxide, oleyldimethylphosphine oxide, 2-hydroxydodecyldimethylphosphine oxide.

6. Longchain dialkyl sulfoxides containing one short chain alkyl or hydroxy alkyl radical of l to about 3 carbon atoms (usually methyl) and one long hydrophobic chain which contains alkyl, alkenyl, hydroxy alkyl, or keto alkyl radicals containing from about 8 to about 20 carbon atoms, from 0 to about ethylene oxide moieties and from, 0 to l glyceryl moiety. Examples include: '1 I i v octadecyl methyl sulfoxide, 2-ketotridecyl methyl sulfoxide, 3,6,9-trioxaoctadecyl 2-hydroxyethyl sulfoxide, dodecyl methyl sulfoxide,

oleyl 3-hydroxypropyl sulfoxide,

tetradecyl methyl sulfoxide,

3-methoxytridecyl methyl sulfoxide 3-hydroxytridecyl methyl sulfoxide,

3-hydroxy4-dodecoxybutyl methyl sulfoxide.

The zwitterionic synthetic detergents useful with the antibacterial agent of the present invention can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight chain or branched, and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate. A general formula for these compounds is:

wherein R contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety; Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms; R is an alkyl or monohydroxyalkyl group containing 1 to about 3 carbon atoms; x is 1 when Y is a sulfur atom and 2 when Y is a nitrogen or phosphorus atom, R is an alkylene or hydroxyalkylene of from 1 to about '4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.

Examples include: 4-[N,N-di(2-hydroxyethyl)-N-octadecylammonio]- butanel-carboxylate; V 5-[S-3-hydroxypropyl-S-hexadecylsulfonio]-3- hydroxypentanel-sulfate; 3-[ P,P-diethyl-P-3 ,6,9-trioxatetradecoxylphosphonio]-2-hydroxy-propane- 1 -phosphate; 3-[N,N-dipropyl-N-3-dodecoxy-2-hydroxypropylammonio -propanel -phosphonate; 3-( N,N-dimethyl-N-hexadecylammonio )propanel sulfonate;

3-( N,N-dimethyl-N-hexadecylammonio )-2-hydroxypropane l-sulfonate;

4- N,N-di( Z-hydroxyethyl )-'N-( Z-hydroxydodecyl- )ammonio]-butanel -carboxylate;

3-[ S-ethyl-S-( 3-dodecoxy-2-hydroxypropyl )sulfonio]-propane- 1 -phosphate;

3- P,P-dimethyl-P-dodecylphosphonio -propanel phosphonate; and

5-[ N,N-di( 3-hydroxypropyl )-N-hexadecylammonio]2-hydroxy-pentanel -sulfate.

The amphoteric synthetic detergents useful in the present invention can be broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to about- 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate,vphosphate, or phosphonate. Examples of compounds falling within this definition are sodium 3-dodecylaminopropionate, sodium. 3- dodecylaminopropane sulfonate, dodecyl-B-alanine, N-alkyltaurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of U.S. Pat. No. 2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of U.S. Pat. No. 2,438,091, and the products sold under the trade name Miranol and described in U.S. Pat. No. 2,528,378.

Cationic synthetic detergents include those quaternary ammonium, quatemary phosphonium, and ternary sulfonium compounds containing a single straight chain or branched aliphatic radical containing from about six to about 20 carbon atoms such as dodecyltrimethylammonium chloride; nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfonium chloride; etc.

Detergent formulations containing the antibacterial compositions of the present invention can also contain from about 0% to about 90%, preferably from about 10% to about 90% of water-soluble alkaline detergency builder salts, either oftheorganic or inorganic types. Examples of such builder salts can be found in U.S. Pat. No. 3,336,233, issued Aug. 15, 1967, column 9, lines 29-66, which is incorporated herein by reference. However, at a very high pH, the compound may undergo alkaline hydrolysis and accordingly, for longterm stability, the detergent formulations should have a pH of less than about 10 preferably the pH should be approximately neutral.

The detergent formulations can also contain any of the usual adjuvants, diluents, and additives, for example, perfumes, anti-tamishing agents, anti-redeposition agents, dyes, fluorescers, suds builders, suds depressors and the like without detracting from the advantageous properties of the antibacterial compositions of the present invention. 1

Examples of diluents which may be incorporated into a synthetic detergent bar in amounts of up to about of the barinclude soaps, especially alkaline earth metal insoluble soaps, (alkaline earth salts of higher fatty acids); starches such as cornstarch; and clays such as china clay or fullers 'earth. Other diluents includev inorganic salts such as sodium and potassium chlorides and sulfates. Such diluents add bulk to the 'bar and improve its cosmetic properties without impairing its detergent or cohesive properties. I

The antibacterial and antifungal efficacyof the phenylantimony bis(2'pyridinethiol l-oxide) is disclosed in the following examples.

EXAMPLE I PREPARATION OF PHENYLANTIMO NY BISQ-PYRIDINETHIOL l-OXIDE) 47.0 g. (.174 mole) of phenylantimony dichloride were dissolved in 200 ml. ofdimethylformamide. 53.7

g. (.348 mole, 96.8% active) of sodium pyridinethiol l-oxide were dissolved in 850 ml. of dimethylformamhot. The residue weighed 21.4 g. The theoretical weight of the NaCl produced in the reaction is 20.3 grams. The filtrate (1000 ml.) was extracted with 1000 ml. of dichloromethane and 2000 ml. of water. The lower layer sat overnight. There was no precipitate. The dichloromethane was taken off the next morning on the steam bath (to 300 ml.). 300 ml. of water was then added and the solution was cooled in ice. The solution was then filtered to separate a green crystal residue. This was dissolved in dimethyl sulfoxide in the concentration of one gram per 100 ml. at low heat on a steam bath. Then the solution was filtered and two volumes of water were added to the filtrate to precipitate out phenylantimony bis(2-pyridinethiol 1-oxide). The solution was cooled in ice and filtered to give a white residue. The residue was washed with water, air-dried, then Washed with ether, and then dried in vacuo to give 48.3 g. (62% yield) of phenylantimony bis(2-pyridinethiol l-oxide) having a melting point of 2046C.

The percents of carbon, hydrogen, nitrogen, antimony, and sulfur present in the phenylantimony bis( 2- pyridinethiol l-oxide) as calculated and found by analysis are:

The phenylantimony bis(2-pyridinethiol l-oxide) prepared according to the process of Example I was tested for antibacterial efficacy in the following tests:

I. Minimal Inhibitory Concentration (MIC) in Agar 10,000 ppm. stock solutions of phenylantimony bis(Z-pyridinethiol l-oxide) were prepared in dimethylformamide (DMF). The active was diluted to the desired test concentration and added to 19-20 ml. of molten trypticase soy agar (TSA) to give a series of graded concentrations (ppm). Thorough rotation of plates assured adequate mixing of the sanitizer before agar solidification. Appropriate control plates containing plain TSA were included. All plates remained at room temperature overnight.

Trypticase soy broth cultures for each test organism (24 hour) were diluted in peptone water to give approximately 100 cells per 0.01 ml. The agar plates, marked in sectors, were inoculated by dropping one drop of each diluted culture from a Kline antigen microdropper onto the appropriate sector of agar. The drops were allowed to dry. The plates were incubated 48 hours at 37C. and then examined for growth. The weakest concentration which completely inhibited growth of an organism was the MIC. The results for the tests were as follows:

Gram-Positive Organisms Mi (pp Slupll \'lot'm'tus aureus (5.21.) 6 SH'L'IIIULOCCUS pyogenex 4 Sarci'ml lulea (Sar. l.) 6 Pseudo/norms ueruginosa (Ps.a.) -100 Escherichia coli (E.c.) l Candida ulbicans 6 Fungistatic tests were performed using a modified gradient plate technique reported by Hunt and Sandham (Applied Microbiology 17 No. 21329-30, 1969). Results were as follows: Aspergillus niger 6.2 ppm; Microsporum gypseum 1 ppm.

EXAMPLE III Shampoo Compositions Composition No. 1 No. 2 No. 3

Sulfated coconut fatty 23 23 alcohol sodium salt Sodium stearate 8.7 8.7

balance Alkyl radicals derived from fatty alcohol, 25.3% from coconut and 3% from tallow.

Acyl radicals derived from coconut fatty acids.

Composition No. 4 Percent Dimethyl coconut amine oxide 8.0 Disodium lauryl beta-iminodipropionate 5.0 Sodium coconut sulfate 4.0 Coconut diethanolamide 1.0 Phenylantimony bis( 2-pyridinethiol l-oxide) 1.0 Perfume 0.5 Color less than 0.01 Citric acid to adjust pH to 7.5

Water balance The alkyl radical is derived from middle Cut coconut alcohol and has approxi mately the following chain length composition: 2% C 66% C 23% C and 99 *Whole cut COMPOSITION NO. 5

A shampoo composition is obtained by uniformly mixing together the following ingredients:

4% triethanolamine salt of the sulfated condensation product of 3 moles of ethylene oxide and one mole of coconut oil fatty alcohol having the following chain length distribution: 2% 121066% C 23% C and 9% C 10% triethanolamine N-acyl sarcosinate', the acyl radicals being derived from coconut oil fatty acids having the following chain length distribution: 10% C 48% C 21% C 10% C and 1l%'C,

3% monoethanolamide of coconut oil fatty acids having the following chain length distribution: 16% C 48% C 17% C 9% C and 10% C 1% Phenylantimony bis( Z-pyridinethiol l-oxide) 3% diethanolamide of coconut oil fatty acids having the following chain length distribution: 16% 48% C 17% C 9% C and 10% C 7% ethanol 9 0.75% methyl cellulose, a 2% solution of which has a viscosity of 4000 cps. at 68F. and a gel point of 140F. 0.75% perfume balance, water. i 5 Shampoo formulations containing phenylantimony bis(2-pyridinethiol l-oxide) are desirable since they will control dandrufi'.

EXAMPLE IV Personal Use Detergent Lotion Composition No. 6

Percent Potassium coconut glyceryl ether 3.0 sulfonate (about 23% diglyceryl and the balance substantially all monoglyceryl) Sodium coconut glyceryl ether sulfonate (diglyceryl and monoglyceryl content as above) Sodium tallow glyceryl ether sulfonate (digylceryl and monoglyceryl content as above); the tallow alkyl radicals correspond to those of substantially saturated tallow alcohols containing approximately 2'7( C 3271 Cm. and 60% C Coconut dimethylamine oxide Sodium salt of sulfated condensation product of one mole of nonylphenol with four moles ethylene oxide Potassium pyrophosphate Phenylantimony bis(Z-pyridinethiol l-oxide) Sodium chloride (in addition to that from detergents) Sodium toluene sulfonate Sodium carboxymethycellulose (degree of substitution 0.65-95; viscosity of 1% soln., l0002800 cps. at 25C.) Acrylamide polymer (contains 5-l0 mole percent acrylic acid radicals; monomer is less than 0.05%; viscosity of 0.5% soln. is about 10-15 cps. at 25C.)

Salts (sodium and potassium chloride and sulfate from detergents) Water balance Coconut indicates alkyl radicals corresponding to those of middle cut coconut fatty alcohol containing approximately 27' Chd I0, 66% C 23% C". and 971 C 4O EXAMPLE V Cream Shampoo 2% c 66% C 23% C... and 9% c v EXAMPLE VI A milled toilet detergent bar is prepared in accordance with methods known and used in the art and having the following composition:

Percent Sodium alkyl glyceryl ether sulfonate 8.0 (alkyl group derived from the middlecut of alcohols obtained by catalytic reduction of coconut oil) Potassium alkyl sulfate (alkyl group 20.0

Phenylantimony bis( 2pyridinethiol l-oxide) Water and minors balance to Middle-cut coconut alcohols having a chain length distribution substantially as follows: 2% C 66% C 23% C and 9% C This bar cleans well and exhibits good odor reducing properties evidencing antibacterial effectiveness. It reduces the number of bacteria on the skin significantly.

EXAMPLE VII A granular built synthetic detergent composition having the following formulation can be prepared and the antibacterial compositions of the present invention can be incorporated therein.

Percent Sodium dodecylbenzene sulfonate 17.5 Sodium tripolyphosphate 50.0 Sodium sulfate 14.0 Sodium silicate (SiO :Na O=2:l 7.0 3.0

Phenylantim ony bis( 2pyridinethiol l-oxide) Water and minors balance to 100 This composition, in addition to performing welliin its' cleaning capacity, imparts considerable antibacterial activity to fabrics cleansed in its solution.

Substantially equivalent results are obtained, i.e., good cleaning and good odor reducing properties, when the sodium dodecylbenzene sulfonate of Example VII is replaced, on an equal weight basis, by the follow-' dodecyltrimethylammonium chloride;

nonlbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfonium chloride;

(hexylphenyl)dimethylbenzylammonium fluoride;

eicosyldimethylbenzylphosphonium chloride;

coconutalkylmethylmorpholinium nitrate; octadecylmethylbenzylsulfonium sulfate; laurylpyridinium chloride;

laurylpyridinium bromide;

laurylpyridinium bisulfate;

laurylpyridinium-S-chloro-Z-mercaptobenzothiazole;

laurylpicolinium-p-toluenesulfonate; tetradecylpyridinium bromide;

cetylpyridinium chloride;

cetylpyridinium bromide;

laurylisoquinolinium bromide;

laurylisoquinolinium saccharinate;

alkylisoquinolinium bromide;

N-cetyl-ethyl-morpholiniurn ethosulfate;

benzalkonium chloride;

monoquaternaries R N X (one R group is fatty);

octadecyltrimethylammonium chloride;

coconut alkyl trimethylammonium chloride;

dodecylbenzyltri(octyldecyl)ammonium chloride;

1 1 monoquaternaries R N X (two R groups are fatty); dihexadecyldimethylammonium chloride; di-coconut alkyl dimethylammonium chloride; monoquatemaries R N X (three R groups are y); tri( hydrogenated tallow) methylammonium chloride; distilled tallow amine acetate; diamine acetates; N-oleyl propylene diamine monoacetate; sodium tallow alkyl sulfate; potassium coconut alkyl glyceryl ether sulfonate; sodium salt of randomly sulfonated paraffin containing an average of 15.2 carbon atoms; ammonium tridecyl sulfate; condensation product of octyl phenol with moles of ethylene, oxide per mole of octyl phenol; dimethyldodecylamine oxide; dodecyldimethylphosphine oxide; tetradecyl methyl sulfoxide; 3 N,N dimethyl-N-hexadecylammonio )propanel sulfonate; 3-dodecylaminopropionate; and dodecyl-B-alanine. The invention has been described above in conjunction with toilet and laundry detergents. It will be obvious to those skilled in the art, however, that the antibacterial compositions of the present invention can also be beneficially employed in such products as Percent Dialkyl dimethylammonium chloride 7 75% active ingredient dispersed in isopropanol and water, the dialkyl groups being approximately 24% octadecenyl The condensation product of 30 4 3 moles of ethylene oxide with one mole of coconut alcohol Color and Perfume 0.3 Phenylantimony bis(Z-p'yridinethiol l.0 l-oxide) Water balance What is claimed is: t i

' 1. An antibacterial and antifungal detergent composition consisting essentially of:

A. an effective amount of a water-soluble detergent from the group consisting of soaps and non-soap synthetic detergents; l

B. an effective amount of a water-soluble, alkaline detergency builder salt; a

C. from about 0.2%to about 3% of phenylantimony bis(Z-pyridinethiol l-oxide); and

D. the balance being water and additives, said detergent composition having a pH of less than about 10. I

2. The antibacterial and antifungal detergent composition of claim 1 wherein the phenylantimony bis(2- pyridinethiol l-oxide) is present in a concentration of about 1.5%. 4

3. An antibacterial and antifungal shampoo composition consisting essentially of:

A. an effective amount of a water-soluble detergent selected from the group consisting of soaps and non-soap synthetic detergents;

B. from about 0.2% to about 3% of phenylantimony bis( Z-pyridinethiol l-oxide); and

C. the balance being water and additives, said shampoo having a pH of less than about 10.

4. A synthetic antibacterial and antifungal detergent toilet bar consisting essentially of:

A. a water-soluble synthetic detergent;

B. diluents; and

C. from about 0.2% to about 3% of phenylantimony bis( Z-pyridinethiol l-oxide.

5. An antibacterial and antifungal soap composition consisting essentially of:

A. an'effective amount of an alkali or alkaline earth metal salt of a fatty acid of fromabout ID to about 20 carbon atoms; I

B. from about 0.2% to about 3% of phenylantimony bis(Z-pyridinethiol l-oxide); and

C. the balance being water and additives.

6. The process of controlling dandruff comprising the step wherein the head of a human subject is shampooed using the shampoo composition of claim 3.

7. The process of controlling bacteria, yeast, and fungal species, comprising the step of contacting said bacteria, yeast and fungal species with an effective amount of phenylantimony bis( Z-pyridinethiol loxide).

8. The process of claim 7 wherein the bacterium is Pseudomonas aeruginosa.

Claims (8)

1. An antibacterial and antifungal detergent composition consisting essentially of: A. an effective amount of a water-soluble detergent from the group consisting of soaps and non-soap synthetic detergents; B. an effective amount of a water-soluble, alkaline detergency builder salt; C. from about 0.2% to about 3% of phenylantimony bis(2-pyridinethiol 1-oxidE); and D. the balance being water and additives, said detergent composition having a pH of less than about 10.

2. The antibacterial and antifungal detergent composition of claim 1 wherein the phenylantimony bis(2-pyridinethiol 1-oxide) is present in a concentration of about 1.5%.

3. An antibacterial and antifungal shampoo composition consisting essentially of: A. an effective amount of a water-soluble detergent selected from the group consisting of soaps and non-soap synthetic detergents; B. from about 0.2% to about 3% of phenylantimony bis(2-pyridinethiol 1-oxide); and C. the balance being water and additives, said shampoo having a pH of less than about 10.

4. A synthetic antibacterial and antifungal detergent toilet bar consisting essentially of: A. a water-soluble synthetic detergent; B. diluents; and C. from about 0.2% to about 3% of phenylantimony bis(2-pyridinethiol 1-oxide.

5. An antibacterial and antifungal soap composition consisting essentially of: A. an effective amount of an alkali or alkaline earth metal salt of a fatty acid of from about 10 to about 20 carbon atoms; B. from about 0.2% to about 3% of phenylantimony bis(2-pyridinethiol 1-oxide); and C. the balance being water and additives.

6. The process of controllng dandruff comprising the step wherein the head of a human subject is shampooed using the shampoo composition of claim 3.

7. THE PROCESS OF CONTROLLING BACTERIAL, YEAST, AND FUNGAL SPECIES, COMPRISING THE STEP OF CONTACTING SAID BACTERIA, YEAST AND FUNGAL SPECIES WITH AN EFFECTIVE AMOUNT OF PHENYLANTIMONY BIS(2-PYRIDINETHIOL L-OXIDE).

8. The process of claim 7 wherein the bacterium is Pseudomonas aeruginosa.