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Patent 2330483 Summary

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(12) Patent Application: (11) CA 2330483
(54) English Title: COSMETIC METHOD FOR TREATING COLOURED HAIR TO REDUCE COLOUR FADE
(54) French Title: PROCEDE COSMETIQUE POUR TRAITER LES CHEVEUX TEINTS AFIN DE REDUIRE L'AFFAIBLISSEMENT DES COULEURS
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • A61K 8/30 (2006.01)
  • A61Q 5/00 (2006.01)
(72) Inventors :
  • CASTAING, BERNARD (United Kingdom)
  • DIAS, LOUIS CARLOS (United Kingdom)
  • LANGSCH, DIETER HANS JOSEF (United Kingdom)
  • MACGILP, NEIL ARCHIBALD (United Kingdom)
  • MONICH, MELISSA SMITH (United Kingdom)
  • SAMI, CHRISTINA HARCHARAN KAUR (United Kingdom)
  • HUGHES, BLAKE GARETH (United Kingdom)
  • BUREIKO, ANDREI S. (United Kingdom)
(73) Owners :
  • THE PROCTER & GAMBLE COMPANY
(71) Applicants :
  • THE PROCTER & GAMBLE COMPANY (United States of America)
(74) Agent: DIMOCK STRATTON LLP
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1998-08-07
(87) Open to Public Inspection: 1999-11-04
Examination requested: 2000-10-27
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/US1998/016496
(87) International Publication Number: WO 1999055295
(85) National Entry: 2000-10-27

(30) Application Priority Data:
Application No. Country/Territory Date
PCT/US98/08128 (United States of America) 1998-04-27

Abstracts

English Abstract


The present invention provides a cosmetic method for treating mammalian
coloured hair to reduce or prevent colour fade and/or colour shift comprising:
(a) treating the hair with a composition comprising a hydrophobic and/or
cationic conditioning agent; followed by (b) wetting the hair. Optionally the
method can include treating the hair, after step (b), with a composition
comprising a conditioning agent and/or an ultraviolet filtering agent. The
method of the present invention provides a reduction or prevention of colour
fade and/or colour shift or coloured hair. The method can help to maintain a
more consistent colour and, therefore, can increase the time between dye
applications.


French Abstract

Cette invention se rapporte à un procédé cosmétique servant à traiter les cheveux teints afin de réduire ou d'empêcher l'affaiblissement des couleurs et/ou la dégradation de la couleur, ce procédé consistant: (a) à traiter les cheveux à l'aide d'une composition contenant un agent traitant hydrophobe et/ou cationique; puis (b) à mouiller les cheveux. Ce procédé peut éventuellement consister à traiter les cheveux, après l'étape (b), avec une composition contenant un agent traitant et/ou un agent filtrant les ultraviolets. Ce procédé permet de réduire ou d'empêcher l'affaiblissement des couleurs et/ou la dégradation de la couleur des cheveux teints. Ce procédé peut contribuer à préserver une couleur plus uniforme et, par conséquent, peut augmenter la période entre les applications de teinture.

Claims

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


42
CLAIMS
1. A cosmetic method of treating mammalian hair to reduce or prevent colour
fade and/or colour shift comprising;
(a) treating the hair with a composition comprising a
hydrophobic and/or cationic conditioning agent; followed by
(b) wetting the hair.
2. A cosmetic method according to Claim 1 wherein the hair of step (a) is wet.
3. A cosmetic method according to Claim 1 or 2 comprising an additional step
(c), to be carried out after step (b), of treating the hair with a composition
comprising a conditioning agent.
4. A cosmetic method according to any of Claims 1 to 3 comprising an
additional step (d), to be carried out after step (b) or (c), of treating the
hair
with a composition comprising a ultra violet filter.
5. A cosmetic method according to any of Claims 1 to 4, wherein the
composition comprising a conditioning agent of step (a) or step (c) is
delivered as a foam.
6. A cosmetic method according to any of Claims 1 to 5, wherein the
composition comprising a conditioning agent of step (a) or step (c)
additionally comprises an ultra violet filter.

43
7. A cosmetic method according to any of Claims 1 to 6, wherein the
conditioning agent is selected from cationic surfactants, cationic polymers,
nonvolatile silicones, volatile silicones, nonvolatile hydrocarbons,
saturated C14 to C22 straight chain fatty alcohols, nonvolatile hydrocarbon
esters, and mixtures thereof.
8. A cosmetic method according to any of Claims 1 to 7, wherein step (b)
comprising washing the hair with a surfactant composition.
9. A cosmetic method according to Claim 8, wherein the surfactant
composition comprises a surfactant selected from anionic, cationic,

nonionic, amphoteric, zwitterionic surfactants.

Description

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


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1
COSMETIC METHOD FOR TREATING COLOURED HAIR TO REDUCE COLOUR FADE
Technical Field
The present invention relates to a cosmetic method of treating mammalian
coloured hair to reduce or prevent colour fade and/or colour shift.
Background of the invention
The desire to alter the colour of human hair is not only a facet of modern
times. Since the days of the Roman Empire the colour of human hair has been
routinely altered to accommodate the changes of fashion and style. However the
attainment of precise initial colours which are retained by the hair for a
desirable
period has proved a more elusive goal.
Once the hair has been coloured there is a desire that the colour be
retained in a consistent manner for a predictable period of time. Further,
there is
a desire for the colour to be resistant to fading, as occasioned by the
actions of
washing (also known as wash fastness) and other exterior factors such as the
action of the sun. It is, therefore, something of a balancing act between the
desire to retain a consistent colour and the necessity of exposing the
coloured
hair to factors which would lead to colour fade and/or colour shift.
Thus, it would be desirable to develop a method of treating coloured hair
that provides improved resistance to colour fade andlor colour shift, as
occasioned, for example, by washing during a regular cleansing regimen,
exposure to rain, exposure to water from other sources (e.g. from swimming) or
by the action of the sun, thereby maintaining a more consistent colouration
inbetween dye applications.

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2
Pre-treatment of hair prior to washing is known in the art. For example,
US-4402936 (Kao) discloses a pre-treatment composition comprising a cyclic
cationic group as having various beneficial conditioning effects. US-5700456
(L'Oreal) discloses a pre-treatment composition comprising a ceramide and a
cationic polymer for providing a de-tangling effect. GB-1570220 (L'Oreal)
discloses a pre-treatment composition comprising cationic materials for the
elimination of the bad effect of discolouration or dyeing treatments. JP-
60087208 (Shiseido) discloses a pre-treatment comprising metal salts for
preventing flux of protein components during shampooing and thereby protect
the hair in addition to improving chemically damaged hair. However, none of
these references disclose the use of pre-treatment compositions on coloured
hair
for the prevention or reduction of colour fade/shift.
It has surprisingly been found that treating the wet or dry coloured hair
with a composition comprising a hydrophobic and/or cationic conditioning agent
prior to washing with shampoo or exposure to water will reduce or prevent
colour
fade and/or colour shift caused by said washing or exposure.
Summary of the Invention
The present invention provides a cosmetic method for treating mammalian
coloured hair to reduce or prevent colour fade and/or colour shift comprising;
(a) treating the hair with a composition comprising a hydrophobic
and/or cationic conditioning agent; followed by
(b) wetting the hair.
Optionally the method can include treating the hair, after step (b), with a
composition comprising a conditioning agent and/or an ultra violet fltering
agent.

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The method of the present invention provides a reduction or prevention of
colour fade and/or colour shift of coloured hair. The method can help to
maintain
a more consistent colour and, therefore, can increase the time between dye
applications.
Description
The method of the present invention comprises at least two essential
steps, firstly a pre-treatment step and secondly a wetting step. Without
intending
necessarily to limit the scope of the invention, it is believed that pre-
treatment
with a composition comprising a conditioning agent 'seals' the hair thereby
preventing or reducing the leaching out of dye molecules that can be caused by
water.
As used herein "coloured hair" means hair which has been treated to alter
its colour. In particular, this can be through a dyeing treatment which,
permanently or temporarily, alters the hair's natural colour.
As used herein "colour fade and/or colour shift" means changes to the
colour of coloured hair caused by the action of external conditions. In
particular,
this can be through exposure of the coloured hair to the sun or water.
As used herein "reduction or prevention of colour fade andlor colour shift"
means impeding, retarding andlor arresting changes to the colour of hair. By
reducing or preventing colour fade andlor colour shift a more consistent
colour is
achieved and the time between dye applications can be increased.
As used herein "wetting of the hair" means exposure of the hair to water.
In particular, this exposure can be during a cleansing regimen with, for
example,

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4
shampoo or through other activities such as swimming. When the method is a
cleansing regimen, it is preferable that such a regimen is carried out
frequently,
preferably from once a day to once a week, more preferably from once a day to
once every three days, most preferably once a day.
Pre-treatment step
An essential step of the present method is a pre-treatment of the coloured
hair with a composition comprising a conditioning agent. Any conditioning
agent
suitable for use on hair may be used herein. Preferably the composition
comprises at least one hydrophobic and/or cationic conditioning agent.
Suitable
conditioning agents include cationic surfactants, cationic polymers, volatile
and
non-volatile silicones (including soluble and insoluble silicones),
nonvolatile
hydrocarbons, saturated C14 to C22 straight chain fatty alcohols, nonvolatile
hydrocarbon esters, liquid polyol carboxylic acid esters, and mixtures
thereof.
Preferred conditioning agents are cationic surfactants, cationic polymers and
silicones (especially insoluble silicones).
Cationic Surfactants
Cationic surfactants useful in the present method, contain amino or
quaternary ammonium moieties. The cationic surfactant will preferably, though
not necessarily, be insoluble in the compositions hereof. Cationic surfactants
among those useful herein are disclosed in the following documents, all
incorporated by reference herein: M.C. Publishing Co., McCutcheon's,
Detergents & Emulsifiers, (North American edition 1979); Schwartz, et al.,
Surface Active Agents, Their Chemistry and Technology, New York: Interscience
Publishers, 1949; U.S. Patent 3,155,591, Hilfer, issued November 3, 1964; U.
S.
Patent 3,929,678, Laughlin et al., issued December 30, 1975; U. S. Patent
3,959,461, Bailey et al., issued May 25, 1976; and U. S. Patent 4,387,090,
Bolich, Jr., issued June 7, 1983.

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Among the quaternary ammonium-containing cationic surfactant materials
useful herein are those of the general formula:
R
R~\N ~ 3 X
R
5 -
wherein R1-R4 are independently an aliphatic group of from about 1 to about 22
carbon atoms or an aromatic, alkoxy, poiyoxyalkylene, alkylamido,
hydroxyalkyl,
aryl or alkylaryl group having from about 1 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, sulfate, and
alkylsulfate
radicals. The aliphatic groups may 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. Especially preferred are di-long chain (e.g., di C12-C22,
preferably
C1g-Clg, aliphatic, preferably alkyl). di-short chain (e.g., C1-C3 alkyl,
preferably
C1-C2 alkyl) quaternary ammonium salts.
Salts of primary, secondary and tertiary fatty amines are also suitable
cationic surfactant materials. The alkyl groups of such amines preferably have
from about 12 to about 22 carbon atoms, and may be substituted or
unsubstituted. Such amines, useful herein, include stearamido propyl dimethyl
amine, diethyl amino ethyl stearamide, dimethyl stearamine, dimethyl soyamine,
soyamine, myristyl amine, tridecyl amine, ethyl stearylamine, N-tallowpropane
diamine, ethoxylated (with 5 moles of ethylene oxide) stearylamine, dihydroxy
ethyl stearylamine, and arachidylbehenylamine. Suitable amine salts include
the
halogen, acetate, phosphate, nitrate, citrate, lactate, and alkyl sulfate
salts. Such

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6
salts include stearylamine hydrochloride, soyamine chloride, stearylamine
formate, N-tallowpropane diamine dichloride and stearamidopropyl
dimethylamine citrate. Cationic amine surfactants included among those useful
in the present invention are disclosed in U.S. Patent 4,275,055, Nachtigal, et
al.,
issued June 23, 1981.
Cationic surfactants are preferably utilized at levels of from about 0.1 % to
about 10%, more preferably from about 0.25% to about 5%, most preferably from
about 0.5% to about 2%, by weight of the composition.
Cationic Polymer Conditioning Agent
The conditioning compositions useful in the present invention can also
comprise one or more cationic polymer conditioning agents. The cationic
polymer conditioning agents will preferably be water soluble. Cationic
polymers
are typically used in the same ranges as disclosed above for cationic
surfactants.
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.
Preferably,
the polymer will be sufficiently soluble to form a substantially clear
solution at
0.5% concentration, more preferably at 1.0% concentration.
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.
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

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nitrogen-containing moieties such as quaternary ammonium or cationic amino
moieties, and mixtures thereof.
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,
Crosiey, 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.

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Amine-substituted vinyl monomers can be polymerised 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
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-Cg 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, monoafkylaminoalkyl 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

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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.
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:
R~
A-O(-R-N~ R3X )
R2
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)

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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
5 their Polymer JR(RTM) and LR(RTM) 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 opoxide, referred to in the
10 industry (CTFA) as Polyquaternium 24. These materials are available from
Amerchol Corp. (Edison, NJ, USA) under the tradename Polymer LM-200(RTM).
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 by reference herein), and copolymers of etherified cellulose and
starch (e.g., as described in U.S. Patent 3,958,581, incorporated herein by
reference).
As discussed above, the cationic polymer hereof is water soluble. This
does not mean, however, that it must be soluble in the composition. Preferably
however, the cationic polymer is either soluble in the composition, or in a
complex coacervate phase in the composition formed by the cationic polymer and
anionic material. Complex coacervates of the cationic polymer can be formed
with anionic surfactants or with anionic polymers that can optionally be added
to
the compositions hereof (e.g., sodium polystyrene sulfonate).
Silicone Conditioning Agients
The conditioning compositions of the present method can also include
soluble or insoluble silicone conditioning agents. By soluble what is meant is
that

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the silicone conditioning agent is miscible with the aqueous 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 aqueous
carrier, such as in the form of an emulsion or a suspension of droplets of the
silicone.
The silicone hair conditioning agent will be used in the compositions
hereof at levels of from about 0.05% to about 10% by weight of the
composition,
preferably from about 0.1 % to about 6%, more preferably from about 0.5% to
about 5%, most preferably from about 0.5% to about 3%.
Soluble silicones include silicone copolyols, such as dimethicone
copolyols, e.g. polyether siloxane-modified polymers, such as polypropylene
oxide, polyethylene oxide modified polydimethylsiloxane, wherein the level of
ethylene and/or propylene oxide sufficient to allow solubility in the
composition.
Preferred, however, are insoluble silicones. The insoluble silicone hair
conditioning agent for use herein will preferably have viscosity of from about
1,000 to about 2,000,000 centistokes at 25°C, more preferably from
about
10,000 to about 1,800,000, even more preferably from about 100,000 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 CTM0004, July
20, 1970.
Suitable volatile silicones include cyclomethicone. Suitable insoluble,
nonvolatile silicone fluids include polyalkyl siloxanes, polyaryl siioxanes,
polyalkylaryl siloxanes, polyether siloxane copolymers, and mixtures thereof.
Other insoluble, nonvolatile silicone fluids having hair conditioning
properties can
also be used. The term "nonvolatile" as used herein shall mean that the
silicone
has a boiling point of at least about 260°C, preferably at least about
275°C, more

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preferably at least about 300°C Such materials exhibit very low or no
significant
vapor pressure at ambient conditions. The term "silicone fluid" shall mean
flowable silicone materials having a viscosity of less than 1,000,000
centistokes
at 25°C. Generally, the viscosity of the fluid will be between about 5
and
1,000,000 centistokes at 25°C, preferably between about 10 and about
300,000
centistokes.
Silicone fluids hereof also include polyalkyl or polyaryl siloxanes with the
following structure:
R R R
I I I
A-Si-O Si-O Si-A
I f
R R XR
wherein R is alkyl or aryl, and x is an integer from about 7 to about 8,000
may
be used. "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) may have any structure as long as the
resulting silicones remain fluid at room temperature, are hydrophobic, are
neither irritating, toxic nor otherwise harmful when applied to the hair, are
compatible with the other components of the composition, are chemically
stable under normal use and storage conditions, and are capable of being
deposited on and of conditioning hair.
Suitable A groups include methyl, methoxy, ethoxy, propoxy, and
aryloxy. The two R groups on the silicone 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 silicones are polydimethyi siloxane,

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polydiethylsiioxane, and polymethylphenylsiloxane. Polydimethylsiloxane is
especially preferred.
The nonvolatile polyalkylsiloxane fluids that may be used include, for
example, polydimethylsiloxanes. These siloxanes 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.
The polyalkylaryl siloxane fluids that may be used, also include, for
example, polymethylphenylsiloxanes. These siloxanes are available, for
example, from the General Electric Company as SF 1075 methyl phenyl fluid
.e .
or from Dow Corning as 556 Cosmetic Grade Fluid.
Especially preferred, for enhancing the shine characteristics of hair,
are highly arylated silicones, such as highly phenylated polyethyl silicone
having refractive indices of about 1.46 or higher, especially about 1.52 or
higher. When these high refractive index silicones 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.
The poiyether siloxane copolymers that may be used include, for
example, a polypropylene oxide modified polydimethylsiioxane (e.g., Dow
Corning DC-1248) although ethylene oxide or mixtures of ethylene oxide and
propylene oxide may also be used. The ethylene oxide and polypropylene
oxide level should be sufficiently low to prevent solubility in the
composition
hereof.
References disclosing suitable silicone fluids include U.S. Patent
2,826,551, Geen; U.S. Patent 3,964,500, Drakoff, issued June 22, 1976; U.S.

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Patent 4,364,837, Pader; and British Patent 849,433, Woolston. All of these
patents are incorporated herein by reference. Also incorporated herein by
reference is Silicon Compounds distributed by Petrarch Systems, Inc., 1984.
This reference provides an extensive (though not exclusive) listing of
suitable
silicone fluids.
Another silicone hair conditioning material that can be especially useful
in the silicone conditioning agents is insoluble silicone gum. The term
"silicone gum", as used herein, means polyorganosiloxane materials having a
viscosity at 25°C of greater than or equal to 1,000,000 centistokes.
Silicone
gums are described by Petrarch and others including U.S. Patent 4,152,476,
Spitzer et al., issued May 1, 1979 and Noll, Walter, Chemistry and
Technology of Silicones, New York: Academic Press 19fi8. Also describing
silicone gums are General Electric Silicone Rubber Product Data Sheets SE
30, SE 33, SE 54 and SE 7fi. All of these described references are
incorporated herein by reference. 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, (polydimethylsiloxane) (methylvinylsiloxane) copolymer,
poly(dimethylsiloxane) (diphenyl siloxane)(methyl vinylsiloxane) copolymer
and mixtures thereof.
Preferably the silicone hair conditioning agent comprises a mixture of a
polydimethylsiloxane gum, having a viscosity greater than about 1,000,000
centistokes and polydimethylsiloxane fluid having a viscosity of from about 10
centistokes to about 100,000 centistokes, wherein the ratio of gum to fluid is
from about 30:70 to about 70:30, preferably from about 40:60 to about 60:40.
An optional ingredient that can be included in the silicone conditioning
agent is silicone resin. Silicone resins are highly crossiinked polymeric

CA 02330483 2000-10-27
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siloxane systems. The cross-linking is introduced through the incorporation of
trifunctional and tetrafunctional silanes with monofunctional or difunctional,
or
both, silanes during manufacture of the silicone resin. As is well understood
in the art, the degree of cross-linking that is required in order to result in
a
5 silicone resin will vary according to the specific silane units incorporated
into
the silicone 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
10 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-,
15 monophenyl-, Biphenyl-, methylphenyl-, monovinyl-, and
methylvinyl-chlorosilanes, 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.
Silicone resins can enhance deposition of silicone on the hair and can
enhance the glossiness of hair with high refractive index volumes.
Background material on silicones including sections discussing silicone
fluids, gums, and resins, as well as manufacture of silicones, can be found in
Encyclopedia of Polymer Science and Engineering, Volume 15, Second

CA 02330483 2000-10-27
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16
Edition, pp 204-308, John Wiley & Sons, Inc., 1989, incorporated herein by
reference.
Silicone materials and silicone resins in particular, can conveniently be
identified according to a shorthand nomenclature system well known to those
skilled in the art as "MDTQ" nomenclature. Under this system, the silicone is
described according to presence of various siloxane monomer units which
make up the silicone. Briefly, the symbol M denotes the monofunctional unit
(CH3)gSiO).5; D denotes the difunctional unit (CHg)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,
phenyls, amines, hydroxyls, 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 molar amounts of T, Q, T'
andlor Q' to D, D', M and/or or M' in a silicone resin is indicative of higher
levels of cross-linking. As discussed before, however, the overall level of
cross-linking 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.
Wetting Step

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17
A second essential step of the present method is a wetting step to be
carried out after the pre-treatment step. This can comprise exposing the pre-
treated hair, which may be wet or dry, to water, for example, rinsing or
wetting
during swimming or washing the pre-treated hair with a shampoo composition
comprising a surfactant. Any shampoo suitable for cleansing the hair may be
used herein. Suitable surfactants for inclusion in the compositions of the
invention generally have a lipophilic chain length of from about 8 to about 22
carbon atoms and can be selected from anionic, cationic, nonionic, amphoteric,
zwitterionic surfactants and mixtures thereof.
Anionic Surfactants
Anionic surfactants suitable for inclusion in the compositions useful in the
present
method include alkyl sulphates, ethoxylated alkyl sulphates, alkyl glyceryl
ether
sulfonates, methyl acyl taurates, fatty acyl giycinates, N-acyl glutamates,
acyl
isethionates, alkyl sulfosuccinates, alkyl ethoxysulphosuccinates, alpha-
sulfonated fatty acids, their salts and/or their esters, alkyl ethoxy
carboxylates,
alkyl phosphate esters, ethoxylated alkyl phosphate esters, alkyl sulphates,
acyl
sarcosinates and fatty acid/protein condensates, and mixtures thereof. Alkyl
and/or acyl chain lengths for these surfactants are C12-C22, preferably C12-
C18
more preferably C12_C14~
Nonionic Surfactants
The compositions useful in the present method can also comprise water-soluble
nonionic surfactant(s). Surfactants of this class include C~2_C~4 fatty acid
mono-and diethanolamides, sucrose polyester surfactants and polyhydroxy fatty
acid amide surfactants having the general formula below.
O R9
R8 C 1V Z2

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18
The preferred N-alkyl, N-alkoxy or N-aryloxy, polyhydroxy fatty acid amide
surfactants according to the above formula are those in which Rg is C5-Cg1
hydrocarbyl, preferably Cg-C1g hydrocarbyl, including straight-chain and
branched chain alkyl and alkenyl, or mixtures thereof and Rg is typically
hydrogen, C1-Cg alkyl or hydroxyalkyl, preferably methyl, or a group of
formula -
R1-O-R2 wherein R1 is C2-Cg hydrocarbyl including straight-chain, branched-
chain and cyclic (including aryl), and is preferably C2-C4 alkyiene, R2 is C1-
Cg
straight-chain, branched-chain and cyclic hydrocarbyl including aryl and
oxyhydrocarbyl, and is preferably C1-C4 alkyl, especially methyl, or phenyl.
Z2 is
a polyhydroxyhydrocarbyl moiety having a linear hydrocarbyl chain with at
least 2
(in the case of glyceraldehyde) or at least 3 hydroxyls (in the case of other
reducing sugars) directly connected to the chain, or an alkoxylated derivative
(preferably ethoxylated or propoxylated) thereof. Z2 preferably will be
derived
from a reducing sugar in a reductive amination reaction, most preferably Z2 is
a
glycityl moiety. Suitable reducing sugars include glucose, fructose, maltose,
lactose, galactose, mannose, and xylose, as well as glyceraldehyde. As raw
materials, high dextrose com syrup, high fructose corn syrup, and high maltose
corn syrup can be utilised as well as the individual sugars listed above.
These
corn syrups may yield a mix of sugar components for Z2. It should be
understood that it is by no means intended to exclude other suitable raw
materials. Z2 preferably will be selected from the group consisting of -CH2-
(CHOH)~-CH20H, -CH(CH20H)-(CHOH)n-1-CH2H,
CH2(CHOH)2(CHOR')CHOH)-CH20H, where n is an integer from 1 to 5,
inclusive, and R' is H or a cyclic mono- or polysaccharide, and alkoxylated
derivatives thereof. As noted, most preferred are glycityls wherein n is 4,
particularly -CH2-{CHOH)4-CH20H.

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19
The most preferred polyhydroxy fatty acid amide has the formula
Rg(CO)N(CH3)CH2(CHOH)4CH20H wherein Rg is a C6-C19 straight chain alkyl
or alkenyl group. In compounds of the above formula, Rg-CO-N< can be, for
example, cocoamide, stearamide, oleamide, iauramide, myristamide,
capricamide, palmiamide, talfowamide, etc.
Suitable oil derived nonionic surfactants for use herein include water soluble
vegetable and animal-derived emollients such as triglycerides with a
polyethyleneglycol chain inserted; ethoxylated mono and di-glycerides,
polyethoxylated lanolins and ethoxylated butter derivatives. One preferred
class
of oil-derived nonionic surfactants for use herein have the general formula
below:
0
RCOCH2 CH ( OH ) CH2 ( OCH2 CH2 ) nOH
wherein n is from about 5 to about 200, preferably from about 20 to about 100,
more preferably from about 30 to about 85, and wherein R comprises an
aliphatic
radical having on average from about 5 to 20 carbon atoms, preferably from
about 7 to 18 carbon atoms.
Suitable ethoxylated oils and fats of this class include polyethyleneglycol
derivatives of glyceryl cocoate, glyceryl caproate, glyceryl caprylate,
glyceryl
tallowate, glyceryl palmate, glyceryl stearate, glyceryl laurate, glyceryl
oleate,
glyceryl ricinoleate, and glyceryl fatty esters derived from triglycerides,
such as
palm oil, almond oil, and corn oil, preferably glyceryl tallowate and giyceryl
cocoate.
Preferred for use herein are polyethyleneglycol based polyethoxylated Cg-C15
fatty alcohol nonionic surfactants containing an average of from about 5 to
about
50 ethyleneoxy moieties per mole of surfactant.

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Suitable polyethylene glycol based polyethoxylated Cg-C15 fatty alcohols
suitable for use herein include Cg-C11 Pareth-3, Cg-C11 Pareth-4, Cg-C11
Pareth-5, Cg-C11 Pareth-6, Cg-C11 Pareth-7, Cg-C11 Pareth-8, C11-C15
5 Pareth-3, C11-C15 Pareth-4, C11-C15 Pareth-5, C1 ~-C15 Pareth-6, C11-C15
Pareth-7, C11-C15 Pareth-8, C11-C15 Pareth-9, C11-C15 Pareth-70, C11-C15
Pareth-11, C11-C15 Pareth-12, C11-C15 Pareth-13 and C11-C15 Pareth-14.
PEG 40 hydrogenated castor oil is commercially available under the tradename
Cremophor (RTM) from BASF. PEG 7 glyceryl cocoate and PEG 20 gfyceryl
10 laurate are commercially available from Henkel under the tradenames Cetiol
(RTM) HE and Lamacit (RTM) GML 20 respectively. Cg-C11 Pareth-8 is
commercially available from Shell Ltd under the tradename Dobanol (RTM) 91-8.
Particulary preferred for use herein are polyethylene glycol ethers of ceteryl
alcohol
such as Ceteareth 25 which is available from BASF under the trade name
Cremaphor
15 A25.
Also suitable for use herein are nonionic surfactants derived from composite
vegetable fats extracted from the fruit of the Shea Tree (Butyrospermum Karkii
Kotschy) and derivatives thereof. Similarly, ethoxylated derivatives of Mango,
20 Cocoa and Illipe butter may be used in compositions according to the
invention.
Although these are classified as ethoxyiated nonionic surfactants it is
understood
that a certain proportion may remain as non-ethoxylated vegetable oil or fat.
Other suitable oil-derived nonionic surfactants include ethoxylated
derivatives of
almond oil, peanut oil, rice bran oil, wheat germ oil, linseed oil, jojoba
oil, oil of
apricot pits, walnuts, palm nuts, pistachio nuts, sesame seeds, rapeseed, cade
oil, corn oil, peach pit oil, poppyseed oil, pine oil, castor oil, soybean
oil, avocado
oil, safflower oil, coconut oil, hazelnut oil, olive oil, grapeseed oil, and
sunflower
seed oil.

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21
Amphoteric Surfactants
Amphoteric surfactants suitable for use in the compositions useful in the
present
method include:
(a) imidazolinium surfactants of formula (VII)
C2H40R2
;CH2Z
R1.. ,~N~
+ '
N
wherein R~ is C7-C22 alkyl or alkenyl, R2 is hydrogen or CH2Z,
each Z is independently COZM or CH2C02M, and M is H, alkali
metal, alkaline earth metal, ammonium or alkanolammonium;
and/or ammonium derivatives of formula (VIII)
C2H40H
R1CONH(CH2)2N+CH2Z
R2
wherein R~, R2 and Z are as defined above;
(b) aminoalkanoates of formula (IX)
R~ NH(CH2)nC02M
iminodialkanoates of formula (X)

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22
R1 N[(CH2)mC02M12
and iminopolyalkanoates of formula (XI)
R 1 _[N(CH2)p]qN[CH2C02M]2
CH2C02M
wherein n, m, p, and q are numbers from 1 to 4, and R1 and M are
independently selected from the groups specified above; and
(c) mixtures thereof.
Suitable amphoteric surfactants of type (a) are marketed under the trade name
Miranol and Empigen and are understood to comprise a complex mixture of
species. Traditionally, the Miranols have been described as having the general
formula (VII), although the CTFA Cosmetic Ingredient Dictionary, 3rd Edition
indicates the non-cyclic structure (VIII) while the 4th Edition indicates yet
another
structural isomer in which R2 is O-linked rather than N-linked. In practice, a
complex mixture of cyclic and non-cyclic species is likely to exist and both
definitions are given here for sake of completeness. Preferred for use herein,
however, are the non-cyclic species.
Examples of suitable amphoteric surfactants of type (a) include compounds of
formula XII and/or XIII in which R1 is CgHl7 (especially iso-capryl), CgHlg
and
C11 H23 alkyl. Especially preferred are the compounds in which R1 is CgH1 g, Z
is C02M and R2 is H; the compounds in which R1 is C11 H23, Z is C02M and
R2 is CH2C02M; and the compounds in which R1 is C11H23, Z is C02M and R2
is H.

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23
In CTFA nomenclature, materials suitable for use in the present invention
include
cocoamphocarboxypropionate, cocoamphocarboxy propionic acid, and especially
cocoamphoacetate and cocoamphodiacetate (otherwise referred to as
cocoamphocarboxyglycinate). Specific commercial products include those sold
under the trade names of Ampholak 7TX (sodium carboxy methyl tallow
polypropyl amine), Empigen CDL60 and CDR 60 (Albright & Wilson), Miranol
H2M Conc. Miranol C2M Conc. N.P., Miranol C2M Conc. O.P., Miranol C2M SF,
Miranol CM Special (Rhone-Poulenc); Alkateric 2CIB (Alkaril Chemicals);
Amphoterge W-2 (Lonza, Inc.); Monateric CDX-38, Monateric CSH-32 (Mona
Industries); Rewoteric AM-2C (Rewo Chemical Group); and Schercotic MS-2
.e .
(Scher Chemicals). Further examples of amphoteric surfactants suitable for use
herein include Octoxynol-1 (RTM), polyoxethylene (1) octyfphenyl ether;
Nonoxynol-4 (RTM), polyoxyethylene (4) nonylphenyl ether and Nonoxynol-9,
polyoxyethylene (9} nonylphenyl ether.
It will be understood that a number of commercially-available amphoteric
surfactants of this type are manufactured and sold in the form of
electroneutral
complexes with, for example, hydroxide counterions or with anionic sulfate or
sulfonate surfactants, especially those of the sulfated Cg-C1g alcohol, Cg-C1g
ethoxylated alcohol or Cg-C1g acyl glyceride types. Note also that the
concentrations and weight ratios of the amphoteric surfactants are based
herein
on the uncomplexed forms of the surfactants, any anionic surfactant
counterions
being considered as part of the overall anionic surfactant component content.
Examples of preferred amphoteric surfactants of type (b) include N-alkyl
polytrimethylene poly-, carboxymethylamines sold under the trade names
Ampholak X07 and Ampholak 7CX by Berol Nobel and also salts, especially the
triethanolammonium salts and salts of N-lauryl-beta-amino propionic acid and N-

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24
lauryl-imino-dipropionic acid. Such materials are sold under the trade name
Deriphat by Henkel and Mirataine by Rhone-Poulenc.
Zwitterionic Surfactants
Water-soluble auxiliary zwitterionic surfactants suitable for inclusion in the
compositions useful in the present method include alkyl betaines of the
formula
R5RgR7N+ (CH2)nC02M and amido betaines of the formula (XII) below:
R6
R~CON(CH2)mN(CH2)nC02M
R~
wherein R5 is C11-C22 alkyl or alkenyl, Rg and R7 are independently C1-C3
alkyl, M is H, alkali metal, alkaline earth metal, ammonium or
alkanolammonium,
and n, m are each numbers from 1 to 4. Preferred betaines include
cocoamidopropyldimethylcarboxymethyl betaine,
laurylamidopropyldimethylcarboxymethyl betaine and Tego betaine (RTM)
Water-soluble auxiliary sultaine surfactants suitable for inclusion in the
compositions of the present invention include alkyl sultaines of the formula
(X111)
below:
R2
R1 CON(CH2)mN+(CH2)nCH(OH)CH2S03-M+
R3

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WO 99/55295 PCT/US98/16496
wherein R1 is C7 to C22 alkyl or alkenyl, R2 and R3 are independently C1 to C3
alkyl, M is H, alkali metal, alkaline earth metal, ammonium or alkanolammonium
and m and n are numbers from 1 to 4. Preferred for use herein is coco amido
5 propylhydroxy sultaine.
Water-soluble auxiliary amine oxide surfactants suitable for inclusion in the
compositions of the present invention include alkyl amine oxide R5RgR7N0 and
amido amine oxides of the formula (XI~ below:
R6
R5CON(CH2)mN ~ O
R~
wherein R5 is C11 to C22 alkyl or alkenyl, Rg and R7 are independently C1 to
~ 5 Cg alkyl, M is H, alkali metal, alkaline earth metal, ammonium or
alkanolammonium and m is a number from 1 to 4. Preferred amine oxides
include cocoamidopropylamine oxide, lauryl dimethyl amine oxide and myristyl
dimethyl amine oxide.
Optional Steps
The present method can additionally comprise one or more optional steps
to be carried out after the wetting step. These additional steps can include
treating the hair with a conditioning composition, treating the hair with a
25 conditioning composition additionally comprising an ultra violet filtering
agent

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26
and/or treating the hair with a composition comprising an ultra violet
filtering
agent.
Any ultra violet filtering agents suitable for topical application are useful
in
the conditioning, shampooing or ultra violet filtering compositions herein. A
wide
variety of ultra violet filtering agents are described in U.S. Patent No.
5,087,445,
to Haffey et al., issued February 11, 1992; U.S. Patent No. 5,073,372, to
Turner
et al., issued December 17, 1991; U.S. Patent No. 5,073,371, to Turner et al.
issued December 17, 1991; and Segarin, et al., at Chapter VIII, pages 189 et
seq., of Cosmetics Science and Technolo4y. Preferred among those ultra violet
filtering agents which are useful in the compositions of the instant invention
are
those selected from 2-ethylhexyl p-methoxycinnamate, 2-ethylhexyl N, N-
dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5- \
sulfonic acid, octocrylene, oxybenzone, homomenthyf salicylate, octyl
salicylate,
4,4'-methoxy-t-butyldibenzoylmethane, 4-isopropyl dibenzoylmethane, 3-
benzyiidene camphor, 3-(4-methylbenzylidene) camphor, titanium dioxide, zinc
oxide, silica, iron oxide, Parsol MCX, Eusolex 6300, Octocrylene, Parsol 1789,
and mixtures thereof.
Still other useful ultra violet filtering agents are those disclosed in U.S.
Patent No. 4,937,370, to Sabatelli, issued June 26, 1990; and U.S. Patent No.
'
4,999,186, to Sabatelli et al., issued March 12, 1991. The ultra violet
filtering
agents disclosed therein have, in a single molecule, two distinct chromophore
moieties which exhibit different ultra-violet radiation absorption spectra.
One of
the chromophore moieties absorbs predominantly in the UVB radiation range and
the other absorbs strongly in the UVA radiation range. These ultra violet
filtering
agents provide higher efficacy, broader UV absorption, lower skin penetration
and longer lasting efficacy relative to conventional ultra violet filtering
agents.
Especially preferred examples of these ultra violet filtering agents include
those
selected from 4-N,N-{2-ethylhexyl)methylaminobenzoic acid ester of 2,4-

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~7
dihydroxybenzophenone, 4-N,N-(2-ethylhexyl) methylaminobenzoic acid ester
with 4-hydroxydibenzoylmethane, 4-N,N-(2-ethylhexyl)methylaminobenzoic acid
ester of 2-hydroxy-4-(2-hydroxyethoxy)benzophenone, 4-N,N-(2-ethylhexyl)-
methylaminobenzoic acid ester of 4-(2-hydroxyethoxy)dibenzoylmethane, and
mixtures thereof.
Other Ingredients
The compositions useful in the present method can contain a variety of
other optional components suitable for rendering such compositions more
cosmetically or aesthetically acceptable or to provide them with additional
usage
benefits. Such conventional optional ingredients are well-known to those
skilled
in the art.
A wide variety of additional ingredients can be formulated into the present
compositions. These include: other conditioning agents; hair-hold polymers;
additional thickening agents and suspending agents such as xanthan gum, guar
gum, hydroxyethyl cellulose, methyl cellulose, hydroxyethylcellulose, starch
and
starch derivatives; viscosity modifiers such as methanolamides of long chain
fatty
acids such as cocomonoethanol amide; crystalline suspending agents;
pearlescent aids such as ethylene glycol distearate; preservatives such as
benzyl
alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; polyvinyl
alcohol; ethyl alcohol; 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; colouring 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; sequestering agents, such as disodium
ethyienediamine tetra-acetate; and polymer plasticizing agents, such as
glycerin,

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28
disobutyl adipate, butyl stearate, and propylene glycol; antioxidants, such as
tocopheryl acetate and butyl hydroxy toluene.
Also suitable for use herein as conditioning agents are liquid polyol
carboxylic acid esters. These polyol esters are derived from a polyol with one
or
more carboxylic acids. In other words, these esters contain a moiety derived
from a poiyol and one or more moieties derived from a carboxylic acid. These
carboxylic acid esters can also be described as liquid polyol fatty acid
esters,
because the terms carboxylic acid and fatty acid are often used
interchangeably
by those skilled in the art. As used herein, the term liquid, means a fluid
which is
visibly flowable (to the naked eye) under ambient conditions (about 1
atmosphere
of pressure at about 25°C).
The liquid polyol polyesters suitable for use herein comprise certain polyols,
especially sugars, sugar alcohols or sugar ethers, esterified with at least
two fatty
acid groups. The polyol starting material, however, preferably has at least
about
four esterifiable hydroxyl groups. Examples of preferred polyols are sugars,
including monosaccharides and disaccharides, sugar alcohols or sugar ethers.
Examples of monosaccharides containing four hydroxyl groups are xylose and
arabinose and the sugar alcohol derived from xylose, which has five hydroxyl
groups, i.e., xylitol. The monosaccharide, erythrose, is also suitable in the
practice of this invention since it contains three hydroxyl groups, as is the
sugar
alcohol derived from erythrose, i.e., erythritol, which contains four hydroxyl
groups. Suitable five hydroxyl group-containing monosaccharides are galactose,
fructose, and sorbose. Sugar alcohols containing six hydroxyl groups derived
from the hydrolysis products of sucrose, as well as glucose and sorbose, e.g.,
sorbitol, are also suitable. Examples of disaccharide polyols which can be
used
include maltose, lactose, and sucrose, all of which contain eight hydroxyl
groups.
In addition, sugar ethers are also suitable for the practise of this
invention, such
as, sorbitan.

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29
The polyols used in such liquid polyol esters preferably have from about 4
to about 12, more preferably from about 4 to about 11, and most preferably
from
about 4 to about 8 hydroxyl groups. Preferred polyols for preparing the
polyesters suitable for use herein are selected from the group consisting of
erythritol, xylitol, sorbitol, glucose, and sucrose. Sucrose is especially
preferred.
The preferred polyol starting material having at least four hydroxyl groups
must be esterified on at least two of the hydroxyl groups with a fatty acid
containing from about 8 to about 22 carbon atoms, preferably from about 8 to
about 14 carbon atoms. Examples of such fatty acids include capryiic, capric,
lauric, myristic, myristoleic, palmitic, palmitoleic, stearic, oleic,
ricinoleic, linoleic,
linolenic, eleostearic, arachidic, arachidonic, behenic, and erucic acids. The
fatty
acids can be derived from naturally occurring or synthetic fatty acids; they
can be
saturated or unsaturated, including positional and geometrical isomers.
However, in order to provide liquid polyesters of the type suitable for use
herein,
at least about half of the fatty acid incorporated into the polyester molecule
must
be unsaturated fatty acids, saturated short chain fatty acids, or mixtures
thereof.
2o The liquid polyol fatty acid polyesters suitable for use as conditioning
agents herein must contain at least two fatty acid ester groups. It is not
necessary that all of the hydroxyl groups of the polyol be esterified with
fatty
acids, but it is preferable that the polyester contain no more than two
unesterified
hydroxyl groups. Most preferably, substantially all of the hydroxyl groups of
the
polyol are esterified with fatty acids, i.e., the polyol moiety is
substantially
completely esterified. The fatty acids esterified to the polyol molecule can
be the
same or mixed, but as noted above, a substantial amount of the unsaturated
acid
ester groups and/or saturated short chain acid ester groups must be present to
provide liquidity.

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To illustrate the above points, a sucrose di-fatty acid ester would be
suitable, but is not preferred because it has more than two unesterified
hydroxyl
groups. A sucrose hexa-fatty acid ester would be preferred because it has no
more than two unesterified hydroxyl groups. Highly preferred compounds in
5 which all the hydroxyl groups are esterified with fatty acids include the
liquid
sucrose octa-substituted fatty acid esters.
The following are non-limiting examples of specific liquid polyol fatty acid
polyesters containing at least two fatty acid ester groups suitable for use in
the
10 present invention: glucose dioleate, the glucose diesters of soybean oil or
cotton
seed oil fatty acids (unsaturated), the mannose diesters of mixed soybean oil
or
cotton seed oil fatty acids, the galactose diesters of oleic acid, the
arabinose
diesters of linoleic acid, xylose dilinoleate, sorbitol dioleate, sucrose
dioleate,
glucose trioleate, the glucose triesters of soybean oil or cotton seed oil
fatty acids
15 (unsaturated), the mannose triesters of mixed soybean oil or cotton seed
oil fatty
acids, the galactose triesters of oleic acid, the arabinose triesters of
linoleic acid,
xylose trilinofeate, sorbitol trioleate, sucrose trioleate, glucose
tetraoleate, the
glucose tetraesters of soybean oil or cotton seed oil fatty acids
(unsaturated), the
mannose tetraesters of mixed soybean oil or cotton seed oil fatty acids, the
20 galactose tetraesters of oleic acid, the arabinose tetraesters of linoieic
acid,
xylose tetralinoleate, gaiactose pentaoleate, sorbitol tetraoleate, the
sorbitol
hexaesters of unsaturated soybean oil or cotton seed oil fatty acids, xylitol
pentaoleate, sucrose tetraoleate, sucrose pentaoletate, sucrose hexaoleate,
sucrose hepatoleate, sucrose octaoleate, and mixtures thereof.
The preferred liquid polyol polyesters of the present invention have
complete melting points below about 30oC, preferably below about 27.5oC, and
more preferably below about 25oC. Complete melting points reported herein are
measured by Differential Scanning Calorimetry (DSC). The term "complete
melting point", as used herein means a melting point as measured by the well-

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
31
known technique of Differential Scanning Calorimetry (DSC). The complete
melting point is the temperature at the intersection of the baseline, i.e. the
specific heat line, with the line tangent to the trailing edge of the
endothermic
peak. Typically a scanning temperature of 5oC/minute is used in the present
invention in measuring the complete melting points. A technique for measuring
complete melting points is more fully described in US-A-5,306,514, to Letton
et
al., issued April 26, 1994.
Exemplary liquid polyol carboxylic acid esters suitable for use herein are
sucrose polysoyate or sucrose polycottonseedoate available from Procter and
Gamble.
The polyol fatty acid polyesters suitable for use herein can be prepared by
a variety of methods well known to those skilled in the art. These methods
include: transesterification of the polyol with methyl, ethyl or glycerol
fatty acid
esters using a variety of catalysts; acylation of the polyol with a fatty acid
chloride; acylation of the polyol with a fatty acid anhydride; and acyiation
of the
polyol with a fatty acid, per se. See US-A-3,463,699, to Rizzi, issued June
15,
1976; and US-A-4,517,360 and 4,518,772 to Volpenhein issued 1985.
The shampoo, conditioning and ultra violet filtering compositions herein can
be in
the form of an emulsion, a cream, a gel or a foam.

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
32
Examples
Example 1
1. As part of a daily cleansing regimen coloured hair is pre-treated using
currently marketed Pantene(RTM) conditioner.
2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) shampoo and rinsed with water.
Example 2
1. As part of a daily cleansing regimen coloured hair is pre-treated using a
conditioning composition of the following formula (A);
Component IIVt.%
Oleyl Alcohol 1.00
PEG-7M1 2.00
Polydimethylsiloxane2 4.20
Silicone Resin3 0.25
Pentaphenyl Trimethyl
Trisiloxane4 0.38
DL Panthenol 0.04
Panthenyl Ethyl Ether 0.34
Fragrance 0.30
Kathon(RTM) CG5 0.03
Cetyl Alcohol 1.20
Stearyl Alcohol 0.80
Ditallow Dimethyl
Ammonium Chloride 0.75
Stearamidopropyl
Dimethylamine 1.00

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
33
Glycerol Monostearate 0.25
Citric Acid 0.19
Water to 100
~ PEG-7M is Polyethylene Glycol where n has an average value of about 7,000
and is commercially available
under the tradename of Polyox WSR(RTM) N-750 from Union Carbide.
2 An 85%I15% (wt. basis) mixture of D5 Cyclomethicone and dimethicone gum
(weight average molecular weight
of about 400,000 to about 600,000).
3 Polytrimethyl hydrosilylsilicate, added as a 50 wt. % solution in
decamethylcyclopentasiloxane, General Electric
Silicone Products, SS 4320.
4 Dow Corning 705. Dow Corning Corp. (Midland, MI, USA).
5 Methylchloroisothiazoline (and) methylisothiazoline, a preservative from
Rohm 8 Haas Co., (Philadelphia, PA,
USA).
2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) Ultra Mild shampoo and rinsed with water.
Example 3
After colouring the coloured hair is pre-treated using currently marketed
Pantene(RTM) conditioner followed by rinsing the hair with water.
Example 4
1. The coloured hair is pre-treated using currently marketed Pantene(RTM)
conditioner.
2. The pre-treated hair is exposed to water through swimming.
Example 5
1. As part of a daily cleansing regimen coloured hair is pre-treated using
currently marketed Oil of Ulay(RTM) Active Hydrogel.
2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) shampoo and rinsed with water.

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
34
Example 6
1. As part of a daily cleansing regimen coloured hair is then pre-treated
using
currently marketed Pantene(RTM) conditioner.
2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) shampoo and rinsed with water.
3. The washed hair is then conditioned using currently marketed
Pantene(RTM) Conditioner.
Example 7
1. As part of a daily cleansing regimen coloured hair is pre-treated using a
conditioning composition of formula (A).
2F The pre-treated hair is then washed with currently marketed
Pantene(RTM) Ultra Mild shampoo and rinsed with water.
3. The washed hair is then conditioned with a conditioning composition of
formula (A).
Example 8
1. As part of a daily cleansing regimen the coloured hair is pre-treated using
currently marketed Oil of Ulay(RTM) Active Hydrogel.
2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) shampoo and rinsed with water.
3. The washed hair is then conditioned using a conditioning composition of
the following formula;
Component (Wt.%~
Oleyl Alcohol 0.25
PEG-7M1 1.00
Polydimethylsiloxane2 4.20
Silicone Resin3 0.25
Pentaphenyl Trimethyl

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
Trisiloxane4 0.38
DL Panthenol 0.04
Panthenyl Ethyl Ether 0.34
Fragrance 0.35
5 Kathon(RTM) CG5 0.03
Cetyl Alcohol 1.80
Stearyl Alcohol 1.20
Ditallow Dimethyl
Ammonium Chloride 0.75
10 Stearamidopropyl
Dimethylamine 1.00
Glycerol Monostearate 0.25
Citric Acid 0.22
Hydroxyethyl Cellulose0.25
15 Water to
100
PEG-7M is Polyethylene Glycol where n has an average value of about 7,000 and
is commercially available
under the tradename of Polyox WSR(RTM) N-750 from Union Carbide.
2' An 85%/15% (wt_ basis) mixture of D5 Cyclomethicone and dimethicone gum
(weight average molecular
20 weight of about 400,000 to about 600,000).
3' Polytrimethyl hydrosilylsilicate, added as a 50 wt. % solution in
decamethylcyGopentasiloxane, General
Electric Silicone Products, SS 4320. -
4 Dow Corning 705, Dow Coming Corp. (Midland, MI, USA).
5 Methylchloroisothiazoline (and) methylisothiazoline, a preservative from
Rohm 8 Haas Co., (Philadelphia,
25 PA, USA).
Examele 9
1. As part of a daily cleansing regimen the coloured hair is pre-treated using
currently marketed Pantene(RTM) conditioner.
30 2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) shampoo and rinsed with water.

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
36
3. The washed hair is then conditioned currently marketed Pantene(RTM)
conditioner and rinsed with water.
4. The hair is then treated with an an ultra violet filtering composition of
the
following formula;
Comaonent (Wt %)
Octyl Methoxycinnamate 6.00
Glycerine 6.00
Zinc oxide 3.00
Isohexadecane 2.00
Isopropyl Palmitate 2.00
Polyacrylamide &
C13-14 Isoparaffin &
Laureth-4 (Sepigel 305) 1.55
Steareth-21 0.90
Cetyi alcohol 0.79
Stearyl alcohol 0.7g %
Behenyl alcohol 0.83
Dimethicone 8~
Dimethiconol (DC - 2 1068 blend)0.75
SEFA Cottonate 0.50 % '
Tocopheryl Acetate 0.20
DMDM Hydantoin & lodopropynyl
Butylcarbamate (Glydant Plus) 0.20
Perfume MOD S/PCV 1745/7 0.20
Disodium EDTA 0.10
Steareth-2 0.10
DEA-Oleth-3 Phosphate 0.06
Water to 100

CA 02330483 2000-10-27
WO 99!55295 PCT/US98/16496
37
Example 10
1. As part of a daily cleansing regimen the coloured hair is pre-treated using
a conditioning composition of the following formula;
Comlaonent Wt.%
Oleyl Alcohol 1.00
PEG-14M1 0.25
Polydimethylsiloxane2 4.20
Silicone Resin3 0.25
Pentaphenyl Trimethyl
Trisiloxane4 0.38
DL Panthenoi 0.04
Panthenyl Ethyl Ether 0.34
Fragrance 0.35
Kathon(RTM) CG5 0.03
Cetyl Alcohol 1.80
Stearyl Alcohol 1.20
Ditallow Dimethyl
Ammonium Chloride 0.75
Stearamidopropyl
Dimethylamine 1.00
Glycerol Monostearate 0.25
Citric Acid 0.22
Hydroxyethyl Cellulose0.25
Water to 100
PEG-14M is Polyethylene Glycol where n has an average value of about 14,000
and is commercially available
under the trade name of Polyox WSR(RTM) N-3000 from Union Carbide.
Z An 85%/15°~ (wt. basis) mixture of DS Cyclomethicone and dimethicone
gum (weight average molecular weight of
about 400,000 to about 600,000).

CA 02330483 2000-10-27
WO 99/55295 PCTNS98/16496
38
3 Polytrimethyl hydrosilylsilicate, added as a 50 wt. % solution in
decamethylcyclopentasiloxane, General Electric
Silicone Products, SS 4320.
4 Dow Corning 705, Dow Corning Corp. (Midland, MI, USA).
Methylchloroisothiazoline (and) methylisothiazoline, a preservative from Rohm
8 Haas Co., (Philadelphia, PA, USA).
5
2. The pre-treated hair is then washed with currently marketed
Pantene(RTM) shampoo and rinsed with water.
3. The washed hair is then conditioned currently marketed Pantene(RTM)
conditioner and rinsed with water.
4. The hair is then treated with currently marketed Pantene(RTM) Serum
Spray.
Examples of other compositions useful herein comprising ultra violet filtering
agents include:
Conditioning Spray
Water QS 100
Polyquatermium 37, propylene glycol 1.000
dicaprylate/dicaprate, PPG-1 trideceth-6
PVPNA copolymer 0.500
DL-Panthenol (10%), Panthenyl ethyl ether0.300
(90%)
Dimethicone & Dimethiconal 0.500
PEG-4 0.450
DMDM Hydantoin 0.204
Fragrance 0.110
Polysorbate 80 0.063
Disodium EDTA 0.140
Octyl methoxycinnamate 0.010
Silk amino acids 0.003
PEG-5M 0.010

CA 02330483 2000-10-27
WO 99/55295 PCTNS98/16496
39
Benzophenone-4 0.010
Tocopheryl Acetate 0.030
Shampoo
Water Purified QS 100
Ammonium Laureth-3 Sulfate 28% 28.402 '
Disodium Cocoamphodiacetate 18.182
38.5%
Glycol Distearate Molten Premix2.000
Dimethicone 40/60 0.900
Tricedeceth-7 Carboxylic Acid 0.560
90%
Polyquaternium-10 0.150
Perfume 0.800
DL Panthenol 0.054
DL Pantyl B 0.066
PEG-78 Glyceryl Cocoate 60% 4.667
PEG-30 Glyceral Cocoate 3.500
Sodium Benzoate 0.250
DMDM Hydantoin 55% 0.200
Tetrasodium EDTA 87% 0.100
Sodium Chloride PVD 1.041
Citric Acid Anhydrous 0.650
Tocopheryl Acetate 0.03
Benzophenone-4 0.1
Octy1 Methoxycinnamate 0.1
Rinse Conditioner
Demineralised Water QS 100
15/85 Dimethicone/Cyciomethicone 4.2000

CA 02330483 2000-10-27
WO 99/55295 PCT/US98/16496
blend
Stearamidopropyl Dimethylamine 1.0000
Cetyl alcohol 0.9600
Quaternium 18 0.7500
Stearyl alcohol 0.6400
PEG-2M 0.5000
Emulsifying Wax (Polawax/Lipowax)0.5000 '
Benzyl Alcohol 0.4000
Pantyl B 0.2500
Hydroxyethylcellulose 0.2500
Glyceryl Monostearate 0.2500
Oleyl alcohol 0.2500
DMDM Hydantoin 0.2000
EDTA 0.1000
Citric acid anhydrous 0.1300
Perfume 0.3000
Octyl Methoxycinnamate 0.1000
Benzophenone 0.1000
Tocopheryl Acetate 0.0300
Intensive Conditioner
Demineraiised Water QS 100
15/85 Dimethicone/Cyclomethicone4.3700
blend
Stearamidopropyl Dimethylamine 2.0000
L-Glutamic Acid 0.6400
Cetyl alcohol 2.5000
Stearyl alcohol 4.5000
Benzyl Alcohol 0.4000

CA 02330483 2000-10-27
WO 99155295 f'CT/US9$/16496
41
Pantyl B 0.2500
DMDM Hydantoin 0.2000
EDTA 0.1000
Perfume 0.3000
Octyi Methoxycinnamate 0. ~ 000
Benzophenone 0.1000
Tocopheryi Acetate 0.0300
Gonditionina S~ rav
Demineralised Water qs100
Hexylene Glycol 4.0000
Keratin Amino Acids 1,0000
PVP 0.5000
PEG 60 Hydrogenated Castor0.5000
Oil
Dicetyldimonium Chiaride 0.3800
DMDM Hydantoin (0.55%) 0.1375
Tetrasodium EDTA (87%) 0.1131
Pantethine 0.1000
Panthenol 0.0100
Silk Amino Acids 0.1000
Lactic Acid (85%) 0.451
Fragrance 0.1000
Tocopherol Acetate 0.03
Octyl Methoxycinnamste 1.00
Benzophenone-4 0.05
In all of the above examples the incidence of colour fade andlor colour shift
was
reduced or eliminated increasing the time between dyeing as a consequence.

Representative Drawing

Sorry, the representative drawing for patent document number 2330483 was not found.

Administrative Status

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Please note that "Inactive:" events refers to events no longer in use in our new back-office solution.

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Event History

Description Date
Inactive: IPC deactivated 2013-01-19
Inactive: First IPC assigned 2012-07-31
Inactive: IPC assigned 2012-07-31
Inactive: IPC assigned 2012-07-31
Inactive: Dead - No reply to s.30(2) Rules requisition 2003-11-17
Application Not Reinstated by Deadline 2003-11-17
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 2003-08-07
Inactive: Abandoned - No reply to s.30(2) Rules requisition 2002-11-18
Inactive: S.30(2) Rules - Examiner requisition 2002-05-17
Letter Sent 2001-11-15
Inactive: Correspondence - Transfer 2001-10-16
Inactive: Courtesy letter - Evidence 2001-07-12
Inactive: Single transfer 2001-06-04
Inactive: Cover page published 2001-02-21
Inactive: First IPC assigned 2001-02-18
Inactive: Courtesy letter - Evidence 2001-02-13
Inactive: Acknowledgment of national entry - RFE 2001-02-12
Application Received - PCT 2001-02-08
All Requirements for Examination Determined Compliant 2000-10-27
Request for Examination Requirements Determined Compliant 2000-10-27
Application Published (Open to Public Inspection) 1999-11-04

Abandonment History

Abandonment Date Reason Reinstatement Date
2003-08-07

Maintenance Fee

The last payment was received on 2002-06-25

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.

Fee History

Fee Type Anniversary Year Due Date Paid Date
Request for examination - standard 2000-10-27
Basic national fee - standard 2000-10-27
MF (application, 2nd anniv.) - standard 02 2000-08-07 2000-10-27
Registration of a document 2001-06-04
MF (application, 3rd anniv.) - standard 03 2001-08-07 2001-06-28
MF (application, 4th anniv.) - standard 04 2002-08-07 2002-06-25
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
THE PROCTER & GAMBLE COMPANY
Past Owners on Record
ANDREI S. BUREIKO
BERNARD CASTAING
BLAKE GARETH HUGHES
CHRISTINA HARCHARAN KAUR SAMI
DIETER HANS JOSEF LANGSCH
LOUIS CARLOS DIAS
MELISSA SMITH MONICH
NEIL ARCHIBALD MACGILP
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 2000-10-26 41 1,566
Claims 2000-10-26 2 46
Abstract 2000-10-26 1 56
Notice of National Entry 2001-02-11 1 203
Request for evidence or missing transfer 2001-10-29 1 109
Courtesy - Certificate of registration (related document(s)) 2001-11-14 1 114
Courtesy - Abandonment Letter (R30(2)) 2003-01-26 1 167
Courtesy - Abandonment Letter (Maintenance Fee) 2003-09-03 1 176
Correspondence 2001-02-08 1 25
PCT 2000-10-26 23 846
Correspondence 2001-07-11 1 23
PCT 2001-11-21 1 64