Note: Descriptions are shown in the official language in which they were submitted.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
1
HYDRATING ORAL CARE COMPOSITIONS COMPRISING PEROXIDE
FIELD OF THE INVENTION
The present invention relates to hydrating oral care compositions comprising
peroxide
and water. The present invention relates to hydrating dentifrice compositions
comprising
peroxide and water.
BACKGROUND OF THE INVENTION
Oral care compositions, such as dentifrice compositions, can include fluoride,
peroxide,
and/or abrasive to clean teeth, prevent cavities, and maintain the aesthetics
and health of the oral
cavity, such as the teeth and gums.
It can be desirable to have dentifrice compositions with a relatively high
level of peroxide,
such as at least about 1%, at least about 3%, or at least about 3.5%, to
achieve high whitening
efficacy. However, it can be challenging to formulate dentifrice compositions
with a relatively
high level of peroxide because peroxide can be reactive with other dentifrice
components, such as
fluoride, metal ions, abrasives, etc. One approach to the formulation
challenges associated with
peroxide can be to separately package and/or apply peroxide from a separate
whitening
composition. However, consumer compliance can be lower when peroxide must be
applied from
a separate composition. Thus, it can be advantageous to provide peroxide in a
dentifrice
composition with other components, such as fluoride.
Another approach to the formulation challenges associated with peroxide can be
to
formulate peroxide as an adduct and/or complex in a nonaqueous chassis.
However, anhydrous
compositions can lead to the dehydration of oral care surfaces that can
contribute to sensitivity,
such as tooth sensitivity. Additionally, the complexation of peroxide can lead
to lower amounts of
available of peroxide to provide health and cosmetic benefits. As such, there
is a need for an
improved hydrating oral care composition, such as an improved hydrating
dentifrice composition,
including non-complexed peroxide.
SUMMARY OF THE INVENTION
Disclosed herein is an oral care composition comprising (a) from about 1% to
about 5%,
by weight of the oral care composition, of peroxide; and (b) water, wherein
the oral care
composition releases at least about 1 % of the peroxide within about 120
seconds according to the
Peroxide Release Method.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
2
Disclosed herein is a hydrating oral care composition comprising (a) from
about 1% to
about 5%, by weight of the oral care composition, of peroxide; and (b) water,
wherein the oral care
composition releases at least about 1 % of the peroxide into an oral cavity of
a user within about
120 seconds of initial application to the oral cavity.
Disclosed herein is an oral care composition comprising (a) from about 1% to
about 5%,
by weight of the oral care composition, of peroxide; and (b) water, wherein
the oral care
composition releases at least about 15 % of the peroxide within about 15
minutes of initial
application according to the Peroxide Release Method.
Disclosed herein is a hydrating oral care composition comprising (a) from
about 1% to
about 5%, by weight of the oral care composition, of peroxide; and (b) water,
wherein the oral care
composition releases at least about 15 % of the peroxide into an oral cavity
of a user within about
15 minutes of initial application to the oral cavity.
Disclosed herein is a jammed oil-in-water emulsion comprising (a) hydrophobic
phase; (b)
aqueous phase; and (c) peroxide, wherein the jammed oil-in-water emulsion
releases at least about
1 % of the peroxide within about 120 seconds according to the Peroxide Release
Method.
Disclosed herein is a jammed oil-in-water emulsion comprising (a) hydrophobic
phase; (b)
aqueous phase; and (c) peroxide, wherein the jammed oil-in-water emulsion
releases at least about
1 % of the peroxide into an oral cavity of a user within about 120 seconds of
initial application to
the oral cavity.
Disclosed herein is an oral care composition comprising: (a) peroxide; (b) at
least about
5%, by weight of the oral care composition, of water; and (c) fluoride and/or
abrasive.
Disclosed herein is a method of delivering peroxide to an oral cavity of a
user comprising
(a) directing the user to apply any of the disclosed oral care compositions to
the oral cavity; (b)
directing the user to continue application of the oral care composition to the
oral cavity for at least
120 seconds.
Disclosed herein is a method of delivering a majority of peroxide to an oral
cavity of a user
instead of a sink comprising (a) directing the user to a apply any of the
disclosed oral care
compositions to the oral cavity; (b) directing the user to continue
application of the oral care
composition to the oral cavity for at least 120 seconds; and (c) directing the
user to expectorate the
oral care composition.
BRIEF DESCRIPTION OF THE FIGURE
Fig. 1 shows the peroxide release over time for Composition A, B, C, and D.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
3
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to hydrating oral care compositions
comprising peroxide
and water. While not wishing to being bound by theory, it is believed that
peroxide that is stabilized
through complexation and placed in an anhydrous chassis can lead to lower
amounts of available
of peroxide to provide health and cosmetic benefits. Additionally, anhydrous
compositions can be
dehydrating, leading to additional sensitivity challenges.
It has been surprisingly found that peroxide in composition including water
can have a high
peroxide release rate and hydrate the oral cavity. While not wishing to being
bound by theory, it
is believed that by minimizing reactivity with the remaining components in the
oral care
composition, including the abrasive, peroxide can be formulated in a
composition including water.
Definitions
To define more clearly the terms used herein, the following definitions are
provided.
Unless otherwise indicated, the following definitions are applicable to this
disclosure. If a term is
used in this disclosure but is not specifically defined herein, the definition
from the IUPAC
Compendium of Chemical Terminology, 2nd Ed (1997), can be applied, as long as
that definition
does not conflict with any other disclosure or definition applied herein, or
render indefinite or non-
enabled any claim to which that definition is applied.
The term "oral care composition", as used herein, includes a product, which in
the ordinary
course of usage, is not intentionally swallowed for purposes of systemic
administration of
particular therapeutic agents, but is rather retained in the oral cavity for a
time sufficient to contact
dental surfaces or oral tissues. Examples of oral care compositions include
dentifrice, tooth gel,
subgingival gel, mouth rinse, mousse, foam, mouth spray, lozenge, chewable
tablet, chewing gum,
tooth whitening strips, floss and floss coatings, breath freshening
dissolvable strips, or denture care
or adhesive product. The oral care composition may also be incorporated onto
strips or films for
direct application or attachment to oral surfaces.
The term "dentifrice composition", as used herein, includes tooth or
subgingival -paste, gel,
or liquid formulations unless otherwise specified. The dentifrice composition
may be a single-
phase composition or may be a combination of two or more separate dentifrice
compositions. The
dentifrice composition may be in any desired form, such as deep striped,
surface striped,
multilayered, having a gel surrounding a paste, or any combination thereof
Each dentifrice
composition in a dentifrice comprising two or more separate dentifrice
compositions may be
contained in a physically separated compartment of a dispenser and dispensed
side-by-side.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
4
"Active and other ingredients" useful herein may be categorized or described
herein by
their cosmetic and/or therapeutic benefit or their postulated mode of action
or function. However,
it is to be understood that the active and other ingredients useful herein
can, in some instances,
provide more than one cosmetic and/or therapeutic benefit or function or
operate via more than
one mode of action. Therefore, classifications herein are made for the sake of
convenience and are
not intended to limit an ingredient to the particularly stated function(s) or
activities listed.
The term "orally acceptable carrier" comprises one or more compatible solid or
liquid
excipients or diluents which are suitable for topical oral administration. By
"compatible," as used
herein, is meant that the components of the composition are capable of being
commingled without
interaction in a manner which would substantially reduce the composition's
stability and/or
efficacy. The carriers or excipients of the present invention can include the
usual and conventional
components of mouthwashes or mouth rinses, as more fully described
hereinafter: Mouthwash or
mouth rinse carrier materials typically include, but are not limited to one or
more of water, alcohol,
humectants, surfactants, and acceptance improving agents, such as flavoring,
sweetening, coloring
and/or cooling agents.
The term "substantially free" as used herein refers to the presence of no more
than 0.05%,
preferably no more than 0.01%, and more preferably no more than 0.001%, of an
indicated material
in a composition, by total weight of such composition.
The term "essentially free" as used herein means that the indicated material
is not
deliberately added to the composition, or preferably not present at
analytically detectable levels.
It is meant to include compositions whereby the indicated material is present
only as an impurity
of one of the other materials deliberately added.
The term "oral hygiene regimen' or "regimen" can be for the use of two or more
separate
and distinct treatment steps for oral health. e.g. toothpaste, mouth rinse,
floss, toothpicks, spray,
water irrigator, massager.
The term "total water content" as used herein means both free water and water
that is bound
by other ingredients in the oral care composition.
For the purpose of the present invention, the relevant molecular weight (MW)
to be used is
that of the material added when preparing the composition e.g., if the chelant
is a citrate species,
which can be supplied as citric acid, sodium citrate or indeed other salt
forms, the MW used is that
of the particular salt or acid added to the composition but ignoring any water
of crystallization that
may be present.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
While compositions and methods are described herein in terms of "comprising"
various
components or steps, the compositions and methods can also "consist
essentially of' or "consist
of' the various components or steps, unless stated otherwise.
As used herein, the word "or" when used as a connector of two or more elements
is meant
to include the elements individually and in combination; for example, X or Y,
means X or Y or
both.
As used herein, the articles "a" and "an" are understood to mean one or more
of the material
that is claimed or described, for example, "an oral care composition" or "a
bleaching agent."
All measurements referred to herein are made at about 23 C (i.e. room
temperature) unless
otherwise specified.
Generally, groups of elements are indicated using the numbering scheme
indicated in the
version of the periodic table of elements published in Chemical and
Engineering News, 63(5), 27,
1985. In some instances, a group of elements can be indicated using a common
name assigned to
the group; for example, alkali metals for Group 1 elements, alkaline earth
metals for Group 2
elements, and so forth.
Several types of ranges are disclosed in the present invention. When a range
of any type is
disclosed or claimed, the intent is to disclose or claim individually each
possible number that such
a range could reasonably encompass, including end points of the range as well
as any sub-ranges
and combinations of sub-ranges encompassed therein.
The dentifrice composition can be in any suitable form, such as a solid,
liquid, powder,
paste, or combinations thereof. The oral care composition can be dentifrice,
tooth gel, subgingival
gel, mouth rinse, mousse, foam, mouth spray, lozenge, chewable tablet, chewing
gum, tooth
whitening strips, floss and floss coatings, breath freshening dissolvable
strips, or denture care or
adhesive product. The components of the dentifrice composition can be
incorporated into a film,
a strip, a foam, or a fiber-based dentifrice composition.
The oral care compositions, as described herein, comprise peroxide and
peroxide
compatible abrasive, such as calcium pyrophosphate. Additionally, the oral
care compositions can
comprise other optional ingredients, as described below. The section headers
below are provided
for convenience only. In some cases, a compound can fall within one or more
sections. For
example, stannous fluoride can be a tin compound and/or a fluoride compound.
Peroxide
The oral care composition comprises peroxide. The peroxide can include any
suitable
source of peroxide, such as solubilized peroxide compounds and/or solid
peroxide sources.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
6
Suitable peroxides include solid peroxides, hydrogen peroxide, urea peroxide,
calcium peroxide,
benzoyl peroxide, sodium peroxide, barium peroxide, inorganic peroxides,
hydroperoxides,
organic peroxides, polyvinylpyrrolidone-peroxide complex, crosslinked
polyvinylpyrrolidone-
peroxide complex, and/or combinations thereof
While not wishing to being bound by theory, it is believed that peroxide
compounds that
are stabilized through the complexation with a stabilizing compound, such as
crosslinked polyvinyl
pyrrolidone-peroxide, are less available to provide an oral health benefit,
such as a whitening
benefit, when applied to the oral cavity. Thus, the peroxide can comprise
solubilized peroxide
compounds, such as aqueous hydrogen peroxide.
Additionally, the oral care composition can be designed, such as through the
selection of
the other components of the oral care composition, to maximize the amount of
remaining peroxide
after a defined period after initially mixing the oral care composition.
Suitable oral care
compositions include oral care compositions comprising at least about 75%, at
least about 80%, at
least about 85%, at least about 90%, from about 90% to about 99%, or from
about 88% to about
99% of hydrogen peroxide remaining in the oral care composition the oral care
composition is
stored at 50 C for 10 days. Other suitable oral care compositions include
oral care compositions
comprising at least about 75%, at least about 80%, at least about 85%, at
least about 90%, at least
about 95%, from about 90% to about 99%, or from about 88% to about 99% of
hydrogen peroxide
remaining in the oral care composition the oral care composition is stored at
50 C for 20 days.
The oral care composition can comprise from about 0.01% to about 20%, from
about 0.01%
to about 10%, from about 1% to about 5%, at least about 1%, at least about 2%,
at least about 3%,
at least about 3.5%, at least about 4%, or greater than 3%, by weight of the
oral care composition,
of the peroxide.
While not wishing to being bound by theory, it is believed that the peroxide,
as described
herein, can be un-bound, uncomplexed, and/or only minimally stabilized by
other components in
the oral care composition. It is additionally believed that oral care
compositions comprising
peroxide that is un-bound, uncomplexed, and/or only minimally stabilized to
other components in
the oral care composition, such as amphiphilic polymer and/or other thickening
agents, can lead to
a greater rate of release of peroxide than compositions that have peroxide
adducts, such as
polyvinylpyrrolidone-peroxide, and/or other sources of bound peroxide.
Desirable oral care
compositions include oral care compositions that have a peroxide release of at
least about 10%, at
least about 15%, at least about 25%, at least about 35%, at least about 50%,
at least about 60 %, at
least about 70%, at least about 75%, at least about 80%, at least about 90%,
at least about 95%,
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
7
from about 10% to about 95%, from about 25% to about 75%, from about 20% to
about 95%, from
about 35% to about 90%, from about 40% to about 95%, from about 50% to about
90%, and from
about 60% to about 99% in a defined period of time corresponding to a single
oral care session,
such as 30 second, 45 second, 60 seconds, 75 seconds, 90 seconds, 120 seconds,
and/or 5 minutes.
Abrasive
The oral care composition can comprise abrasive, such as a peroxide-compatible
abrasive.
Abrasives can be added to oral care formulations to help remove surface stains
from teeth. The
abrasive can comprise calcium abrasive, silica abrasive, carbonate abrasive,
phosphate abrasive,
alumina abrasive, other suitable abrasives, and/or combinations thereof
The calcium abrasive can comprise calcium carbonate, dicalcium phosphate,
tricalcium
phosphate, calcium orthophosphate, calcium metaphosphate, calcium
pyrophosphate, calcium
polyphosphate, calcium hydroxyapatite, and combinations thereof.
The calcium abrasive can comprise calcium carbonate. The calcium-containing
abrasive can
be selected from the group consisting of fme ground natural chalk, ground
calcium carbonate,
precipitated calcium carbonate, and combinations thereof.
The calcium abrasive can comprise calcium pyrophosphate. While not wishing to
be bound
by theory, it is believed that particular sources of calcium pyrophosphate can
be sufficiently
compatible with peroxide to be used in an oral care composition comprising
peroxide. Calcium
pyrophosphate has at least three polymorphic phases: alpha (a), beta (13), and
gamma (y). It has been
unexpectedly found that calcium pyrophosphate with a higher proportion of the
y phase are more
compatible with peroxide, such as hydrogen peroxide. Suitable sources of
calcium pyrophosphate
can comprise a ratio of gamma phase calcium pyrophosphate to beta phase
calcium pyrophosphate
of at least about 0.75, at least about 0.8. at least about 0.9, at least about
1, from about 0.75 to about
1.5, from about 0.9 to about 1.5, or from about 1 to about 1.5.
While not wishing to being bound by theory, it is believed that abrasives that
include high
amounts of soluble metal ions are less compatible with peroxide due to
reactivity between peroxide
and metal ions. Thus, suitable sources of abrasives, such as calcium
pyrophosphate, can comprise
less than about 0.001%, less than about 0.00075%, less than about 0.0006%,
less than about
0.0005%, or less than about 0.0001%, by weight of the abrasive. Additionally,
the abrasive can be
free of, substantially free of, or essentially free of soluble metal ions.
Examples of trace metal ions
that might be present in abrasives and have been previously reported to induce
peroxide
degradation include Cr, Mn, Fe, Co, Ni, Cu, Mo, and/or combinations thereof
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
8
As described herein, it has also been unexpectedly found that abrasives with a
slurry pH of
from about 5.4 to about 7 were more compatible with peroxide. The slurry pH
was determined by
creating a 1:3 abrasive:water slurry and determining the pH.
The carbonate abrasive can comprise sodium carbonate, sodium bicarbonate,
calcium
carbonate, strontium carbonate, and/or combinations thereof
The phosphate abrasive can comprise calcium phosphate, sodium
hexametaphosphate,
dicalcium phosphate, tricalcium phosphate, calcium orthophosphate, calcium
metaphosphate,
calcium polyphosphate, a polyphosphate, a pyrophosphate, and/or combinations
thereof.
The silica abrasive can comprise fused silica, fumed silica, precipitated
silica, hydrated silica,
and/or combinations thereof
The alumina abrasive can comprise polycrystalline alumina, calcined alumina,
uncalcined
alumina, fused alumina, levigated alumina, hydrated alumina, and/or
combinations thereof.
Other suitable abrasives include diatomaceous earth, barium sulfate,
wollastonite, perlite,
polymethylmethacrylate particles, tospearl, and combinations thereof
The oral care composition can comprise from about 0.01% to about 30%, from
about 0.01%
to about 15%, from about 0.01% to less than 15%, from about 1% to about 30%,
from about 1% to
less than 15%, from about 1% to about 12%, or from about 0.01% to about 10%,
by weight of the
oral care composition of the abrasive.
The oral care composition can have a Pellicle Cleaning Ratio (PCR) of at least
about 75, at
least about 90, at least about 100, from about 75 to about 250, or from about
100 to about 250.
The oral care composition can have a Relative Dentin Abrasion value of up to
about 250, up
to about 150, from about 70 to about 150, or from about 50 to about 250.
Alumina
The oral care composition can include alumina as an abrasive. The alumina can
be the sole
abrasive or used in combination with other abrasives, as described herein. The
abrasivity of alumina
can be higher than silica, thus a lower amount of alumina abrasive can be
added.
An oral care composition comprising alumina can have a hard tissue safety
value (REA) of
at least about 15, at least about 20, at least about 25, or at least about 40.
An oral care composition comprising alumina can have a pellicle cleaning ratio
(PCR) of at
least about 75, at least about 100, from about 75 to about 250, from about 50
to about 175, from
about 50 to about 150, or rom about 65 to about 155.
An oral care composition comprising alumina can have a Relative Dentin
Abrasion (RDA)
of less than about 150, less than about 125, less than about 100, or less than
about 90.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
9
While not wishing to be bound by theory, it is believed that alumina can be
reactive with
peroxide and/or fluoride. Thus, desirable alumina abrasives include those that
are compatible with
peroxide and/or fluoride. Suitable oral care compositions include oral care
compositions comprising
at least about 75%, at least about 80%, at least about 85%, at least about
90%, at least about 95%,
from about 90% to about 99%, or from about 88% to about 99% of hydrogen
peroxide remaining
in the oral care composition the oral care composition is stored at 40 C for
30 and/or 60 days.
Other suitable oral care compositions include oral care compositions that
comprise
peroxide and alumina and have % loss of peroxide after 30 days and/or 90 days
at 40 C of less
than about 10%, less than about 5%, less than about 4%, less than about 3%,
from about 0.5% to
about 10%, from about 0.5% to about 5%, or from about 0.1% to about 5%. While
not wishing to
being bound by theory, it is believed that alumina is unexpectedly stable with
alumina, such that
only a minimal amount of peroxide is lost to peroxide decomposition and/or
degradation.
Other suitable oral care compositions include oral care compositions that
comprise
peroxide, fluoride, and alumina and have % loss of fluoride after 30 days
and/or 90 days at 40 C
of less than about 20%, less than about 18%, less than about 15%, less than
about 10%, less than
about 5%, from about 0.5% to about 10%, from about 0.5% to about 20%, or from
about 0.1% to
about 15%. While not wishing to being bound by theory, it is believed that
alumina and peroxide
are unexpectedly stable with certain fluoride sources, such that only a
minimal loss of fluoride is
observed.
Other suitable oral care compositions include oral care compositions
comprising peroxide
and alumina and have a % increase of viscosity 30 days and/or 90 days at 40 C
of at least about
5%, at least about 10%, at least about 15%, at least about 20%, at least about
25%, at least about
35%, at least about 50%, at least about 75%, at least about 100%, from about
5% to about 125%,
from about 5% to about 50%, or from about 1%, to about 75%. While not wishing
to being bound
by theory, it is believed that the combination of alumina and peroxide are
unexpectedly stable,
which can minimize the decrease in viscosity in meta-stable peroxide
compositions normally
observed due to the decomposition of peroxide.
The oral care composition can comprise from about 0.01% to about 10%, from
about 0.01%
to about 5%, from about 0.1% to about 5%, from about 0.01% to about 3%, or
from about 0.01% to
about 1%, by weight of the oral care composition, of alumina.
Water
The oral care composition of the present invention can be a dentifrice
composition that is
anhydrous, a low water formulation, or a high water formulation. In total, the
oral care composition
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
can comprise from 0% to about 99%, from about 5% to about 60%, from about 5%
to about 75%,
about 20% or greater, about 30% or greater, about 50% or greater, up to about
45%, or up to about
75%, by weight of the composition, of water. Preferably, the water is USP
water.
The oral care composition of the present invention can include water. While
not wishing
to be bound by theory, it is believed that including water in the oral care
composition can lead to
greater availability of peroxide to provide oral health benefits, such as
whitening, while also
hydrating the oral cavity. While one option to stabilize peroxide is to
provide a complexed
peroxide in an anhydrous dentifrice composition, it is believed that peroxide
can be more
effectively delivered through the selection of the other ingredients of the
oral care composition
while simultaneously hydrating the oral cavity.
In a high water dentifrice formulation, the dentifrice composition comprises
from about
45% to about 75%, by weight of the composition, of water. The high water
dentifrice composition
can comprise from about 45% to about 65%, from about 45% to about 55%, or from
about 46% to
about 54%, by weight of the composition, of water. The water may be added to
the high water
dentifrice formulation and/or may come into the composition from the inclusion
of other
ingredients.
In a low water dentifrice formulation, the dentifrice composition comprises
from about 5%
to about 45% or from about 10% to about 45%, by weight of the composition, of
water. The low
water dentifrice composition can comprise from about 10% to about 35%, from
about 15% to about
25%, or from about 20% to about 25%, by weight of the composition, of water.
The water may be
added to the low water dentifrice formulation and/or may come into the
composition from the
inclusion of other ingredients.
In an anhydrous dentifrice formulation, the dentifrice composition comprises
less than
about 10%, by weight of the composition, of water. The anhydrous dentifrice
composition
comprises less than about 5%, less than about 1%, or 0%, by weight of the
composition, of water.
The water may be added to the anhydrous formulation and/or may come into the
dentifrice
composition from the inclusion of other ingredients.
The dentifrice composition can also comprise other orally acceptable carrier
materials, such
as alcohol, humectants, polymers, surfactants, and acceptance improving
agents, such as flavoring,
sweetening, coloring and/or cooling agents.
The oral care composition can also be a mouth rinse formulation. A mouth rinse
formulation can comprise from about 75% to about 99%, from about 75% to about
95%, or from
about 80% to about 95% of water.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
11
Amphiphilic Polymer
The oral care composition can comprise amphiphilic polymer. The amphiphilic
polymer
can be included as a peroxide compatible thickening agent. The amphiphilic
polymer can
comprise a polymer that has a hydrophobic portion and a hydrophilic portion.
For example, the
polymer can comprise a polymer macromolecule that comprises a hydrophilic
backbone and
hydrophobic subunits. This can allow the amphiphilic polymer to remain soluble
in water while
preventing strong interactions with the peroxide.
As described herein, it is believed that peroxide can be effectively delivered
in an aqueous
chassis if the other components are designed to minimize reactivity with the
peroxide. As such, it
is desirable for the amphiphilic polymer to not strongly react with the
peroxide. Thus, it is desirable
for the amphiphilic polymer to not form an isolatable complex with the
peroxide.
The amphiphilic polymer can include polymers that are at least partially
soluble and/or
fully soluble in water.
Suitable amphiphilic polymers include 2-acrylamido-2-methylpropane sulfonic
acid
(AMPS) polymer, copolymer, cross-polymer, or combination thereof. In one
example, the oral
care composition can contain polyacrylate crosspolymer-6 ( commercially
available as
SepiMAXTm ZEN from SEPPIC S.A., a subsidiary of the Air Liquide group, Puteaux
Cedex,
France).
The oral care composition can comprise from about 0.01% to about 10%, from
about 0.1%
to about 5%, from about 1% to about 10%, or from about 1% to about 5%, by
weight of the oral
care composition, of the amphiphilic polymer.
Alkyl Alcohol
The oral care composition can comprise alkyl alcohol. While not wishing to be
bound by
theory, it is believed that the addition of alkyl alcohol in combination with
the amphiphilic polymer
can lead to oral care compositions with unexpectedly high viscosities.
The alkyl alcohol can include compounds with an alkyl functional group and an
alcohol
functional group. The alkyl functional can be linear, branched, cyclical, or
combinations thereof.
The alkyl alcohol can include a primary alcohol, a secondary alcohol, and/or a
tertiary alcohol.
The alkyl alcohol can be represented by the general formula of CnH2n-10H,
wherein n can
be any whole number from 1 to 30, from 10 to 20, or from 10 to 25.
Specific examples of alkyl alcohols can include 1-heptacosanol, 1-hexacosanol,
1-
nonacosanol, 1-octacosanol, 1-tetracosanol, docosanol, heneicosan-l-ol,
pentacosan-l-ol,
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
12
tricosan-l-ol, 1,4-butanediol, 1-heptanol, 1-hexanol, 1-nonanol, 1-octanol, 1-
pentanol, 1-propanol,
2,4-dichlorobenzyl alcohol, 2-ethylhexanol, 3-nitrobenzyl alcohol, allyl
alcohol, anisyl alcohol,
arachidyl alcohol, benzyl alcohol, cetyl alcohol, cinnamyl alcohol, crotyl
alcohol, furfuryl alcohol,
isoamyl alcohol, neopentyl alcohol, nicotinyl alcohol, perillyl alcohol,
phenethyl alcohol,
propargyl alcohol, salicyl alcohol, stearyl alcohol, tryptophol, vanillyl
alcohol, veratrole alcohol,
and/or combinations thereof The alkyl alcohol can comprise stearyl alcohol,
cetyl alcohol, and/or
combinations thereof.
The alkyl alcohol can be provided through commercial mixtures of alkyl
alcohols, such as
Lanette W, which includes cetyl alcohol: stearyl alcohol: sodium lauryl
sulfate at a 45:45:10 ratio
(available from BASF, Florham Park, NJ).
The oral care composition can comprise from about 0.01% to about 10%, from
about 0.1%
to about 5%, from about 1% to about 10%, or from about 1% to about 5%, by
weight of the oral
care composition, of the alkyl alcohol.
The combination of amphiphilic polymer and alkyl alcohol can lead to oral care
compositions with unexpectedly high viscosities. Suitable ratios of
amphiphilic polymer:alkyl
alcohol can be at least about 0.25, at least about 0.5, at least about 0.75,
at least about 1, from about
0.25 to about 5, about 0.5 to 1.5, or about 1.
The oral care composition can have a viscosity of at least about 5 cP, at
least about 10 cP,
at least about 20 cP, from about 5 cP to about 20 cP, or from about 1 cP to
about 25 cP.
pH
The pH of the disclosed composition can be from about 4 to about 10, from
about 4 to about
7, from about 4 to about 8, or from about 7 to about 10.
Fluoride
The oral care composition can comprise fluoride, which can be provided by a
fluoride ion
source. The fluoride ion source can comprise one or more fluoride containing
compounds, such
as stannous fluoride, sodium fluoride, potassium fluoride, amine fluoride,
sodium
monofluorophosphate, zinc fluoride, and/or mixtures thereof
The fluoride ion source and the tin ion source can be the same compound, such
as for
example, stannous fluoride, which can generate tin ions and fluoride ions.
Additionally, the
fluoride ion source and the tin ion source can be separate compounds, such as
when the tin ion
source is stannous chloride and the fluoride ion source is sodium
monofluorophosphate or sodium
fluoride.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
13
The fluoride ion source and the zinc ion source can be the same compound, such
as for
example, zinc fluoride, which can generate zinc ions and fluoride ions.
Additionally, the fluoride
ion source and the zinc ion source can be separate compounds, such as when the
zinc ion source is
zinc phosphate and the fluoride ion source is stannous fluoride.
The fluoride ion source can be essentially free of, or free of stannous
fluoride. Thus, the
oral care composition can comprise sodium fluoride, potassium fluoride, amine
fluoride, sodium
monofluorophosphate, zinc fluoride, and/or mixtures thereof.
The oral care composition can comprise a fluoride ion source capable of
providing from
about 50 ppm to about 5000 ppm, and preferably from about 500 ppm to about
3000 ppm of free
fluoride ions. To deliver the desired amount of fluoride ions, the fluoride
ion source may be present
in the oral care composition at an amount of from about 0.0025% to about 5%,
from about 0.01%
to about 10%, from about 0.2% to about 1%, from about 0.5% to about 1.5%, or
from about 0.3%
to about 0.6%, by weight of the oral care composition. Alternatively, the oral
care composition
can comprise less than 0.1%, less than 0.01%, be essentially free of, be
substantially free of, or free
of a fluoride ion source.
Metal
The oral care composition, as described herein, can comprise metal, which can
be provided
by a metal ion source comprising one or more metal ions. The metal ion source
can comprise or
be in addition to the tin ion source and/or the zinc ion source, as described
herein. Suitable metal
ion sources include compounds with metal ions, such as, but not limited to Sn,
Zn, Cu, Mn, Mg,
Sr, Ti, Fe, Mo, B, Ba, Ce, Al, In and/or mixtures thereof. The metal ion
source can be any
compound with a suitable metal and any accompanying ligands and/or anions.
Suitable ligands and/or anions that can be paired with metal ion sources
include, but are
not limited to acetate, ammonium sulfate, benzoate, bromide, borate,
carbonate, chloride, citrate,
gluconate, glycerophosphate, hydroxide, iodide, oxalate, oxide, propionate, D-
lactate, DL-lactate,
orthophosphate, pyrophosphate, sulfate, nitrate, tartrate, and/or mixtures
thereof.
The oral care composition can comprise from about 0.01% to about 10%, from
about 1%
to about 5%, or from about 0.5% to about 15% of metal and/or a metal ion
source.
Tin
The oral care composition of the present invention can comprise tin, which can
be provided
by a tin ion source. The tin ion source can be any suitable compound that can
provide tin ions in
an oral care composition and/or deliver tin ions to the oral cavity when the
oral care composition
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
14
is applied to the oral cavity. The tin ion source can comprise one or more tin
containing
compounds, such as stannous fluoride, stannous chloride, stannous bromide,
stannous iodide,
stannous oxide, stannous oxalate, stannous sulfate, stannous sulfide, stannic
fluoride, stannic
chloride, stannic bromide, stannic iodide, stannic sulfide, and/or mixtures
thereof. Tin ion source
can comprise stannous fluoride, stannous chloride, and/or mixture thereof The
tin ion source can
also be a fluoride-free tin ion source, such as stannous chloride.
The oral care composition can comprise from about 0.0025% to about 5%, from
about
0.01% to about 10%, from about 0.2% to about 1%, from about 0.4% to about 1%,
or from about
0.3% to about 0.6%, by weight of the oral care composition, of tin and/or a
tin ion source.
Alternatively, the oral care composition can be essentially free of,
substantially free of, or free of
tin.
Zinc
The oral care composition can comprise zinc, which can be provided by a zinc
ion source.
The zinc ion source can comprise one or more zinc containing compounds, such
as zinc fluoride,
zinc lactate, zinc oxide, zinc phosphate, zinc chloride, zinc acetate, zinc
hexafluorozirconate, zinc
sulfate, zinc tartrate, zinc gluconate, zinc citrate, zinc malate, zinc
glycinate, zinc pyrophosphate,
zinc metaphosphate, zinc oxalate, and/or zinc carbonate. The zinc ion source
can be a fluoride-
free zinc ion source, such as zinc phosphate, zinc oxide, and/or zinc citrate.
The zinc and/or zinc ion source may be present in the total oral care
composition at an
amount of from about 0.01% to about 10%, from about 0.2% to about 1%, from
about 0.4% to
about 1 %, or from about 0.3% to about 0.6%, by weight of the dentifrice
composition.
Alternatively, the oral care composition can be essentially free of,
substantially free of, or free of
zinc.
Polyphosphate
The oral care composition can comprise polyphosphate, which can be provided by
a
polyphosphate source. A polyphosphate source can comprise one or more
polyphosphate
molecules. Polyphosphates are a class of materials obtained by the dehydration
and condensation
of orthophosphate to yield linear and cyclic polyphosphates of varying chain
lengths. Thus,
polyphosphate molecules are generally identified with an average number (n) of
polyphosphate
molecules, as described below. A polyphosphate is generally understood to
consist of two or more
phosphate molecules arranged primarily in a linear configuration, although
some cyclic derivatives
may be present.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
Preferred polyphosphates are those having an average of two or more phosphate
groups so
that surface adsorption at effective concentrations produces sufficient non-
bound phosphate
functions, which enhance the anionic surface charge as well as hydrophilic
character of the
surfaces. Preferred in this invention are the linear polyphosphates having the
formula:
X0(XP03)X, wherein X is sodium, potassium, ammonium, or any other alkali metal
cations and
n averages from about 2 to about 21. Alkali earth metal cations, such as
calcium, are not preferred
because they tend to form insoluble fluoride salts from aqueous solutions
comprising a fluoride
ions and alkali earth metal cations. Thus, the oral care compositions
disclosed herein can be free
of or substantially free of calcium pyrophosphate.
Some examples of suitable polyphosphate molecules include, for example,
pyrophosphate
(n-2), tripolyphosphate (n=3), tetrapolyphosphate (n=4), sodaphos
polyphosphate (n-6), hexaphos
polyphosphate (n=13), benephos polyphosphate (n=14), hexametaphosphate (n=21),
which is also
known as Glass H. Polyphosphates can include those polyphosphate compounds
manufactured by
FMC Corporation, ICL Performance Products, and/or Astaris.
The oral care composition can comprise from about 0.01% to about 15%, from
about 0.1%
to about 10%, from about 0.5% to about 5%, from about 1 to about 20%, or about
10% or less, by
weight of the oral care composition, of the polyphosphate source.
Alternatively, the oral care
composition can be essentially free of; substantially free of, or free of
polyphosphate.
Orthophosphate
The oral care composition can comprise orthophosphate, which can be provided
by an
orthophosphate source. An orthophosphate source can comprise a salt including
the
orthophosphate anion, a salt including a phosphate anion (H2PO4-, HP042, and
Pah, a
phosphoric acid compound, a polyphosphate source, which can breakdown into
orthophosphate
under a variety of conditions, and/or another suitable orthophosphate source.
The oral care composition can comprise from about 0.01% to about 15%, from
about 0.1%
to about 10%, from about 0.5% to about 5%, from about 1 to about 20%, or about
10% or less, by
weight of the oral care composition, of the orthophosphate. Alternatively, the
oral care
composition can be essentially free of, substantially free of, or free of
orthophosphate.
Surfactant
The oral care composition can comprise one or more surfactants. The
surfactants can be
used to make the compositions more cosmetically acceptable. The surfactant is
preferably a
detersive material which imparts to the composition detersive and foaming
properties. Suitable
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
16
surfactants are safe and effective amounts of anionic, cationic, nonionic,
zwitterionic, amphoteric
and betaine surfactants, such as sodium lauryl sulfate, sodium lauryl
isethionate, sodium lauroyl
methyl isethionate, sodium cocoyl glutamate, sodium dodecyl benzene sulfonate,
alkali metal or
ammonium salts of lauroyl sarcosinate, myristoyl sarcosinate, palmitoyl
sarcosinate, stearoyl
sarcosinate and oleoyl sarcosinate, polyoxyethylene sorbitan monostearate,
isostearate and laurate,
sodium lauryl sulfoacetate, N-lauroyl sarcosine, the sodium, potassium, and
ethanolamine salts of
N-lauroyl, N-myristoyl, or N-palmitoyl sarcosine, polyethylene oxide
condensates of alkyl
phenols, cocoamidopropyl betaine, lauramidopropyl betaine, palmityl betaine,
sodium cocoyl
glutamate, and the like. Sodium lauryl sulfate is a preferred surfactant. The
oral care composition
can comprise one or more surfactants each at a level from about 0.01% to about
15%, from about
0.3% to about 10%, or from about 0.3% to about 2.5 %, by weight of the oral
care composition.
It was surprisingly found that additional amounts of anionic surfactant, such
as alkyl
sulfate surfactant and/or sodium lauryl sulfate, can lead to increased
peroxide stability. As such,
desirable compositions include compositions that comprise at least about 1.5%,
greater than
1.5%, from about 1.5% to about 10%, or greater than 1.5% to about 10%, by
weight of the oral
care composition, of anionic surfactant.
Amino Acid
The oral care composition can comprise amino acid. The amino acid can comprise
one or
more amino acids, peptide, and/or polypeptide, as described herein.
Amino acids, as in Formula II, are organic compounds that contain an amine
functional
group, a carboxyl functional group, and a side chain (R in Formula II)
specific to each amino acid.
Suitable amino acids include, for example, amino acids with a positive or
negative side chain,
amino acids with an acidic or basic side chain, amino acids with polar
uncharged side chains, amino
acids with hydrophobic side chains, and/or combinations thereof Suitable amino
acids also
include, for example, arginine, histidine, lysine, aspartic acid, glutamic
acid, serine, threonine,
asparagine, glutamine, cysteine, selenocysteine, glycine, proline, alanine,
valine, isoleucine,
leucine, methionine, phenylalanine, tyrosine, tryptophan, citrulline,
ornithine, creatine,
diaminobutanoic acid, diaminoproprionic acid, salts thereof, and/or
combinations thereof.
Suitable amino acids include the compounds described by Formula I, either
naturally
occurring or synthetically derived. The amino acid can be zwitterionic,
neutral, positively charged,
or negatively charged based on the R group and the environment. The charge of
the amino acid,
and whether particular functional groups, can interact with tin at particular
pH conditions, would
be well known to one of ordinary skill in the art.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
17
E.) 0
H3N
0
Formula I. Amino Acid. R is any suitable functional group
Suitable amino acids include one or more basic amino acids, one or more acidic
amino
acids, one or more neutral amino acids, or combinations thereof
The oral care composition can comprise from about 0.01% to about 20%, from
about 0.1%
to about 10%, from about 0.5% to about 6%, or from about 1% to about 10 % of
amino acid, by
weight of the oral care composition.
The term "neutral amino acids" as used herein include not only naturally
occurring neutral
amino acids, such as alanine, asparagine, cysteine, glutamine, glycine,
isoleucine, leucine,
methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine,
valine, but also
biologically acceptable amino acids which have an isoelectric point in range
of pH 5.0 to 7Ø The
biologically preferred acceptable neutral amino acid has a single amino group
and carboxyl group
in the molecule or a functional derivative hereof, such as functional
derivatives having an altered
side chain albeit similar or substantially similar physio chemical properties.
In a further
embodiment the amino acid would be at minimum partially water soluble and
provide a pH of less
than 7 in an aqueous solution of lg/1000m1 at 25 C.
Accordingly, neutral amino acids suitable for use in the invention include,
but are not limited
to, alanine, aminobutyrate, asparagine, cysteine, cystine, glutamine, glycine,
hydroxyproline,
isoleucine, leucine, methionine, phenylalanine, proline, serine, taurine,
threonine, tryptophan,
tyrosine, valine, salts thereof, or mixtures thereof. Preferably, neutral
amino acids used in the
composition of the present invention may include asparagine, glutamine,
glycine, salts thereof, or
mixtures thereof. The neutral amino acids may have an isoelectric point of
5.0, or 5.1, or 5.2, or
5.3, or 5.4, or 5.5, or 5.6, or 5.7, or 5.8, or 5.9, or 6.0, or 6.1, or 6.2,
or 6.3, or 6.4, or 6.5, or 6.6, or
6.7, or 6.8, or 6.9, or 7.0, in an aqueous solution at 25 C. Preferably, the
neutral amino acid is
selected from proline, glutamine, or glycine, more preferably in its free form
(i.e. uncomplexed).
If the neutral amino acid is in its salt form, suitable salts include salts
known in the art to be
pharmaceutically acceptable salts considered to be physiologically acceptable
in the amounts and
concentrations provided.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
18
Humectant
The oral care composition can comprise one or more humectants, have low levels
of a
humectant, or be free of a humectant. Humectants serve to add body or "mouth
texture" to an oral
care composition or dentifrice as well as preventing the dentifrice from
drying out. Suitable
humectants include polyethylene glycol (at a variety of different molecular
weights), propylene
glycol, glycerin (glycerol), erythritol, xylitol, sorbitol, mannitol, butylene
glycol, lactitol,
hydrogenated starch hydrolysates, and/or mixtures thereof. The oral care
composition can
comprise one or more humectants each at a level of from 0 to about 70%, from
about 5% to about
50%, from about 10% to about 60%, or from about 20% to about 80%, by weight of
the oral care
composition.
Thickening Agents
The oral care composition can comprise one or more thickening agents in
addition to the
amphiphilic polymer and alkyl alcohol, as described herein. Thickening agents
can be useful in
the oral care compositions to provide a gelatinous structure that stabilizes
the dentifrice and/or
toothpaste against phase separation. Suitable thickening agents include
polysaccharides, polymers,
and/or silica thickeners.
The thickening agent can comprise one or more polysaccharides. Some non-
limiting
examples of polysaccharides include starch; glycerite of starch; gums such as
gum karaya (sterculia
gum), gum tragacanth, gum arabic, gum ghatti, gum acacia, xanthan gum, guar
gum and cellulose
gum; magnesium aluminum silicate (Veegum); carrageenan; sodium alginate; agar-
agar; pectin;
gelatin; cellulose compounds such as cellulose, microcrystalline cellulose,
carboxymethyl
cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxymethyl
cellulose,
hydroxymethyl carboxypropyl cellulose, methyl cellulose, ethyl cellulose, and
sulfated cellulose;
natural and synthetic clays such as hectorite clays; and mixtures thereof
Other polysaccharides that are suitable for use herein include carageenans,
gellan gum,
locust bean gum, xanthan gum, carbomers, poloxamers, modified cellulose, and
mixtures thereof.
Carageenan is a polysaccharide derived from seaweed. There are several types
of carageenan that
may be distinguished by their seaweed source and/or by their degree of and
position of sulfation.
The thickening agent can comprise kappa carageenans, modified kappa
carageenans, iota
carageenans, modified iota carageenans, lambda carrageenan, and mixtures
thereof. Carageenans
suitable for use herein include those commercially available from the FMC
Company under the
series designation "Viscarin," including but not limited to Viscarin TP 329,
Viscarin TP 388, and
Viscarin TP 389.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
19
The thickening agent can comprise one or more polymers. The polymer can be a
polyethylene glycol (PEG), a polyvinylpyrrolidone (PVP), polyacrylic acid, a
polymer derived
from at least one acrylic acid monomer, a copolymer of maleic anhydride and
methyl vinyl ether,
a crosslinked polyacrylic acid polymer, of various weight percentages of the
oral care composition
as well as various ranges of average molecular ranges. Alternatively, the oral
care composition
can be free of, essentially free of, or substantially free of a copolymer of
maleic anhydride and
methyl vinyl ether.
The thickening agent can comprise one or more inorganic thickening agents.
Some non-
limiting examples of suitable inorganic thickening agents include colloidal
magnesium aluminum
silicate, silica thickeners. Useful silica thickeners include, for example,
include, as a non-limiting
example, an amorphous precipitated silica such as ZEODENT 165 silica. Other
non-limiting
silica thickeners include ZEODENT 153, 163, and 167, and ZEOFREE 177 and 265
silica
products, all available from Evonik Corporation, and AEROSIL fumed silicas.
The oral care composition can comprise from 0.01% to about 15%, from 0.1% to
about
10%, from about 0.2% to about 5%, or from about 0.5 % to about 2% of one or
more thickening
agents.
Dicarboxylic acid
The oral care composition can comprise dicarboxylic acid. The dicarboxylic
acid
comprises a compound with two carboxylic acid functional groups. The
dicarboxylic acid can
comprise a compound or salt thereof defined by Formula II.
0 0
HO R
Formula II. Dicarboxylic acid
R can be null, alkyl, alkenyl, allyl, phenyl, benzyl, aliphatic, aromatic,
polyethylene
glycol, polymer, 0, N, P, or combinations thereof.
The dicarboxylic acid can comprise oxalic acid, malonic acid, succinic acid,
glutaric acid,
adipic acid, pimelic acid, suberic acid, azerlaic acid, sebacic acid,
undecanedioic acid,
dodecanedioic acid, brassylic acid, thapsic acid, japanic acid, phellogenic
acid, equisetolic acid,
malic acid, tartaric acid, salts thereof, or combinations thereof. The
dicarboxylic acid can comprise
suitable salts of dicarboxylic acid, such as, for example, monoalkali metal
oxalate, dialkali metal
oxalate, monopotassium monohydrogen oxalate, dipotassium oxalate, monosodium
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
monohydrogen oxalate, disodium oxalate, titanium oxalate, and/or other metal
salts of oxalate.
The dicarboxylic acid can also include hydrates of the dicarboxylic acid
and/or a hydrate of a salt
of the dicarboxylic acid.
The oral care composition can comprise from about 0.01% to about 10%, from
about 0.1%
to about 15%, from about 1% to about 5%, or from about 0.0001 to about 25%, of
dicarboxylic
acid.
Other Ingredients
The oral care composition can comprise a variety of other ingredients, such as
flavoring
agents, sweeteners, colorants, preservatives, buffering agents, or other
ingredients suitable for use
in oral care compositions, as described below.
Flavoring agents also can be added to the oral care composition. Suitable
flavoring agents
include oil of wintergreen, oil of peppermint, oil of spearmint, clove bud
oil, menthol, anethole,
methyl salicylate, eucalyptol, cassia, 1-menthyl acetate, sage, eugenol,
parsley oil, oxanone, alpha-
irisone, marjoram, lemon, orange, propenyl guaethol, cinnamon, vanillin, ethyl
vanillin,
heliotropine, 4-cis-heptenal, diacetyl, methyl-para-tert-butyl phenyl acetate,
and mixtures thereof.
Coolants may also be part of the flavor system. Preferred coolants in the
present compositions are
the paramenthan carboxyamide agents such as N-ethyl-p-menthan-3-carboxamide
(known
commercially as "WS-3") or N-(Ethoxycarbonylmethyl)-3-p-menthanecarboxamide
(known
commercially as "WS-5"), and mixtures thereof A flavor system is generally
used in the
compositions at levels of from about 0.001 % to about 5%, by weight of the
oral care composition.
These flavoring agents generally comprise mixtures of aldehydes, ketones,
esters, phenols, acids,
and aliphatic, aromatic and other alcohols.
Sweeteners can be added to the oral care composition to impart a pleasing
taste to the
product. Suitable sweeteners include saccharin (as sodium, potassium or
calcium saccharin),
cyclamate (as a sodium, potassium or calcium salt), acesulfame-K, thaumatin,
neohesperidin
dihydrochalcone, ammoniated glycyrrhizin, dextrose, levulose, sucrose,
marmose, sucralose,
stevia, and glucose.
Colorants can be added to improve the aesthetic appearance of the product.
Suitable
colorants include without limitation those colorants approved by appropriate
regulatory bodies
such as the FDA and those listed in the European Food and Pharmaceutical
Directives and include
pigments, such as TiO2, and colors such as FD&C and D&C dyes.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
21
Preservatives also can be added to the oral care compositions to prevent
bacterial growth.
Suitable preservatives approved for use in oral compositions such as
methylparaben,
propylparaben, benzoic acid, and sodium benzoate can be added in safe and
effective amounts.
Titanium dioxide may also be added to the present composition. Titanium
dioxide is a
white powder which adds opacity to the compositions. Titanium dioxide
generally comprises from
about 0.25% to about 5%, by weight of the oral care composition.
Other ingredients can be used in the oral care composition, such as
desensitizing agents,
healing agents, other caries preventative agents, chelating/sequestering
agents, vitamins, amino
acids, proteins, other anti-plaque/anti-calculus agents, opacifiers,
antibiotics, anti-enzymes,
enzymes, pH control agents, oxidizing agents, antioxidants, and the like.
Hydrating Oral Care Composition
The oral care composition can be a hydrating oral care composition. Suitable
hydrating
oral care compositions can deliver a high amount of peroxide and/or other
suitable active agent
while hydrating or without removing water from the oral cavity upon
expectoration of the oral care
composition. Suitable oral care compositions can also include oral care
compositions that can
deliver a majority of the included active agent, such as peroxide, to the oral
cavity, and not to the
sink upon expectoration of the oral care composition to the sink.
Suitable oral care compositions include dentifrice compositions, toothpaste
compositions,
and/or jammed oil-in-water emulsions.
Multi-phase Oral Composition
The oral care composition can comprise multi-phase oral composition. The multi-
phase
oral composition can comprise multi-phase compositions, such as in U.S. Patent
Application
Publication Number 2018/0133121, U.S. Patent Number 10,849,729, and/or U.S.
Patent
Application Publication Number 10,780,032, which are each herein incorporated
by reference in
their entirety.
Suitable multi-phase oral compositions include water-in-oil emulsions, oil-in-
water
emulsions, soluble particle dispersions in hydrophobic phase, jammed oil-in-
water emulsions,
and/or jammed water-in-oil emulsions. In particular, jammed oil-in-water
emulsions, as described
in TABLE 5 and TABLE 6, have a high peroxide release rate.
Traditional oil-in-water emulsions are multi-phase compositions with a
discontinuous
hydrophobic phase and a continuous aqueous phase. Stable oil-in-water
emulsions can be prepared
by combining a minority hydrophobic phase with a majority aqueous phase.
Traditional oil-in-
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
22
water emulsions are discontinuous droplets of hydrophobic phase suspended
and/or stabilized
within a continuous aqueous phase. As the hydrophobic and aqueous phases are
immiscible,
generally only a small portion of the hydrophobic phase can be stabilized
within the aqueous phase
before macroscopic separation occurs.
A high internal phase emulsion can be either oil-in-water or water-in-oil
emulsion, wherein
there is a high amount of the internal, discontinuous phase, by volume or
weight of the multi-phase
composition, relative to a traditional emulsion. A high internal phase
emulsion can have more of
the internal, discontinuous phase, by volume or weight of the total multi-
phase composition than
the external, continuous phase, by volume or weight of the multi-phase
composition. However,
the stability of high internal phase emulsions can prove challenging. High
internal phase emulsions
can suffer from macroscopic separation upon mixing or during storage of the
high internal phase
emulsions prior to use by a consumer.
As described herein, a jammed emulsion may be an unexpectedly stable high
internal phase
emulsion. As the concentration of the discontinuous phase of a high internal
phase emulsion is
increased, regions of discontinuous phase can become sufficiently crowded,
such that they can jam
against each other with a region of continuous phase between them and deform
each other with a
region of continuous phase between them. If both the continuous phase and
discontinuous phase
are liquids, the emulsion can transition into an at least a partially
semisolid structure when the
jamming transition occurs. The jammed emulsion, as described herein, can be
prepared by the
portion-wise addition or gradual addition or slow addition of the
discontinuous phase to the
continuous phase. Simply combining the entire discontinuous phase to the
continuous phase will
not necessarily result in jammed emulsion.
The multi-phase oral care composition and/or jammed oil-in-water emulsion can
comprise
hydrophobic phase, aqueous phase, active agent, such as peroxide, and
optionally emulsifier.
Aqueous Phase
The aqueous phase can be at least partially continuous, essentially
continuous, or preferably
continuous. The multi-phase oral care composition and/or jammed oil-in-water
emulsion can
comprise from about 0.01% to about 25%, from about 1% to about 20%, from about
2.5% to about
20 %, or preferably from about 5% to about 15%, by weight or volume of the
multi-phase oral care
composition and/or jammed oil-in-water emulsion, of the aqueous phase.
The aqueous phase may also include other water-soluble solvents, such as for
example,
polyalkylene glycols with molecular weights from about 200 to about 20,000,
humectants, or
combinations thereof Suitable humectants generally include edible polyhydric
alcohols such as
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
23
glycerin, sorbitol, xylitol, butylene glycol, and propylene glycol, and
mixtures thereof. The
aqueous phase may comprise at least about 10%, at least about 20%, or at least
about 30%, of
water, by weight or volume of the aqueous phase. The multi-phase oral
compositions may
comprise an aqueous solution of a bleaching agent, such as hydrogen peroxide,
optionally
including emulsifier.
Hydrophobic Phase
The multi-phase oral care composition and/or jammed oil-in-water emulsion can
comprise
a hydrophobic phase. The hydrophobic phase can be at least partially
discontinuous, essentially
discontinuous, or preferably discontinuous.
The multi-phase oral care composition can comprise about 75% to about 99%,
from about
80% to about 97.5%, greater than about 80%, greater than about 90%, or
preferably, from about
85% to about 95%, by weight or volume of the multi-phase oral care composition
or jammed oil-
in-water emulsion, of the hydrophobic phase.
The density of the hydrophobic phase, as described herein, may be in the range
of from
about 0.8 g/cm3 to about 1.0 g/cm3, from about 0.85 g/cm3 to about 0.95 g/cm3,
or about 0.9 g/cm3,
or any other numerical range, which is narrower, and which falls within such
broader numerical
range, as if such narrower numerical ranges were all expressly written herein.
The hydrophobic phase can comprise a non-toxic oil, such as non-toxic edible
oil. The
hydrophobic phase can comprise non-toxic edible oils, saturated or unsaturated
fatty alcohols,
aliphatic hydrocarbons, long chain triglycerides, fatty esters, and
combinations thereof The
hydrophobic phase may also comprise silicones, polysiloxanes, and mixtures
thereof The
hydrophobic phase may be preferably selected from mineral oil, petrolatum, and
combinations
thereof.
Emulsifier
The multi-phase oral care composition and/or jammed oil-in-water emulsion can
comprise
one or more emulsifiers. Depending on the design of the multi-phase oral care
composition, the
hydrophobic phase can have emulsifying properties. Thus, the emulsifier and
the hydrophobic
phase can comprise the same compound.
The multi-phase oral care composition and/or jammed oil-in-water emulsion, as
described
herein, can comprise from about 0.001% to about 20%, from about 0.01% to about
10%, up to
about 10%, up to about 5%, or preferably from about 0.1% to about 10%, by
weight of the multi-
phase oral care composition or jammed oil-in-water emulsion, of the
emulsifier.
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
24
Classes of surfactants useful as emulsifiers include nonionic, anionic,
cationic, amphoteric,
polymeric, synthetic emulsifiers, and mixtures thereof. Many suitable nonionic
and amphoteric
surfactants are disclosed by U.S. Pat. No. 3,988,433; U.S. Pat No. 4,051,234,
and many suitable
nonionic surfactants are also disclosed by U.S. Pat. No. 3,959,458.
The emulsifier can comprise a polysorbate, an alkyl sulfate, Lipowax D, or
combinations
thereof. Suitable polysorbate compounds include, polysorbate 20, 40, 60, 80,
or combinations
thereof, such as Tween 20, 40, 60, 80, or combinations thereof.
The emulsifier can comprise natural emulsifiers, such as acacia, gelatin,
lecithin and
cholesterol; finely dispersed solids, such as colloidal clays, bentonite,
veegum (magnesium
aluminum silicate; and synthetic emulsifiers, such as salts of fatty acids,
sulfates such as sorbitan
trioleate, sorbitan tristearate, sucrose distearate, propylene glycol
monostearate, glycerol
monostearate, propylene glycol monolaurate, sorbitan monostearate, sorbitan
monolaurate,
polyoxyethylene-4-lauryl ether, sodium lauryl sulfate, sulfonates such as
dioctyl sosium
sulfosuccinate, glyceryl esters, polyoxyethylene glycol esters and ethers,
diethylene glycol
monostearate, PEG 200 distearate, and sorbitan fatty acid esters, such as
sorbitan monopalmitate,
and their polyoxyethylene derivatives, polyoxyethylene glycol esters such as
the monostearate,
Polysorbate 80 (ethoxylated sorbitan monooleate) (supplied by Spectrum, etc.);
and combinations
thereof.
The emulsifier can be a surfactant that is non-reactive with a bleaching
agent. For example,
surfactants that are non-reactive with a bleaching agent may be substantially
free of hydroxy
groups, nitrogen groups and linkages, double or triple covalent bonds between
adjacent carbon
atoms, metals such as Zn, etc., or combinations thereof.
Peroxide Release
Suitable oral care compositions include oral care compositions that have a
high amount of
peroxide release into the oral cavity. Suitable compositions include
Compositions A and B, as
described in TABLE 6. Other suitable compositions include oral care
compositions that have a %
peroxide diffusion of at least about 0.25%, at least about 0.5%, at least
about 1%, at least about
1.5%, at least about 2.5%, at least about 5%, and/or at least about 10% after
2 minutes. Other
suitable compositions include oral care compositions that have a % peroxide
diffusion of greater
than 13%, at least about 15%, at least about 25%, or at least about 45% after
15 minutes.
Other suitable compositions include oral care compositions that release at
least about
0.25%, at least about 0.5%, at least about 1%, at least about 1.5%, at least
about 2.5%, at least
about 5%, and/or at least about 10% of peroxide into an oral cavity of a user
within about 120
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
seconds of initial application to the oral cavity. Other suitable compositions
include oral care
compositions that release greater than 13%, at least about 15%, at least about
25%, or at least about
45% of peroxide into an oral cavity of a user within about 15 minutes of
initial application to the
oral cavity.
While not wishing to being bound by theory, it is believed that compositions
with a high %
peroxide diffusion according to the Peroxide Release Rate Method, as described
herein, will also
release a high amount of peroxide to the oral cavity.
EXAMPLES
The invention is further illustrated by the following examples, which are not
to be construed
in any way as imposing limitations to the scope of this invention. Various
other aspects,
modifications, and equivalents thereof which, after reading the description
herein, may suggest
themselves to one of ordinary skill in the art without departing from the
spirit of the present
invention or the scope of the appended claims.
Peroxide Release
A 15 mL dialysis cell (2K MWCO, Slide-A-Lyzer G2 Dialysis Cassette) was filled
with
WFI MilliQ Water (16 grams) and the cap affixed. To one side of the cassette a
test product was
applied covering the entire cell membrane surface at a depth defined by the
cell plastic housing by
leveling the applied product with a spatula. A piece of parafilm was applied
over the product
composition to protect it during cassette mixing during sampling. The cell was
placed either
vertically or horizontally product facing down on a tared balanced. A timer
was started post
product application and samples of the WFI MilliQ water within the cassette
were taken at the
defmed time points.
At each defined sample point, the cell was taken and inverted 180 degrees
twice, the lid
removed and a sample (0.3 ¨ 0.50g) pulled via a pipet. Following sampling, the
dialysis cell was
returned to the balance until the next sample was required. Each sample was
assayed for percent
peroxide as outlined below.
A Reflectoquant RQ Flex peroxide test strip reader (Millipore Sigma) was
calibrated using
both 0.2 ¨ 0.20 mg/L (604) and 100¨ 1000 mg/L (609) test strips (Supelco) with
peroxide standard
solutions as follows:
0.2 ¨ 20.0 mg/L strips:
1. 5 grams of 35% Hydrogen Peroxide was diluted to 500 grams total with WFI
MilliQ water.
2. 1 gram from (1) was diluted to 500 grams total weight using WFI MilliQ
water
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
26
3. 2 drops from (2) were applied to a 0.2 ¨ 20.0 mg/L test strip for 5
seconds and the excess
solution dabbed on a paper towel.
4. The test strip was inserted into a RQ Flex 10 with the 0.2 ¨ 20.0 mg/L
test strip program
loaded and the measurement recorded. Note total strip development and program
is 15 seconds in
duration. 5. 2 grams from solution (1) were diluted to 500 grams with WFI
MilliQ water and steps
(3) and (4) were repeated.
100¨ 1000 mg/L strips:
1. 0.5 grams of 35% Hydrogen Peroxide was diluted to 500 grams total with
USP water.
2. 2 drops from (1) were applied to a 0.2 ¨ 20.0 mg/L test strip for 10
seconds and the
excess solution dabbed on a paper towel. The strip was developed by sitting
for an additional 50
seconds.
3. The test strip was inserted into a RQ Flex 10 with 10 seconds remaining
on the 100 -
1000 mg/L test strip program and the measurement recorded. Note total strip
development and
program was approximately 60 seconds in duration for this test strip.
4. 1 gram of 35% Hydrogen Peroxide was diluted to 500 grams total with WFI
MilliQ water
5. The test strip was inserted into a RQ Flex 10 with the 100 - 1000 mg/L
test strip program
loaded and the measurement recorded.
Sample analysis
1. 2 drops from a given test sample time point were applied to a either a
0.2 ¨ 20.0 mg/L or
100 - 1000 mg/L test strip following the development time period and analysis
steps defined
above (a3-a4 & b2-b3).
2. The diffused peroxide concentration defined the appropriate strip to
use. If
concentrations exceeded the respective strip concentration ranges, serial
dilutions were
performed to bring the concentration into range.
The peroxide release rate was determined for four compositions. Composition A,
TABLE
1, and Composition B, TABLE 2A, are inventive compositions. Composition C and
Composition
D, TABLE 3, are commercial products marketed by the Colgate-Palmolive Company.
Composition C is Colgate Optic White Renewal Toothpaste, which is marketed to
include
hydrogen peroxide at 3% wt%. Composition D is Colgate Optic White Overnight,
which is also
marketed to include hydrogen peroxide at 4 wt%.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
27
TABLE 1. Composition A
Composition A
(wt%)
Mineral Oil 81.357
Water 14.141
Hydrogen Peroxide 3.0
Sucralose 0.35
Polysorbate 20 1.0
Flavor 1.4
Yield Stress 12.70 Pa
TABLE 1 shows the formulation for Composition A, a jammed oil-in-water
emulsion.
Composition A was produced by combining polysorbate 20, water, sucralose and
the aqueous
solution of H202 in a 20 gallon premix tank. The premix mixture was
transferred to a 400L vessel
and agitated while mineral oil was slowly added over 30 minutes. Flavor was
added next and the
batch stirred for 5 minutes. An oil-in-water emulsion was formed during this
step, and the
composition developed a lotion-like, semisolid consistency.
TABLE 2A. Composition B
Composition B
(wt%)
Water 62.365
Glycerin 10.0
Amphiphilic Polymer' 1.375
Sodium Lauryl Sulfate (28%) 7.0
Alkyl Alcohol2 1.25
Sodium Monofluorophosphate 1.14
Disodium Pyrophosphate 0.7
Tetrasodium Pyrophosphate 0.3
Sucralose 0.33
Calcium Pyrophosphate 10.0
H202 4.0
Flavor 1.54
Total 100
1Sepimax ZenTM
2Cetyl Alcohol:Stearyl Alcohol:SLS (45:45:10)
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
28
TABLE 2A shows the formulation of Composition B, a dentifrice composition
including
fluoride, 4 wt% peroxide, water, and abrasive. The release of peroxide into
the dialysis cell is
shown in TABLE 5, and additionally shown in Fig. 1.
TABLE 2B. Compositions
Example Example Example Example Example Example
1 2 3 4 5 6
(wt %) (wt%) (wt%) (wt%) (wt%) (wt%)
Water 56.33 56.83 57.33 56.58 56.83 57.08
Glycerin 10 10 10 10 10 10
Amphiphilic
2.25 2.25 1.25 2.25 1.75 1.5
Polymer'
SLS (28%) 5 5 5 5 5 5
Alkyl Alcohol2 1.25 0.75 1.25 1 1.25 1.25
Sodium
1.14 1.14 1.14 1.14 1.14 1.14
Monofluorophosphate
Disodium
0.7 0.7 0.7 0.7 0.7 0.7
Pyrophosphate
Tetrasodium
0.4 0.4 0.4 0.4 0.4 0.4
Pyrophosphate
Sucralose 0.3 0.3 0.3 0.3 0.3 0.3
Calcium
10 10 10 10 10
Pyrophosphate
H202(35%) 11.43 11.43 11.43 11.43 11.43 11.43
Flavor 1.2 1.2 1.2 1.2 1.2 1.2
1Sepimax ZenTM
2Cetyl Alcohol:Stearyl Alcohol:SLS (45:45:10)
TABLE 2B shows a variety of exemplary compositions that include different
amounts of
amphiphilic polymer (from 1.25 wt% to 2.25 wt%) and alkyl alcohol (from 0.75
wt% to 1.25 wt%).
Ex. 1-6 include sodium monofluorophosphate (1.14 wt%) , sodium lauryl sulfate
(1.4 wt%),
calcium pyrophosphate (10 wt%), and hydrogen peroxide (4 wt%).
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
29
TABLE 3. Comparative Compositions
Composition C Composition D
Colgate Optic White Renewal Colgate Optic White Overnight
Toothpaste
Propylene Glycol Alcohol
Calcium Pyrophosphate Acrylates/Octylacrylamide
PVP Water
PEG/PPG-116/66 Copolymer Hydrogen Peroxide
Hydrogen Peroxide
Flavor
Sodium Lauryl Sulfate
Tetrasodium Pyrophosphate
Sodium Saccharin
Disodium Pyrophosphate
Silica
Sucralose
BHT
TABLE 3 shows the ingredients listed on the carton for comparative examples
and
commercial products Composition C, Colgate Optic White Renewal toothpaste, and
Composition
D, Colgate Optic White Overnight whitening pen.
TABLE 4. Composition A, Peroxide Release Rate Sampling
Adjusted
Sample
Time Weight Strip Dilution Readings Readings
Avg
(s) (g) (mg/L) Factor (mg/L)
(mg/L)
Reading (mg/L)
Non-
1 0 0.33 0.2 - 20 NA NA 0
Detect
163
2 30 0.34 100 - 1000 NA NA 166
169
402
3 60 0.44 100 - 1000 NA NA 390
377
701
4 120 0.37 100 - 1000 NA NA 717
733
121 941
180 0.42 100 - 1000 7.77 983
132 1026
161 1368
6 240 0.41 100 - 1000 8.50
1334
153 1301
158 1511
7 300 0.37 100 - 1000 9.56
1525
161 1539
240 2040
8 450 0.46 100 - 1000 8.50
2015
234 1989
285 2722
9 600 0.49 100 - 1000 9.55
2799
301 2875
336 3531
900 0.50 100 - 1000 10.51 3263
285 2995
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
TABLE 4 shows an example of the procedure utilized to calculate the amount of
peroxide
(ppm) in the dialysis cell. As shown in TABLE 4, Composition A led to 717 ppm
of peroxide after
120 seconds, 1525 ppm of peroxide after 300 seconds, and 3263 ppm peroxide
after 900 seconds.
The same method of quantification shown in TABLE 4, was used to determine the
concentration
of the dialysis cell at various times with Composition B, Composition C, and
Composition D.
TABLE 5. Peroxide Release
Peroxide Concentration (ppm) at Diffusion Time
Composition Al Composition B
Composition C Composition D
Time
Inventive Inventive Comparative
Comparative
0 0 0 0 0
30 166 15 0 0
60 390 39 0 0
120 717 150 0 2
180 983 268 1 10
240 1334 392 5 18
300 1525 513 9 45
450 2015 795 28 135
600 2799 1003 65 181
900 3263 1529 219 252
TABLE 5 shows the peroxide concentration of each dialysis cell after a loading
of
Composition A-D after a defined period of time. As shown in TABLE 5,
Composition A and
Composition B, resulted in 717 ppm and 150 ppm, respectively, of hydrogen
peroxide in the
dialysis cell after 120 seconds. Compositions C and D resulted in less than 1
ppm and 2 pm,
respectively, of peroxide in the dialysis cell after 120 seconds.
Additionally, Composition A and
Composition B resulted in 3263 ppm and 1529 ppm, respectively, of peroxide in
the dialysis cell
after 900 seconds. Composition C and Composition D resulted in 219 ppm and 252
ppm,
respectively, of peroxide in the dialysis cell after 900 seconds. Thus,
membranes loaded with
Compositions A and Composition B, both including hydrogen peroxide in
solution, led to increased
delivery of hydrogen peroxide across the membrane.
CA 03211176 2023-08-16
WO 2022/178530
PCT/US2022/070717
31
TABLE 6. % Peroxide Diffused after 2 Minutes
Composition Product Loading Product % % Peroxide % Peroxide
(grams) Peroxide Diffused
after Diffused after 15
2 minutes minutes
A 3.55 3 10.8% 49%
B 3.99 4 1.5% 15%
C 4.61 3 0.001% 2.5%
D 0.76 4 0.13% 13%
TABLE 6 shows the relative amount of peroxide that diffused into the dialysis
cell after a
defined period of time. 9.3-10.8% of the total amount of peroxide in
Compositions A diffused into
the dialysis cell after 2 minutes. 49% of the total amount of peroxide in
Composition A diffused
into the dialysis cell after 15 minutes. 1.5% of the total amount of peroxide
in Composition B
diffused into the dialysis cell after 2 minutes. 16% of the total amount of
peroxide in Composition
B diffused into the dialysis cell after 15 minutes. In contrast, 0.001% and
0.13% of Composition
C and Composition D diffused into the dialysis cell after 2 minutes and 2.5%
and 13% of
Composition C and Composition D diffused into the dialysis cell after 15
minutes.
Thus, compositions, such as toothpaste compositions and jammed oil-in-water
emulsion
compositions, that included peroxide and water led to an increased diffusion
of peroxide into the
dialysis cell. It has been surprisingly found that peroxide in composition
including water can have
a high peroxide release rate, as shown in TABLE 6 with Composition A and
Composition B, and
hydrate the oral cavity. While not wishing to being bound by theory, it is
believed that by
minimizing reactivity with the remaining components in the oral care
composition, including the
abrasive, peroxide can be formulated in a composition including water.
While not wishing to being bound by theory, it is believed that peroxide that
is stabilized
through complexation and placed in an anhydrous chassis can lead to lower
amounts of available
of peroxide to provide health and cosmetic benefits, as shown in TABLE 6 with
Composition C
and Composition D. Additionally, anhydrous compositions can be dehydrating,
leading to
additional sensitivity challenges.
The dimensions and values disclosed herein are not to be understood as being
strictly
limited to the exact numerical values recited. Instead, unless otherwise
specified, each such
dimension is intended to mean both the recited value and a functionally
equivalent range
surrounding that value. For example, a dimension disclosed as "40 mm" is
intended to mean "about
40 mm."
CA 03211176 2023-08-16
WO 2022/178530 PCT/US2022/070717
32
Every document cited herein, including any cross referenced or related patent
or application
and any patent application or patent to which this application claims priority
or benefit thereof, is
hereby incorporated herein by reference in its entirety unless expressly
excluded or otherwise
limited. The citation of any document is not an admission that it is prior art
with respect to any
invention disclosed or claimed herein or that it alone, or in any combination
with any other
reference or references, teaches, suggests or discloses any such invention.
Further, to the extent
that any meaning or definition of a term in this document conflicts with any
meaning or definition
of the same term in a document incorporated by reference, the meaning or
defmition assigned to
that term in this document shall govern.
While particular embodiments of the present invention have been illustrated
and described,
it would be obvious to those skilled in the art that various other changes and
modifications can be
made without departing from the spirit and scope of the invention. It is
therefore intended to cover
in the appended claims all such changes and modifications that are within the
scope of this
invention.
