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Patent 2772119 Summary

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(12) Patent: (11) CA 2772119
(54) English Title: ORAL CARE COMPOSITIONS AND METHODS
(54) French Title: COMPOSITIONS ET PROCEDES POUR SOINS BUCCODENTAIRES
Status: Granted and Issued
Bibliographic Data
(51) International Patent Classification (IPC):
  • A61K 8/96 (2006.01)
  • A61K 8/30 (2006.01)
  • A61K 8/31 (2006.01)
  • A61K 8/34 (2006.01)
  • A61K 8/49 (2006.01)
  • A61Q 11/00 (2006.01)
(72) Inventors :
  • RAJAIAH, JAYANTH (United States of America)
  • BAIG, ARIF ALI (United States of America)
(73) Owners :
  • THE PROCTER & GAMBLE COMPANY
(71) Applicants :
  • THE PROCTER & GAMBLE COMPANY (United States of America)
(74) Agent: WILSON LUE LLP
(74) Associate agent:
(45) Issued: 2014-07-15
(86) PCT Filing Date: 2010-08-17
(87) Open to Public Inspection: 2011-02-24
Examination requested: 2012-02-16
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US2010/045677
(87) International Publication Number: US2010045677
(85) National Entry: 2012-02-16

(30) Application Priority Data:
Application No. Country/Territory Date
61/234,512 (United States of America) 2009-08-17

Abstracts

English Abstract

Advantageous oral care composition can include a water insoluble carrier, sweetener, and an additional component selected from the group consisting of flavors, sensates, and combinations thereof.


French Abstract

L'invention concerne une composition avantageuse pour soins buccodentaires qui peut comprendre un support insoluble dans l'eau, un édulcorant et un composant supplémentaire choisi dans le groupe constitué par les arômes, les agents sensoriels et leurs combinaisons.

Claims

Note: Claims are shown in the official language in which they were submitted.


20
What is claimed is:
1. An oral care composition, comprising:
a) from about 80% to about 99%, by weight of the composition, of a water
insoluble carrier selected from microcrystalline wax, paraffin wax, bees wax,
petrolatum, mineral oil, polybutene, silicone, natural oil, synthetic oil,
polyethylene, or combinations thereof,
b) from about 0.5% to about 10%, by weight of the composition, of a sweetener
selected from saccharin, sucralose, Rebiana, xylitol, aspartame, Acesulfame
K, mono ammoniated glycyrrhizinate, or mixtures thereof, and
c) an additional component selected from a combination of a sensate selected
from menthol; 3-1-menthoxypropane-1,2-diol, menthyl lactate; N,2,3-
trimethyl-2-isopropylbutanamide; N-ethyl-p-menthan-3-carboxamide; N-(4-
cyanomethylphenyl)-p-menthanecarboxamide, and combinations thereof and a
flavor selected from mint, wintergreen, spice, vanilla, fruit, citrus, cocoa,
tea,
or a combination thereof;
wherein the ratio of sensate to flavor is from about 0.25 to about 2.0, the
ratio
by weight of flavor to sweetener is from about 1.0 to about 4.0, the ratio by
weight of sensate to sweetener is from about 1.0 to about 4.0, and the ratio
by
weight of the flavor plus the sensate to sweetener is from about 0.4 to about
40.
2. The oral care composition of claim 1, further comprising monoalkyl
phosphate.
3. The oral care composition of claim 1 or 2, wherein the ratio by weight of
flavor to
sweetener is from about 1.5 to about 2.5.
4. The oral care composition of any one of claims 1 to 3, wherein the ratio by
weight
of sensate to sweetener is from about 1.5 to about 2.5.

21
5. The oral care composition of any one of claims 1 to 4, wherein the
composition
comprises from about 1% to about 10% by weight of flavor and from about 1% to
about 10% by weight of sensate.
6. The oral care composition of any one of claims 1 to 5, wherein the ratio by
weight
of flavor plus sensate to sweetener is from about 2.0 to about 8Ø
7. The oral care composition of claim 1, wherein the oral care composition
consists
of petrolatum as the water insoluble carrier, saccharin as the sweetener, mint
as
the flavor, and menthol as the sensate.
8. The oral care composition of claim 1, wherein the oral care composition
consists
of the water insoluble carrier, sweetener, and additional component.

Description

Note: Descriptions are shown in the official language in which they were submitted.


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1
ORAL CARE COMPOSITIONS AND METHODS
FIELD OF THE INVENTION
This application relates to oral care compositions with a water insoluble
component and
varying combinations of sweetener, flavor, and/or sensate, and methods
relating thereto.
BACKGROUND OF THE INVENTION
Historically, oral care products like dentifrices and rinses have been used
for cleansing
the oral cavity. Because these products often get their cleaning effect from
surfactants and
surfactants generally give a better result in a water based environment, these
products generally
utilize water soluble components as their base. For deposition, however, these
water soluble
chassis have several disadvantages. For one, the water soluble chassis are
quickly washed away
in the mouth due to interaction with saliva meaning the residence time for
anything deposited in
these chassis is often very short. As such, there is a need for oral care
compositions and methods
which give a better deposition profile in the oral cavity.
Additionally, in order to promote consumer use and acceptance, taste is an
import aspect
of an oral care product. Thus, consumer product companies work to not only
provide a product
with a benefit, but to make that product acceptable to the consumer. Thus,
there is a need for
improved flavor combinations for oral care products.
SUMMARY OF THE INVENTION
One embodiment of the present invention is directed to an oral care
composition,
consisting essentially of a water insoluble carrier, a sweetener, and an
additional component
selected from the group consisting of a sensate, a flavor, and combinations
thereof. The oral care
composition is configured for application within the oral cavity.
According to another embodiment, the present invention is directed to an oral
care
composition which includes from about 50 % to about 99 % of a water insoluble
carrier, from
about 0.5% to about 10% a sweetener, and an additional component selected from
the group
consisting of a sensate, a flavor, and combinations thereof. The oral care
composition is
configured for application to the teeth.
In yet another embodiment, the present invention is directed to an oral care
composition,
consisting essentially of: petrolatum; saccharin; mint oil; and menthol. The
oral care
composition is configured for application to the teeth.
These and other embodiments will be better understood in light of the
disclosure below.

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DETAILED DESCRIPTION
DEFINITIONS
The term "sensate" as used herein refers to a material in which its
predominant effect in
the oral cavity is to impart a sensation, for example, a warming, cooling,
and/or tingling
sensation.
The term "flavor" as used here refers to a material in which its predominant
effect in the
oral cavity is to impart a taste, excluding sweeteners.
The term "sweetener" as used herein refers to a material in which its
predominant effect
in the oral cavity is to impart a sweet taste.
The term "water-insoluble" as used herein refers to a material that is less
than about 10%
soluble in water, unless specifically stated otherwise.
The term "about", when used in conjunction with a numerical value, refers to a
range of
+/- 10% of the value it precedes; so "about 10%" would mean from 9.0% to
11.0%.
All percentages and ratios herein are by weight of total composition, unless
otherwise
indicated.
DESCRIPTION OF THE INVENTION
Oral care products have variable functions within the oral cavity. For
instance, when
looking to clean the oral cavity, a consumer will generally look to toothpaste
or a mouth rinse.
To provide this cleaning benefit, both pastes and rinses generally use a
foaming water soluble
chassis. The foam provided in these chassis provides a cleaning action which
can be used in
combination with a brush or actives to provide a further cleaning benefit.
Other oral care
products provide more of an aesthetic function, like breath freshening. These
products come in
many forms from dissolvable strips to mints. The one thing most all of these
products have in
common is that they are generally water soluble. The water soluble nature of
these products
limits the length of time for which they can provide their benefit as the
benefit providing
components are solubilized and/or washed away by the saliva in the oral
cavity.
It has now been surprisingly discovered that water insoluble carriers can be
used in oral
care compositions to give improved delivery of oral care components to the
oral cavity. Some of
these oral care components include, for example, sensates, flavors, and
sweeteners. The use of
the water insoluble carrier allows for a longer residence time in the oral
cavity for the oral care
components and thus provides a longer lasting benefit. For example, in some
instances, the
water-insoluble carrier can be detected in the mouth even an hour or more
after application.

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WATER INSOLUBLE CARRIER
Water insoluble components can be used as a carrier in the present invention.
In varying
embodiments, the water insoluble carrier is less than about 10%, 8%, 5%, 4%,
3%, 2% or 1%
soluble in water. In one embodiment the water-insoluble carrier is at a level
from about 25, 30,
35, 40, 45, 50, 55, 60, 65% to about 45, 50, 55, 60, 65, 70, 75, 80, 85, 90,
95, 99%, and/or any
combination thereof, by weight of the composition. In varying embodiments the
water-insoluble
carrier level is from about 80% to about 99%, from about 80% to about 95%, or
from about 85%
to about 95% by weight of the composition. In another embodiment, the water
insoluble carrier
is at least about 75% by weight of the oral care composition. In yet another
embodiment the
water-insoluble carrier is both water-insoluble and non-swellable in water.
In other
embodiments, the water insoluble carrier comprises a gel, liquid, or mixtures
thereof. The water-
insoluble carrier may be a combination of two or more water-insoluble
components.
In one embodiment, the water insoluble carrier is selected from the group
consisting of:
natural wax, synthetic wax, petrolatum, rubber, elastomer, plastomer,
polyvinyl chloride, nylon,
polyvinyl acetate, natural oils, synthetic oils, fats, silicone, hydrocarbons,
essential oils,
caprilic/capric triglycerides, polybutene, oleic acid, stearic acid,
fluorocarbon, polyurethane
prepolymer, polyethylene, polystyrene, polypropylene, and mixtures thereof. In
another
embodiment the water-insoluble carrier is a PDMS gum, or a mixture of PDMS gum
with an MQ
resin cast from a solvent such as volatile isoparrafin (see US Patent
6,074,654).
In one embodiment the water-insoluble carrier comprises a natural wax,
synthetic wax, or
a combination thereof. Natural waxes include, for example, animal, vegetable,
and mineral wax.
Animal waxes include, for example, beeswax, lanolin, shellac wax, Chinese wax,
etc. Vegetable
waxes include carnauba, candelilla, bayberry, sugar cane, etc., and mineral
waxes include fossil
and earth waxes (ozocerite, ceresin, montan), and petroleum waxes such as
paraffin,
microcrystalline, etc. In one embodiment the waxes herein are natural waxes
selected from the
group consisting of beeswax, candelilla, candela, carnauba, paraffin,
microcrystalline wax,
Fischer-Tropsch waxes, and mixtures thereof.
Examples of natural oils include, but are not limited to, vegetable oils (ex.
corn oil), soy
bean oils, cottonseed oils, palm oils, coconut oils, mineral oils, animal oils
(ex. fish oils), etc.
Examples of synthetic oils include, but are not limited to, silicone oils,
etc. In one embodiment,
the water insoluble component comprises a natural oil. In a further
embodiment, the natural oil
comprises mineral oil. In one embodiment, mineral oil is present in the
composition at an

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amount from about 30% to about 50% and in another embodiment, from about 35%
to about
45%.
Examples of elastomers include, but are not limited to, Ethylene-Ethylene-
Propylene
rubber, Ethylene-Propylene rubber, Styrene-Ethylene¨Propylene-Styrene rubber,
and
combinations thereof, and these may optionally be further combined with waxes.
In one embodiment, the water insoluble carrier comprises microcrystalline wax,
paraffin
wax, bees wax, petrolatum, mineral oil, polybutene, silicone, natural oil,
synthetic oil,
polyethylene, or combinations thereof. In a further embodiment, the water
insoluble carrier is
selected from the group consisting of polybutene, silicones, petrolatum, and
combinations
thereof. In another embodiment, the carrier comprises petrolatum. In yet
another embodiment,
the carrier consists essentially of petrolatum.
While several specific embodiments of water insoluble carriers are listed
herein, it is
envisioned other suitable combinations are also possible and within the scope
of invention.
SENSATES
The present invention may include one or more components that provide a
sensory
benefit, often called a sensate. Sensates can have sensory attributes such as
a warming, tingling,
or cooling sensation. Suitable sensates include, for example, menthol, menthyl
lactate, leaf
alcohol, camphor, clove bud oil, eucalyptus oil, anethole, methyl salicylate,
eucalyptol, cassia, 1-
8 menthyl acetate, eugenol, oxanone, alpha-irisone, propenyl guaethol, thymol,
linalool,
benzaldehyde, cinnamaldehyde glycerol acetal known as CGA, and mixtures
thereof.
In one embodiment, the sensate comprises a coolant. The coolant can be any of
a wide
variety of materials. Included among such materials are carboxamides, menthol,
ketals, diols,
and mixtures thereof. Some examples of carboxamide coolants include, for
example,
paramenthan carboxyamide agents such as N-ethyl-p-menthan-3-carboxamide, known
commercially as "WS-3", N,2,3-trimethy1-2-isopropylbutanamide, known as "WS-
23," and N-(4-
cyanomethylpheny1)-p-menthanecarboxamide, known as G-180 and supplied by
Givaudan. G-
180 generally comes as a 7.5% solution in a flavor oil, such as spearmint oil
or peppermint oil.
Examples of menthol coolants include, for example, menthol; 3-1-
menthoxypropane-1,2-diol
known as TK-10, manufactured by Takasago; menthone glycerol acetal known as
MGA
manufactured by Haarmann and Reimer; and menthyl lactate known as Frescolat
manufactured
by Haarmann and Reimer. The terms menthol and menthyl as used herein include
dextro- and
levorotatory isomers of these compounds and racemic mixtures thereof.
In one embodiment, the sensate comprises a coolant selected from the group
consisting of

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menthol; 3- 1-menthoxypropane- 1,2-diol , menthyl
lactate; N,2,3-trimethy1-2-
isopropylbutanamide; N-ethyl-p-menthan-3-c arboxamide ;
N-(4-cyanomethylpheny1)-p-
menthanecarboxamide, and combinations thereof. In a further embodiment, the
sensate
comprises menthol; N,2,3-trimethy1-2-isopropylbutanamide; N-(4-
cyanomethylphenye-p-
5 menthanecarboxamide; or a combination thereof. In one embodiment, the
sensate comprises
menthol. In another embodiment, the sensate consists essentially of menthol.
The amount of sensate employed is normally a matter of preference subject to
such
factors as type and strength of effect desired. Sensates can be present in
amounts up to about
40% by weight of the oral care composition. In varying embodiments, the
sensates can be
present from about 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10%, to about 2, 5,
6, 7, 8, 9, 10, 12, 15, 20,
30, or 40%, or any combination thereof. In varying embodiments, the sensate is
present in an
amount from about 0.1% to about 20.0%, from about 1% to about 10%, or from
about 3% to
about 6% by weight of the total composition.
FLAVORS
The present invention may include one or more components that provide a flavor
benefit.
The flavoring component can be chosen from natural and synthetic flavorings.
Natural flavors
can include, for example, oils derived from plant leaves, flowers, fruits and
so forth. Some
representative flavorings include, for example, vanilla, sage, marjoram,
parsley oil, spearmint oil,
cinnamon oil, wintergreen oil (methylsalicylate), and peppermint oils. Also
useful herein are
artificial, natural or synthetic fruit flavors. These include, for example,
citrus oil including
lemon, orange, banana, grape, lime, apricot and grapefruit and fruit essences
including apple,
strawberry, cherry, orange, pineapple and so forth; bean and nut derived
flavors such as coffee,
cocoa, cola, peanut, almond and so forth. These can be in any form including
liquid, powder, etc.
Additionally, flavor adsorbed onto a hydrophilic matrix may be included, e.g.
"spray-dried"
flavors. Furthermore, encapsulated flavors may be included.
In one embodiment, the flavor is selected from mint, wintergreen, spice,
vanilla, fruit,
citrus, cocoa, tea, or a combination thereof. In one embodiment, the flavor
component is selected
from the group consisting of peppermint, spearmint, vanilla, cinnamon,
wintergreen, mint,
strawberry, grape, apple, and combinations thereof. In a further embodiment,
the flavor
component comprises mixed mint, peppermint, spearmint, wintergreen, or a
combination thereof.
In an additional embodiment, the flavor component comprises peppermint.
The amount of flavor employed is normally a matter of preference subject to
such factors
as type and strength of effect desired. Flavors can be present in amounts up
to about 40%. In

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varying embodiments, the flavor can be present from about 0.1, 0.5, 1, 2, 3,
4, 5, 6, 7, 8, 9, or
10%, to about 2, 5, 6, 7, 8, 9, 10, 12, 15, 20, 30, or 40%, or any combination
thereof. In varying
embodiments, the flavor is present in an amount from about 0.1% to about
20.0%, from about 1%
to about 10%, or from about 3% to about 6% by weight of the total composition.
SWEETENERS
The present invention may include one or more components that provide a
sweetening
benefit. Suitable sweeteners include both natural and artificial sweeteners.
The sweeteners can
be water-soluble or water-insoluble. The sweetener may also be an intense
sweetener.
Some examples of sweeteners include dextrose, sucrose, maltose, dextrin, dried
invert
Intense sweeteners are often dipeptide based. Some examples of intense
sweeteners
include monellin, haumatoccous danielli, and L-aspartyl L-phenylalanine methyl
ester and
In one embodiment, the sweetener is selected from the group consisting of
dextrose,
sucrose, maltose, dextrin, dried invert sugar, mannose, xylose, ribose,
glucose, fructose, levulose,
galactose, corn syrup, high fructose corn syrup, corn syrup solids, partially
hydrolyzed starch,
aspartame, saccharin, sugar alcohols, hydrogenated starch, monellin,
haumatoccous danielli, L-
The amount of the sweetener will vary with the type of sweetener selected and
the desired
level of sweetness. Sweeteners can be present in amounts up to about 20%. In
other
embodiments the sweeteners can be present from about 0.1, 0.15, 0.25, 0.5,
0.75, 1, 1.25, 1.5,
1.75, 2, 2.25, 2.5, 2.75, 3, 4, 5, or 10%, to about 1, 2, 3, 4, 5, 10, or 20%,
or any combination

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OTHER COMPONENTS
In addition to those components listed above, the oral care composition may
additionally
include other components. One example of these additional components includes
substantivity
agents. One group of substantivity agents is organophosphates. Suitable
organophosphate
compounds have a strong affinity for the tooth surface and have sufficient
surface binding
propensity to desorb pellicle proteins and remain affixed thereon. The
phosphate groups of the
organophosphate attach themselves to cations, in particular calcium ions in
teeth or some other
positively charged sites such as protein residues on the mucosal surface and
thus serve to anchor
the hydrophobic portion of the molecule onto the surface thereby modifying it
to be hydrophobic.
The phosphate groups provide ready bonding/binding to cationic and charged
surfaces via
electrostatic interaction, hydrogen bonding, or complexation, which leads to
ready deposition of
the organophosphate upon application to form a coating on the treated surface.
The strong bond
results in longer retention or durability and substantivity of the coating.
Examples of suitable organophosphate compounds are mono-, di- or triesters
represented
by the following general structure wherein Z1, Z2, or Z3 may be identical or
different, at least one
being an organic moiety, preferably selected from linear or branched, alkyl or
alkenyl group of
from 6 to 22 carbon atoms, optionally substituted by one or more phosphate
groups; alkoxylated
alkyl group or alkoxylated alkenyl group.
0
I
Z1-0¨PI-0¨Z2
I
0¨Z3
Some preferred agents include alkoxylated alkyl or alkenyl phosphate esters
represented by the
following structure:
0
II
R1¨(0CnH2n)a(0CmH2m)b¨O¨P-0¨Z2
I
0¨Z3
wherein Rl represents a linear or branched, alkyl or alkenyl group of from 6
to 22 carbon atoms,
optionally substituted by one or more phosphate groups; n and m, are
individually and separately,

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2 to 4, and a and b, individually and separately, are 0 to 20; Z2 and Z3 may
be identical or
different, each represents hydrogen, alkali metal, ammonium, protonated alkyl
amine or
protonated functional alkyl amine such as an alkanolamine, or a
R1¨(0C,1112,1)a(OCmH2m)b¨
group. Preferably, Rl is an alkyl group of at least 10 carbon atoms and a and
b are each no more
than 10 in order to maintain overall hydrophobic character of the
organophosphate and the degree
of hydrophobicity imparted to the surface.
In one embodiment, the substantivity agent includes mono- di- and tri- alkyl
and alkyl
(poly)alkoxy phosphates such as dodecyl phosphate, lauryl phosphate; laureth-1
phosphate;
laureth-3 phosphate; laureth-9 phosphate; dilaureth-10 phosphate; trilaureth-4
phosphate; C12-18
PEG-9 phosphate and salts thereof. Many are commercially available from
suppliers including
Croda; Rhodia; Nikkol Chemical; Sunjin; Alzo; Huntsman Chemical; Clariant and
Cognis. In
one embodiment, the substantivity agent comprises monoalkyl phosphate.
Another example of an additional component includes actives. Some examples of
actives
include various fluoride salts for caries prevention and remineralization;
gingivitis prevention by
the use of antimicrobial agents such as triclosan, cetylpyridinium chloride,
stannous fluoride,
zinc citrate or essential oils; and hypersensitivity control through the use
of ingredients such as
strontium chloride, stannous fluoride, or potassium nitrate; pyrophosphate
salts can be used as
antitartar agents; peroxides can be used for bleaching and antiseptics; and
polymeric mineral
surface active agents such as phosphorylated polymers, in particular
polyphosphates that bind to
teeth, or metal ions such as stannous, zinc or copper that form insoluble
compounds that deposit
onto teeth, can be used for erosion protection or sensitivity protection.
These actives can be used
alone or in combination.
Another example of an additional component includes adhesive components. The
present
invention may comprise a safe and effective amount of an adhesive component,
generally at a level of
from about 1% to about 75% by weight of the composition. In other embodiments,
the adhesive
component is in the range of from about 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%,
40% to about 10%,
15%, 20%, 50%, 60%, 75%, or any combination thereof. In one particular
embodiment, the adhesive
component is in an amount from about 10.0% to about 60.0%. In another
embodiment, the adhesive
component is in an amount from about 1% to about 15%.
In general, adhesive components are hydrophilic particles that become sticky
when activated by
moisture or are hydrophilic liquids. For those that activate with moisture,
moisture can be present, for
example, in the oral care composition itself as well as in the oral cavity of
the user. In varying
embodiments, the adhesive components herein are mucoadhesive, adhesive to the
teeth, hydrophilic, water
soluble, have the property of swelling upon exposure to moisture, or any
combination thereof.

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In one embodiment the adhesive component is selected from the group consisting
of: glycerin,
polyoxamer, sorbitol, polyox, carbomer, polyacrylamides, polypeptides, natural
gums; synthetic
polymeric gums; AVE/MA; AVE/MA/IB; copolymers of maleic acid or anhydride and
ethylene, styrene,
and/or isobutylene, polyacrylic acid and/or polyacrylates thereof;
polyitaconic acid, mucoadhesive
.. polymers; water-soluble hydrophilic colloids; saccharide; cellulose;
cellulosic resin, acrylic resin, their
derivatives, and mixtures thereof. Examples of such materials include karaya
gum; guar gum; gelatin;
algin; sodium alginate; tragacanth; chitosan; acrylamide polymers;
carboxypolymethylene; polyvinyl
alcohol; polyamines; polyquarternary compounds; polyvinylpyrrolidone or its
copolymers; cationic
polyacrylamide polymers; salts and mixed salts of AVE/MA; polymeric acids,
polymeric salts, and
.. copolymers thereof; polyitaconic acid salts; polyhydroxy compounds; their
derivatives; and mixtures
thereof.
In another embodiment, the adhesive component is selected from the group
consisting of:
cellulose, cellulose derivatives (such as methylcellulose,
carboxymethylcellulo se, hydroxyethylcellulose,
hydroxypropylcellulose, hydroxy-propylmethylcellulose, corn starch, and
mixtures thereof), starch, starch
.. derivatives, saccharide, saccharide derivatives, polyethylene oxides,
polyethylene glycols, polyvinyl
alcohols, carrageenan, alginates, karaya gums, xanthan gums, guar gums,
gelatins, algins, tragacanth,
chitosan, acrylamide polymers, carboxypolymethylenes, polyamines, poly
quaternary compounds,
polyvinylpyrrolidone, AVE/MA, salts of AVE/MA, mixed salts of AVE/MA,
polymeric acids, polymeric
salts, polyhydroxy compounds, and mixtures thereof.
RATIOS
Furthermore, it has been surprisingly discovered that specific combinations
and/or ratios
of sweeteners, sensates, and/or flavors, delivered via water-insoluble
carriers to the oral cavity
provide a high level of consumer recognizable benefits such as fresh feeling,
clean feeling, slick
teeth, smooth teeth, and fresh breath. In addition, it was also surprisingly
discovered that
.. consumer acceptability of a water insoluble carrier based oral care
composition was highest when
a sweetener is present.
Thus, even though water insoluble carrier systems offer some additional
flexibility in
formulation from water soluble carrier based systems, there appears to be a
particular range of
ratios within the system for the sweetener, flavor, and sensate in order to
produce a consumer
.. acceptable product. Thus, the compositions of the present invention with
the components present
in the specific ratios disclosed herein are believed to offer superior flavor
benefits to those
compositions that do not contain the components disclosed herein or are
present in different
ratios, and thus, give a more consumer acceptable product. Since consumer
acceptance helps
drive the use of the product, it is an important feature in the development of
a successful product.
The first ratio is the weight of sensate to the weight of flavor ("R1"). This
ratio is

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WO 2011/022343 PCT/US2010/045677
calculated by dividing the weight percentage of sensate by the weight
percentage of flavor. In
one embodiment, this ratio is from about 0 to about 4Ø In another
embodiment, this ratio is
from about 0.25 to about 2Ø In another embodiment, this ratio is about 1Ø
The second ratio is for the weight of flavor to the weight of sweetener in the
oral care
5 composition ("R2"). To calculate this ratio, the weight percentage of
flavor is divided by the
weight percentage of sweetener. In one embodiment, this ratio is from about 0
to about 20. In
another embodiment, the ratio is from about 1.0 to about 4Ø In another
embodiment, the ratio is
from about 1.5 to about 2.5. In a further embodiment, the ratio is about 2Ø
The next ratio is for the weight of sensate to the weight of sweetener ("R3").
This ratio is
10 calculated by dividing the weight percentage of sensate by the weight
percentage of sweetener.
In one embodiment, this ratio is from about 0 to about 20. In another
embodiment, the ratio is
from about 1.0 to about 4Ø In another embodiment, the ratio is from about
1.5 to about 2.5. In
a further embodiment, the ratio is about 2Ø
The last ratio is the weight of sensates and weight of flavors to the weight
of sweetener
("R4"). This ratio is calculated by adding the weight percentage of sensates
to the weight
percentage of flavors and dividing that total by the weight percentage of
sweeteners. In one
embodiment, this ratio is from about 0.4 to about 40. In varying embodiments,
this ratio is from
about 2.0 to about 8Ø, from about 3.0 to about 7.0, or from about 3.0 to
about 5Ø In an
additional embodiment, the ratio is about 4Ø
These ratios can be used to help define a consumer acceptable oral care
product for a
water insoluble base. For example, in one embodiment, R1 is from about 0.25 to
about 4.0, R2 is
from about 0.2 to about 20, and R3 is from about 0.2 to about 20. In another
embodiment, R1 is
from about 0.5 to about 2.0, R2 is from about 1.0 to about 4.0, and R3 is from
about 1.0 to about
4Ø In another embodiment, R1 is about 1.0, R2 is about 2.0, and R3 is about

ORAL CARE COMPOSITIONS
Various combinations of the water insoluble carrier, sweetener, flavor, and/or
sensate are
possible and are considered within the scope of the invention, a few specific
combinations are
discussed below.
In one embodiment, an oral care composition comprises a water insoluble
carrier, a
sweetener, and an additional component selected from a sensate, a flavor, or
combination thereof.
In another embodiment, an oral care composition consists essentially of a
water insoluble carrier,
a sweetener, and an additional component selected from a sensate, a flavor, or
a combination
thereof. Both of these embodiments are configured for application within the
oral cavity. In one

CA 02772119 2012-02-16
WO 2011/022343 PCT/US2010/045677
11
embodiment, the oral care compositions are configured for application to the
teeth.
In a further embodiment, the oral care composition comprises at least 75% by
weight of
the water insoluble carrier. In another embodiment, the water insoluble
carrier is from about
70% to about 99% by weight of the oral care composition. In an additional
embodiment, the
water insoluble carrier is from about 50% to about 99% by weight of the oral
care composition.
In another embodiment, the water insoluble carrier is rubber and/or natural
wax and/or
synthetic wax and/or polyvinyl chloride and/or nylon and/or fluorocarbon
and/or polyurethane
prepolymer and/or polyethylene and/or polystyrene and/or polypropylene and/or
petrolatum
and/or polyvinyl acetate and/or natural oil and/or synthetic oil and/or fats
and/or silicone and/or
hydrocarbons and/or caprilic/capric triglycerides and/or oleic acid and/or
stearic acid and/or
mixtures thereof. In one embodiment, the water insoluble carrier comprises
microcrystalline wax
and/or paraffin wax and/or bees wax and/or petrolatum and/or mineral oil
and/or polybutene
and/or silicone and/or natural oil and/or synthetic oil and/or polyethylene
and/or combinations
thereof. In a further embodiment, the water insoluble carrier is selected from
the group
consisting of polybutene and/or silicones and/or petrolatum and/or
combinations thereof. In
another embodiment, the carrier comprises petrolatum. In yet another
embodiment, the carrier
consists essentially of petrolatum.
In a further embodiment, the oral care composition comprises from about 0.5%
to about
10% by weight of a sweetener. In one embodiment, the sweetener is selected
from a group
consisting of dextrose, fructose, corn syrup, high fructose corn syrup,
aspartame, saccharin, sugar
alcohols, and mixtures thereof. In a one embodiment, the sweetener is selected
from the group
consisting of saccharin, sucralose, Rebiana, xylitol, aspartame, Acesulfame K,
mono ammoniated
glycyrrhizinate, and mixtures thereof.
In another embodiment, the sweetener comprises
saccharin, sucralose, Rebiana, or a combination thereof.
In another embodiment, the sum of the weight percentages of the sweetener and
the
additional component is less than about 25%. In another embodiment the sum of
the weight
percentages of the sweetener and the additional component is less than 25%. In
an additional
embodiment, the sum of the weight percentages of the sweetener and the
additional component is
from about 8% to about 15%.
In one embodiment, the additional component comprises a flavor. In a further
embodiment, the flavor is selected from the group consisting of: peppermint,
spearmint, vanilla,
cinnamon, wintergreen, mint, strawberry, grape, apple, and combinations
thereof. In a further
embodiment, the flavor component comprises mixed mint, peppermint, spearmint,
wintergreen,

CA 02772119 2012-02-16
WO 2011/022343 PCT/US2010/045677
12
or a combination thereof. In an additional embodiment, the flavor component
consists essentially
of mint. In one embodiment, the ratio of flavor to sweetener is from about 0.2
to about 20.
In one embodiment, the additional component comprises a sensate. In one
embodiment,
the sensate comprises a coolant. In another embodiment, the sensate is
selected from the group
consisting of menthol, menthyl lactate, leaf alcohol, camphor, clove bud oil,
eucalyptus oil,
anethole, methyl salicylate, eucalyptol, cassia, 1-8 menthyl acetate, eugenol,
oxanone, alpha-
irisone, propenyl guaethol, thymol, linalool, benzaldehyde, cinnamaldehyde
glycerol acetal, and
mixtures thereof. In another embodiment, the sensate is selected from the
group consisting of
menthol; 3 -1 -menthoxyprop ane-1,2-diol ; methyl lactate; N,2,3-trimethy1-2-
isopropylbutanamide;
N-ethyl-p-menthan-3-c arboxamide ; N-(4-cyanomethylphenye- p-
menthanecarboxamide, and
combinations thereof. In a further embodiment, the sensate comprises menthol;
N,2,3-trimethy1-
2-isopropylbutanamide; N-(4-cyanomethylpheny1)-p-menthanecarboxamide; or a
combination
thereof. In an additional embodiment, the ratio of sensate to sweetener is
from about 0.2 to about
20.
In another embodiment, the additional component comprises a combination of
flavor and
sensate. In one embodiment, the ratio by weight of flavor plus sensate to
sweetener is from about
0.4 to about 40. In another embodiment, the ratio by weight of sensate to
flavor is from about 0.5
to about 2.0, the ratio by weight of flavor to sweetener is from about 1.0 to
about 4.0, the ratio by
weight of sensate to sweetener is from about 1.0 to about 4.0, and the ratio
by weight of flavor
plus sensate to sweetener is from about 2.0 to about 8Ø In an additional
embodiment, the oral
care composition comprises from about 1% to about 10% by weight of flavor and
from about 1%
to about 10% by weight of sensate.
In one embodiment, the oral care composition comprises a water soluble carrier
comprising microcrystalline wax and/or paraffin wax and/or bees wax and/or
petrolatum and/or
mineral oil and/or polybutene and/or silicone and/or natural oil and/or
synthetic oil and/or
polyethylene; and a flavor comprising peppermint and/or spearmint and/or
vanilla and/or
cinnamon and/or wintergreen and/or mint and/or strawberry and/or grape and/or
apple; and a
sweetener comprising dextrose and/or fructose and/or corn syrup and/or high
fructose corn syrup
and/or aspartame and/or saccharin and/or sugar alcohols; and a sensate
comprising menthol
and/or menthyl lactate and/or leaf alcohol and/or camphor and/or clove bud oil
and/or eucalyptus

CA 02772119 2012-02-16
WO 2011/022343 PCT/US2010/045677
13
oil and/or anethole and/or methyl salicylate and/or eucalyptol and/or cassia
and/or 1-8 menthyl
acetate and/or eugenol and/or oxanone and/or alpha-irisone and/or propenyl
guaethol and/or
thymol and/or linalool and/or benzaldehyde and/or cinnamaldehyde glycerol
acetal; wherein the
ratio by weight of sensate to flavor is from about 0.5 to about 2.0 and/or the
ratio by weight of
flavor to sweetener is from about 1.0 to about 4.0 and/or the ratio by weight
of sensate to
sweetener is from about 1.0 to about 4.0 and/or and the ratio by weight of
flavor plus sensate to
sweetener is from about 2.0 to about 8Ø
In one specific embodiment, the oral care composition consists of a water
insoluble
carrier, a sweetener, and an additional component selected from the group
consisting of sensate,
flavor, and combinations thereof, wherein the ratio by weight of sensate to
flavor is from about
0.5 to about 2.0 and/or the ratio by weight of flavor to sweetener is from
about 1.0 to about 4.0
and/or the ratio by weight of sensate to sweetener is from about 1.0 to about
4.0 and/or and the
ratio by weight of flavor plus sensate to sweetener is from about 2.0 to about
8Ø In another
specific embodiment, an oral care composition consists essentially of
petrolatum, saccharin, mint
oil, and menthol and is configured for application to the teeth, wherein the
ratio by weight of
sensate to flavor is from about 0.5 to about 2.0 and/or the ratio by weight of
flavor to sweetener
is from about 1.0 to about 4.0 and/or the ratio by weight of sensate to
sweetener is from about 1.0
to about 4.0 and/or and the ratio by weight of flavor plus sensate to
sweetener is from about 2.0
to about 8Ø In another embodiment, the ratio by weight of flavor plus
sensate to sweetener is
from about 0.4 to about 40. In another embodiment, the ratio by weight of
sensate to flavor is
about 1.0, the ratio by weight of flavor to sweetener is about 2.0, the ratio
by weight of sensate to
sweetener is about 2.0, and the ratio by weight of flavor plus sensate to
sweetener is about 4Ø
In one embodiment the composition is free of surfactants, abrasives, fluoride
sources,
therapeutic actives, muco-adhesives, polybutenes, silicones, and/or
antimicrobial agents. In one
embodiment, the oral care composition is not a dentifrice. In another
embodiment, the oral care
composition is not a rinse. In another embodiment, the oral care composition
is not a denture
adhesive.
In one embodiment, the oral care composition will be in the form of a liquid
or gel. The
liquid or gel form of the oral care composition may be applied with an
applicator. The applicator

CA 02772119 2013-07-24
14
may be used with any oral care applicator, for example, a swab, brush, foam
tipped applicator, etc.
While a few embodiments are discussed above, additional embodiments enabled
based on
the discussion above, for example specific types of each component, its weight
percentages, and
ratios, are believed to also be within the scope of the invention.
METHODS OF USE
The oral care composition as discussed herein may be used to deliver any oral
care
components compatible with the water insoluble carrier to the oral cavity. For
example, an oral
care composition may be used as a breath freshener by including a breath
freshening agent, like a
flavor, in the oral care composition or the composition may be used as an
active delivery vehicle
by including an active.
Without being limited by theory, it is also believed there will be benefits to
a consumer
due to the formation of a water insoluble layer on the teeth upon application.
Thus, the oral care
composition can be used to form a water insoluble barrier on the teeth. Some
benefits expected
from such a barrier include: reduction in caries, plaque, and calculus due at
least in part to the
inability of bacteria to stick to the teeth, reduction in sensitivity due at
least in part to the
blocking of dentin tubules, reduction in erosion and prevention of staining
due at least in part to
the coating operating as a barrier to erosive agents, and overall improvements
in mouth feel
impression and/or appearance which can be broadly characterized as aesthetics,
such as shine,
gloss, luster, smoothness, slickness, and clean mouth feel.
EXAMPLES
Example 1 ¨ Various Compositions of the Invention
The following non-limiting examples further illustrate and describe the
embodiments of
the subject invention wherein both essential and optional ingredients are
combined. It is to be
understood that the examples are given solely for the purpose of illustration
and are not to be
construed as limiting the invention described herein, as many variations
thereof are possible
without departing from the invention described herein.

CA 02772119 2013-07-24
A BCDEF GH,I J K
% % % % % % % % % % ...
%
Microcrystalline
Wax W835 0 48 0 0 48 0 0 0 10 10 0
Mineral Oil 0 42 0 0 34 0 0 0 0 0 0
Petrolatum 90 0 0 82 0 90 89 88 80 79 94
Mixed Mint
Flavor 4 4 4 8 8 8 2 4 4 4 4
Menthol 4 4 4 8 8 1 8 4 4 4 0
Saccharin
(Powder) 2 2 2 2 2 1 1 4 2 2 2
Versagel 750 M
(or 1600 M) 0 0 90 0 0 0 0 _ 0 0 1 0
100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0
RI 1.00
1.00 1.00 1.00 1.00 0.13 4.00 1.00 1.00 1.00 0.00
R2 2.00
2.00 2.00 4.00 4.00 8.00 2.00 1.00 2.00 2.00 2.00
R3 2.00
2.00 2.00 4.00 4.00 1.00 8.00 1.00 2.00 2.00 0.00
R4 4.00
4.00 4.00 8.00 8.00 9.00 10.00 2.00 4.00 4.00 2.00
To make the above example compositions B, E, I, and 3 the wax is melted at 95
C and the
other components are mixed into it at the elevated temperature. To make the
above examples A,
5 C, D, F, G, H, and K the petrolatum and/or VersagelTm is heated to about
70 C and the other
components are mixed in at the elevated temperature. For all examples, the
compositions are
allowed to come to room temperature prior to use.
Furthermore, each of the above example formulations may also be mixed with
each other
to provide hybrid-examples.
EXAMPLE 2 - RATIOS
A B C
% % %
Petrolatum 90 92 94
Saccharin 2 0 2
Mint 4 4 0
Menthol 4 4 4
100.0 100.0 100.0
RI 1.00 1.00 >100
R2 2.00 >100 0.00
R3 2.00 >100 2.00
R4 4.00 >100 2.00

CA 02772119 2012-02-16
WO 2011/022343 PCT/US2010/045677
16
To make the above examples A, B, and C, the petrolatum is heated to about 70 C
and the
other components are mixed in at the elevated temperature. For all examples,
the compositions
are allowed to come to room temperature prior to use. After the samples are
made, they are
placed into a container. The consumer preference for taste is tested by
allowing a consumer to
dip a disposable lip gloss applicator into the container and tasting the
sample. The consumer
then picks the sample they prefer. The consumer also rates each sample on a
scale of -4 to +4
(with -4 being "Dislike Extremely" and +4 being "Like Extremely"). Each of
Samples B and C
are directly compared with Sample A, so each consumer tests Sample A versus
Sample B, then
Sample A versus Sample C. The preferences and ratings for these comparisons
are below.
Sample A vs. Sample B Sample A vs. Sample C
Rating Sample A is preferred over Sample A is preferred over
Sample B by 100% of the Sample C by 67% of the
Panelists Panelists
Sample A is rated: 2.4 Sample A is rated: 2.11
Sample B is rated: -1.8 Sample C is rated: 0.67
The above results indicate Sample A is strongly preferred over and rated much
higher
than Sample B. Specifically, Sample A, with R1/R2/R3/R4 ratios of 1/2/2/4, is
strongly
preferred over and rated much higher than Sample B with R1/R2/R3/R4 ratios of
1/>100/>100/>100.
The above results also indicate that Sample A is preferred over and rated
higher than
Sample C. Specifically, Sample A, with R1/R2/R3/R4 ratios of 1/2/2/4, is
preferred over and
rated higher than Sample B with R1/R2/R3/R4 ratios of >100/0/2/2.

CA 02772119 2012-02-16
WO 2011/022343 PCT/US2010/045677
17
EXAMPLE 3 - RATIOS
A
Petrolatum 91.8 98.5 91.8 90
Saccharin 0.16 0.3 0.16 2
Mint 4 0.6 4 4
Menthol 4 0.6 4 4
100.0 100.0 100.0 100.0
R1 1.00 1.00 1.00 1.00
R2 25.00 2.00 25.00 2.00
R3 25.00 2.00 25.00 2.00
R4 50.00 4.00 50.00 4.00
To make the above examples A, B, C, and D, the petrolatum is heated to about
70 C and
the other components are mixed in at the elevated temperature. For all
examples, the
compositions are allowed to come to room temperature prior to use. After the
samples are made,
they are placed into a container. The consumer preference for taste is tested
by allowing a
consumer to dip a disposable lip gloss applicator into the container and
tasting the sample. The
consumer then picks the sample they prefer. The consumer also rates each
sample on a scale of -
4 to +4 (with -4 being "Dislike Extremely" and +4 being "Like Extremely"). The
preferences
and ratings for these comparisons are below.
Sample A vs. Sample B Sample C vs. Sample D
Rating Sample B is preferred over Sample D is preferred over
Sample A by 75% of the Sample C by 90% of the
Panelists Panelists
Sample A is rated: 0.63 Sample C is rated : 0.9
Sample B is rated: 1.75 Sample D is rated: 2.3
The above results indicate Sample B is preferred over and rated higher than
Sample A.
Specifically, Sample B, with R1/R2/R3/R4 ratios of 1/2/2/4, is preferred over
and rated higher
than Sample A with R1/R2/R3/R4 ratios of 1/25/25/50.

CA 02772119 2012-02-16
WO 2011/022343 PCT/US2010/045677
18
The above results also indicate that Sample D is strongly preferred over and
rated much
higher than Sample C. Specifically, Sample D, with R1/R2/R3/R4 ratios of
1/2/2/4, is strongly
preferred over and rated much higher than Sample C with R1/R2/R3/R4 ratios of
1/25/25/50.
EXAMPLE 4- LEVEL
A
Petrolatum 98.5 90.0
Saccharin 0.3 2
Mint 0.6 4
Menthol 0.6 4
100.0 100.0
R1 1.00 1.00
R2 2.00 2.00
R3 2.00 2.00
R4 4.00 4.00
To make the above examples A and B, the petrolatum is heated to about 70 C and
the
other components are mixed in at the elevated temperature. For all examples,
the compositions
are allowed to come to room temperature prior to use. After the samples are
made, they are
placed into a container. The consumer preference for taste is tested by
allowing a consumer to
dip a disposable lip gloss applicator into the container and tasting the
sample. The consumer
then picks the sample they prefer. The consumer also rates each sample on a
scale of -4 to +4
(with -4 being "Dislike Extremely" and +4 being "Like Extremely"). The
preferences and
ratings for these comparisons are below.
Sample A vs. Sample B
Rating Sample B is preferred over
Sample A by 80% of the
Panelists
Sample A is rated: 0.5
Sample B is rated: 1.8

CA 02772119 2012-02-16
19
The above results indicate Sample B is preferred over and rated higher than
Sample A.
Specifically, Sample B, with a total Saccharin+Mint+Menthol level of 10% [and
R 1/R2/R3/R4
ratios of 1/2/2/4], is preferred over and rated higher than Sample A with
total
Saccharin+Mint+Menthol level of 1.5% [and the same RI /R2/R3/R4 ratios of
1/2/2/4].
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.
The citation of any document, including any cross referenced or related patent
or
application, 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 cited herein, the meaning or definition 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 invention described
herein. It is therefore
intended to cover in the appended claims all such changes and modifications
that are within the
invention described herein.

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Administrative Status

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Event History

Description Date
Common Representative Appointed 2019-10-30
Common Representative Appointed 2019-10-30
Appointment of Agent Requirements Determined Compliant 2016-12-22
Inactive: Office letter 2016-12-22
Inactive: Office letter 2016-12-22
Revocation of Agent Requirements Determined Compliant 2016-12-22
Revocation of Agent Request 2016-12-01
Change of Address or Method of Correspondence Request Received 2016-12-01
Appointment of Agent Request 2016-12-01
Inactive: Office letter 2016-11-28
Inactive: Adhoc Request Documented 2016-11-28
Revocation of Agent Request 2016-11-03
Appointment of Agent Request 2016-11-03
Grant by Issuance 2014-07-15
Inactive: Cover page published 2014-07-14
Inactive: Final fee received 2014-04-25
Pre-grant 2014-04-25
Notice of Allowance is Issued 2013-10-29
Letter Sent 2013-10-29
4 2013-10-29
Notice of Allowance is Issued 2013-10-29
Inactive: Approved for allowance (AFA) 2013-10-25
Inactive: Q2 passed 2013-10-25
Amendment Received - Voluntary Amendment 2013-07-24
Inactive: S.30(2) Rules - Examiner requisition 2013-01-24
Inactive: Cover page published 2013-01-03
Inactive: IPC assigned 2012-07-24
Inactive: IPC assigned 2012-07-24
Inactive: IPC assigned 2012-07-24
Inactive: IPC assigned 2012-07-24
Inactive: IPC assigned 2012-07-24
Inactive: IPC removed 2012-07-24
Inactive: First IPC assigned 2012-07-04
Inactive: IPC assigned 2012-07-04
Letter Sent 2012-04-25
Letter Sent 2012-04-25
Letter Sent 2012-04-25
Inactive: Acknowledgment of national entry - RFE 2012-04-25
Inactive: IPC assigned 2012-04-03
Application Received - PCT 2012-04-03
National Entry Requirements Determined Compliant 2012-02-16
Request for Examination Requirements Determined Compliant 2012-02-16
All Requirements for Examination Determined Compliant 2012-02-16
Application Published (Open to Public Inspection) 2011-02-24

Abandonment History

There is no abandonment history.

Maintenance Fee

The last payment was received on 2013-08-14

Note : If the full payment has not been received on or before the date indicated, a further fee may be required which may be one of the following

  • the reinstatement fee;
  • the late payment fee; or
  • additional fee to reverse deemed expiry.

Patent fees are adjusted on the 1st of January every year. The amounts above are the current amounts if received by December 31 of the current year.
Please refer to the CIPO Patent Fees web page to see all current fee amounts.

Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
THE PROCTER & GAMBLE COMPANY
Past Owners on Record
ARIF ALI BAIG
JAYANTH RAJAIAH
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 2012-02-15 19 943
Abstract 2012-02-15 1 50
Claims 2012-02-15 3 77
Description 2012-02-16 19 942
Claims 2012-02-16 2 78
Cover Page 2012-10-25 1 27
Description 2013-07-23 19 951
Claims 2013-07-23 2 51
Cover Page 2014-06-18 1 27
Maintenance fee payment 2024-07-01 30 1,219
Acknowledgement of Request for Examination 2012-04-24 1 177
Notice of National Entry 2012-04-24 1 203
Courtesy - Certificate of registration (related document(s)) 2012-04-24 1 104
Courtesy - Certificate of registration (related document(s)) 2012-04-24 1 104
Commissioner's Notice - Application Found Allowable 2013-10-28 1 161
Correspondence 2014-04-24 1 34
Correspondence 2016-11-02 3 128
Correspondence 2016-11-30 3 131
Courtesy - Office Letter 2016-12-21 2 379
Courtesy - Office Letter 2016-12-21 2 394
Courtesy - Office Letter 2016-11-27 138 5,840