USOO6616922B2

12) United States Patent 10) Patent No.: US 6,616,922

9 9 B2
Taylor et al. (45) Date of Patent: Sep. 9, 2003

(54) ANTIBACTERIAL COMPOSITIONS 6,106,851 A 8/2000 Beerse et al. ............... 424/401

6,107.261 A * 8/2000 Taylor et al. ............... 510/131
(75) Inventors: Timothy J. Taylor, Phoenix, AZ (US); 6,113.933 A 9/2000 Beerse et al. ............... 424/404
Priscilla S. Fox, Phoenix, AZ (US); E. 4.
2-a-s-s-?
A : 1838 yet al. - - - - - - - - - - - - SR;
aylor et al. . . . . . . . . . . . . . . .
Ef SYNC, (S), AZ
s ael J. Slayton, Uave Ureek,
6,204.230 B1 * 3/2001 Taylor et al. ............... 510/131
6,451,748 B1 * 9/2002 Taylor et al. ............... 510/131
FOREIGN PATENT DOCUMENTS
(73) Assignee: The
(US)
Dial Corporation, Scottsdale, AZ EP O SOS 935 9/1992 ............ C11D/3/48
EP O 651 048 5/1995 ........... C11D/1/835
(*) Notice: Subject to any disclaimer, the term of this E. St. A1 * :1998
/1998
patent is extended or adjusted under 35 WO WO 92/16182 10/1992
U.S.C. 154(b) by 0 days. WO WO 92/16201 10/1992 ......... A61 K/31/205
WO WO95/09605 4/1995 ... A61K/7/50
(21) Appl. No.: 09/818,366 WO WO95/32705 12/1995 ... A61K/7/50
WO WO 96/06152 2/1996 ... C11D/3/00
(22) Filed: Mar 27, 2001 WO WO 97/15647 5/1997 ... C11D/1/62
O O WO WO 97/46218 12/1997 ... A61K/7/48
(65) Prior Publication Data WO WO 98/O1110 1/1998 ... A61K/7/48
WO WO 98/55.096 12/1998 ............ A61 K/7/50
US 2003/0022941 A1 Jan. 30, 2003 WO WO 99/19438 * 4/1999
(51) Int. Cl. ............................. A61K 7/50; A61K 7/40 OTHER PUBLICATIONS
(52) U.S. Cl. ................ 424/7028; 424/70.1; 424/70.27;
424/400; 424/404 Allawala et al., Journal of the American Pharmaceutical
(58) Field of Search ....................... 514/358; 424/7028, Association, vol. XIII, No. 5, pp. 267-275 (1953).
424/70.1, 70.27, 400, 404 Mitchell, J. Pharm. Pharmacol. 16, pp. 533–537 (1964).
(56) References Cited * cited by examiner
U.S. PATENT DOCUMENTS Primary Examiner Thurman K. Page
ASSistant Examiner-Rachel M. Bennett
4,062.976 A 12/1977 Michaels - - - - - - - - - - - - - - - - - - - - 424/319 (74) Attorney, Agent, or Firm-Marshall, Gerstein & Borun
4,075,350 A 2/1978 Michaels ... ... 424/316
4,107,328 A 8/1978 Michaels ... ... 424/316 (57) ABSTRACT
4,145,436 A 3/1979 Michaels ... 424/273 R
5.244.652 A 9/1993 Michaels ..................... 424/54 Antibacterial compositions having enhanced antibacterial
5,314.917 A 5/1994 Michaels et al. ........... 514/556 effectiveness are disclosed. The antibacterial compositions
5,389,676 A 2/1995 Michaels .................... 514/556 contain an antibacterial agent, an alkamine oxide, a nonionic
5. A S.S. s - - - SR and/or cationic coSurfactant, an optional polymeric
5908,854. A 6/1999 M.C.A. E, thickener, and water.
5,929,016 A 7/1999 Harrison ..................... 510/384
5,968,539 A 10/1999 Beerse et al. ............... 424/405 37 Claims, No Drawings
 US 6,616,922 B2
1 2
ANTIBACTERIAL COMPOSITIONS It should be noted that high log reductions have been
achieved at pH values of 4 and 9, but Such log reductions are
attributed at least in part to these relatively extreme pH
FIELD OF THE INVENTION values. Compositions having Such pH values can irritate the
The present invention is directed to antibacterial skin or damage other Surfaces, and, therefore, typically are
compositions, like personal care compositions, having avoided. It has been difficult to achieve a high log reduction
using an antibacterial composition having a neutral pH of
improved antibacterial effectiveness and excellent esthetic about 5.5 to about 7.5, and especially about 6 to about 7.3.
properties. More particularly, the present invention is Antibacterial compositions having a near neutral pH are
directed to antibacterial compositions comprising an anti disclosed in U.S. Pat. Nos. 6,107,261 and 6,136,771.
bacterial agent, an alkamine oxide, a coSurfactant, and an In addition to an antibacterial agent, antibacterial personal
optional polymeric thickener. Preferred compositions have a care compositions typically contain an anionic Surfactant for
pH of about 5.5 to about 7.5. A present composition provides cleansing and foam generation, Skin conditioning agents for
a Substantial reduction, e.g., greater than 99%, in Gram cosmetic effects, and dyes, perfumes, and optional thicken
positive and Gram negative bacterial populations within one 15
ing agents, Such as clays, polymers, or colloids, for esthetic
minute. effects. The most common antibacterial agents are Selected
BACKGROUND OF THE INVENTION
from the classes of phenolic compounds, carbanalide
compounds, lower alcohols, and quaternary ammonium
Antibacterial personal care compositions are known in the compounds. Quaternary ammonium germicides are not
art. Especially useful are antibacterial cleansing widely used in antibacterial personal care compositions,
compositions, which typically are used to cleanse the skin predominantly because of an inherent chemical incompat
and to destroy bacteria and other microorganisms present on ibility with the commonly used, and preferred, anionic
the skin, especially the hands, arms, and face of the user. Surfactants, Such as Soaps, alcohol Sulfates, alcohol ether
Antibacterial compositions are used, for example, in the Sulfates, and the like.
health care industry, food Service industry, meat processing 25
Although a composition containing a quaternary ammo
industry, and in the private Sector by individual consumers. nium compound and a Selected anionic Surfactant has been
The widespread use of antibacterial compositions indicates disclosed as being effective in Some applications (e.g., U.S.
the importance consumers place on controlling bacteria and Pat. No. 5,798,329), no reference disclosing such a combi
other microorganism populations on Skin. It is important, nation for use in personal care compositions has been found.
however, that antibacterial compositions provide a Substan Accordingly, antibacterial personal care compositions based
tial and broad Spectrum reduction in microorganism popu on quaternary ammonium germicides generally incorporate
lations quickly and without problems associated with tox nonionic or amphoteric Surfactants, and avoid anionic Sur
icity and skin irritation. factants because of chemical incompatibility problems.
In particular, antibacterial cleansing compositions typi However, personal care compositions based on nonionic
cally contain an active antibacterial agent, a Surfactant, and 35 and/or amphoteric Surfactants Suffer in comparison to
various other ingredients, for example, dyes, fragrances, pH anionic Surfactant-based compositions with respect to
adjusters, thickeners, Skin conditioners, and the like, in an acceptable consumer properties, especially foam generation.
aqueous carrier. Several different classes of antibacterial It also is difficult to provide phase Stable compositions
agents have been used in antibacterial cleansing composi having a consumer acceptable Viscosity using a low to
tions. Examples of antibacterial agents include bis 40 moderate level of nonionic and amphoteric Surfactants.
guanidines (e.g., chlorhexidine digluconate), diphenyl In particular, when the nonionic/amphoteric Surfactant
compounds, benzyl alcohols, trihalocarbanilides, quaternary level is low to moderate, the compositions initially are
ammonium compounds, ethoxylated phenols, and phenolic Viscous, or thick, when first prepared, but often undergo
compounds, Such as halo-Substituted phenolic compounds, phase Separation under ambient, and especially under
like PCMX (i.e., p-chloro-m-xylenol) and triclosan (i.e., 45 stressed (i.e., high temperature) storage conditions. Further,
2,4,4'-trichloro-2'hydroxy-diphenylether). Present-day anti present-day antibacterial personal care compositions do not
microbial compositions based on Such antibacterial agents provide an effective antibacterial activity, especially against
exhibit a wide range of antibacterial activity, ranging from pathogenic Gram negative bacteria. Thus, a need exists for
low to high, depending on the microorganism to be con phase Stable, efficacious antibacterial personal care compo
trolled and the particular antibacterial composition. 50 Sitions containing a quaternary ammonium germicide and a
Most commercial antibacterial compositions, however, low or moderate level of nonionic or amphoteric Surfactant,
generally offer a low to moderate antibacterial activity. and that further are consumer acceptable and mild to the
Antibacterial activity is assessed against a broad Spectrum of skin. A need also exists for phase Stable compositions having
microorganisms, including both Gram positive and Gram a high Viscosity and containing a phenolic antibacterial
negative microorganisms. The log reduction, or alternatively 55 agent and an alkamine oxide Surfactant.
the percent reduction, in bacterial populations provided by An example of patents and published applications dis
the antibacterial composition correlates to antibacterial closing compositions comprising triclosan, Surfactants,
activity. A log reduction of 3-5 is most preferred, a 1-3 Solvents, chelating agents, thickeners, buffering agents, and
reduction is preferred, whereas a log reduction of less than water is WO 98/01110. WO98/01110 is directed to reducing
1 is least preferred, for a particular contact time, generally 60 skin irritation by employing a reduced amount of Surfactant.
ranging from 15 Seconds to 5 minutes. Thus, a highly Fendler et al. U.S. Pat. No. 5,635,462 discloses compo
preferred antibacterial composition exhibits a 3–5 log reduc sitions comprising PCMX and selected Surfactants. The
tion against a broad spectrum of microorganisms in a short compositions disclosed therein are devoid of anionic Sur
contact time. Prior disclosures illustrate attempts to provide factants and nonionic Surfactants.
Such antibacterial compositions, which, to date, do not 65 WO 97/46218 and WO 96/06152 disclose compositions
provide the rapid, broad range control of microorganisms based on triclosan, organic acids or Salts, hydrotropes, and
desired by consumers. hydric solvents.
 US 6,616,922 B2
3 4
EP 0505935 discloses compositions containing PCMX More particularly, the present invention relates to antimi
in combination with nonionic and anionic Surfactants, par crobial compositions containing a phenolic or quaternary
ticularly nonionic block copolymer Surfactants. ammonium antibacterial agent, an alkamine oxide
WO95/32705 discloses a mild Surfactant combination Surfactant, a coSurfactant, an optional-polymeric thickener,
that can be combined with antibacterial compounds, like and water. The present antimicrobial compositions are free
triclosan. of anionic Surfactants and Zwitterionic Surfactants, are phase
WO95/09605 discloses antibacterial compositions con Stable, and possess excellent esthetic properties, Such as
taining anionic Surfactants and alkylpolyglycoside Surfac foam height and Stability.
tantS. Accordingly, one aspect of the present invention is to
WO 98/55096 discloses antimicrobial wipes having a provide a stable, liquid antibacterial composition compris
porous sheet impregnated with an antibacterial composition ing: (a) about 0.05% to about 5%, by weight, of an antibac
containing an active antimicrobial agent, an anionic terial agent; (b) about 1% to about 15%, by weight, of an
Surfactant, an acid, and water, wherein the composition has alkamine oxide surfactant; (c) about 1% to about 10%, by
a pH of about 3.0 to about 6.0. weight, of a nonionic coSurfactant, a cationic coSurfactant,
Beerse et al. U.S. Pat. Nos. 5,968,539; 6,106,851; and
15 or a mixture thereof; (d) 0% to about 5%, by weight, of a
polymeric thickening agent, Such as a hydrophobically
6,113,933 disclose antibacterial compositions having a pH modified alkoxylated compound; and (e) water. A present
of about 3 to about 6. The compositions contain an antibac composition also is free of anionic and Zwitterionic Surfac
terial agent, an anionic Surfactant, and a proton donor. tantS.
N. A. Allawala et al., J. Amer: Pharm. ASSOc.- Sci. Ed., A present antibacterial composition is phase Stable, has a
Vol. XLII, no. 5, pp. 267-275, (1953) discusses the anti pH of about 5.5 to about 7.5, and has a viscosity of about 0.1
bacterial activity of active antibacterial agents in combina to about 100 centipoise (cp) in the absence of a polymeric
tion with Surfactants. thickener, and up to about 10,000 cp when an optional
A. G. Mitchell, J. Pharm. Pharmacol, Vol. 16, pp. thickening agent is present. The present compositions also
533–537, (1964) discloses compositions containing PCMX 25
exhibit excellent esthetic properties, Such as foam character,
and a nonionic Surfactant that exhibit antibacterial activity. which is unexpected for compositions free of anionic Sur
The compositions disclosed in the Mitchell publication factants.
exhibit antibacterial activity in at least 47 minutes contact Yet another aspect of the present invention is to provide
time, thus the compositions are not highly effective. an antibacterial composition that exhibits a log reduction
Patents and published applications disclosing germicidal against Gram positive bacteria (i.e., S. aureus) of at least 2
compositions containing a quaternary ammonium antibac after 30 seconds of contact.
terial agent include U.S. Pat. Nos. 5,798,329; 5,929,016; Still another aspect of the present invention is to provide
WO 97/15647; and EPO 651 048, directed to antibacterial an antibacterial composition that exhibits a log reduction
laundry detergents and antibacterial hard Surface cleaners. 35 against Gram negative bacteria (i.e., E. coli) of at least 2.5
Antibacterial compositions containing amphoteric Surfac after 30 seconds of contact.
tants are disclosed in U.S. Pat. Nos. 5,244,652; 5,389,676; Another aspect of the present invention is to provide an
4,075,350; 4,062,976; 4,107,328; and 4,145,436. antibacterial composition that exhibits a Substantial log
Prior disclosures have not addressed the issue of provid reduction against Gram positive and Gram negative bacteria,
ing an antibacterial composition that (a) affords an effective, 40 and has a pH of about 5.5 to about 7.5.
fast, and broad Spectrum control of bacteria at a neutral pH Another aspect of the present invention is to provide
of about 5.5 to about 7.5, and especially at about 6.5 to about personal use products based on an antibacterial composition
7.3, (b) is phase stable, and (c) exhibits excellent esthetic of the present invention, for example, a skin cleanser, a body
properties, Such as a high Viscosity and a stable, copious Splash, a Surgical Scrub, a wound care agent, a hand Sanitizer
foam generation. 45 gel, a disinfectant, a mouth wash, a pet shampoo, a hard
An efficacious antibacterial composition having excellent Surface Sanitizer, and the like.
esthetic properties has been difficult to achieve because of A further aspect of the present invention is to provide a
the chemical properties of the antibacterial agents and the method of reducing the Gram positive and/or Gram negative
Surfactants, and the effects of a Surfactant on an antibacterial bacteria populations on animal tissue, including human
agent. For example, nonionic and amphoteric Surfactants do 50 tissue, by contacting the tissue, like the dermis, with a
not provide a high foam level desired by consumers, and it composition of the present invention for a Sufficient time,
is difficult to provide a phase Stable, Viscous composition. Such as about 15 Seconds to 5 minutes, to reduce the bacteria
Anionic Surfactants provide Such properties, but cannot be level to a desired level.
formulated with quaternary ammonium antibacterial agents. The above and other novel aspects and advantages of the
Accordingly, a need exists for an antibacterial composi 55 present invention are illustrated in the following, nonlimit
tion that is highly efficacious against a broad spectrum of ing detailed description of the preferred embodiments.
Gram positive and Gram negative bacteria in a short time
period, and wherein the composition is Viscous, phase DETAILED DESCRIPTION OF THE
Stable, and provides consumer-acceptable esthetic PREFERRED EMBODIMENTS
properties, even in the absence of anionic Surfactants. The 60 Personal care products incorporating an active antibacte
present invention is directed to Such antibacterial composi rial agent have been known for many years. Since the
tions. introduction of antibacterial personal care products, many
SUMMARY OF THE INVENTION
claims have been made that Such products provide antibac
terial properties. However, to be most effective, an antibac
The present invention relates to antibacterial composi 65 terial composition should provide a high log reduction
tions that provide a Substantial reduction in Gram positive against a broad Spectrum of organisms in as short a contact
and Gram negative bacteria in less than about one minute. time as possible.
 US 6,616,922 B2
S 6
The antibacterial composition also should exhibit excel cationic coSurfactant, or a mixture thereof; (d) 0% to about
lent esthetic properties in order to achieve consumer accep 5%, by weight, of a-polymeric thickener; and (e) water.
tance. The features of antibacterial efficacy and esthetic The compositions also can further include additional
properties often are competing, wherein enhancing one optional ingredients disclosed hereafter, for example, a
feature is detrimental to the other. The present invention is conditioning agent, a hydric Solvent, a preservative, a
directed to antibacterial compositions that unexpectedly hydrotrope, a pH adjuster, a dye, and a perfume. The
exhibit both features. compositions exhibit a log reduction against Gram positive
AS presently formulated, commercial liquid antibacterial bacteria of about 2 after 30 seconds contact. The composi
Soap compositions provide a poor to marginal time kill tions exhibit a log reduction against Gram negative bacteria
efficacy, i.e., rate of killing bacteria. Table 1 Summarizes the of about 2.5 after 30 seconds contact.
kill efficacy of commercial products, each of which contains
about 0.2% to 0.3%, by weight, triclosan (an antibacterial The following illustrates nonlimiting embodiments of the
agent). present invention.
TABLE 1. 15 A. Antibacterial Agent
An antibacterial agent is present in a composition of the
Time Kill Efficacy of Commercial Liquid Hand Soaps present invention in an amount of about 0.05% to about 5%,
Organism and preferably about 0.1% to about 3%, by weight of the
(Log Reductions after composition. To achieve the full advantage of the present
1 Minute Contact Time
invention, the antibacterial agent is present in an amount of
Gram Positive Gram negative Grain negative about 0.2% to about 2%, by weight, of the composition.
Product S. aureus E. coil K. pneum.
The antibacterial compositions can be ready to use
Commercial 1.39 O.OO O.04 compositions, which typically contain about 0.05% to about
Product A
Commercial 2.20 O.OO O.O1
25 2%, preferably about 0.1% to about 1.5%, and most pref
Product B erably about 0.2% to about 1%, of an antibacterial agent, by
Commercial 1.85 O.OO O.OO weight of the composition. The antibacterial compositions
Product C also can be formulated as concentrates that are diluted
before use with one to about 100 parts water to provide an
Present-day products especially lack efficacy against end use composition. The concentrated compositions typi
Gram negative bacteria, Such as E. coli, which are of cally contain greater than about 0.1% and up to about 5%,
particular concern to human health. The present invention, by weight, of the antibacterial agent. Applications also are
therefore, is directed to antibacterial compositions having envisioned wherein the end use composition contains greater
high broad Spectrum antibacterial efficacy, as measured by a 35 than 2%, by weight, of the antibacterial agent.
rapid kill of bacteria (i.e., time kill), which is to be distin The amount of antibacterial agent in the composition is
guished from persistent kill. The present antibacterial com related to the end use of the composition, the identity and
positions provide Significantly improved time kill efficacy amount of alkamine oxide and coSurfactant in the
compared to prior compositions.
An important ingredient in antibacterial cleansing com composition, and the presence of optional ingredients in the
40
positions is the Surfactant, which acts as a Solubilizer, composition. The amount of antibacterial agent is Sufficient
cleanser, and foaming agent. Typically, the Surfactant is an to achieve a bacteria kill in a short contact time, like 15 to
60 seconds.
anionic Surfactant, which provides excellent foam
generation, good cleaning, and Viscosity enhancement. The antimicrobial agents useful in the present invention
However, the use of an anionic Surfactant limits the range of 45 are exemplified by the following classes of compounds used
useful antibacterial agents. For example, anionic Surfactants alone or in combination.
and quaternary ammonium antibacterial agents are chemi
cally incompatible. In addition, anionic Surfactants tend to (1) Phenolic Antibacterial Agents
be harsh to the skin. (a) 2-Hydroxydiphenyl Compounds
The Substitution of a nonionic or amphoteric Surfactant 50
for an anionic Surfactant in an antibacterial composition is Y
not Straightforward. For example, the Substitution of a Zip n/2 Y.
nonionic Surfactant often leads to phase instability in a
composition. In addition, nonionic and amphoteric Surfac
tants do not generate the high foam levels that consumers
equate to cleaning efficacy.
The present compositions are antibacterial compositions
having an excellent effectiveness against both Gram nega
55
(OH)
O-O. OH
(OH),

tive and Gram positive bacteria, and that exhibit a rapid wherein Y is chlorine or bromine, Z is SOH, NO, or
bacteria kill. The compositions also are phase Stable, and 60 C-C alkyl, r is 0 to 3, o is 0 to 3, p is 0 or 1, m is 0
exhibit excellent esthetic properties, Such as Viscosity and or 1, and n is 0 or 1.
foam generation, even in the absence of anionic Surfactants. In preferred embodiments, Y is chlorine or bromine, m is
AS illustrated hereafter, an antibacterial composition of the 0, n is 0 or 1, o is 1 or 2, r is 1 or 2, and p is 0.
present invention comprises: (a) about 0.05% to about 5%, In especially preferred embodiments, Y is chlorine, m is
by weight, of an antibacterial agent; (b) about 1% to about 65 0, n is 0, o is 1, r is 2, and p is 0.
15%, by weight, of an alkamine oxide Surfactant; (c) about A particularly useful 2-hydroxydiphenyl compound has
1% to about 10%, by weight, of a nonionic coSurfactant, a the Structure:
 US 6,616,922 B2

C O Cl

OH C

having the adopted name, triclosan, and available commer wherein at least one of R, R2, R, and R is an alkyl, aryl,
cially under the tradename IRGASAN DP100, from Ciba or alkaryl Substituent containing 6 to 26 carbon atoms.
Specialty Chemicals Corp., Greensboro, N.C. Another use 1O Alternatively, any two of the R substituents can be taken
ful 2-hydroxydiphenyl compound is 2,2'-dihydroxy-5,5'- together, with the nitrogen atom, to form a five- or Six
dibromodiphenyl ether. Additional bisphenolic compounds membered aliphatic or aromatic ring. Preferably, the entire
are disclosed in U.S. Pat. No. 6,113,933, incorporated herein ammonium cation portion of the antibacterial agent has a
by reference. molecular weight of at least 165.
15 The Substituents R, R2, R, and R can be Straight
(b) Phenol Derivatives chained or can be branched, but preferably are Straight
OH
chained, and can include one or more amide, ether, or ester
linkage. In particular, at least one Substituent is C-C alkyl,
C-Calkoxyaryl, C-C alkaryl, halogen-Substituted
Co-Calkaryl, C-C alkylphenoxyalkyl, and the like. The
remaining Substituents on the quaternary nitrogen atom
other than the above-mentioned Substituent typically contain
no more than 12 carbon atoms. In addition, the nitrogen
atom of the quaternary ammonium antibacterial agent can be
25 present in a ring System, either aliphatic, e.g., piperdinyl, or
aromatic, e.g., pyridinyl. The anion X can be any Salt
wherein R is hydro, hydroxy, C-C alkyl, chloro, forming anion which renders the quaternary ammonium
nitro, phenyl, or benzyl, R is hydro, hydroxy, C-C, compound water Soluble. Anions include, but are not limited
alkyl, or halo, R is hydro, C-C alkyl, hydroxy, to, a halide, for example, chloride, bromide, or iodide,
chloro, nitro, or a Sulfur in the form of an alkali metal methoSulfate, and ethoSulfate.
Salt or ammonium salt; R is hydro or methyl; and Rs Preferred quaternary ammonium antibacterial agents have
is hydro or nitro. Halo is bromo or, preferably, chloro. a structural formula:
Specific examples of phenol derivatives include, but are
not limited to, chlorophenols (o-, m-, p-), 2,4- CH
dichlorophenol, p-nitrophenol, picric acid, Xylenol, 35
p-chloro-m-Xylenol, cresols (o-, m-, p-), p-chloro-m-cresol, R-N-R X,
pyrocatechol, resorcinol, 4-n-hexylresorcinol, pyrogallol,
phloroglucin, car Vacrol, thy mol, p-chlorothy mol, CH
o-phenylphenol, O-benzylphenol, p-chloro-O-benzylphenol,
phenol, 4-ethylphenol, and 4-phenolsulfonic acid. Other 40 wherein R and R, independently, are C-C-alkyl, or R is
phenol derivatives are listed in WO98/55096 and U.S. Pat. C 2-C alkyl, Cs-C is alkyl eth oxy, O
No. 6,113,933, incorporated herein by reference. Cs-Calkylphenylethoxy, and R is benzyl, and X is halo,
(c) Diphenyl Compounds methoSulfate, ethoSulfate, or p-toluenesulfonate. The alkyl
groups R and R can be straight chained or branched, and
R2 R1 45 preferably are linear.
The quaternary ammonium antibacterial agent in a present
R's X
composition can be a single quaternary ammonium
compound, or a mixture of two or more quaternary ammo
nium compounds. Particularly useful quaternary ammonium
R4 R's R5 R4 50 antibacterial agents include dialkyl(Cs-Co) dimethyl
ammonium chlorides (e.g., dioctyl dimethyl ammonium
chloride), alkyl dimethylbenzyl ammonium chlorides (e.g.,
wherein X is Sulfur or a methylene group, R and R' benzalkonium chloride and myristyl dimethylbenzyl ammo
are hydroxy, and R2, R2, Ra, R's, R., R., Rs, and R's, nium chloride), alkyl methyl dodecyl benzyl ammonium
independent of one another, are hydro or halo. Specific, 55 chloride, methyl dodecyl Xylene-bis-trimethyl ammonium
nonlimiting examples of diphenyl compounds are chloride, benzethonium chloride, dialkyl methyl benzyl
hexachlorophene, tetrachlorophene, dichlorophene, ammonium chloride, alkyl dimethyl ethyl ammonium
2,3-dihydroxy-5,5'-dichlorodiphenyl sulfide, 2,2'- bromide, and an alkyl tertiary amine. Polymeric quaternary
dihydroxy-3,3', 5,5'-tetrachlorodiphenyl sulfide, 2,2'- ammonium compounds based on these monomeric Struc
dihydroxy-3,5".5,5,6,6'-hexachlorodiphenyl sulfide, 60 tures also can be used in the present invention. One example
and 3,3'-dibromo-5,5'-dichloro-2,2'- of a polymeric quaternary ammonium compound is
dihydroxydiphenylamine. Other diphenyl compounds POLYOUATOR, e.g., a 2-butenyl dimethyl ammonium chlo
are listed in WO 98/55096, incorporated herein by ride polymer. The above quaternary ammonium compounds
reference. are available commercially under the trade names
(2) Quaternary Ammonium Antibacterial Agents 65 BARDAC(R), BTC(R), HYAMINE(R), BARQUATOR, and
Useful quaternary ammonium antibacterial agents have a LONZABAC(R), from suppliers such as Lonza, Inc.,
general Structural formula: Fairlawn, N.J. and Stepan Co., Northfield, Ill.
 US 6,616,922 B2
10
Additional examples of quaternary ammonium antibacte
rial agents include, but are not limited to, alkyl ammonium CH
halides, Such as cetyl trimethyl ammonium bromide, alkyl CH(CH), 2 N->O.
aryl ammonium halides, Such as octadecyl dimethylbenzyl
ammonium bromide, N-alkyl pyridinium halides, Such as CH
N-cetyl pyridinium bromide; and the like. Other suitable
quaternary ammonium antibacterial agents have amide, Another class of useful amine oxides includes alkyl
ether, or ester moieties, Such as octylphenoxyethoxy ethyl di(hydroxy lower alkyl)amine oxides in which the alkyl
dimethyl benzyl ammonium chloride, N-(laurylcoco group contains 8 to 22, and preferably about 10 to about 16
aminoformylmethyl)pyridinium chloride, and the like. Other carbon atoms, and can be Straight or branched chain, Satu
classes of quaternary ammonium antibacterial agents rated or unsaturated. Specific examples, include, but are not
include those containing a Substituted aromatic nucleus, for limited to, bis(2-hydroxyethyl)cocoamine oxide, bis(2-
example, lauryloxyphenyl trimethyl ammonium chloride, hydroxyethyl)tallow amine oxide, and bis(2-hydroxyethyl)
15 Stearylamine oxide. These alkamine oxides have a general
cetylaminophenyl trimethyl ammonium methoSulfate, dode Structural formula
cylphenyl trimethyl ammonium methoSulfate, dodecylben
Zyl trimethyl ammonium chloride, chlorinated dodecylben CH2CH2OH
Zyl trimethyl ammonium chloride, and the like.
Specific quaternary ammonium antibacterial agents
include, but are not limited to, behenalkonium chloride, CH2CH2OH.
cetalkonium chloride, cetarylalkonium bromide, cetrimo
nium tosylate, cetyl pyridinium chloride, lauralkonium Additional useful amine oxides are termed alkamidopro
bromide, lauralkonium chloride, lapyrium chloride, lauryl pyl di(lower alkyl)amine oxides in which the alkyl group
pyridinium chloride, myristalkonium chloride, olealkonium 25
contains 8 to 22, and preferably about 10 to about 16 carbon
chloride, and isostearyl ethyldimonium chloride. Preferred atoms, and can be Straight or branched chain, Saturated or
quaternary ammonium antibacterial agents include benza unsaturated. Examples are cocoamidopropyl dimethyl
Ikonium chloride, benzethonium chloride, cetyl pyridinium amine oxide and tallowamidopropyl dimethyl amine oxide.
bromide, and methylbenzethonium chloride. These alkamine oxides have a general Structural formula
B. Alkamine Oxide Surfactant
CH
In addition to an antibacterial agent, a present antimicro
bial composition also contains an alkamine oxide Surfactant.
The alkamine oxide Surfactant is present in an amount of CH
about 1% to about 15%, and preferably about 1.5% to about 35
10%, by weight, of the composition. To achieve the full
advantage of the present invention, a present antibacterial Further useful amine oxides are termed alkylmorpholine
composition contains about 2% to about 8%, by weight, of oxides in which the alkyl group contains 8 to 22, and
the alkamine oxide Surfactant. preferably about 10 to about 16, carbon atoms, and can be
Ready-to-use compositions typically contain about 1% to 40 Straight or branched chain, Saturated or unsaturated. Alka
about 10%, preferably about 1% to about 5%, and most mine oxides are commercially available, for example, from
preferably, 1% to about 3%, of alkamine oxide surfactant, by Stepan Co., Northfield, Ill., and Lonza Inc., Fairlawn, N.J.
The above classes of alkamine oxide Surfactants contain
weight, of the composition. Concentrated compositions Suit a C-C-alkyl group Selected from, for example, octyl,
able for dilution typically contain greater than about 5%, by 45 decyl, undecyl, lauryl, tridecyl, myristyl, cetyl, Stearyl,
weight, of an alkamine oxide Surfactant. isoStearyl, oleyl, and mixtures thereof. Examples of amine
The amount of alkamine oxide Surfactant present in the oxide Surfactants include, but are not limited to, decyl
composition is related to the amount and identity of the dimethylamine oxide, lauryl dimethylamine oxide, Stearyl
antibacterial agent in the composition, to the identity of the dimethylamine oxide, oleyl dimethylamine oxide, coco
alkamine oxide Surfactant, and the end use of the composi 50 dihydroxyethylamine oxide, cetyl N,N-
tion. dihydroxyethylamine oxide, oleyl N,N-
An alkamine oxide useful in the present invention con dihydroxyethylamine oxide, cocamine oxide, cocamidopro
tains at least one long hydrocarbon chain containing at least pylamine oxide, lauramidopropylamine oxide, oleamine
eight carbon atoms. One class of amine oxides is the alkyl oxide, oleamidopropylamine oxide, wheat germamidopro
di(lower alkyl)amine oxides, wherein the alkyl group con 55 pylamine oxide, isoStearamido-propylamine oxide, Stear
tains 8 to 22, and preferably about 10 to about 16, carbon amine oxide, Stearamido-propylamine oxide, cocomorpho
atoms, and can be Straight or branched chain, Saturated or line oxide, de cylamine oxide, dihydroxyethyl
Cs-Coalkoxypropylamine oxide, dihydroxyethyl
unsaturated. The lower alkyl groups contain 1 to 7 carbon Co-Calkoxypropylamine oxide, dihydroxyethyl
atoms, and typically are methyl. Specific examples include, 60 C-C alkoxypropylamine oxide, dihydroxyethyl cocam
but are not limited to, lauryl dimethyl amine oxide, myristyl ine oxide, dihydroxyethyl Stearamine oxide, dihydroxyethyl
dimethyl amine oxide, dimethyl cocoamine oxide, dimethyl tallowamine oxide, hydrogenated tallow amine oxide,
(hydrogenated tallow)amine oxide, myristyl/palmityl dim hydroxyethyl hydroxypropylC-C salkoxypropylamine
ethyl amine oxide, myristyl/lauryl dimethyl amine oxide, oxide, isoStearamidopropyl morpholine oxide, myristami
cetyl dimethyl amine oxide, Stearyl dimethyl amine oxide, 65 dopropylamine oxide, myristamine oxide, palmitamidopro
and myristyl/cetyl dimethyl amine oxide. These alkamine pylamine oxide, palmitamine oxide, PEG-3 lauramine
oxides have a general Structural formula oxide, tallow amidopropylamine oxide, tallow amine oxide,
 US 6,616,922 B2
11 12
undecylenamidopropylamine oxide, and mixtures thereof. Numerous other nonionic Surfactants are disclosed in
Preferred alkamine oxide surfactants are the alkyl di(lower McCutcheon's Detergents and Emulsifiers, 1993 Annuals,
alkyl)amine oxides in which the alkyl group contains about published by McCutcheon Division, MC Publishing Co.,
12 to about 16 carbon atoms, including lauramine oxide, Glen Rock, N.J., pp. 1-246 and 266-273; in the CTEA
myristamine oxide, cocamine oxide, cetamine oxide, and 5 International Cosmetic Ingredient Dictionary, Fourth Ed.,
mixtures thereof. Most preferably, the alkamine oxide Sur Cosmetic, Toiletry and Fragrance ASSociation, Washington,
factant comprises lauramine oxide. D.C. (1991) (hereinafter the CTEA Dictionary) at pages
In Some preferred embodiments, an antibacterial compo 1–651; and in the CTFA Cosmetic Ingredient Handbook,
Sition of the present invention contains a blend of alkamine First Ed., Cosmetic, Toiletry and Fragrance ASSociation,
oxide Surfactants. In most preferred embodiments, a first Washington, D.C. (1988) (hereafter the CTFA Handbook), at
component of the alkamine oxide blend contains twelve or pages 86-94, each incorporated herein by reference.
fewer carbon atoms and a Second component contains more Cationic coSurfactants include a quaternary Surfactant
than twelve carbon atoms. having a structural formula
C. CoSurfactant
O
In addition to the antibacterial agent and alkamine oxide, 15
the antibacterial composition contains about 1% to about CH O
10%, and preferably about 1.5% to about 8%, by weight, of
a nonionic and/or cationic coSurfactant. To achieve the full N- cu-- cucua--c-cals C
advantage of the present invention, the composition contains CH H
about 2% to about 6%, by weight of the composition, of a
coSurfactant.
The coSurfactant can be (a) a nonionic Surfactant, Such as a quaternized phosphate ester, such as PHOSPHOLIPID SV,
a polyoxyethylene alcohol condensate, an alkylpolygluco available from Mona Industries, PaterSon, N.J., e.g., Steara
Side (APG) Surfactant, and the like, (b) a cationic Surfactant, midopropyl phosphatidyl PG-dimonium chloride, linoleami
Such as an amine Salt, a quaternary ammonium Surfactant, an 25 dopropyl phosphatidyl PG-dimonium chloride, coco phos
amidopropyl betaine monoethanolamide, and the like, or (c) phatidyl PG-dimonium chloride, cocamidopropyl
a mixture thereof. Examples of coSurfactants include, but are phosphatidyl PG-dimonium chloride, borage amidopropyl
not limited to, lauryl polyglucose, decyl polyglucose (e.g., phosphatidyl PG-dimonium chloride, and cocohydroxyethyl
PLANTAREN 2000N from Cognis Care Chemicals, phosphatidyl PG-imidazolinium chloride; and other quater
Ambler, Pa.), cocamidopropylbetaine MEA chloride nized phosphate esters disclosed in Mayhew et al. U.S. Pat.
No. 4,209,449. Additional quaternary ammonium surfac
(MONTALAINE C40 from Seppic, Paris, France), and tants can be found in the CTEA Handbook at pages 40-42,
Sunflower Seed amidopropylethyldimonium ethoSulfate incorporated herein by reference.
(MACKERNIUM DY83, McIntyre Chemical Co., Univer In accordance with an important feature of the present
sity Park, Ill.). If the coSurfactant is a quaternary ammonium invention, a present antibacterial composition is free of
Surfactant, Such a Surfactant does not exhibit the typical 35 anionic Surfactants and Zwitterionic Surfactants. The phrase
antibacterial properties of a quaternary ammonium antibac “free” of an anionic and Zwitteronic Surfactant is defined as
terial agent. meaning that the composition contains 0% to about 0.25%
Typically, a nonionic coSurfactant has a hydrophobic by weight, in total, of an anionic Surfactant and/or Zwitte
base, Such as a long chain alkyl group or an alkylated aryl rionic Surfactant. In particular, an anionic Surfactant and/or
group, and a hydrophilic chain comprising a ethoxy and/or 40 Zwitterionic Surfactant may be present in an antibacterial
propoxy moieties. The hydrophilic chain preferably contains composition in a total amount of 0.25% or less either as a
ethoxy moieties. AS defined herein, a “nonionic coSurfac by-product or as a component of an ingredient in the
tant has a hydrophobic base having an alkyl group con composition, but an anionic or Zwitterionic Surfactant is not
taining Six to eighteen carbon atoms, and an average of one intentionally introduced into the composition. For example,
to about twenty ethoxy and/or propoxy moieites. Examples 45 the present compositions are free of Sarcosinates, taurates,
of classes of nonionic coSurfactants include ethoxylated amide Sulfo Succinate S, alko amphoglycinate S,
alkylphenols, ethoxylated and propoxylated fatty alcohols, alkoamphopropionates, alkoamphocarboxy glycinates,
alkylpolyglucosides, polyethylene glycol ethers of Sorbitol, alkoamphocarboxypropionates, alkoamphopropylsulonates,
ethylene oxide-propylene oxide block copolymers, ethoxy alkamidopropyl betaines, alkamidopropyl hydroxySultaines,
lated esters of fatty (C-C) acids, condensation products 50 alkylaminopropionate S, alky liminopropio nate S,
of ethylene oxide with long chain amines or amides, and phosphobetaines, phosphitaines, alkyl Sulfates, alkyl
mixtures thereof. Sulfonates, Salts of fatty acids, alpha-olefin Sulfonates, alkyl
Examples of nonionic coSurfactants include, but are not ether Sulfates, and alkyl carbonates.
limited to, C-C spareth-20, ceteth-12, dodoxynol-12, Preferred compositions of the present invention contain
laureth-15, polySorbate 20, an ethoxylated nonylphenol, 55 decyl polyglucose, Sunflower Seed amidopropylethyldimo
ethoxylated octylphenol, ethoxylated dodecylphenol, or nium ethoSulfate, or a mixture thereof as the coSurfactant.
ethoxylated fatty (C-C) alcohol, including 4 to 20 eth D. Optional Polymeric Thickener
ylene oxide moieties, glycereth-12, trideceth-9, trideceth-10, In addition to the antibacterial agent, alkamine oxide
trideceth-11, trideceth-12, trideceth-15, Sorbeth-20, Surfactant, and coSurfactant, an antibacterial composition of
dodoxynol-9, dodoxynol-12, chlorodeceth-14, chloeth-10, 60 the present invention optionally can contain a thickener. The
dihydrocholeth-15, isoceteth-10, isoceteth-20, isolaureth thickener is present in an amount of 0% to about 5%, and
10, isosteareth-10, isosteareth-12, isosteareth-20, laneth-10, preferably 0.25% to about 4%, by weight, of the composi
laneth-15, laneth-16, laneth-20, oleth-9, oleth-10, oleth-12, tion. To achieve the full advantage of the present invention,
oleth-15, oleth-16, oleth-20, Steareth-10, Steareth-11, the thickener is present in an amount of about 0.5% to about
Steareth-13, Steareth-15, Steareth-16, Steareth-20, talloweth 65 3%, by weight, of the composition.
6, laureth-9, laureth-10, laureth-11, laureth-12, laureth-13, A polymeric thickener typically is present in a Sufficient
laureth-14, laureth-15, laureth-20, and mixtures thereof. amount to provide a composition having a Viscosity of about
 US 6,616,922 B2
13 14
100 to about 10,000 centipoise, preferably about 300 to ether, PPG-50 oleyl ether, PPG-20 methyl glucose ether,
about 6000 centipoise, and more preferably about 500 to PPG-20 methylglucose ether acetate, PEG-20 lanolin, PEG
about 5000 centipoise. To achieve the full advantage of the 24 lanolin, PEG-27 lanolin, PEG-30 lanolin, PEG-40
present invention, an antimicrobial composition has a vis lanolin, PEG-50 lanolin, PEG-60 lanolin, PEG-75 lanolin,
cosity of about 2000 to about 5000 centipoise. In the absence PEG-85 lanolin, PEG-10 lanolin, PEG-75 lanolin oil, PEG
of a polymeric thickener, a present composition has a 75 lanolin wax, PEG-20 methyl glucose sesquistereate,
viscosity of about 0.1 to about 100 centipoise. PEG-20-PPG-10 glyceryl Stearate, PEG-25 propylene gly
For Some applications, a polymeric thickener is an impor col stearate, PEG-75 propylene glycol stearate, PEG-120
tant ingredient of the present invention because composi propylene glycol stearate, PEG-25 soya sterol, PEG-40 soya
tions containing an alkamine oxide often have a low 1O Sterol, talloweth-60 myristylglycol, and mixtures thereof.
Viscosity, i.e., appear “watery,” and hence have a reduced E. Optional Ingredients
consumer appeal. The addition of a thickener to the com An antibacterial composition of the present invention also
position is not Straightforward, however, because the thick can contain optional ingredients known to perSons skilled in
the art. For example, the composition can contain a hydric
ener must perform multiple functions, Such as increasing the Solvent and/or a hydrotrope. The present compositions also
Viscosity of the composition, without adversely affecting the 15 can contain other optional ingredients, Such as Skin
phase Stability of the composition and without reducing the conditioners, dyes, and fragrances, that are present in a
typical low foam height generated by an alkamine oxide. Sufficient amount to perform their intended function and do
Surprisingly, various polymeric thickenerS Successfully not adversely affect the antibacterial efficacy or consumer
increase the Viscosity of a present antibacterial composition, acceptance of the composition. Such optional ingredients
while maintaining excellent phase Stability and providing typically are present, individually, from 0% to about 5%, by
excellent foam properties. weight, of the composition, and, collectively, from 0% to
A polymeric thickener of the present invention can be (a) about 20%, by weight, of the composition.
a cellulose thickener, (b) a hydrophobically modified poly Classes of optional ingredients include, but are not limited
ethylene glycol (PEG) or hydrophobically modified to, dyes, fragrances, pH adjusters, Skin conditioners and
polypropylene glycol (PPG), or (c) a hydrophobic alkoxy 25 emollients, buffering agents, foam Stabilizers, antioxidants,
lated alcohol. A cellulose thickener can be a nonionic preservatives, foam enhancers, hydrotropes, water Softening
cellulose or a cationic cellulose. Useful cellulose thickeners agents, chelating agents, opacifiers, and Similar classes of
include, but are not limited to, hydroxyethylcellulose, optional ingredients known to perSons skilled in the art.
hydroxybutyl methylcellulose, hydroxypropyl Specific optional ingredients include alkanolamides as
methylcellulose, hydroxypropylcellulose, polyguaternium foam boosters and Stabilizers, inorganic phosphates,
10, polygulaternium 4, hydroxypropyl methylcellulose, and Sulfates, and carbonates as buffering agents, mono-, di-, and
hydroxyethyl ethylcellulose. triglycerides (e.g., glycerol monolaurate) as opacifiers, vis
A hydrophobic PEG, PPG, or alkoxylated alcohol con cosity modifiers, or skin conditioners; EDTA and phosphates
tains a hydrophobic hydrocarbon moiety, either alkyl or as chelating agents, and acids and baseS as pH adjusters.
alkylated aryl. The alkyl group of the hydrophobic moiety 35 Examples of preferred basic pH adjusters are ammonia;
contains fourteen carbon atoms, or more (e.g., up to thirty mono-, di-, and tri-alkyl amines, mono-, di-, and tri
carbon atoms). Such thickeners further contain an average of alkanolamines, alkali metal and alkaline earth metal hydrox
at least twenty ethoxy and/or propoxy moieties. ides; and mixtures thereof. However, the identity of the basic
Examples of a hydrophobically modified PEG or hydro pH adjuster is not limited, and any basic pH adjuster known
phobically modified PPG include, for example, PEG-20 40 in the art, alone or in combination, can be used. Specific,
through PEG-200, or PPG-20 through PPG-34, either hav nonlimiting examples of basic pH adjusters are ammonia;
ing a hydrophobic moiety attached thereto or copolymerized Sodium, potassium, and lithium hydroxide; monoethanola
with a hydrophobic monomer. The hydrophobic monomer mine; triethylamine, isopropanolamine; diethanolamine;
can be a C-C glycol, for example. The hydrophobic and triethanolamine.
moiety can be an alkylated phenol residue, Such as a 45 Examples of preferred acidic pH adjusters are the mineral
nonylphenol residue, a fatty acid residue, a fatty amide acids and polycarboxylic acids. Nonlimiting examples of
residue, a fatty amine residue, and Similar residues having a mineral acids are hydrochloric acid, nitric acid, phosphoric
long-chain alkyl (e.g., C-C2) and/or an aryl component. acid, and Sulfuric acid. Nonlimiting examples of polycar
Examples of an alkoxylated alcohol include a C-Co boxylic acids are citric acid, glycolic acid, and lactic acid.
alcohol alkoxylate with 20 to 100 moles of ethylene oxide 50 The identity of the acidic pH adjuster is not limited and any
and/or propylene oxide, and having a hydrophobic moiety acidic pH adjuster known in the art, alone or in combination,
present in the molecule. can be used.
Specific examples of hydrophobically modified polymeric With respect to pH adjusters, a present composition has a
thickeners include, but are not limited to, PEG-120 methyl pH of about 5.5 to about 7.5 to provide a high, broad
glucose dioleate, PPG-14 palmeth-60 alkyl, ceteareth-60 55 Spectrum antibacterial efficacy. An optional pH adjuster can
myristyl glycol, methoxy PEG-22/dodecyl glycol be used in a sufficient amount to provide a pH of about 5.5
copolymer, methyl gluceth-20, PEG-20 castor oil, PEG-25 to about 7.5, or a preferred pH of about 6 to about 7.3.
castor oil, PEG-30 castor oil, PEG-36 castor oil, PEG-40 An alkanolamide used to provide foam enhancement and
castor oil, PEG-50 castor oil, PEG-60 castor oil, PEG-100 foam stability can be, but is not limited to, cocamide MEA,
castor oil, PEG-45/dodecyl glycol copolymer, PEG-20 60 cocamide DEA, soyamide DEA, lauramide DEA, oleamide
hydrogenated castor oil, PEG-25 hydrogenated castor oil, MIPA, Stearamide MEA, myristamide MEA, lauramide
PEG-30 hydrogenated castor oil, PEG-40 hydrogenated MEA, capramide DEA, ricinoleamide DEA, myristamide
castor oil, PEG-50 hydrogenated castor oil, PEG-60 hydro DEA, Stearamide DEA, oleylamide DEA, tallowamide
genated castor oil, PEG-80 hydrogenated castor oil, PEG DEA, lauramide MIPA, tallowamide MEA, isostearamide
100 hydrogenated castor oil, PPG-20 lanolin alcohol PPG 65 DEA, isostearamide MEA, and mixtures thereof.
30 lanolin alcohol ether, PPG-25-laureth-25, PPG-20 oleyl Optional skin conditioners and emollients include, but are
ether, PPG-23 oleyl ether, PPG-30 oleyl ether, PPG-37 oleyl not limited to, an ester having at least 10 carbon atoms, and
 US 6,616,922 B2
15 16
preferably 10 to about 32 carbon atoms. Suitable esters toluene Sulfonate, Sodium Xylene Sulfonate, toluene Sulfonic
include those comprising an aliphatic alcohol having about acid, and Xylene Sulfonic acid. Other useful hydrotropes
8 to about 20 carbon atoms and an aliphatic or aromatic include Sodium polynaphthalene Sulfonate, Sodium polySty
carboxylic acid including 2 to about 12 carbon atoms, or rene Sulfonate, Sodium methyl naphthalene Sulfonate, and
conversely, an aliphatic alcohol having 2 to about 12 carbon 5 disodium Succinate.
atoms with an aliphatic or aromatic carboxylic acid includ A present antibacterial composition also can contain a
ing 8 to about 20 carbon atoms. The ester is either Straight preservative in an amount of 0% to about 0.5% by weight.
chained or branched. Preferably, the ester has a molecular Examples of preservatives include, but are not limited to,
weight of less than about 500 and provides emollient prop Sorbic acid, potassium Sorbate, the parabens (like
erties. Suitable esters, therefore, include, for example, but ben Zyl paraben), imida Zo liny lure a,
are not limited to: methylchloroisothiazolinone, and the hydantoins, like
(a) aliphatic monohydric alcohol esters, including, but not DMDM hydantoin. Additional preservatives as disclosed in
limited to, myristyl propionate, isopropyl isoStearate, the CTFA Handbook at page 78, incorporated herein by
isopropyl myristate, isopropyl palmitate, cetyl acetate, reference.
cetyl propio nate, cetyl Ste a rate, isode cyl 15 A present antibacterial composition further can contain an
neopentanoate, cetyl octanoate, and isocetyl Stearate; antioxidant and/or an ultraviolet light (UV) absorber, each
(b) aliphatic di- and triesters of polycarboxylic acids, independently in an amount of 0% to about 0.5% by weight.
including, but not limited to, diisopropyl adipate, di Examples of antioxidants and UV absorbers include, but are
SoStearyl fumarate, dioctyl adipate, and trisoStearyl not limited to, BHA, BHT, sodium ascorbate, potassium
citrate; Sulfite, erythorbic acid, ben Zophenone-1 through
(c) aliphatic polyhydric alcohol esters, including, but not benzophenone-12, and PABA. Additional antioxidants and
limited to, propylene glycol dipelargonate, UV absorbers can be found in the CTEA Handbook at pages
(d) aliphatic esters of aromatic acids, including, but not 78 and 98, incorporated herein by reference.
limited to, C-C alcohol esters of benzoic acid, octyl F. Carrier
Salicylate, Sucrose benzoate, and dioctyl phthalate. 25 The carrier of a present antibacterial composition com
Numerous other esters are listed in the CTEA Handbook at prises water.
pages 24 through 26, incorporated herein by reference. An antibacterial composition of the present invention
A present antibacterial composition also optionally can does not rely upon a low pH or a high pH to provide a rapid
include an oil. Examples of oils that can be included in the reduction in bacterial populations. Antibacterial composi
composition include, but are not limited to, apricot kernel tions of the present invention have a pH of about 5.5 to about
oil, avocado oil, Co-Caspiscine oil, castor oil, chaulmoogra 7.5, and preferably about 6 to about 7.3. Within this pH
oil, cherry pit oil, coconut oil, corn oil, cottonseed oil, egg range, the present compositions effectively reduce Gram
oil, ethiodized oil, grape Seed oil, hazel nut oil, hybrid positive and Gram negative bacterial populations, and are
Safflower oil, lanolin oil, linSeed oil, menhaden oil, mink oil, consumer acceptable, i.e., have a consumer acceptable
moringa oil, neatsfoot oil, olive husk oil, olive oil, palm 35 Viscosity, are mild to the Skin, are phase Stable, and generate
kernel oil, palm oil, peach kernel oil, peanut oil, pengawar a high, Stable foam. Such results are Surprising for an
dambi oil, rapeseed oil, rice bran oil, Safflower oil, Sesame antibacterial composition that is free of an anionic Surfac
oil, Soybean oil, Sunflower Seed oil, Sweet almond oil, tant.
walnut oil, wheat germ oil, cod liver oil, hydrogenated castor To demonstrate the new and unexpected results provided
oil, hydrogenated coconut oil, hydrogenated cottonseed oil, 40 by the antibacterial compositions of the present invention,
hydrogenatedjojoba oil, hydrogenated menhaden oil, hydro the following Examples were prepared, and the ability of the
genated palm kernel oil, white petrolatum, hydrogenated compositions to control Gram positive and Gram negative
palm oil, hydrogenated peanut oil, hydrogenated Shark liver bacteria was determined. The weight percentage listed in
oil, hydrogenated Soybean oil, hydrogenated vegetable oil, each of the following examples represents the actual, or
jojoba oil, Shark liver oil, Synthetic jojoba oil, tall oil, 45 active, weight amount of each ingredient present in the
vegetable oil, bay oil, cottonseed oil, and mixtures thereof. composition. The compositions were prepared by blending
A composition of the present invention also optionally can the ingredients, as understood by those skilled in the art and
contain 0% to about 20%, by weight, of a hydric solvent, and as described below.
0% to about 20%, by weight, of a hydrotrope. The following materials were used as ingredients in the
As used herein, the term “hydric solvent' is defined as a 50 examples. The Source of each ingredient, and its
water-Soluble organic compound containing one to Six, and abbreviation, are Summarized below:
typically one to three, hydroxyl groups. The term “hydric
Solvent therefore encompasses water-Soluble alcohols,
diols, triols, and polyols. Specific examples of hydric Sol
vents include, but are not limited to, methanol, ethanol, 55
Chemical Name Tradename
Active
% Supplier
isopropyl alcohol, n-butanol, n-propyl alcohol, ethylene
glycol, propylene glycol, glycerol, diethylene glycol, dipro (a) Benzethonium Sale 100 Lonza
pylene glycol, tripropylene glycol, heXylene glycol, buty chloride (BZC)
lene glycol, 1,2,6-hexanetriol, Sorbitol, PEG-4, and Similar (b) Decyl polyglucose PLANTAREN 50 Cognis
2OOON
hydroxyl-containing compounds. 60
(c) Glycerin Sale 100 Dial
A hydrotrope is a compound that has the ability to (d) Lauramine oxide MACKAMINE LO 30 McIntyre
enhance the water Solubility of other compounds. An (e) Sunflower seed MACKERNIUM 80 McIntyre
optional hydrotrope utilized in the present invention typi amidopropyl SFES
cally is a short-chain alkyl aryl Sulfonate. Specific examples ethyldimonium
ethylsulfate
of hydrotropes include, but are not limited to, Sodium 65 (f) Orchophenylphenol DOWICIDE 1 1OO Dow
cumene Sulfonate, ammonium cumene Sulfonate, ammo (g) Triclosan (TCS) IRGASAN DP3OO 100 Ciba
nium Xylene Sulfonate, potassium toluene Sulfonate, Sodium
 US 6,616,922 B2
17 18
ATCC (American Type Culture Collection) identification
-continued number, and the abbreviation for the name of the organism
used hereafter.
Active
Chemical Name Tradename % Supplier
(h) PEG-120 methyl GLUCAMATE 100 Americhol
glucose dioleate DOE12O Organism Name ATCC # Abbreviation
(i) Hydroxyethyl ELFACOS CD481 100 Akzo Nobel
ethylcellulose Staphylococcus aureus 6538 S. aureus
(i) Ceteareth-60 ELFACOS GT282S 100 Akzo Nobel Escherichia coli 11229 E. coil
myristylglycol Klebsiella pneumoniae 1OO31 K. pneum.
(k) PPG-14 palmeth-60 ELFACOST212 100 Akzo Nobel
Alkyl
(T) Hydroxypropyl METHOCEL 40- 100 Dow S. aureuS is a Gram positive bacteria, whereas E. coli and K.
methylcellulose 101 pneum. are Gram negative bacteria.
(m) Polyquaternium 10 CELQUATSC- 100 National The beaker containing the test composition is placed in a
23OM Starch
(n) Cocamidopropyl MONTALAINE 40 Seppic
15 water bath (if constant temperature is desired), or placed on
betaine MEA C-40 a magnetic stirrer (if ambient laboratory temperature is
chloride desired). The sample then is inoculated with 1.0 ml of the
(o) Stearyldimethyl- ARQUAD HTL8- 80 Akzo Nobel test bacteria Suspension. The inoculum is Stirred with the test
ethylhexyl ammo- MS composition for the predetermined contact time. When the
nium methosulfate
(p) Water-unless contact time expires, 1.0 ml of the test composition/bacteria
otherwise indicated, mixture is transferred into 9.0 ml of Tryptone-Histidine
the water was pre Tween Neutralizer Solution (THT). Decimal dilutions to a
pared as follows: countable range then are made. The dilutions can differ for
deionized (DI) water
was distilled once different organisms. Plate Selected dilutions in triplicate on
through a Corning
AG-3 water still
25 TSA+ plates (TSA+ is Trypticase Soy Agar with Lecithin
and Polysorbate 80). The plates then are incubated for 25+2
hours, and the colonies are counted for the number of
The following methods were used in the preparation and Survivors and the calculation of percent or log reduction.
testing of the examples: The control count (numbers control) is determined by con
a) Determination of Rapid Germicidal (Time Kill) Activ ducting the procedure as described above with the exception
ity of Antibacterial Products. The activity of antibac that THT is used in place of the test composition. The plate
terial compositions was measured by the time kill counts are converted to cfu/ml for the numbers control and
method, whereby the Survival of challenged organisms samples, respectively, by standard microbiological methods.
exposed to an antibacterial test composition is deter The log reduction is calculated using the formula
mined as a function of time. In this test, a diluted 35
aliquot of the composition is brought into contact with Log reduction=logo (numbers control)-logo (test sample survi
a known population of test bacteria for a specified time vors).
period at a Specified temperature. The test composition
is neutralized at the end of the time period, which The following table correlates percent reduction in bac
arrests the antibacterial activity of the composition. The 40 teria population to log reduction:
percent or, alternatively, log reduction from the original
bacteria population is calculated. In general, the time
kill method is known to those skilled in the art.
The composition can be tested at any concentration from % Reduction Log Reduction
0-100%. The choice of which concentration to use is at the 45 90 1.
discretion of the investigator, and Suitable concentrations are 99 2
readily determined by those skilled in the art. For example, 99.9 3
Viscous Samples usually are tested at 50% dilution, whereas 99.99
99.999
4
5
nonviscous Samples are not diluted. The test Sample is
placed in a Sterile 250 ml beaker equipped with a magnetic 50
stirring bar and the sample volume is brought to 100 ml, if
needed, with Sterile deionized water. All testing is performed EXAMPLE 1.
in triplicate, the results are combined, and the average log
reduction is reported. This example shows that compositions thickened with an
The choice of contact time period also is at the discretion optional hydrophobically modified polymeric thickener (i.e.,
of the investigator. Any contact time period can be chosen. 55 ELFACOS CD 481) are phase stable.
Typical contact times range from 15 Seconds to 5 minutes,
with 30 Seconds and 1 minute being typical contact times.
The contact temperature also can be any temperature, typi
cally room temperature, or about 25 degrees Celsius. Wt. Percent
The bacterial Suspension, or test inoculum, is prepared by 60
Ingredient A. B C D E
growing a bacterial culture on any appropriate Solid media
(e.g., agar). The bacterial population then is washed from the BZC 0.25 O.25 0.25 O.25 O.25
agar with Sterile physiological Saline and the population of ELFACOS CD 481
(polymeric thickener)
1.O 1.O 1.O 1.O 1.O
the bacterial suspension is adjusted to about 10 colony PLANTAREN2OOON 1.44 3.25
forming units per ml (cfu/ml). 65 Glycerin 2.5 2.5 2.5 2.5 2.5
The table below lists-the test bacterial cultures used in the MACKAMINE LO 6.O 2.25 4.5 5.04 4.5
following tests and includes the name of the bacteria, the
 US 6,616,922 B2
20
-continued
Wt. Percent Wt. 2%

Ingredient A. B C D E Ingredient A. B
Citric acid (25%) 1.75 0.75 1.75 2.O 1.65 BZC O.25
MACKERNIUMSFES 3.2 TCS (antibacterial agent) O.25
(cosurfactant) MACKAMINE LO 4.5 4.5
Water C.S. C.S. C.S. C.S. C.S. Glycerin 2.5 2.5
1O GLUCAMATE DOE 120 3.0 5.0
NaCl 1.O
Citric Acid (25%) 1.5 1.O
All Samples 1A-1E exhibited a consumer acceptable MACKERNIUMSFES 3.2
Water C.S. C.S.
Viscosity and were physically stable with no indications of
phase Separation, even when Stored under accelerated aging 15
conditions (10 days at 60° C.) Both Samples 3A and 3B were clear, phase stable, and had
a consumer acceptable Viscosity.
EXAMPLE 2 EXAMPLE 4
This example Summarizes the exceptional antibacterial
This example shows a Surprising increase in Viscosity in efficacy of a composition of the present invention. Antibac
compositions containing an optional polymeric thickener terial efficacy was assessed by time kill tests. The compo
Sitions exhibit an antibacterial efficacy considerably Superior
and a viscosity-enhancing additive (i.e., Sodium chloride). A to that provided by present-day commercial antibacterial
different polymeric thickener (i.e., GLUCAMATE compositions. Table 1 Summarizes the log reductions mea
DOE120) was used than in Example 1. 25 Sured in time kill tests at contact times of 30 Seconds and 1
minute.

TABLE 1.
Wt. 2%
Log Reduction
Ingredient A. B
S. aureus E. coli
BZC 0.25 O.25
MACKAMINE LO 4.5 4.5 Sample 30 sec 1 min 30 sec 1 min
Glycerin 2.5 2.5
MACKERNIUMSFES 3.2 3.2 1A (pH-5.99) >4.95 >4.95 >5.00 >5.00
GLUCAMATE DOE120 (polymeric thickener) 3.0 3.0 35 1B 3.94 4.75 >4.85 4.7O
Sodium chloride (NaCl) (viscosity enhancer) O.1 O1 1C 4.52 4.85 >4.85 >4.85
Citric Acid (25%) 1.5 1.5 1D 3.64 4.85 >4.85 >4.85
DOWICIDE 1 (antibacterial agent) O.25 1E 3.39 4.06 >5.00 >5.00
Water C.S. C.S. 2A 3.50 4.23 >4.62 >4.62
2B 3.38 3.48 >4.62 >4.62
orthophenylphenol 40 3A 3.43 4.06 4.88 4.68
3B (pH-5.82) 1.6 2.23 >5.0 >5.0

The viscosity of Sample 2A was 511 cp, and the viscosity

of Sample 2B was 2770 cp. An unexpected increase in Preferred compositions of the present invention contain,
viscosity was observed upon addition of 0.25% DOWICIDE by total weight of the composition:
45 about 0.05 to about 5% of an antibacterial agent selected
1 to the composition (Sample 2B). from the group consisting of benzethonium chloride,
All Viscosity measurements herein were obtained using a o-phenylphenol, triclosan, benzalkonium chloride, and
Brookfield Viscometer, Model DV II (digital), LVT, Speed mixtures thereof;
12, Spindle Number #3. When determining viscosity, a 200 about 1 to about 15% of a (C-C)alkamine oxide,
50 preferably comprising lauramine oxide;
ml sample is poured into a 250 ml beaker and allowed to about 1 to about 10% of a coSurfactant selected from the
equilibrate temperature to 25 C.+/-0.5 C. The Brookfield group consisting of an alkyl polyglucose, preferably
Viscometer is Standardized according to the manufacturer's comprising decyl polyglucose, cocamidopropyl betaine
directions. The Sample is placed under the Spindle and is MEA chloride, stearyl dimethyl ethylhexyl ammonium
raised until the surface of the liquid is at the “notch.” 55 methoSulfate, and mixtures thereof;
ensuring that no air bubbles are trapped underneath the 0 to about 5% glycerin; and
Spindle. The Viscometer is engaged and the reading for 0 to about 3% of a polymeric thickener selected from the
Viscosity is taken after one minute. If the reading is unstable, group consisting of PEG-120 methyl glucose dioleate,
readings are taken at 30–45 seconds, and again at 75 hydroxyethyl ethylcellulose, Sunflower Seed amidopro
Seconds, and the range of readings is reported. 60 pyl ethyldimonium ethylsulfate, PPG-14 palmeth-60
alkyl, ceteareth-60 myristyl glycol, and mixtures
EXAMPLE 3 thereof; and having a pH of about 5.5 to about 7.5,
preferably about 6 to about 7.3.
This example shows that triclosan can be substituted for 65 EXAMPLE 5
benzethonium chloride as the antibacterial agent in a com This example illustrates the relationship between pH and
position of the present invention. antibacterial activity of 2% active acqueous lauramine oxide
 US 6,616,922 B2
21
solutions. The efficacy data are log reductions after 30
Seconds against the indicated bacteria. -continued
Material Composition wt.%
MONTALAINE C-40 2.3
pH S. aureus E. coli Hydroxymethyl cellulose 1.25
4.93 2.11 >5.32
Fragrance O.3
5.50 >4.38 >4.70 Sodium hydroxide O.05
6.02 >439 >4.70 FD&C Yellow 5 (dye) O.OO62
6.5 >439 >4.70 FD&C Red 4 (dye) O.OO33
7.0 >439 >5.32
1O DMDM Hydantoin (preservative) O.22
7.53 >439 O.88
8.94 4.33 0.27
10.14 3.75 O.11 The composition of Example 7 was tested for time kill at
50% dilution against S. aureus, E. coli, and K. Pneum., and
15 achieved respective log reduction of >4.69, >4.74, and
This example shows that lauramine oxide exhibits a high, >4.43, respectively, after 30 seconds.
broad-spectrum efficacy at a 2% active concentration within
a pH range of about 5.5 to about 7.5. EXAMPLE 8

EXAMPLE 6 This example illustrates that a composition having a pH

outside of the preferred 6 to 7.3 pH range exhibits a good,
This example illustrates the relationship between pH and but reduced, level of broad-spectrum antibacterial efficacy.
antibacterial efficacy for an unthickened composition of the The following compositions were prepared and tested for
present invention. time-kill at 50% dilution against the bacteria indicated in the
following table.
25

Material A. B C
Composition wt %
Water CS CS CS
Decyl polyglucose 1.44 1.44 1.44 Ingredient A. B C D E F
BZC O.25 O.25 O.25
Glycerin 2.5 2.5 2.5 Water CS CS CS CS CS CS
Lauramine oxide 2.25 2.25 2.25 PLANTAREN2OOON 1.5 3.25 1.5 1.5 1.5
Citric acid CS CS CS BZC 0.25 0.25 0.25 - O.25
pH 6.0 6.5 7.0 TCS - 0.2 0.25
Glycerin 2.5 2.5 2.5 2.5 2.5 2.5
'added in a sufficient amount, typically 0-0.5% by weight of the 35 MACKAMINE LO 2.25 5.0 2.25 2.25 5.0 2.25
composition, to adjust the pH to the desired value. Citric acid 1.O3 O.S O.2 O.2 0.65 0.175
MONTELAINE C-40 - 2.3 2.3
Samples 6A-6C were tested for time kill at 50% dilution. AROUAD HTL8-MS 3.2 - 4.2 4.2
The results are summarized in the following table. MACKERNIUM DY-83 - 3.2 3.2
STANDAMOX CAW) 0.54 -
ELFACOS GT282S 2.55 -
40 ELFACOST212 2.55
DOWICIDE 1 O.25
Log Reduction at 30 seconds GLUCAMATE DOE-120 - 2.55 3.06 3.06 5.0
Sodium Chloride 1.OS 1.O 0.51 0.51 - O1
Sample pH S. aureus E. coli pH 5.66 5.67 5.84 5.84 5.86 5.74
6A 6.O 3.37 >4.86 45 STANDAMOX CAW is cocamidopropyl amine oxide, 30% active, avail
6B 6.5 4.41 >4.86
6C 7.0 4.51 1.21
able from Cognis Care Chemicals.

This example shows that an unthickened composition of

the present invention exhibits a more effective broad Spec 50 Log Reduction at 30 seconds
trum antibacterial activity at pH 6 and 6.5 than at pH 7. Composition S. aureus E. coil
EXAMPLE 7
8B 2.27 4.55
This example illustrates that a composition of the present 55 8C 2.01 >4.84
invention exhibits an excellent broad-spectrum activity at 8D
8E
1.45
18
>4.84
>5.0
pH 7.12.

Material Composition wt.%

60 Example 8 clearly demonstrates the role pH plays in the
efficacy of compositions of the invention.
Water 77.96
Decyl polyglucose 148 EXAMPLE 9
BZC O.25
Glycerin 2.5 The following two compositions of the present invention
Lauramine oxide 2.25 65 contain a combination of amine oxides. The compositions
Citric acid O.O75 were prepared by admixing procedures well known to
perSons Skilled in the art. Stearamine oxide is available as
 US 6,616,922 B2
23 24
Mackamine SO (about 25% active amine oxide), from propoxylated fatty alcohol, an alkyl polyglucoside, a
McIntyre Chemicals, University Park, Ill. polyethylene glycol ether of Sorbitol, an ethylene
Oxide-propylene oxide block copolymer, an ethoxy
lated ester of a fatty (C-C) acid, a condensation
product of ethylene oxide with a long chain amine or
Composition (wt.% amide, and mixtures the reof, (ii) a cationic
Chemical A. B
coSurfactant, or (iii) a mixture thereof;
(d) 0% to about 5%, by weight, of a polymeric thickener;
Benzethonium Chloride O.25 0.25 and
Deionized Water 83.55 84.48
Decyl Polyglucose 2.5 2.5 (e) water,
Glycerin 2.O 2.O wherein the antibacterial composition has a pH of about
Lauramine Oxide 5.0 3.75 5.5 to about 7.5, and is free of an anionic Surfactant.
Stearamine Oxide 2.5 3.75 2. The composition of claim 1 having a log reduction
Glyceryl Laurate 0.5 0.5 against Gram positive bacteria of at least 2 after 30 Seconds
Sunflower amindopropyl 1.O 1.1
ethonium sulfate 15 of contact, as measured against S. aureus, and a log reduc
PEG 120 methyl gluceth 1.5 1.5 tion against Gram negative bacteria of at least 2.5 after 30
dioleate Seconds of contact, as measured against E. coli.
Fragrane O.2 3. The composition of claim 1 comprising about 0.1% to
Dye Solution O.7 about 3%, by weight, of the phenolic antibacterial agent.
Citric acid O.30 0.17
4. The composition of claim 1 wherein the phenolic
antibacterial agent is Selected from the group consisting of:
Compositions 9A and 9B had good viscosity and good (a) a 2-hydroxydiphenyl compound having the structure
lather properties.
The data presented in the above examples and tables show Yo
that a present antibacterial composition can exhibit a log
reduction of at least about 2 (after 30 seconds) or at least
about 3 (after 60 seconds) vs. S. aureus, or of at least about
2.5 (after 30 seconds) or at least about 3.5 (after 60 seconds)
vs. E. coli.
25

(OH)'E)--O.
C-O. OH
(OH)n,

The antibacterial compositions of the present invention

have Several practical end uses, including hand cleansers, wherein Y is chlorine or bromine, Z is SOH, NO, or
mouthwashes, Surgical Scrubs, body Splashes, hand Sanitizer C-C alkyl, r is 0 to 3, o is 0 to 3, p is 0 or 1, m is 0
gels, and Similar personal care products. Additional types of or 1, and n is 0or 1;
compositions include foamed compositions, Such as creams, (b) a phenol derivative having the structure
mousses, and the like, and compositions containing organic 35
and inorganic filler materials, Such as emulsions, lotions, OH
creams, pastes, and the like. The compositions further can be
used as an antibacterial cleanser for hard Surfaces, for
example, SinkS and countertops in hospitals, food Service
areas, and meat processing plants. The present antibacterial 40
compositions can be manufactured as dilute ready-to-use
compositions, or as concentrates that are diluted prior to use.
The compositions also can be incorporated into a web
material to provide an antibacterial wiping article. The 45
wiping article can be used to clean and Sanitize skin or wherein R is hydro, hydroxy, C-C alkyl, chloro,
inanimate Surfaces. nitro, phenyl, or benzyl, R is hydro, hydroxy, C-C,
The present antimicrobial compositions provide the alkyl, or halo; R is hydro, C-C alkyl, hydroxy,
advantages of a broad Spectrum kill of Gram positive and chloro, nitro, or a Sulfur in the form of an alkali metal
Gram negative bacteria in Short contact times. The short 50 Salt or ammonium salt; R is hydro or methyl; and Rs
contact time for a Substantial log reduction of bacteria is is hydro or nitro,
important in view of the typical 15 to 60 second time frame (c) a diphenyl compound having the structure
used to cleanse and Sanitize the skin and inanimate Surfaces.
Obviously, many modifications and variations of the R2 R1 R1 R2
invention as hereinbefore set forth can be made without

-O-O-
55
departing from the Spirit and Scope thereof, and, therefore,
only Such limitations should be imposed as are indicated by
the appended claims.
What is claimed is:
1. An antimicrobial composition comprising: R4 R's R5 R4
60
(a) about 0.05% to about 5%, by weight, of a phenolic
antibacterial agent; wherein X is Sulfur or a methylene group, R and R'
(b) about 1% to about 15%, by weight, of an alkamine are hydroxy, and R2, R2, Ra, R's, R., R., Rs, and R's,
oxide Surfactant; independent of one another, are hydro or halo, and
(c) about 1% to about 10%, by weight, of (i) a nonionic 65 (d) mixtures thereof.
coSurfactant Selected from the group consisting of an 5. The composition of claim 1 wherein the phenolic
ethoxylated alkylphenol, an ethoxylated fatty alcohol, a antibacterial agent is Selected from the group consisting of
 US 6,616,922 B2
25 26
triclosan, 2,2'-dihydroxy-5,5'-dibromodiphenyl ether, 11. The composition of claim 1 wherein the nonionic
p-chloro-m-Xylenol, ortho-phenylphenol, and mixtures coSurfactant is Selected from the group consisting of
thereof. C-C spareth-20, ceteth-12, dodoxynol-12, laureth-15,
6. The composition of claim 1 wherein the alkamine oxide polySorbate 20, an ethoxylated nonylphenol, an ethoxylated
Surfactant is present in an amount of about 1.5% to about octylphenol, an ethoxylated dodecylphenol, an ethoxylated
10%, by weight of the composition. fatty (C-C) alcohol containing 9 to 50 ethylene oxide
7. The composition of claim 1 wherein the alkamine oxide moieties, glycereth-12, glycereth-26, trideceth-9, trideceth
is Selected from the group consisting of: 10, trideceth-11, trideceth-12, trideceth-15, Sorbeth-20,
dodoxynol-9, dodoxynol-12, chlorodeceth-14, chloeth-10,
(a) 1O dihydrocholeth-15, isoceteth-10, isoceteth-20, isoceteth-30,
CH isolaureth-10, isoSteareth-10, isoSteareth-12, isoSteareth-20,
laneth-10, laneth-15, laneth-16, laneth-20, oleth-9, oleth-10,
oleth-12, oleth-15, oleth-16, oleth-20, Steareth-10, Steareth
circus -o CH
11, Steareth-13, Steareth-15, Steareth-16, Steareth-20,
(b) 15
talloweth-6, laureth-9, laureth-10, laureth-11, laureth-12,
CH2CH2OH laureth-13, laureth-14, laureth-15, laureth-20, and mixtures
thereof.
12. The composition of claim 1 wherein the cosurfactant
cucus is Selected from the group consisting of decyl polyglucose,
lauryl polyglucose, Sunflower Seed amidopropylethyldimo
CH nium ethoSulfate, and a mixture thereof.
13. The composition of claim 1 wherein the composition
is free of a Zwitterionic Surfactant.
CH 14. The composition of claim 1 wherein the polymeric
thickener is present in an amount of about 0.25% to about
25 4%, by weight of the composition.
(d) an alkylmorpholine oxide, wherein the alkyl group 15. The composition of claim 1 having a viscosity of
contains 8 to 22 carbon atoms, and about 0.1 to about 10,000 centipoise.
(e) mixtures thereof. 16. The composition of claim 1 wherein the polymeric
8. The composition of claim 1 wherein the alkamine oxide thickener is Selected from the group consisting of a cellulose
is Selected from the group consisting of lauryl dimethyl thickener, a hydrophobically modified polyethylene glycol,
amine oxide, myristyl dimethyl amine oxide, dimethyl a hydrophobically modified polypropylene glycol, a hydro
cocoamine oxide, dimethyl (hydrogenated tallow)amine phobic alkoxylated alcohol, and mixtures thereof.
oxide, myristyl/palmityl dimethyl amine oxide, myristyl/ 17. The composition of claim 1 wherein the thickener is
lauryl dimethyl amine oxide, cetyl dimethyl amine oxide, Selected from the group consisting of hydroxyethylcellulose,
Stearyl dimethylamine oxide, myristyl/cetyl dimethylamine 35 hydroxyethyl ethylcellulose, hydroxybutyl methylcellulose,
oxide, bis(2-hydroxyethyl)cocoamine oxide, bis(2- hydroxypropyl methylcellulose, hydroxypropylcellulose,
hydroxyethyl)tallow amine oxide, bis(2-hydroxyethyl) polygulaternium 10, polygulaternium 4, hydroxypropyl
Stearylamine oxide, cocoamidopropyl dimethyl amine methylcellulose, PEG-120 methylglucose dioleate, PPG-14
oxide, tallowamidopropyl dimethyl amine oxide, decyl dim palmeth-60 alkyl, ceteareth-60 myristyl glycol, methoxy
ethylamine oxide, lauryl dimethylamine oxide, Stearyl dim 40 PEG-22/dodecyl glycol copolymer, methyl gluceth-20,
ethylamine oxide, oleyl dimethylamine oxide, coco dihy PEG-20 castor oil, PEG-25 castor oil, PEG-30 castor oil,
droxyethylamine oxide, cetyl dihydroxyethylamine oxide, PEG-36 castor oil, PEG-40 castor oil, PEG-50 castor oil,
oleyl dihydroxyethylamine oxide, cocamine oxide, cocami PEG-60 castor oil, PEG-100 castor oil, PEG-45/dodecyl
dopropylamine oxide, lauramidopropylamine oxide, oleam glycol copolymer, PEG-20 hydrogenated castor oil, PEG-25
ine oxide, oleamidopropylamine oxide, wheat germami 45 hydrogenated castor oil, PEG-30 hydrogenated castor oil,
dopropylamine oxide, isoStearamidopropylamine oxide, PEG-40 hydrogenated castor oil, PEG-50 hydrogenated
Stearamine oxide, Stearamidopropylamine oxide, cocomor castor oil, PEG-60 hydrogenated castor oil, PEG-80 hydro
pholine oxide, decylamine oxide, dihydroxyethyl genated castor oil, PEG-100 hydrogenated castor oil, PPG
Cs-Coalkoxypropylamine oxide, dihydroxyethyl 20 lanolin alcohol ether, PPG-30 lanolin alcohol ether,
Co-Calkoxypropylamine oxide, dihydroxyethyl 50 PPG-25-laureth-25, PPG-20 oleyl ether, PPG-23 oleyl ether,
C-Calkoxypropylamine oxide, dihydroxyethyl cocam PPG-30 oleyl ether, PPG-37 oleyl ether, PPG-50 oleyl ether,
ine oxide, dihydroxyethyl Stearamine oxide, dihydroxyethyl PPG-20 methylglucose ether, PPG-20 methylglucose ether
tallowamine oxide, hydrogenated tallow amine oxide, acetate, PEG-10 lanolin, PEG-20 lanolin, PEG-24 lanolin,
hydroxyethyl hydroxypropylC-C-alkoxypropylamine PEG-27 lanolin, PEG-30 lanolin, PEG-40 lanolin, PEG-50
oxide, isoStearamidopropyl morpholine oxide, myristami 55 lanolin, PEG-60 lanolin, PEG-75 lanolin, PEG-85 lanolin,
dopropylamine oxide, myristamine oxide, palmitamidopro PEG-100 lanolin, PEG-75 lanolin oil, PEG-75 lanolin wax,
pylamine oxide, palmitamine oxide, PEG-3 lauramine PEG-20 methyl glucose sesquistereate, PEG-20-PPG-10
oxide, tallow amidopropylamine oxide, tallow amine oxide, glyceryl Stearate, PEG-25 propylene glycol Stearate, PEG
undecylenamidopropylamine oxide, and mixtures thereof. 75 propylene glycol Stearate, PEG-120 propylene glycol
9. The composition of claim 1 wherein the alkamine oxide 60 Stearate, PEG-25 soya sterol, PEG-40 soya sterol, talloweth
is Selected from the group consisting of lauramine oxide, 60 myristylglycol, and mixtures thereof.
myristamine oxide, cocamine oxide, cetamine oxide, Stear 18. The composition of claim 1 further comprising one or
amine oxide, oleamine oxide, Steard mine oxide, oleamine more of a hydric Solvent, a hydrotrope, a pH adjuster, a skin
oxide, and mixtures thereof. conditioner, an oil, and an emollient, each in an amount of
10. The composition of claim 1 wherein the coSurfactant 65 5% or less by weight of the composition.
is present in an amount of about 1.5% to about 8%, by 19. The composition of claim 1 having a pH of about 6 to
weight of the composition. about 7.3.
 US 6,616,922 B2
27 28
20. An antimicrobial composition comprising: 31. The composition of claim 29 wherein R, R, and R,
(a) about 0.05% to about 5%, by weight, of a quaternary independently, contain one or more amide, ether, or ester
ammonium antibacterial agent; linkage.
(b) about 1% to about 15%, by weight, of a (C-C) 32. The composition of claim 20 wherein the quaternary
alkamine oxide; ammonium antibacterial agent has a structure:
(c) about 1% to about 10%, by weight, of a coSurfactant
Selected from the group consisting of an alkyl CH
polyglucose, cocamidopropyl betaine MEA chloride,
polyguaternium 10, Stearyl dimethyl ethylhexyl ammo R-N-R
nium methoSulfate, Sunflower Seed amidopropyl eth 1O
yldimonium ethylsulfate, and mixtures thereof; CH
(d) 0 to about 5%, by weight, glycerin; and
(e) 0 to about 3%, by weight, of a polymeric thickener;
and having a pH of about 6 to about 7.3. wherein R and R, independently, are C-C-alkyl, or R is
21. A method of reducing a bacteria population on a 15 C 2-C alkyl, Cs-C is alkyl eth oxy, O
Surface comprising contacting the Surface with a composi Cs-Calkylphenylethoxy, and R is benzyl, and X is halo,
tion of claim 20 for a sufficient time to provide a log methoSulfate, ethoSulfate, or p-toluenesulfonate.
reduction of bacteria of at least 2, then rinsing the compo 33. The composition of claim 20 wherein the quaternary
Sition from the Surface.
22. The method of claim 21 wherein the Surface is a skin ammonium antibacterial agent is Selected from the group
of a mammal. consisting of an alkyl ammonium halide, an alkyl aryl
23. The method of claim 21 wherein the Surface is a hard, ammonium halide, an N-alkyl pyridinium halide, and mix
inanimate Surface. tures thereof.
24. The method of claim 21 wherein the composition 34. The composition of claim 20 wherein the quaternary
contacts the Surface for 30 Seconds to achieve a log reduc 25 ammonium antibacterial agent is Selected from the group
tion of at least 2 against S. aureus. consisting of cetyl trimethyl ammonium bromide, octadecyl
25. The method of claim 21 wherein the composition dimethyl benzyl ammonium bromide, N-cetyl pyridinium
contacts the Surface for 60 Seconds to achieve a log reduc bromide, octylphenoxyethoxyethyl dimethylbenzyl ammo
tion of at least 3 against S. aureus. nium chloride, N-(laurylcoco-aminoformylmethyl)
26. The method of claim 21 wherein the composition pyridinium chloride, lauryloxyphenyl-trimethyl ammonium
contacts the Surface for 30 Seconds to achieve a log reduc chloride, cetylaminophenyl trimethyl ammonium
tion of at least 2.5 against E. coil. methoSulfate, dodecylphenyl trimethyl ammonium
27. The method of claim 21 wherein the composition methoSulfate, dodecylbenzyl trimethyl ammonium chloride,
contacts the Surface for 60 Seconds to achieve a log reduc chlorinated dodecylbenzyl trimethyl ammonium chloride,
tion of at least 3.75 against E. coli. 35 dioctyl dimethyl ammonium chloride, benzalkonium
28. The composition of claim 20 comprising about 0.2% chloride, myristyl dimethylbenzyl ammonium chloride,
to about 2% by weight, of the quaternary ammonium anti methyl dodecyl Xylene-bis-trimethyl ammonium chloride,
bacterial agent. benzethonium chloride, a 2-butenyl dimethyl ammonium
29. The composition of claim 20 wherein the quaternary chloride polymer, behenalkonium chloride, cetalkonium
ammonium antibacterial agent has a structure: 40 chloride, cetarylalkonium bromide, cetrimonium tosylate,
cetylpyridinium chloride, lauralkonium bromide, lauralko
nium chloride, lapyrium chloride, lauryl pyridinium
chloride, myristalkonium chloride, olealkonium chloride,
isoStearyl ethyldimonium chloride, and mixtures thereof.
45
35. The composition of claim 20 wherein the (C-C)
alkamine oxide is present in an amount of about 2% to about
8%, by weight of the composition.
wherein R is an alkyl, aryl, or alkaryl Substituent con 36. The composition of claim 20 wherein the coSurfactant
taining 6 to 26 carbon atoms, R., R., and R, is present in an amount of about 2% to about 6%, by weight
independently, are Substituents containing no more than 50
of the composition.
twelve carbon atoms, and X is an anion Selected from
the group consisting of halo, methoSulfate, ethoSulfate, 37. The composition of claim 20 wherein the polymeric
and p-toluenesulfonyl. thickener is present in an amount of about 0.5% to about 3%,
30. The composition of claim 29 wherein R is selected by weight of the composition, and the composition has a
from the group consisting of C-C alkyl, 55 viscosity of about 500 to about 5,000 centipoise.
Co-Calkoxyaryl, Co-Calkaryl, halogen-Substituted
C-C alkaryl, and C-C alkylphenoxyalkyl.
 UNITED STATES PATENT AND TRADEMARK OFFICE
CERTIFICATE OF CORRECTION

PATENT NO. : 6,616,922 B2 Page 1 of 1

DATED : September 9, 2003
INVENTOR(S) : Timothy J. Taylor et al.

It is certified that error appears in the above-identified patent and that said Letters Patent is
hereby corrected as shown below:

Column 24,
Line 34, "Oor" should be -- 0 or --
Column 25,
Line 19,
CH2CH2OH y

CH3(CH2)-2-N - O
should be

CH2CH2OH
Chich ---- O
CH2CH2OH

Line 54, "Cis-alkoxypropylamine' Should be -- Cisalioxyproplyamine --

Column 27,
Line 32, “E COil.” Should be -- E coli. --
Column 28,
Line 29, “laurylcoco-aminoformylmethyl” should be -- laurylcocoaminoformylmethyl --

Signed and Sealed this

Thirteenth Day of April, 2004

WDJ
JON W. DUDAS
Acting Director of the United States Patent and Trademark Office