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Patent 2373863 Summary

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(12) Patent Application: (11) CA 2373863
(54) English Title: HAIR CONDITIONING COMPOSITION COMPRISING CATIONIC SILICONE EMULSION
(54) French Title: COMPOSITION POUR LE CONDITIONNEMENT DES CHEVEUX COMPRENANT UNE EMULSION CATIONIQUE DE SILICONE
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • A61K 8/895 (2006.01)
  • A61K 8/891 (2006.01)
(72) Inventors :
  • VENKATESWARAN, ANANTHANARAYAN (Japan)
  • NAKAMURA, KIICHIRO (Japan)
(73) Owners :
  • THE PROCTER & GAMBLE COMPANY (United States of America)
(71) Applicants :
  • THE PROCTER & GAMBLE COMPANY (United States of America)
(74) Agent: DIMOCK STRATTON LLP
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 2000-06-27
(87) Open to Public Inspection: 2001-01-11
Examination requested: 2001-12-21
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US2000/017648
(87) International Publication Number: WO2001/001937
(85) National Entry: 2001-12-21

(30) Application Priority Data:
Application No. Country/Territory Date
PCT/US99/15112 United States of America 1999-07-02

Abstracts

English Abstract




Disclosed is a hair conditioning composition comprising by weight: a) from
about 0.1 % to about 20 % of a cationic silicone emulsion comprising by weight
of the cationic silicone emulsion from about 1 % to about 20 % of a cationic
surfactant; and an emulsifiable amount of a silicone compound having a
particle size of less than about 50 microns; b) from about 0.1 % to about 15 %
of a high melting point fatty compound having a melting point of 25 ~C or
higher; c) from about 0.1 % to about 10 % of a cationic conditioning agent;
and d) an aqueous carrier.


French Abstract

L'invention concerne une composition pour le conditionnement des cheveux, comprenant en poids a) environ 0,1 % à 20 % d'une émulsion cationique de silicone qui renferme environ 1 % à 20 % d'un tensioactif cationique, et une quantité d'un composé de silicone émulsionnable dont la taille de particule est inférieure à environ 50 microns; b) environ 0,1 % à 15 % d'un composé gras à point de fusion élevé égal ou supérieur à 25 ·C; c) environ 0,1 % à 10 % d'un agent cationique de conditionnement; et d) un milieu aqueux.

Claims

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





WHAT IS CLAIMED IS:

1. A hair conditioning composition comprising by weight:
(a) from about 0.1% to about 20% of a cationic silicone emulsion comprising
by weight of the cationic silicone emulsion from about 1% to about 20% of
a cationic surfactant; and an emulsifiable amount of a silicone compound
having a particle size of less than about 50 microns;
(b) from about 0.1% to about 15% of a high melting point fatty compound
having a melting point of 25°C or higher;
(c) from about 0.1% to about 10% of a cationic conditioning agent; and
(d) an aqueous carrier.

2. The hair conditioning composition according to Claim 1 wherein the
cationic silicone emulsion comprises by weight from about 2% to about 8% of
the
cationic surfactant.

3. The hair conditioning composition according to Claim 1 wherein the
silicone compound has a particle size of from about 0.2 microns to about 2.5
microns.

4. The hair conditioning composition according to Claim 1 wherein the
silicone compound comprises a mechanically emulsified polydimethylsiloxane.

5. The hair conditioning composition according to Claim 1-4 comprising by
weight from about 0.55% to about 7% of the cationic conditioning agent; the
cationic conditioning agent comprising:
an amidoamine having the following general formula:

R1 CONH (CH2)m N (R2)2
wherein R1 is a residue of C11 to C24 fatty acids, R2 is a C1 to C4 alkyl, and
m
is an integer from 1 to 4; and
a acid selected from the group consisting of L-glutamic acid, lactic acid,
hydrochloric acid, malic acid, succinic acid, acetic acid, fumaric acid, L-
glutamic
acid hydrochloride, tartaric acid, and mixtures thereof.



32



6. The hair conditioning composition according to Claim 1-4 further
comprising by weight from about 0.1% to about 10% of a low melting point oil
having a melting point of less than 25°C.

7. The hair conditioning composition according to Claim 6 wherein the low
melting point oil is an unsaturated fatty alcohol.

8. The hair conditioning composition according to Claim 6 wherein the low
melting point oil is selected from the group consisting of:
(a) pentaerythritol ester oils having a molecular weight of at least about
800,
and having the following formula:

Image

wherein R1, R2, R3, and R4, independently, are branched, straight, saturated,
or
unsaturated alkyl, aryl, and alkylaryl groups having from 1 to about 30
carbons;
(b) trimethylol ester oils having a molecular weight of at least about 800,
and
having the following formula:

Image

wherein R11 is an alkyl group having from 1 to about 30 carbons, and R12, R13,
and R14, independently, are branched, straight, saturated, or unsaturated
alkyl,
aryl, and alkylaryl groups having from 1 to about 30 carbons;
(c) poly .alpha.-olefin oils derived from 1-alkene monomers having from about
6 to
about 16 carbons, the poly .alpha.-olefin oils having a viscosity of from
about 1 to
about 35,000 cst, a molecular weight of from about 200 to about 60,000, and a
polydispersity of no more than about 3;
(d) citrate ester oils having a molecular weight of at least about 500, and
having the following formula:



33



Image

wherein R21 is OH or CH3COO, and R22, R23, and R24, independently, are
branched, straight, saturated, or unsaturated alkyl, aryl, and alkylaryl
groups
having from 1 to about 30 carbons;
(e) glyceryl ester oils having a molecular weight of at least about 500, and
having the following formula:

Image

wherein R41, R42, and R43, independently, are branched, straight, saturated,
or
unsaturated alkyl, aryl, and alkylaryl groups having from 1 to about 30
carbons;
and mixtures thereof.

9. The hair conditioning composition according to Claim 7 further comprising
by weight from about 0.1% to about 10% of a polyethylene glycol having the
formula:

H(OCH2CH2)n -OH

wherein n has an average value of from 2,000 to 14,000.

10. A method of increasing hair volume by applying the hair conditioning
composition according to any of the preceding claims to the hair.



34

Description

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



CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
HAIR CONDITIONING COMPOSITION COMPRISING
CATIONIC SILICONE EMULSION
TECHNICAL FIELD
The present invention relates to hair conditioning composition comprising
a cationic silicone emulsion.
BACKGROUND
Human hair becomes soiled due to its contact with the surrounding
environment and from the sebum secreted by the scalp. The soiling of hair
causes it to have a dirty feel and an unattractive appearance. The soiling of
the
hair necessitates shampooing with frequent regularity.
Shampooing cleans the hair by removing excess soil and sebum.
However, shampooing can leave the hair in a wet, tangled, and generally
unmanageable state. Once the hair dries, it is often left in a dry, rough,
lusterless, or frizzy condition due to removal of the hair's natural oils and
other
natural conditioning and moisturizing components. The hair can further be left
with increased levels of static upon drying, which can interfere with combing
and
result in a condition commonly referred to as "fly-away hair", or contribute
to an
undesirable phenomena of "split ends", particularly for long hair.
A variety of approaches have been developed to alleviate these after-
shampoo problems. These approaches range from post-shampoo application of
hair conditioners such as leave-on and rinse-off products, to hair
conditioning
shampoos which attempt to both clean and condition the hair from a single
p rod a ct.
Although some consumers prefer the ease and convenience of a
shampoo which includes conditioners, a substantial proportion of consumers
prefer the more conventional conditioner formulations which are. applied to
the
hair as a separate step from shampooing, usually subsequent to shampooing.
Conditioning formulations can be in the form of rinse-off products or leave-on
products, and can be in the form of an emulsion, cream, gel, spray, and
mousse.
Such consumers who prefer the conventional conditioner formulations value the
relatively higher conditioning effect, or convenience of changing the amount
of
conditioning depending on the condition of hair or amount of hair.


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
Japanese Patent Publication (laid-open) No.10-7534 discloses a hair
conditioning composition containing a cationic surfactant and an emulsion
polymerized silicone emulsion. It is disclosed this composition provides
shining,
smoothness, softness, and free-flowing feeling to the hair.
Generally, hair conditioner compositions which provide benefits described
above are also known to provide hair volume-down. For consumers who desire
hair volume-up such as consumers having fine hair, the effect of hair volume-
down is not desirable. The term "hair volume-up" as used herein is not equal
to
fly-away hair. Fly-away hair is due to the increased level of static, and
represents
volume increase of only very minor amount of the hair as a whole, and is not
desirable. On the other hand, hair volume-up as used herein relates to
increase
of the bulk of the hair volume. Consumers having fine hair have the desire to
achieve hair volume-up while controlling undesirable fly-away of the hair.
Based on the foregoing, there remains a desire to provide hair
conditioning compositions which provide hair volume-up while not deteriorating
conditioning benefits such as softness, moisturized feel, and fly-away
control.
There is also a desire to provide such hair conditioning compositions while
maintaining acceptable rheology profiles so as to satisfactory spreadability
on the
hair, and so as to be made by a convenient manufacturing method.
None of the existing art provides all of the advantages and benefits of the
present invention.
SUMMARY
The present invention is directed to a hair conditioning composition
comprising by weight:
(a) from about 0.1 % to about 20% of a cationic silicone emulsion comprising
by weight of the cationic silicone emulsion from about 1 % to about 20% of
a cationic surfactant; and an emulsifiable amount of a silicone compound
having a particle size of less than about 50 microns;
(b) from about 0.1 % to about 15% of a high melting point fatty compound
having a melting point of 25°C or higher;
(c) from about 0.1 % to about 10% of a cationic conditioning agent; and
(d) an aqueous carrier.
These and other features, aspects, and advantages of the present
invention will become evident to those skilled in the art from a reading of
the
present disclosure.
2


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
DETAILED DESCRIPTION
While the specification concludes with claims which particularly point out
and distinctly claim the invention, it is believed the present invention will
be better
understood from the following description.
All cited references are incorporated herein by reference in their entireties.
Citation of any reference is not an admission regarding any determination as
to
its availability as prior art to the claimed invention.
Herein, "comprising" means that other steps and other ingredients which
do not affect the end result can be added. This term encompasses the terms
"consisting of and "consisting essentially of'.
All percentages, parts and ratios are based upon the total weight of the
compositions of the present invention, unless otherwise specified. All such
weights as they pertain to listed ingredients are based on the active level
and,
therefore, do not include carriers or by-products that may be included in
commercially available materials.
CATIONIC SILICONE EMULSION
The hair conditioning composition of the present invention comprises a
cationic silicone emulsion. The cationic silicone emulsion herein is a pre-
dispersed stable emulsion comprising at least a cationic surfactant, a
silicone
compound, and water.
The cationic silicone emulsion herein provides increase in bulk hair
volume while not deteriorating conditioning benefits such as fly-away control.
It is
of particular significance that, in the present invention the cationic
surfactant is
present in the silicone emulsion, and not just in the bulk of the composition.
Cationic surfactant is typically included in the bulk of a conditioning
composition
for hair conditioning benefits such as fly-away control, however can also
reduce
bulk hair volume. It has been surprisingly found that when cationic surfactant
is
included in the silicone emulsion, increase in bulk hair volume is
significantly
improved than when the same amount of cationic surfactant is included in the
bulk of the composition.
The cationic silicone emulsion herein also provides acceptable rheology
profiles in the conditioning composition of this invention, so this
composition
provides satisfactory spreadability on the hair, and can be made by a
convenient
manufacturing method.
3


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
The cationic silicone emulsion comprises, by weight of the cationic silicone
emulsion, from about 1 % to about 20%, preferably from about 2% to about 8%,
of a cationic surfactant; and an emulsifiable amount of silicone compound. The
silicone compound is preferably comprised from about 0.1 % to about 70%, more
preferably from about 5% to about 60% by weight of the cationic silicone
emulsion. The amount of silicone compound to the entire composition is
preferably from about 0.1 % to about 10% by weight.
The cationic silicone emulsion is included in the composition at a level by
weight from about 0.1 % to about 20%, more preferably from about 0.5% to about
5%.
The cationic silicone emulsion can be made by any convenient method
known in the art.
For example, the cationic silicone emulsion may be made by mechanical
emulsification by taking a polysiloxane polymer and emulsifying it in water in
the
presence of at least one emulsifying agent using mechanical means such as
agitation, shaking and homogenization. The emulsifying agent can be the
cationic surfactant comprised in the cationic silicone emulsion, or other
suitable
surfactant. Mechanical emulsification may require use of two or more
surfactants, and two or more mixing processes using different surfactants. Two
or more types of silicone compounds, such as a highly viscous silicone
compound and a low viscosity silicone compound, may be used. One particularly
preferred process for obtaining the cationic silicone emulsion of the present
invention via mechanical emulsification is through the process disclosed in EP
Publication 460,683A, which is incorporated herein by reference in its
entirety. In
this reference, it is disclosed that the emulsion is prepared by combining the
polysiloxane, water, and a primary nonionic surfactant having an HLB value of
15-19 to form a first mixture, adding to the first mixture a co-surfactant
selected
from the group consisting of nonionic, cationic and anionic surfactants having
an
HLB value of 1.8-15 to form a second mixture and mixing the second mixture at
a
temperature of about 40°C, until the particle size of the polysiloxane
in the
emulsion is less than about three hundred nanometers.
The cationic silicone emulsion herein may be made by emulsion
polymerization. An emulsion polymerization process includes taking a
polysiloxane monomer and/or oligomer and emulsifying it in water in the
presence of a catalyst to form the polysiloxane polymer. It is understood that
unreacted monomers and oligomers may remain in an emulsion polymerized
4


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
silicone emulsion. One particularly preferred process for obtaining the
cationic
silicone emulsion of the present invention via emulsion polymerization is
through
the process disclosed in GB application 2,303,857, which is incorporated
herein
by reference in its entirety. This reference discloses a process for making
stable
cationic silicone oil-in-water emulsion comprising: 1 ) blending a mixture of
silicones selected from the group consisting of cyclic silicone oligomers,
mixed
silicone hydrolyzates, silanol stopped oligomers, high molecular weight
silicone
polymers, and functionalized silicones with 2) water, and 3) an anionic
surfactant;
4) heating the blend to a temperature ranging from about 75 to about
98°C for a
period of time ranging from about 1 hours to about 5 hours; 5) cooling the
heated
blend to a temperature ranging from 0 to about 25°C for a period of
time ranging
from about 3 hours to about 24 hours; 6) adding a compatibilizing surfactant
selected from the group consisting of nonionic surfactant having an HLB ratio
greater than 9; and 7) adding a cationic surfactant.
The silicone compound in the cationic silicone emulsion has a particle size
of less than about 50 microns, preferably from about 0.2 to about 2.5 microns,
more preferably from about 0.2 to about 0.5 microns. The particle size of the
silicone compound is believed to affect the deposition of the silicone
compound
on the hair. The particle size of the silicone compound is determined based on
the desired deposition and uniformity of distribution of the silicone
compound.
The silicone particle size herein is measured by a laser analyzing
equipment using Coulter Model N4SD available from Coulter Electronics, Inc.
(Hialeah, FL, U.S.A.) using a spectrophotometer containing a Laser 4mW helium
neon (632.8nm) and RS-232C serial interface. The particle size is analyzed via
unimodal fit.


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
Cationic Surfactant
The cationic silicone emulsion herein comprises a cationic surfactant. The
cationic surfactant useful herein is any known to the artisan, and is
preferably
included in the cationic silicone emulsion at a level by weight from about 1 %
to
about 20%, more preferably from about 2% to about 8%.
Among the cationic surfactants useful herein are those corresponding to
the general formula (I):
R


N _


R R X


14


R


wherein at least one of R1, R2, R3, and R4 is selected from an aliphatic group
of
from 8 to 30 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido,
hydroxyalkyl, aryl or alkylaryl group having up to about 22 carbon atoms, the
remainder of R1, R2, R3, and R4 are independently selected from an aliphatic
group of from 1 to about 22 carbon atoms or an aromatic, alkoxy,
polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up
to
about 22 carbon atoms; and X is a salt-forming anion such as those selected
from halogen, (e.g. chloride, bromide), acetate, citrate, lactate, glycolate,
phosphate, nitrate, sulfonate, sulfate, alkylsulfate, and alkyl sulfonate
radicals.
The aliphatic groups can contain, in addition to carbon and hydrogen atoms,
ether linkages, and other groups such as amino groups. The longer chain
aliphatic groups, e.g., those of about 12 carbons, or higher, can be saturated
or
unsaturated. Preferred is when R1, R2, R3, and R4 are independently selected
from C1 to about C22 alkyl. Nonlimiting examples of cationic surfactants
useful
in the present invention include the materials having the following CTFA
designations: quaternium-8, quaternium-14, quaternium-18, quaternium-18
methosulfate, quaternium-24, and mixtures thereof.
Among the cationic surfactants of general formula (I), preferred are those
containing in the molecule at least one alkyl chain having at least 16
carbons.
Nonlimiting examples of such preferred cationic surfactants include: behenyl
trimethyl ammonium chloride available, for example, with tradename
INCROQUAT TMC-80 from Croda and ECONOL TM22 from Sanyo Kasei; cetyl
trimethyl ammonium chloride available, for example, with tradename CA-2350
from Nikko Chemicals, hydrogenated tallow alkyl trimethyl ammonium chloride,
6


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
dialkyl (14-18) dimethyl ammonium chloride, ditallow alkyl dimethyl ammonium
chloride, dehydrogenated tallow alkyl dimethyl ammonium chloride, distearyl
dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride,
di(behenyl/arachidyl) dimethyl ammonium chloride, dibehenyl dimethyl
ammonium chloride, stearyl dimethyl benzyl ammonium chloride, stearyl
propyleneglycol phosphate dimethyl ammonium chloride, stearoyl amidopropyl
dimethyl benzyl ammonium chloride, stearoyl amidopropyl dimethyl
(myristylacetate) ammonium chloride, and N-(stearoyl colamino formyl methy)
pyridinium chloride.
Also preferred are hydrophilically substituted cationic surfactants in which
at least one of the substituents contain one or more aromatic, ether, ester,
amido, or amino moieties present as substituents or as linkages in the radical
chain, wherein at least one of the R1 - R4 radicals contain one or more
hydrophilic moieties selected from alkoxy (preferably C1 - C3 alkoxy),
polyoxyalkylene (preferably C1 - C3 polyoxyalkylene), alkylamido,
hydroxyalkyl,
alkylester, and combinations thereof. Preferably, the hydrophilically
substituted
cationic conditioning surfactant contains from 2 to about 10 nonionic
hydrophile
moieties located within the above stated ranges. Preferred hydrophilically
substituted cationic surfactants include those of the formula (II) through
(VIII)
below:
CH3(CHZ)n-CH2 N~ (CH2CH20)xH X
(CH2CH20)yH
wherein n is from 8 to about 28, x+y is from 2 to about 40, Z1 is a short
chain
alkyl, preferably a C1 - C3 alkyl, more preferably methyl, or (CH2CH20)zH
wherein x+y+z is up to 60, and X is a salt forming anion as defined above;
6
R
R N~ CH2 m-~+ R 2X
R ( ) R~ (
wherein m is 1 to 5, one or more of R5, R6, and R7 are independently an C1 -
C30 alkyl, the remainder are CH2CH20H, one or two of R8, R9, and R10 are
7


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
independently an C~ - C30 alkyl, and remainder are CH2CH20H, and X is a salt
forming anion as mentioned above;
2
R 1 ~NH- CH -~~ CH2 -NH~RZ X
2)p I3 ~ )q
Z
2
R 1 ~-O- CH -~+ CH -O-~-R12
2)p I3 ~ 2)q
Z
wherein, independently for formulae (IV) and (V), Z2 is an alkyl, preferably a
C~ -
C3 alkyl, more preferably methyl, and Z3 is a short chain hydroxyalkyl,
preferably
hydroxymethyl or hydroxyethyl, p and q independently are integers from 2 to 4,
inclusive, preferably from 2 to 3, inclusive, more preferably 2, R~ ~ and R~2
,
independently, are substituted or unsubstituted hydrocarbyls, preferably C~2
C20 alkyl or alkenyl, and X is a salt forming anion as defined above;
4
13
R-~5 (CH2~H0)aH X
IZ CH3
wherein R~ 3 is a hydrocarbyl, preferably a C~ - C3 alkyl, more preferably
methyl,
Z4 and Z5 are, independently, short chain hydrocarbyls, preferably C2 - C4
alkyl
or alkenyl, more preferably ethyl, a is from 2 to about 40, preferably from
about 7
to about 30, and X is a salt forming anion as defined above;
14
Z lrT~CH2~HCH2 A X
is
R OH
wherein R~4 and RCS, independently, are C~ - C3 alkyl, preferably methyl, Z6
is
a C~2 - C22 hydrocarbyl, alkyl carboxy or alkylamido, and A is a protein,
preferably a collagen, keratin, milk protein, silk, soy protein, wheat
protein, or
hydrolyzed forms thereof; and X is a salt forming anion as defined above;
8


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
16
~+
HOCH2 (CHOH)a CNH(CH2)b-N 7 CHzCH20H X (~)
R
wherein b is 2 or 3, R16 and R17, independently are C1 - Cg hydrocarbyls
preferably methyl, and X is a salt forming anion as defined above. Nonlimiting
examples of hydrophilically substituted cationic surfactants useful in the
present
invention include the materials having the following CTFA designations:
quaternium-16, quaternium-26, quaternium-27, quaternium-30, quaternium-33,
quaternium-43, quaternium-52, quaternium-53, quaternium-56, quaternium-60,
quaternium-61, quaternium-62, quaternium-70, quaternium-71, quaternium-72,
quaternium-75, quaternium-76 hydrolyzed collagen, quaternium-77, quaternium-
78, quaternium-79 hydrolyzed collagen, quaternium-79 hydrolyzed keratin,
quaternium-79 hydrolyzed milk protein, quaternium-79 hydrolyzed silk,
quaternium-79 hydrolyzed soy protein, and quaternium-79 hydrolyzed wheat
protein, quaternium-80, quaternium-81, quaternium-82, quaternium-83,
quaternium-84, and mixtures thereof.
Highly preferred hydrophilically substituted cationic surfactants include
dialkylamido ethyl hydroxyethylmonium salt, dialkylamidoethyl dimonium salt,
dialkyloyl ethyl hydroxyethylmonium salt, dialkyloyl ethyldimonium salt, and
mixtures thereof; for example, commerically available under the following
tradenames; VARISOFT 110, VARIQUAT K1215 and 638 from Witco Chemical,
MACKPRO KLP, MACKPRO WLW, MACKPRO MLP, MACKPRO NSP,
MACKPRO NLW, MACKPRO WWP, MACKPRO NLP, MACKPRO SLP from
Mclntyre, ETHOQUAD 18/25, ETHOQUAD O/12PG, ETHOQUAD C/25,
ETHOQUAD S/25, and ETHODUOQUAD from Akzo, DEHYQUAT SP from
Henkel, and ATLAS 6265 from ICI Americas.
Salts of primary, secondary, and tertiary fatty amines are also suitable
cationic surfactants. The alkyl groups of such amines preferably have from
about 12 to about 22 carbon atoms, and can be substituted or unsubstituted.
Particularly useful are amidoamines of the following general formula:
R1 CONH (CH2)m N (R2)2
wherein R1 is a residue of C11 to C24 fatty acids, R2 is a C1 to C4 alkyl, and
m
is an integer from 1 to 4.
9


CA 02373863 2001-12-21
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Preferred amidoamine useful in the present invention includes
stearamidopropyldimethylamine, stearamidopropyldiethylamine,
stearamidoethyldiethylamine, stearamidoethyldimethylamine,
palmitamidopropyldimethylamine, palmitamidopropyldiethylamine,
palmitamidoethyldiethylamine, palmitamidoethyldimethylamine,
behenamidopropyldimethylamine, behenamidopropyldiethylamine,
behenamidoethyldiethylamine, behenamidoethyldimethylamine,
arachidamidopropyldimethylamine, arachidamidopropyldiethylamine,
arachidamidoethyldiethylamine, arachidamidoethyldimethylamine, and mixtures
thereof; more preferably stearamidopropyldimethylamine,
stearamidoethyldiethylamine, and mixtures thereof.
The amidoamines herein are preferably partially quaternized with the acids
selected from the group consisting of L-glutamic acid, lactic acid,
hydrochloric
acid, malic acid, succinic acid, acetic acid, fumaric acid, L-glutamic acid
hydrochloride, tartaric acid, and mixtures thereof; preferably L-glutamic
acid,
lactic acid, hydrochloric acid, and mixtures thereof.
Preferably, the mole ratio of amidoamine to acid is from about 1:0.3 to
about 1:1, more preferably from about 1:0.5 to about 1:0.9.
Silicone Com~~ound
The cationic silicone emulsion herein comprises a silicone compound in
an amount capable of providing a stable emulsion, preferably from about 0.1 %
to
about 70%, more preferably from about 5% to about 60% by weight of the
cationic silicone emulsion. The amount of silicone compound to the entire
composition is preferably from about 0.1 % to about 10% by weight. The
silicone
compounds hereof can include volatile soluble or insoluble, or nonvolatile
soluble
or insoluble silicone conditioning agents. By soluble what is meant is that
the
silicone compound is miscible with the carrier of the composition so as to
form
part of the same phase. By insoluble what is meant is that the silicone forms
a
separate, discontinuous phase from the carrier, such as in the form of an
emulsion or a suspension of droplets of the silicone. The silicone compounds
herein may be made by conventional polymerization, or emulsion polymerization.
The silicone compounds for use herein will preferably have a viscosity of
from about 1,000 to about 2,000,000 centistokes at 25oC, more preferably from
about 10,000 to about 1,800,000, and even more preferably from about 25,000
to about 1,500,000. The viscosity can be measured by means of a glass
capillary viscometer as set forth in Dow Corning Corporate Test Method


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
CTM0004, July 20, 1970, which is incorporated by reference herein in its
entirety.
Silicone compound of high molecular weight may be made by emulsion
polymerization.
Silicone compounds useful herein include polyalkyl polyaryl siloxanes,
polyalkyleneoxide-modified siloxanes, silicone resins, amino-substituted
siloxanes, and mixtures thereof. The silicone compound is preferably selected
from the group consisting of polyalkyl polyaryl siloxanes, polyalkyleneoxide-
modified siloxanes, silicone resins, and mixtures thereof, and more preferably
from one or more polyalkyl polyaryl siloxanes.
Polyalkyl polyaryl siloxanes useful here in include those with the following
structure (I)
A ~ -O-f ~ -O-lx ~ -A (I )
R R R
wherein R is alkyl or aryl, and x is an integer from about 7 to about 8,000.
"A"
represents groups which block the ends of the silicone chains. The alkyl or
aryl
groups substituted on the siloxane chain (R) or at the ends of the siloxane
chains
(A) can have any structure as long as the resulting silicone remains fluid at
room
temperature, is dispersible, is neither irritating, toxic nor otherwise
harmful when
applied to the hair, is compatible with the other components of the
composition,
is chemically stable under normal use and storage conditions, and is capable
of
being deposited on and conditions the hair. Suitable A groups include hydroxy,
methyl, methoxy, ethoxy, propoxy, and aryloxy. The two R groups on the silicon
atom may represent the same group or different groups. Preferably, the two R
groups represent the same group. Suitable R groups include methyl, ethyl,
propyl, phenyl, methylphenyl and phenylmethyl. The preferred silicone
compounds are polydimethylsiloxane, polydiethylsiloxane, and
polymethylphenylsiloxane. Polydimethylsiloxane, which is also known as
dimethicone, is especially preferred. The polyalkylsiloxanes that can be used
include, for example, polydimethylsiloxanes. These silicone compounds are
available, for example, from the General Electric Company in their ViscasilR
and
SF 96 series, and from Dow Corning in their Dow Corning 200 series.
Polymethylphenylsiloxanes, for example, from the General Electric Company as
11


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
SF 1075 methyl phenyl fluid or from Dow Corning as 556 Cosmetic Grade Fluid,
are useful herein.
Also preferred, for enhancing the shine characteristics of hair, are highly
arylated silicone compounds, such as highly phenylated polyethyl silicone
having
refractive index of about 1.46 or higher, especially about 1.52 or higher.
When
these high refractive index silicone compounds are used, they should be mixed
with a spreading agent, such as a surfactant or a silicone resin, as described
below to decrease the surface tension and enhance the film forming ability of
the
material.
Another polyalkyl polyaryl siloxane that can be especially useful is a
silicone gum. The term "silicone gum", as used herein, means a
polyorganosiloxane material having a viscosity at 25°C of greater than
or equal to
1,000,000 centistokes. It is recognized that the silicone gums described
herein
can also have some overlap with the above-disclosed silicone compounds. This
overlap is not intended as a limitation on any of these materials. Silicone
gums
are described by Petrarch, and others including U.S. Patent No. 4,152,416, to
Spitzer et al., issued May 1, 1979 and Noll, Walter, Chemistry and Technology
of
Silicones, New York: Academic Press 1968. Also describing silicone gums are
General Electric Silicone Rubber Product Data Sheets SE 30, SE 33, SE 54 and
SE 76. All of these described references are incorporated herein by reference
in
their entirety. The "silicone gums" will typically have a mass molecular
weight in
excess of about 200,000, generally between about 200,000 and about
1,000,000. Specific examples include polydimethylsiloxane,
poly(dimethylsiloxane methylvinylsiloxane) copolymer, poly(dimethylsiloxane
diphenylsiloxane methylvinylsiloxane) copolymer and mixtures thereof.
Polyalkyleneoxide-modified siloxanes useful herein include, for example,
polypropylene oxide modified and polyethylene oxide modified
polydimethylsiloxane. The ethylene oxide and polypropylene oxide level should
be sufficiently low so as not to interfere with the dispersibility
characteristics of
the silicone. These material are also known as dimethicone copolyols.
Silicone resins, which are highly crosslinked polymeric siloxane systems,
are useful herein. The crosslinking is introduced through the incorporation of
tri
functional and tetra-functional silanes with mono-functional or di-functional,
or
both, silanes during manufacture of the silicone resin. As is well understood
in
the art, the degree of crosslinking that is required in order to result in a
silicone
resin will vary according to the specific silane units incorporated into the
silicone
12


CA 02373863 2001-12-21
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resin. In general, silicone materials which have a sufficient level of
trifunctional
and tetrafunctional siloxane monomer units, and hence, a sufficient level of
crosslinking, such that they dry down to a rigid, or hard, film are considered
to be
silicone resins. The ratio of oxygen atoms to silicon atoms is indicative of
the
level of crosslinking in a particular silicone material. Silicone materials
which
have at least about 1.1 oxygen atoms per silicon atom will generally be
silicone
resins herein. Preferably, the ratio of oxygenailicon atoms is at least about
1.2:1Ø Silanes used in the manufacture of silicone resins include monomethyl-
,
dimethyl-, trimethyl-, monophenyl-, diphenyl-, methylphenyl-, monovinyl-, and
methylvinylchlorosilanes, and tetrachlorosilane, with the methyl substituted
silanes being most commonly utilized. Preferred resins are offered by General
Electric as GE SS4230 and SS4267. Commercially available silicone resins will
generally be supplied in a dissolved form in a low viscosity volatile or
nonvolatile
silicone fluid. The silicone resins for use herein should be supplied and
incorporated into the present compositions in such dissolved form, as will be
readily apparent to those skilled in the art. Without being bound by theory,
it is
believed that the silicone resins can enhance deposition of other silicone
compounds on the hair and can enhance the glossiness of hair with high
refractive index volumes.
Other useful silicone resins are silicone resin powders such as the
material given the CTFA designation polymethylsilsequioxane, which is
commercially available as TospearITM from Toshiba Silicones.
Silicone resins can conveniently be identified according to a shorthand
nomenclature system well known to those skilled in the art as the "MDTQ"
nomenclature. Under this system, the silicone is described according to the
presence of various siloxane monomer units which make up the silicone.
Briefly,
the symbol M denotes the mono-functional unit (CH3)3Si0).5; D denotes the
difunctional unit (CH3)2Si0; T denotes the trifunctional unit (CH3)Si01.5; and
Q
denotes the quadri- or tetra-functional unit Si02. Primes of the unit symbols,
e.g., M', D', T', and Q' denote substituents other than methyl, and must be
specifically defined for each occurrence. Typical alternate substituents
include
groups such as vinyl, phenyl, amino, hydroxyl, etc. The molar ratios of the
various units, either in terms of subscripts to the symbols indicating the
total
number of each type of unit in the silicone, or an average thereof, or as
specifically indicated ratios in combination with molecular weight, complete
the
description of the silicone material under the MDTQ system. Higher relative
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CA 02373863 2001-12-21
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molar amounts of T, Q, T' and/or Q' to D, D', M and/or or M' in a silicone
resin is
indicative of higher levels of crosslinking. As discussed before, however, the
overall level of crosslinking can also be indicated by the oxygen to silicon
ratio.
The silicone resins for use herein which are preferred are MQ, MT, MTQ,
MQ and MDTQ resins. Thus, the preferred silicone substituent is methyl.
Especially preferred are MQ resins wherein the M:Q ratio is from about 0.5:1.0
to
about 1.5:1.0 and the average molecular weight of the resin is from about 1000
to about 10,000.
Amino-substituted siloxanes useful herein include those represented by
the following structure (II)
~H3 R
HO-[-$i-O]x-[-$i-O-]y-H
ICH3 ( I~HZ)a ( II )
NH
(~H~b
NHZ
wherein R is CH3 or OH, x and y are integers which depend on the molecular
weight, the average molecular weight being approximately between 5,000 and
10,000. This polymer is also known as "amodimethicone".
Suitable amino-substituted siloxane fluids include those represented by
the formula (III)
(R1 )aG3-a-Si-(-OSiG2)n-(-OSiGb(R1 )2-b)m-O-SiG3_a(R1 )a (I II)
in which G is chosen from the group consisting of hydrogen, phenyl, OH, C1-Cg
alkyl and preferably methyl; a denotes 0 or an integer from 1 to 3, and
preferably
equals 0; b denotes 0 or 1 and preferably equals 1; the sum n+m is a number
from 1 to 2,000 and preferably from 50 to 150, n being able to denote a number
from 0 to 1,999 and preferably from 49 to 149 and m being able to denote an
integer from 1 to 2,000 and preferably from 1 to 10; R1 is a monovalent
radical
of formula CqH2qL in which q is an integer from 2 to 8 and L is chosen from
the
groups
-N(R2)CH2-CH2-N(R2)2
-N(R2)2
-N(R2)3A
-N(R2)CH2-CH2-NR2H2A
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CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
in which R2 is chosen from the group consisting of hydrogen, phenyl, benzyl, a
saturated hydrocarbon radical, preferably an alkyl radical containing from 1
to 20
carbon atoms, and A denotes a halide ion.
An especially preferred amino-substituted siloxane corresponding to
formula (III) is the polymer known as "trimethylsilylamodimethicone", of
formula
(IV):
_~H3 r H3
(CH3)3Si O[ ~Si O-]n-[-~Si O-lm- Si 1CH3)3 (N)
CH3 (~H2)a
NH
(~H2)b
NH2
In this formula n and m are selected depending on the molecular weight of
the compound desired.
Other amino-substituted siloxane which can be used are represented by
the formula (V):
R CHZ-CHOH-CHZ N+(R)3Q
3
R
R Si-O-[-~ i-O-]r-[-I i-O-]s-Si(R )3 ( V )
~3 y~
~3
where R3 denotes a monovalent hydrocarbon radical having from 1 to 18 carbon
atoms, preferably an alkyl or alkenyl radical such as methyl; Rq. denotes a
hydrocarbon radical, preferably a C1 - C1g alkylene radical or a C1 - Clg, and
more preferably C1 - Cg, alkyleneoxy radical; Q is a halide ion, preferably
chloride; r denotes an average statistical value from 2 to 20, preferably from
2 to
8; s denotes an average statistical value from 20 to 200, and preferably from
20
to 50. A preferred polymer of this class is available from Union Carbide under
the name "UCAR SILICONE ALE 56."


CA 02373863 2001-12-21
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HIGH MELTING POINT FATTY COMPOUND
The composition of the present invention comprises a high melting point
fatty compound. The high melting point fatty compound useful herein have a
melting point of 25°C or higher, and is selected from the group
consisting of fatty
alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and
mixtures
thereof. It is understood by the artisan that the compounds disclosed in this
section of the specification can in some instances fall into more than one
classification, e.g., some fatty alcohol derivatives can also be classified as
fatty
acid derivatives. However, a given classification is not intended to be a
limitation
on that particular compound, but is done so for convenience of classification
and
nomenclature. Further, it is understood by the artisan that, depending on the
number and position of double bonds, and length and position of the branches,
certain compounds having certain required carbon atoms may have a melting
point of less than 25°C. Such compounds of low melting point are not
intended
to be included in this section. Nonlimiting examples of the high melting point
compounds are found in International Cosmetic Ingredient Dictionary, Fifth
Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992.
These high melting point fatty compounds, together with the cationic
conditioning agent, provide a gel network suitable for providing various
conditioning benefits such as slippery and slick feel on wet hair, and
softness,
moisturized feel, and fly-away control on dry hair.
The high melting point fatty compound is included in the composition at a
level by weight of from about 0.1 % to about 15%, preferably from about 0.5%
to
about 10%, more preferably from about 1 % to about 7%.
The fatty alcohols useful herein are those having from about 14 to about
30 carbon atoms, preferably from about 16 to about 22 carbon atoms. These
fatty alcohols are saturated and can be straight or branched chain alcohols.
Nonlimiting examples of fatty alcohols include, cetyl alcohol, stearyl
alcohol,
behenyl alcohol, and mixtures thereof.
The fatty acids useful herein are those having from about 10 to about 30
carbon atoms, preferably from about 12 to about 22 carbon atoms, and more
preferably from about 16 to about 22 carbon atoms. These fatty acids are
saturated and can be straight or branched chain acids. Also included are
diacids, triacids, and other multiple acids which meet the requirements
herein.
Also included herein are salts of these fatty acids. Nonlimiting examples of
fatty
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acids include lauric acid, palmitic acid, stearic acid, behenic acid, sebacic
acid,
and mixtures thereof.
The fatty alcohol derivatives and fatty acid derivatives useful herein
include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl
ethers of
alkoxylated fatty alcohols, esters of fatty alcohols, fatty acid esters of
compounds
having esterifiable hydroxy groups, hydroxy-substituted fatty acids, and
mixtures
thereof. Nonlimiting examples of fatty alcohol derivatives and fatty acid
derivatives include materials such as methyl stearyl ether; the ceteth series
of
compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers
of cetyl alcohol, wherein the numeric designation indicates the number of
ethylene glycol moieties present; the steareth series of compounds such as
steareth-1 through 10, which are ethylene glycol ethers of steareth alcohol,
wherein the numeric designation indicates the number of ethylene glycol
moieties present; ceteareth 1 through ceteareth-10, which are the ethylene
glycol
ethers of ceteareth alcohol, i.e. a mixture of fatty alcohols containing
predominantly cetyl and stearyl alcohol, wherein the numeric designation
indicates the number of ethylene glycol moieties present; C~-C3o alkyl ethers
of
the ceteth, steareth, and ceteareth compounds just described; polyoxyethylene
ethers of behenyl alcohol; ethyl stearate, cetyl stearate, cetyl palmitate,
stearyl
stearate, myristyl myristate, polyoxyethylene cetyl ether stearate,
polyoxyethylene stearyl ether stearate, polyoxyethylene lauryl ether stearate,
ethyleneglycol monostearate, polyoxyethylene monostearate, polyoxyethylene
distearate, propyleneglycol monostearate, propyleneglycol distearate,
trimethylolpropane distearate, sorbitan stearate, polyglyceryl stearate,
glyceryl
monostearate, glyceryl distearate, glyceryl tristearate, and mixtures thereof.
High melting point fatty compounds of a single compound of high purity
are preferred. Single compounds of pure fatty alcohols selected from the group
of pure cetyl alcohol, stearyl alcohol, and behenyl alcohol are highly
preferred.
By "pure" herein, what is meant is that the compound has a purity of at least
about 90%, preferably at least about 95%. These single compounds of high
purity provide good rinsability from the hair when the consumer rinses off the
composition.
Commercially available high melting point fatty compounds useful herein
include: cetyl alcohol, stearyl alcohol, and behenyl alcohol having tradenames
KONOL series available from Shin Nihon Rika (Osaka, Japan), and NAA series
available from NOF (Tokyo, Japan); pure behenyl alcohol having tradename 1
17


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DOCOSANOL available from WAKO (Osaka, Japan), various fatty acids having
tradenames NEO-FAT available from Akzo (Chicago Illinois, USA), HYSTRENE
available from Witco Corp. (Dublin Ohio, USA), and DERMA available from Vevy
(Genova, Italy).
CATIONIC CONDITIONING AGENT
The composition of the present invention comprises a cationic
conditioning agent. This cationic conditioning agent, together with the high
melting point fatty compounds, provide a gel network suitable for providing
various conditioning benefits such as slippery and slick feel on wet hair, and
such as softness, moisturized feel, and fly-away control on dry hair.
The cationic conditioning agent is included in the composition at a level by
weight of from about 0.1 % to about 10%, preferably from about 0.25% to about
8%, more preferably from about 0.5% to about 3%.
The cationic conditioning agent is selected from the group consisting of
cationic surfactants, cationic polymers, and mixtures thereof.
Cationic Surfactant
The cationic surfactant useful herein is any known to the artisan, and is
selected from the species disclosed above under the title "Cationic
Surfactant".
Cationic Polymer
The cationic polymer useful herein is described below. As used herein,
the term "polymer" shall include materials whether made by polymerization of
one type of monomer or made by two (i.e., copolymers) or more types of
monomers.
Preferably, the cationic polymer is a water-soluble cationic polymer. By
"water soluble" cationic polymer, what is meant is a polymer which is
sufficiently
soluble in water to form a substantially clear solution to the naked eye at a
concentration of 0.1 % in water (distilled or equivalent) at 25°C. The
preferred
polymer will be sufficiently soluble to form a substantially clear solution at
0.5%
concentration, more preferably at 1.0% concentration.
The cationic polymers hereof will generally have a weight average
molecular weight which is at least about 5,000, typically at least about
10,000,
and is less than about 10 million. Preferably, the molecular weight is from
about
100,000 to about 2 million. The cationic polymers will generally have cationic
nitrogen-containing moieties such as quaternary ammonium or cationic amino
moieties, and mixtures thereof.
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The cationic charge density is preferably at least about 0.1 meq/gram,
more preferably at least about 1.5 meq/gram, even more preferably at least
about 1.1 meq/gram, still more preferably at least about 1.2 meq/gram.
Cationic
charge density of the cationic polymer can be determined according to the
Kjeldahl Method. Those skilled in the art will recognize that the charge
density of
amino-containing polymers may vary depending upon pH and the isoelectric
point of the amino groups. The charge density should be within the above
limits
at the pH of intended use.
Any anionic counterions can be utilized for the cationic polymers so long
as the water solubility criteria is met. Suitable counterions include halides
(e.g.,
CI, Br, I, or F, preferably CI, Br, or I), sulfate, and methylsulfate. Others
can also
be used, as this list is not exclusive.
The cationic nitrogen-containing moiety will be present generally as a
substituent, on a fraction of the total monomer units of the cationic hair
conditioning polymers. Thus, the cationic polymer can comprise copolymers,
terpolymers, etc. of quaternary ammonium or cationic amine-substituted
monomer units and other non-cationic units referred to herein as spacer
monomer units. Such polymers are known in the art, and a variety can be found
in the CTFA Cosmetic Ingredient Dictionary, 3rd edition, edited by Estrin,
Crosley, and Haynes, (The Cosmetic, Toiletry, and Fragrance Association, Inc.,
Washington, D.C., 1982).
Suitable cationic polymers include, for example, copolymers of vinyl
monomers having cationic amine or quaternary ammonium functionalities with
water soluble spacer monomers such as acrylamide, methacrylamide, alkyl and
dialkyl acrylamides, alkyl and dialkyl methacrylamides, alkyl acrylate, alkyl
methacrylate, vinyl caprolactone, and vinyl pyrrolidone. The alkyl and dialkyl
substituted monomers preferably have C1 - C7 alkyl groups, more preferably C1
- C3 alkyl groups. Other suitable spacer monomers include vinyl esters, vinyl
alcohol (made by hydrolysis of polyvinyl acetate), malefic anhydride,
propylene
glycol, and ethylene glycol.
The cationic amines can be primary, secondary, or tertiary amines,
depending upon the particular species and the pH of the composition. In
general, secondary and tertiary amines, especially tertiary amines, are
preferred.
Amine-substituted vinyl monomers can be polymerized in the amine form,
and then optionally can be converted to ammonium by a quaternization reaction.
Amines can also be similarly quaternized subsequent to formation of the
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CA 02373863 2001-12-21
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polymer. For example, tertiary amine functionalities can be quaternized by
reaction with a salt of the formula R'X wherein R' is a short chain alkyl,
preferably
a C1 - C7 alkyl, more preferably a C1 - C3 alkyl, and X is an anion which
forms a
water soluble salt with the quaternized ammonium.
Suitable cationic amino and quaternary ammonium monomers include, for
example, vinyl compounds substituted with dialkylaminoalkyl acrylate,
dialkylaminoalkyl methacrylate, monoalkylaminoalkyl acrylate,
monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salt,
trialkyl acryloxyalkyl ammonium salt, diallyl quaternary ammonium salts, and
vinyl
quaternary ammonium monomers having cyclic cationic nitrogen-containing rings
such as pyridinium, imidazolium, and quaternized pyrrolidone, e.g., alkyl
vinyl
imidazolium, alkyl vinyl pyridinium, alkyl vinyl pyrrolidone salts. The alkyl
portions
of these monomers are preferably lower alkyls such as the C1 - C3 alkyls, more
preferably C1 and C2 alkyls. Suitable amine-substituted vinyl monomers for use
herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate,
dialkylaminoalkyl acrylamide, and dialkylaminoalkyl methacrylamide, wherein
the
alkyl groups are preferably C1 - C7 hydrocarbyls, more preferably C1 - C3,
alkyls.
The cationic polymers hereof can comprise mixtures of monomer units
derived from amine- and/or quaternary ammonium-substituted monomer and/or
compatible spacer monomers.
Suitable cationic hair conditioning polymers include, for example:
copolymers of 1-vinyl-2-pyrrolidone and 1-vinyl-3-methylimidazolium salt
(e.g.,
chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and
Fragrance
Association, "CTFA", as Polyquaternium-16), such as those commercially
available from BASF Wyandotte Corp. (Parsippany, NJ, USA) under the
LUVIQUAT tradename (e.g., LUVIQUAT FC 370); copolymers of 1-vinyl-2-
pyrrolidone and dimethylaminoethyl methacrylate (referred to in the industry
by
CTFA as Polyquaternium-11 ) such as those commercially available from Gaf
Corporation (Wayne, NJ, USA) under the GAFQUAT tradename (e.g.,
GAFQUAT 755N); cationic diallyl quaternary ammonium-containing polymers,
including, for example, dimethyldiallylammonium chloride homopolymer and
copolymers of acrylamide and dimethyldiallylammonium chloride, referred to in
the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively;
and mineral acid salts of amino-alkyl esters of homo- and co-polymers of
unsaturated carboxylic acids having from 3 to 5 carbon atoms, as described in
U.S. Patent 4,009,256, incorporated herein by reference.


CA 02373863 2001-12-21
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Other cationic polymers that can be used include polysaccharide
polymers, such as cationic cellulose derivatives and cationic starch
derivatives.
Cationic polysaccharide polymer materials suitable for use herein include
those of the formula:



~


A -O-(R-+ R X
)


~2


R


wherein: A is an anhydroglucose residual group, such as a starch or cellulose
anhydroglucose residual, R is an alkylene oxyalkylene, polyoxyalkylene, or
hydroxyalkylene group, or combination thereof, R1, R2, and R3 independently
are alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each
group
containing up to about 18 carbon atoms, and the total number of carbon atoms
for each cationic moiety (i.e., the sum of carbon atoms in R1, R2 and R3)
preferably being about 20 or less, and X is an anionic counterion, as
previously
described.
Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) in
their Polymer JR~ and LR~ series of polymers, as salts of hydroxyethyl
cellulose
reacted with trimethyl ammonium substituted epoxide, referred to in the
industry
(CTFA) as Polyquaternium 10. Another type of cationic cellulose includes the
polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with
lauryl dimethyl ammonium-substituted epoxide, referred to in the industry
(CTFA)
as Polyquaternium 24. These materials are available from Amerchol Corp.
(Edison, NJ, USA) under the tradename Polymer LM-200~.
Other cationic polymers that can be used include cationic guar gum
derivatives, such as guar hydroxypropyltrimonium chloride (commercially
available from Celanese Corp. in their Jaguar R series). Other materials
include
quaternary nitrogen-containing cellulose ethers (e.g., as described in U.S.
Patent
3,962,418, incorporated herein by reference), and copolymers of etherified
cellulose and starch (e.g., as described in U.S. Patent 3,958,581,
incorporated
herein by reference.)
AQUEOUS CARRIER
The composition of the present invention comprises an aqueous carrier.
The level and species of the carrier are selected according to the
compatibility
with other components, and other desired characteristic of the product.
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The carrier useful in the present invention include water and water
solutions of lower alkyl alcohols and polyhydric alcohols. The lower alkyl
alcohol
useful herein are monohydric alcohols having 1 to 6 carbons, more preferably
ethanol and isopropanol. The polyhydric alcohols useful herein include
propylene glycol, hexylene glycol, glycerin, and propane diol.
Preferably, the aqueous carrier is substantially water. Deionized water is
preferably used. Water from natural sources including mineral cations can also
be used, depending on the desired characteristic of the product. Generally,
the
compositions of the present invention comprise from about 20% to about 95%,
preferably from about 30% to about 92%, and more preferably from about 50% to
about 90% water.
LOW MELTING POINT OIL
The hair conditioning composition of the present invention may further
comprise a low melting point oil, which has a melting point of less than
25°C, and
is preferably included in the composition at a level by weight of from about
0.1
to about 10%, more preferably from about 0.25% to about 6%.
The low melting point oil useful herein is selected from the group
consisting of hydrocarbon having from 10 to about 40 carbon atoms, unsaturated
fatty alcohols having from about 10 to about 30 carbon atoms, unsaturated
fatty
acids having from about 10 to about 30 carbon atoms, fatty acid derivatives,
fatty
alcohol derivatives, ester oils, poly a-olefin oils, and mixtures thereof.
Fatty alcohols useful herein include those having from about 10 to about
30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more
preferably from about 16 to about 22 carbon atoms. These fatty alcohols are
unsaturated and can be straight or branched chain alcohols. Suitable fatty
alcohols include, for example, oleyl alcohol, isostearyl alcohol,
tridecylalcohol,
decyl tetradecyl alcohol, and octyl dodecyl alcohol. These alcohols are
available,
for example, from Shinnihon Rika.
Low melting point oils useful herein include pentaerythritol ester oils,
trimethylol ester oils, poly a-olefin oils, citrate ester oils, glyceryl ester
oils, and
mixtures thereof, and the ester oil useful herein is water-insoluble. As used
herein, the term "water-insoluble" means the compound is substantially not
soluble in water at 25°C; when the compound is mixed with water at a
concentration by weight of above 1.0%, preferably at above 0.5%, the compound
is temporarily dispersed to form an unstable colloid in water, then is quickly
separated from water into two phases.
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Pentaerythritol ester oils useful herein are those having the following
formula:
O
C H20-C-R2
O I O
R~ C-OCH2-C-CH20-C-R3
O
H O-C-R 4
2
wherein R', R2, R3, and R4, independently, are branched, straight, saturated,
or
unsaturated alkyl, aryl, and alkylaryl groups having from 1 to about 30
carbons.
Preferably, R', R2, R3, and R4, independently, are branched, straight,
saturated,
or unsaturated alkyl groups having from about 8 to about 22 carbons. More
preferably, R', R2, R3 and R4 are defined so that the molecular weight of the
compound is from about 800 to about 1200.
Trimethylol ester oils useful herein are those having the following formula:
O
C H20-C-R~ 2
O
R1 ~ ~ H2-CH20-C-R13
O
H20-C-R ~ 4
wherein R" is an alkyl group having from 1 to about 30 carbons, and R'2, R'3,
and R'4, independently, are branched, straight, saturated, or unsaturated
alkyl,
aryl, and alkylaryl groups having from 1 to about 30 carbons. Preferably, R"
is
ethyl and R'2, R'3, and R'4, independently, are branched, straight, saturated,
or
unsaturated alkyl groups having from 8 to about 22 carbons. More preferably,
R", R'2, R'3 and R'4 are defined so that the molecular weight of the compound
is
from about 800 to about 1200.
Particularly useful pentaerythritol ester oils and trimethylol ester oils
herein
include pentaerythritol tetraisostearate, pentaerythritol tetraoleate,
trimethylolpropane triisostearate, trimethylolpropane trioleate, and mixtures
thereof. Such compounds are available from Kokyo Alcohol with tradenames
KAKPTI, KAKTTI, and Shin-nihon Rika with tradenames PTO, ENUJERUBU
TP3S0.
Poly a-olefin oils useful herein are those derived from 1-alkene monomers
having from about 6 to about 16 carbons, preferably from about 6 to about 12
carbons atoms. Nonlimiting examples of 1-alkene monomers useful for
23


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
preparing the poly a-olefin oils include 1-hexene, 1-octene, 1-decene, 1-
dodecene, 1-tetradecene, 1-hexadecene, branched isomers such as 4-methyl-1-
pentene, and mixtures thereof. Preferred 1-alkene monomers useful for
preparing the poly a-olefin oils are 1-octene, 1-decene, 1-dodecene, 1-
tetradecene, 1-hexadecene, and mixtures thereof. Poly a-olefin oils useful
herein further have a viscosity of from about 1 to about 35,000 cst, a
molecular
weight of from about 200 to about 60,000, and a polydispersity of no more than
about 3.
Poly a-olefin oils having a molecular weight of at least about 800 are
useful herein. Such high molecular weight poly a-olefin oils are believed to
provide long lasting moisturized feel to the hair. Poly a-olefin oils having a
molecular weight of less than about 800 are useful herein. Such low molecular
weight poly a-olefin oils are believed to provide a smooth, light, clean feel
to the
hair.
Particularly useful poly a-olefin oils herein include polydecenes with
tradenames PURESYN 6 having a number average molecular weight of about
500 and PURESYN 100 having a number average molecular weight of about
3000 and PURESYN 300 having a number average molecular weight of about
6000 available from Mobil Chemical Co.
Citrate ester oils useful herein are those having a molecular weight of at
least about 500 having the following formula:
O
C H2-C-O-R22
O
R2~ ~ -C-O-R 23
O
H2-C-O-R24
wherein R2~ is OH or CH3C00, and R22, R23, and R24, independently, are
branched, straight, saturated, or unsaturated alkyl, aryl, and alkylaryl
groups
having from 1 to about 30 carbons. Preferably, R2' is OH, and R22, R23, and
R2a,
independently, are branched, straight, saturated, or unsaturated alkyl, aryl,
and
alkylaryl groups having from 8 to about 22 carbons. More preferably, R2', R22,
R23 and R24 are defined so that the molecular weight of the compound is at
least
about 800.
Particularly useful citrate ester oils herein include triisocetyl citrate with
tradename CITMOL 316 available from Bernel, triisostearyl citrate with
24


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
tradename PELEMOL TISC available from Phoenix, and trioctyldodecyl citrate
with tradename CITMOL 320 available from Bernel.
Glyceryl ester oils useful herein are those having a molecular weight of at
least
about 500 and having the following formula:
O
C H20-C-R41
O
H ~ -O-C-R 42
O
H20-C-R43
wherein R4', R42, and R43, independently, are branched, straight, saturated,
or
unsaturated alkyl, aryl, and alkylaryl groups having from 1 to about 30
carbons.
Preferably, R4', R42, and R43, independently, are branched, straight,
saturated, or
unsaturated alkyl, aryl, and alkylaryl groups having from 8 to about 22
carbons.
More preferably, R4', R42, and R43 are defined so that the molecular weight of
the
compound is at least about 800.
Particularly useful glyceryl ester oils herein include triisostearin with
tradename SUN ESPOL G-318 available from Taiyo Kagaku, triolein with
tradename CITHROL GTO available from Croda Surfactants Ltd., trilinolein with
tradename EFADERMA-F available from Vevy, or tradename EFA-
GLYCERIDES from Brooks.
POLYETHYLENE GLYCOL
The composition of present invention may further comprise a polyethylene
glycol having the formula:
H(OCH2CH2)n -OH
wherein n has an average value of from 2,000 to 14,000, preferably from about
5,000 to about 9,000, more preferably from about 6,000 to about 8,000.
The polyethylene glycol is preferably included in the composition at a level
by weight of from about 0.1 % to about 10%, more preferably from about 0.25%
to about 6%.
The polyethylene glycol described above is also known as a polyethylene
oxide, and polyoxyethylene. Polyethylene glycols useful herein that are
especially preferred are PEG-2M wherein n has an average value of about 2,000
(PEG-2M is also known as Polyox WSR~ N-10 from Union Carbide and as PEG-
2,000); PEG-5M wherein n has an average value of about 5,000 (PEG-5M is also
known as Polyox WSR~ N-35 and as Polyox WSR~ N-80, both from Union


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
Carbide and as PEG-5,000 and Polyethylene Glycol 300,000); PEG-7M wherein
n has an average value of about 7,000 (PEG-7M is also known as Polyox WSR~
N-750 from Union Carbide); PEG-9M wherein n has an average value of about
9,000 (PEG-9M is also known as Polyox WSR~ N-3333 from Union Carbide);
and PEG-14M wherein n has an average value of about 14,000 (PEG-14M is
also known as Polyox WSR~ N-3000 from Union Carbide).
COMPOSITIONS
In one preferred embodiment of the present invention, the composition
comprises:
(a) from about 0.1 % to about 20%, preferably from about 0.5% to about 5% of
a cationic silicone emulsion;
(b) from about 0.1 % to about 10%, preferably from about 1 % to about 7% of a
high melting point fatty compound;
(c) from about 0.1 % to about 10%, preferably from about 0.25% to about 8%,
more preferably from about 0.5% to about 3% of a cationic conditioning
agent;
(d) an aqueous carrier.
This composition can provide increase in bulk hair volume, softness,
moisturized feel, and fly-away control. It can also provide satisfactory
spreadability on the hair, and can be made by a convenient manufacturing
method.
In another preferred embodiment of the present invention, the composition
comprises:
(a) from about 0.1 % to about 20%, preferably from about 0.5% to about 5% of
a cationic silicone emulsion;
(b) from about 0.1 % to about 10% of a high melting point fatty compound;
(c) from about 0.55% to about 7%, preferably from about 1.2% to about 4.5%
of a cationic conditioning agent, the cationic conditioning agent comprising
an amidoamine and an acid; and
(d) the aqueous carrier.
This composition may further contain a low melting point oil selected from
the group consisting of pentaerythritol ester oils, trimethylol ester oils,
poly a-
olefin oils, citrate ester oils, glyceryl ester oils, and mixtures thereof,
which is
preferably included in the composition at a level by weight of from about 0.1
% to
about 10%, more preferably from about 0.25% to about 6%.
26


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
This composition can provide provide the same benefits as those of the
first embodiment, and further can provide the benefits such as slippery and
slick
feel on wet hair.
In another preferred embodiment of the present invention, the composition
comprises:
A hair conditioning composition comprising:
(a) from about 0.1 % to about 20%, preferably from about 0.5% to about 5% of
a cationic silicone emulsion;
(b) from about 0.1 % to about 5%, preferably from about 0.25% to about 2% of
a high melting point fatty compound;
(c) from about 0.1 % to about 10%, preferably from about 0.25% to about 5%
of a cationic conditioning agent;
(d) an aqueous carrier;
(e) from about 0.1 % to about 10%, preferably from about 0.25% to about 6%
of a low melting point oil, the low melting point oil being an unsaturated
fatty alcohol; and
(f) from about 0.1 % to about 10%, preferably from about 0.25% to about 6%
of a polyethylene glycol.
This composition can provides the same benefits as those of the first
embodiment, and further can provide the benefits such as increase in bulk hair
volume, softness, moisturized feel, and fly-away control on dry hair.
ADDITIONAL COMPONENTS
The composition of the present invention may include other additional
components, which may be selected by the artisan according to the desired
characteristics of the final product and which are suitable for rendering the
composition more cosmetically or aesthetically acceptable or to provide them
with additional usage benefits. Such other additional components generally are
used individually at levels of from about 0.001 % to about 10%, preferably up
to
about 5% by weight of the composition.
A wide variety of other additional components can be formulated into the
present compositions. These include: other conditioning agents such as
hydrolysed collagen with tradename Peptein 2000 available from Hormel, vitamin
E with tradename Emix-d available from Eisai, panthenol available from Roche,
panthenyl ethyl ether available from Roche, a mixture of Polysorbate 60 and
Cetearyl Alcohol with tradename Polawax NF available from Croda Chemicals,
glycerylmonostearate available from Stepan Chemicals, hydroxyethyl cellulose
27


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
available from Aqualon, hydrolysed keratin, proteins, plant extracts, and
nutrients; hair-fixative polymers such as amphoteric fixative polymers,
cationic
fixative polymers, anionic fixative polymers, nonionic fixative polymers, and
silicone grafted copolymers; preservatives such as benzyl alcohol, methyl
paraben, propyl paraben and imidazolidinyl urea; pH adjusting agents, such as
citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide,
sodium carbonate; salts, in general, such as potassium acetate and sodium
chloride; coloring agents, such as any of the FD&C or D&C dyes; hair oxidizing
(bleaching) agents, such as hydrogen peroxide, perborate and persulfate salts;
hair reducing agents such as the thioglycolates; perfumes; and sequestering
agents, such as disodium ethylenediamine tetra-acetate; ultraviolet and
infrared
screening and absorbing agents such as octyl salicylate, antidandruff agents
such as zinc pyridinethione; and optical brighteners, for example
polystyrylstilbenes, triazinstilbenes, hydroxycoumarins, aminocoumarins,
triazoles, pyrazolines, oxazoles, pyrenes, porphyrins, imidazoles, and
mixtures
thereof.
EXAMPLES
The following examples further describe and demonstrate embodiments
within the scope of the present invention. The examples are given solely for
the
purpose of illustration and are not to be construed as limitations of the
present
invention, as many variations thereof are possible without departing from the
spirit and scope of the invention. Ingredients are identified by chemical or
CTFA
name, or otherwise defined below.
The compositions of the present invention are suitable for rinse-off
products and leave-on products, and are particularly useful for making
products
in the form of emulsion, cream, gel, spray or, mousse.
Examples 1 through 8 are hair conditioning compositions of the present
invention which are particularly useful for rinse-off use.
Compositions
Com onents Ex. 1 Ex. Ex. 3 Ex.4
2


Cationic Silicone Emulsion-1 1.05 1.05 1.05
*1


Cationic Silicone Emulsion-2*2 0.63


Cet I Alcohol *3 4.5 1.5 5.5 4.5


Stea I Alcohol *4 2.5 2.7 2.5 1.5


Behen I Alcohol *5 1.0


Stearamido ro I Dimeth lamine2.0 1.2 2.3 2.0
*6


28


CA 02373863 2001-12-21
WO 01/01937 PCT/LTS00/17648
~-Glutamic Acid *7 0.64 0.384 0.73 0.64


Pentae hritol Tetraisostearate1.0 1.0 1.0
*8


Preservatives 0.033 0.033 0.033 0.033


Benz I alcohol 0.4 0.4 0.4 0.4


Perfume 0.6 0.6 0.6 0.6


H drol zed colla en *9 0.01 0.01 0.01 0.01


Vitamin E *10 0.01 0.01 0.01 0.01


Panthenol *11 0.05 0.05 0.05 0.05


Panthen I Eth I Ether *12 0.05 0.05 0.05 0.05


Citric Acid *13 amount
necessa
to ad'ust
H 3
7


Deionized Water q.s.
to 100%



Com onents Ex. 5 Ex. Ex. 7 Ex.8
6


Cationic Silicone Emulsion-1*11.05 0.8


Cationic Silicone Emulsion-2*2 1.05 3.0


Cet I Alcohol *3 0.96 0.96 1.2 0.7


Stea I Alcohol *4 0.64 0.64 0.8 0.5


Behen I Alcohol *5 0.2


Stearamido ro I Dimeth lamine 1.0 1.2 0.75
*6


Ditallow dimethyl ammonium 0.75 0.82 0.46 0.5
chloride
*14


Pentae hritol Tetraisostearate 0.2 0.5 0.5
*8


Pentae hritol Tetraoleate *15 0.5


Ole I alcohol *16 0.25 0.25 0.25


Trimeth lol ro ane Triisostearate 0.25
*17


PEG 2M *18 0.5 0.5 0.25 0.5


Pol sorbate 60 *19 0.25 0.25 0.125 0.125


Cetea I Alcohol *19 0.25 0.25 0.125 0.125


GI ce Imonostearate *20 0.25 0.25 0.25 0.25


H drox eth I Cellulose *21 0.25 0.25


Preservatives 0.04 0.04 0.04 0.04


Benz I alcohol 0.4 0.4 0.4 0.4


Perfume 0.6 0.6 0.6 0.6


Acid EDTA 0.1 0.01 0.02 0.01


H drol zed colla en *9 0.01 0.01 0.01 0.01


Vitamin E *10 0.01 0.025 0.01 0.01


Panthenol *11 0.05 0.2 0.1 0.05


Panthen I Eth I Ether *12 0.05 0.05 0.01 0.05


29


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
Citric Acid *13 amount necessa to ad'ust H
3 7


Deionized Water .s. to 100%


Definitions of Components
*1 Cationic Silicone Emulsion-1: PE2006 obtained from Dow Corning;
mechanically emulsified emulsion containing 60% silicone compound and
3.0% cationic surfactant, wherein the silicone compound has a particle size
of about 280 nm, and is made by using polydimethylsiloxane having about
900 repeating units and polydimethylsiloxane having about 100 repeating
units, in a ratio of 27:73.
*2 Cationic Silicone Emulsion-2: PE2016 obtained from Dow Corning; is
mechanically emulsified emulsion containing 55% silicone compound and
3.0% cationic surfactant, wherein the silicone compound has a particle size
of about 280 nm, and is made by using polydimethylsiloxane having about
900 repeating units and polydimethylsiloxane having about 100 repeating
units, in a ratio of 27:73.
*3 Cetyl Alcohol: Konol series obtained by Shin Nihon Rika.
*4 Stearyl Alcohol: Konol series obtained by Shin Nihon Rika.
*5 Behenyl Alcohol: 1-Docosanol (97%) obtained by Wako.
*6 Stearamidopropyl Dimethylamine: Amidoamine MPS obtained by Nikko.
*7 ~-Glutamic Acid: ~-Glutamic acid (cosmetic grade) obtained by Ajinomoto.
*8 Pentaerythritol Tetraisostearate: KAK PTI obtained by Kokyu alcohol.
*9 Hydrolyzed collagen: Peptein 2000 obtained by Hormel.
*10 Vitamin E: Emix-d obtained by Eisai.
*11 Panthenol: Available from Roche.
*12 Panthenyl Ethyl Ether: Available from Roche.
*13 Citric Acid: Anhydrous Citric acid obtained by Haarman & Reimer.
*14 Ditallow dimethyl ammonium chloride: Available from Witco Chemicals.
*15 Pentaerythritol Tetraoleate: Available from Shin NihonRika.
*16 Oleyl alcohol: Available from New Japan Chemical.
*17 Trimethylolpropane Triisostearate: KAK TTI obtained by Kokyu alcohol.
*18 PEG-2M: Polyox obtained by Union Carbide.
*19 Polysorbate 60, Cetearyl Alcohol: mixture sold as Polawax NF obtained by
Croda Chemicals.
*20 Glycerylmonostearate: Available from Stepan Chemicals.
*21 Hydroxyethyl Cellulose: Available from Aqualon.


CA 02373863 2001-12-21
WO 01/01937 PCT/US00/17648
Method of Preparation
The compositions of Examples 1 through 8 as shown above can be
prepared by any conventional method well known in the art. They are suitably
made as follows: If included in the composition, polymeric materials such as
hydroxyethyl cellulose and polyethylene glycol are dispersed in water at room
temperature to make a polymer solution, and heated up to above 70°C.
Amidoamine and acid, or other cationic conditioning agents, and if present,
ester
oil of low melting point oil are added in the solution with agitation. Then
high
melting point fatty compound, and if present, other low melting point oils and
benzyl alcohol are also added in the solution with agitation. The mixture thus
obtained is cooled down to below 60°C, and the remaining components
such as
cationic silicone emulsion are added with agitation, and further cooled down
to
about 30°C.
A triblender and/or mill can be used in each step, if necessary to disperse
the materials.
The embodiments disclosed and represented by the previous examples
have many advantages. For example, they can provide increase in bulk hair
volume, softness, moisturized feel, and fly-away control. They can also
provide
satisfactory spreadability on the hair, and can be made by a convenient
manufacturing method.
It is understood that the examples and embodiments described herein are
for illustrative purposes only and that various modifications or changes in
light
thereof will be suggested to one skilled in the art without departing from its
spirit
and scope.
31

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 2000-06-27
(87) PCT Publication Date 2001-01-11
(85) National Entry 2001-12-21
Examination Requested 2001-12-21
Dead Application 2004-06-28

Abandonment History

Abandonment Date Reason Reinstatement Date
2003-06-27 FAILURE TO PAY APPLICATION MAINTENANCE FEE

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Request for Examination $400.00 2001-12-21
Registration of a document - section 124 $100.00 2001-12-21
Application Fee $300.00 2001-12-21
Maintenance Fee - Application - New Act 2 2002-06-27 $100.00 2001-12-21
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
THE PROCTER & GAMBLE COMPANY
Past Owners on Record
NAKAMURA, KIICHIRO
VENKATESWARAN, ANANTHANARAYAN
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) 
Cover Page 2002-06-17 1 33
Description 2001-12-21 31 1,589
Abstract 2001-12-21 1 56
Claims 2001-12-21 3 99
PCT 2001-12-21 11 416
Assignment 2001-12-21 6 237