U.S. patent number 3,928,605 [Application Number 05/483,596] was granted by the patent office on 1975-12-23 for phenylantimony bis(2-pyridinethiol-1-oxide in antibacterial and antifungal compositions.
This patent grant is currently assigned to The Procter & Gamble Company. Invention is credited to John Downing Curry.
United States Patent |
3,928,605 |
Curry |
December 23, 1975 |
Phenylantimony bis(2-pyridinethiol-1-oxide in antibacterial and
antifungal compositions
Abstract
Phenylantimony bis(2-pyridinethiol 1-oxide) in antibacterial and
antifungal compositions.
Inventors: |
Curry; John Downing (Oxford,
OH) |
Assignee: |
The Procter & Gamble
Company (Cincinnati, OH)
|
Family
ID: |
26968064 |
Appl.
No.: |
05/483,596 |
Filed: |
June 27, 1974 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
|
|
293633 |
Sep 29, 1972 |
3833565 |
Sep 3, 1974 |
|
|
Current U.S.
Class: |
514/188; 510/319;
546/6; 424/DIG.4; 514/852; 987/25; 510/123; 510/492; 510/390;
510/132; 510/133; 510/382; 510/191; 510/119 |
Current CPC
Class: |
A61K
8/58 (20130101); A61Q 5/006 (20130101); C11D
3/48 (20130101); C07F 9/92 (20130101); C11D
17/006 (20130101); A61Q 17/005 (20130101); A61Q
19/10 (20130101); A61Q 5/02 (20130101); Y10S
514/852 (20130101); Y10S 424/04 (20130101) |
Current International
Class: |
A61K
8/58 (20060101); C11D 3/48 (20060101); A61K
8/30 (20060101); C07F 9/00 (20060101); A61Q
5/02 (20060101); A61Q 19/10 (20060101); C07F
9/92 (20060101); A61K 031/44 () |
Field of
Search: |
;424/245,DIG.4 ;260/27A
;252/106,107 |
References Cited
[Referenced By]
U.S. Patent Documents
Primary Examiner: Meyers; Albert T.
Assistant Examiner: Clarke; Vera C.
Attorney, Agent or Firm: Allen; George W. Witte; Richard C.
Hemingway; Ronald L.
Parent Case Text
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 "PHENYLANTIMONY BIS (2-PYRIDINETHIOL 1-OXIDE", now
U.S. Pat. No. 3,833,565, issued Sept. 3, 1974.
Claims
What is claimed is:
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 bacteria, yeast, and fungal species,
comprising the step of contacting said bacteria, yeast and fungal
species with an effective amount of phenylantimony
bis(2-pyridinethiol 1-oxide).
8. The process of claim 7 wherein the bacterium is Pseudomonas
aeruginosa.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a new compound, phenylantimony
bis(2-pyridinethiol 1-oxide), which can be formed by the reaction
of a phenylantimony dihalide and an alkali metal 2-pyridinethiol
1-oxide salt in a suitable solvent such as dimethylformamide. 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 U.S. Pat. No. 3,753,990, issued Aug. 21, 1973, teaches
phenylbismuth bis(2-pyridinethiol 1-oxide) and its antibacterial
and antifungal activities; Schroder et al.'s U.S. Pat. No.
3,321,480 teaches triphenyl tin 2-pyridinethiol 1-oxide.
SUMMARY OF THE INVENTION
Phenylantimony bis(2-pyridinethiol 1-oxide) has the formula:
##SPC1## Compositions containing phenylantimony bis(2-pyridinethiol
1-oxide) have excellent broad-sprectrum antibacterial and
antifungal action.
Phenylantimony bis(2-pyridinethiol 1-oxide), hereinafter referred
to as PADP, is a stable white powder having a melting point of
about 204.degree.-6.degree.C.
Phenylantimony bis(2-pyridinethiol 1-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 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 PHENYLANTIMONY BIS(2-PYRIDINETHIOL 1-OXIDE)
Reactions to form phenylantimony bis(2-pyridinethiol 1-oxide)
include the reaction of sodium, potassium, ammonium, or lithium
2-pyridinethiol 1-oxide or any other salt containing a loosely held
cation with a phenylantimony dihalide (e.g., a chloride, bromide,
or iodide).
COMPOSITIONS CONTAINING PHENYLANTIMONY BIS(2-PYRIDINETHIOL
1-OXIDE)
Phenylantimony bis (2-pyridinethiol 1-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 1-oxide), most preferably
from about 1% 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.sub.10 -C.sub.20). 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 as the water-soluble 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 10 to
about 14 carbon atoms, especially those of the types described in
U.S. 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 U.S. Pat. No. 3,332,880; and others
known in the art, a number being specifically set forth in U.S.
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 elements.
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 formed 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 insolubility has a molecular weight of from
about 1,500 to about 1,800. The addition of polyoxyethylene
radicals to this hydrophobic portion tends to increase the water
solubility of the molecule as a whole and the liquid character of
the products is retained up to the point where polyoxyethylene
content is about 50% of the total weight of the condensation
product.
Other suitable nonionic synthetic detergents include:
1. 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 elements
which is desired. For example, compounds containing from about 40%
to about 80% 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,
5. Long chain tertiary phosphine oxides corresponding to the
following general formula
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 1 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. Long chain dialkyl sulfoxides containing one short chain alkyl
or hydroxy alkyl radical of 1 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 10 ethylene oxide
moieties and from 0 to 1 glyceryl moiety. Examples include:
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-hydroxy-4-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: ##EQU1## wherein R.sup.2 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 1 glyceryl moiety; Y is selected from the group consisting of
nitrogen, phosphorus, and sulfur atoms; R.sup.3 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.sup.4 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]-butane-1-carboxylate;
5-[S-3-hydroxypropyl-S-hexadecylsulfonio]-3-hydroxypentane-1-sulfate;
3-[P,P-diethyl-P-3,6,9-trioxatetradecoxylphosphonio]-2-hydroxy-propane-1-ph
osphate;
3-[N,N-dipropyl-N-3-dodecoxy-2-hydroxypropylammonio]-propane-1-phosphonate;
3-(N,N-dimethyl-N-hexadecylammonio)propane-1-sulfonate;
3-(N,N-dimethyl-N-hexadecylammonio)-2-hydroxypropane-1-sulfonate;
4-[N,N-di(2-hydroxyethyl)-N-(2-hydroxydodecyl)ammonio]-butane-1-carboxylate
;
3-[S-ethyl-S-(3-dodecoxy-2-hydroxypropyl)sulfonio]-propane-1-phosphate;
3-[P,P-dimethyl-P-dodecylphosphonio]-propane-1-phosphonate; and
5-[N,N-di(3-hydroxypropyl)-N-hexadecylammonio]2-hydroxy-pentane-1-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, phosphate, or phosphonate. Examples of compounds falling
within this definition are sodium 3-dodecylaminopropionate, sodium
3-dodecylaminopropane sulfonate, dodecyl-.beta.-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,
quaternary 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 of the organic 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
long-term 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-tarnishing 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.
Examples of diluents which may be incorporated into a synthetic
detergent bar in amounts of up to about 80% of the bar include
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 fuller's earth. Other diluents
include 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.
The antibacterial and antifungal efficacy of the phenylantimony
bis(2-pyridinethiol 1-oxide) is disclosed in the following
examples.
EXAMPLE I
PREPARATION OF PHENYLANTIMONY BIS(2-PYRIDINETHIOL 1-OXIDE)
47.0 g. (.174 mole) of phenylantimony dichloride were dissolved in
200 ml. of dimethylformamide. 53.7 g. (.348 mole, 96.8% active) of
sodium pyridinethiol 1-oxide were dissolved in 850 ml. of
dimethylformamide. The phenylantimony dichloride solution was then
poured into the sodium pyridinethiol 1-oxide solution in a 2000 ml.
3-neck reaction flask equipped with a drying tube and an argon
line. The color of the solution changed from dark brown to light
yellow as the phenylantimony dichloride solution was added. The
solution was stirred at room temperature for one and one-half
hours, heated to 65.degree.C. for one hour and filtered while hot.
The residue weighed 21.4 g. The theoretical weight of the NaC1
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
1-oxide) having a melting point of 204.degree.- 6.degree.C.
The percents of carbon, hydrogen, nitrogen, antimony, and sulfur
present in the phenylantimony bis(2-pyridinethiol 1-oxide) as
calculated and found by analysis are:
Calculated Found ______________________________________ C 42.6 42.4
H 2.9 2.9 N 6.2 6.2 Sb 14.2 14.2 S 27.0 27.0
______________________________________
EXAMPLE II
The phenylantimony bis(2-pyridinethiol 1-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(2-pyridinethiol
1-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 37.degree.C. 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 ______________________________________ MIC
(ppm) Staphylococcus aureus (S.a.) 6 Streptococcus pyogenes 4
Sarcina lutea (Sar. 1.) 6 Pseudomonas aeruginosa (Ps.a.) 100
Escherichia coli (E.c.) 10 Candida albicans 6
______________________________________
Fungistatic tests were performed using a modified gradient plate
technique reported by Hunt and Sandham (Applied Microbiology 17 No.
2:329-30, 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 Sodium alkyl glyceryl
ether sulfonate.sup.1 28.3 Sodium acyl sarcosinate.sup.2 5.0 Sodium
sulfate 0.8 0.8 2.6 Sodium chloride 6.6 Trisodium phosphate 2.1 2.1
Diethanolamide of coconut fatty acids 2.0 Acetylated lanolin 1.0
1.0 1.0 Perfume 1.0 1.0 0.4 Phenylantimony bis(2- 0.5 1.0 1.5
pyridinethiol 1-oxide) Water balance pH 7.7 7.7 7.4
______________________________________ .sup.1 Alkyl radicals
derived from fatty alcohol, 25.3% from coconut and 3% from tallow.
.sup.2 Acyl radicals derived from coconut fatty acids.
______________________________________ Composition No. 4 Percent
______________________________________ Dimethyl coconut.sup.1 amine
oxide 8.0 Disodium lauryl beta-iminodipropionate 5.0 Sodium
coconut.sup.1 sulfate 4.0 Coconut.sup.2 diethanolamide 1.0
Phenylantimony bis(2-pyridinethiol 1-oxide) 1.0 Perfume 0.5
Colorless than 0.01 Citric acid to adjust pH to 7.5 Water balance
______________________________________ .sup.1 The alkyl radical is
derived from middle cut coconut alcohol and has approximately the
following chain length composition: 2% C.sub.10, 66 C.sub.12, 23%
C.sub.14, and 9% C.sub.16. .sup.2 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% 1210 66%
C.sub.12, 23% C.sub.14, and 9% C.sub.16.
10% triethanolamine N-acyl sarcosinate, the acyl radicals being
derived from coconut oil fatty acids having the following chain
length distribution: 10% C.sub.8.sub.- 10, 48% C.sub.12, 21%
C.sub.14, 10% C.sub.16, and 11% C.sub.18.
3% monoethanolamide of coconut oil fatty acids having the following
chain length distribution: 16% C.sub.6.sub.- 10, 48% C.sub.12, 17%
C.sub.14, 9% C.sub.16, and 10% C.sub.18.
1% phenylantimony bis(2-pyridinethiol 1-oxide)
3% diethanolamide of coconut oil fatty acids having the following
chain length distribution: 16% .sub.6.sub.- 10, 48% C.sub.12, 17%
C.sub.14, 9% C.sub.16, and 10% C.sub.18.
7% ethanol
0.75% methyl cellulose, a 2% solution of which has a viscosity of
4000 cps. at 68.degree.F. and a gel point of 140.degree.F.
0.75% perfume
balance, water.
Shampoo formulations containing phenylantimony bis(2-pyridinethiol
1-oxide) are desirable since they will control dandruff.
EXAMPLE IV ______________________________________ Personal Use
Detergent Lotion Composition No. 6 Percent
______________________________________ Potassium coconut.sup.1
glyceryl ether 3.0 sulfonate (about 23% diglyceryl and the balance
substantially all monoglyceryl) Sodium coconut.sup.1 glyceryl ether
sulfo- 4.0 nate (diglyceryl and monoglyceryl content as above)
Sodium tallow glyceryl ether sulfonate 3.0 (digylceryl and
monoglyceryl content as above); the tallow alkyl radicals corres-
pond to those of substantially saturated tallow alcohols containing
approximately 2% C.sub.14, 32% C.sub.16, and 60% C.sub.18
Coconut.sup.1 dimethylamine oxide 5.0 Sodium salt of sulfated
condensation 2.0 product of one mole of nonylphenol with four moles
ethylene oxide Potassium pyrophosphate 1.0 Phenylantimony
bis(2-pyridinethiol 2.0 1-oxide) Sodium chloride (in addition to
3.0 that from detergents) Sodium toluene sulfonate 2.5 Sodium
carboxymethycellulose (degree of 0.3 substitution 0.65-95;
viscosity of 1% soln., 1000-2800 cps. at 25.degree.C.) Acrylamide
polymer (contains 5-10 0.1 mole percent acrylic acid radicals;
monomer is less than 0.05%; viscosity of 0.5% soln. is about 10-15
cps. at 25.degree.C.) Salts (sodium and potassium chloride 1-2 and
sulfate from detergents) Water balance
______________________________________ .sup.1 Coconut indicates
alkyl radicals corresponding to those of middle cut coconut fatty
alcohol containing approximately 2% Chd 10, 66% C.sub.12, 23%
C.sub.14, and 9% C.sub.16.
EXAMPLE V ______________________________________ Cream Shampoo
Composition Percent ______________________________________ Sodium
coconut glyceryl ether 14.8 sulfonate (about 29% diglyceryl and the
balance substantially monoglyceryl) Sodium tallow glyceryl ether
sulfonate 2.0 (about 28% diglyceryl and the balance substantially
monoglyceryl) Sodium chloride 6.7 Sodium sulfate 3.5 Sodium
N-lauroyl sarcosinate 3.0 Phenylantimony bis(2-pyridinethiol
1-oxide) 2.0 Middle-cut coconut.sup.1 diethanolamine 0.5 Acetylated
lanolin 1.0 Perfume 0.4 Water balance
______________________________________ .sup.1 2% C.sub.10, 66%
C.sub.12, 23% C.sub.14, and 9% C.sub.16.
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 middle-
cut.sup.1 of alcohols obtained by catalytic reduction of coconut
oil) Potassium alkyl sulfate (alkyl group 20.0 derived from the
middle-cut.sup.1 of alcohols obtained by catalytic reduction of
coconut oil) Magnesium soap of 80:20 tallow: 17.0 coconut fatty
acids Inorganic salts (sodium and potassium 32.0 chlorides and
sulfates) Phenylantimony bis(2-pyridinethiol 1.0 1-oxide) Water and
minors balance to 100 ______________________________________ .sup.1
Middle-cut coconut alcohols having a chain length distribution
substantially as follows: 2% C.sub.10, 66% C.sub.12, 23% C.sub.14,
and 9% C.sub.16.
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.sub.2 :Na.sub.2 O=2:1) 7.0 Phenylantimony
bis(2-pyridinethiol 3.0 1-oxide) Water and minors balance to 100
______________________________________
This composition, in addition to performing well in 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 following:
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-5-chloro-2-mercaptobenzothiazole;
laurylpicolinium-p-toluenesulfonate;
tetradecylpyridinium bromide;
cetylpyridinium chloride;
cetylpyridinium bromide;
laurylisoquinolinium bromide;
laurylisoquinolinium saccharinate;
alkylisoquinolinium bromide;
N-cetyl-ethyl-morpholinium ethosulfate;
benzalkonium chloride;
monoquaternaries R.sub.4 N.sup.+X.sup.- (one R group is fatty);
octadecyltrimethylammonium chloride;
coconut alkyl trimethylammonium chloride;
dodecylbenzyltri(octyldecyl)ammonium chloride;
monoquaternaries R.sub.4 N.sup.+X.sup.- (two R groups are
fatty);
dihexadecyldimethylammonium chloride;
di-coconut alkyl dimethylammonium chloride;
monoquaternaries R.sub.4 N.sup.+X.sup.- (three R groups are
fatty);
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 15 moles of ethylene
oxide per mole of octyl phenol;
dimethyldodecylamine oxide;
dodecyldimethylphosphine oxide;
tetradecyl methyl sulfoxide;
3-(N,N-dimethyl-N-hexadecylammonio)propane-1-sulfonate;
3-dodecylaminopropionate; and
dodecyl-.beta.-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
shampoos, foot powders, antiseptic ointments, cosmetic products and
the like.
A fabric softening composition having the following formulation can
be prepared. The antibacterial and antifungal effectiveness of the
phenylantimony bis(2-pyridinethiol 1-oxide) is especially desirable
since the antibacterial and antifungal compound is extremely
substantive to cloth.
______________________________________ 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 3 moles of ethylene oxide with one mole
of coconut alcohol Color and Perfume 0.3 Phenylantimony
bis(2-pyridinethiol 1.0 1-oxide) Water balance
______________________________________
* * * * *