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Sommaire du brevet 2196982 

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Disponibilité de l'Abrégé et des Revendications

L'apparition de différences dans le texte et l'image des Revendications et de l'Abrégé dépend du moment auquel le document est publié. Les textes des Revendications et de l'Abrégé sont affichés :

  • lorsque la demande peut être examinée par le public;
  • lorsque le brevet est émis (délivrance).
(12) Demande de brevet: (11) CA 2196982
(54) Titre français: COMPOSITIONS COSMETIQUES ANTI-ACNEIQUES
(54) Titre anglais: ANTI-ACNE COSMETIC COMPOSITIONS
Statut: Réputée abandonnée et au-delà du délai pour le rétablissement - en attente de la réponse à l’avis de communication rejetée
Données bibliographiques
(51) Classification internationale des brevets (CIB):
  • A61K 9/107 (2006.01)
  • A61K 8/06 (2006.01)
  • A61K 9/113 (2006.01)
  • A61K 31/19 (2006.01)
  • A61K 31/191 (2006.01)
  • A61K 31/192 (2006.01)
  • A61K 31/194 (2006.01)
  • A61K 31/20 (2006.01)
  • A61K 31/203 (2006.01)
  • A61K 31/60 (2006.01)
(72) Inventeurs :
  • BRIGGS, GILLIAN SCOTT (Royaume-Uni)
  • CROOK, TERESA BARBARA (Royaume-Uni)
  • SMITH, GRAEME DOUGLAS TELFER (Royaume-Uni)
(73) Titulaires :
  • THE PROCTER & GAMBLE COMPANY
(71) Demandeurs :
  • THE PROCTER & GAMBLE COMPANY (Etats-Unis d'Amérique)
(74) Agent: GOWLING WLG (CANADA) LLP
(74) Co-agent:
(45) Délivré:
(86) Date de dépôt PCT: 1995-08-08
(87) Mise à la disponibilité du public: 1996-02-22
Requête d'examen: 1997-02-06
Licence disponible: S.O.
Cédé au domaine public: S.O.
(25) Langue des documents déposés: Anglais

Traité de coopération en matière de brevets (PCT): Oui
(86) Numéro de la demande PCT: PCT/US1995/010135
(87) Numéro de publication internationale PCT: WO 1996004894
(85) Entrée nationale: 1997-02-06

(30) Données de priorité de la demande:
Numéro de la demande Pays / territoire Date
9416050.4 (Royaume-Uni) 1994-08-09

Abrégés

Abrégé français

On décrit une composition cosmétique anti-acnéique qui prend la forme d'un émulsion huileuse à plusieurs phases, ainsi que son procédé de préparation. Cette composition comprend deux phases aqueuses ou plus et un inhibiteur de coalescence destiné à prevenir la coalescence de ces phases aqueuses. Une première phase aqueuse au moins comprend la substance active contre l'acné qui prend la forme d'une solution aqueuse/alcoolique. Cette composition présente des propriétés d'hydratation, anti-acné et anti-vieillissement de la peau, ainsi qu'une stabilité du produit et de sa couleur.


Abrégé anglais


An anti-acne cosmetic composition in the form of a multiple phase water-in-oil
emulsion and process for preparing thereof, wherein the composition comprises
two or more aqueous phases and a coalescence inhibitor for preventing
coalescence of the aqueous phases and wherein at least a first aqueous phase
comprises the anti-acne active in the form of an aqueous/alcoholic solution.
The composition exhibits moisturisation, anti-acne activity and skin anti-
ageing benefits, together with product and colour stability.

Revendications

Note : Les revendications sont présentées dans la langue officielle dans laquelle elles ont été soumises.


23
CLAIMS
1. An anti-acne cosmetic composition in the form of a multiple phase
water-in-oil emulsion, wherein the composition comprises:
(a) two or more aqueous phases; and
(b) a coalescence inhibitor for preventing coalescence of the
aqueous phases;
and wherein at least a first aqueous phase comprises an anti-acne
active in the form of an aqueous/alcoholic solution.
2. An anti-acne cosmetic composition according to Claim 1 wherein the
coalescence inhibitor is an electrolyte or mixture of electrolytes.
3. An anti-acne cosmetic composition according to Claim 2 wherein the
electrolyte is sodium chloride.
4. An anti-acne cosmetic composition according to any of Claims 1 to 3
wherein the coalescence inhibitor is present at a level of from about
0.05 % to about 5 % by weight of composition.
5. An anti-acne cosmetic composition according to any of Claims 1 to 4
wherein the coalescence inhibitor is present at a level of from 0.01%
to about 1% by weight of composition,
6. An anti-acne cosmetic composition according to any of Claims 1 to 5
wherein the first aqueous phase comprises no more than 20% by
weight of composition of water.
7. An anti-acne cosmetic composition according to any of Claim 1 to 6
comprising a second aqueous phase which comprises at least about
15 % by weight of composition of water.
8. An anti-acne cosmetic composition according to any of Claims 1 to 7
comprising in total from about 30% to about 50% by weight of water
and from about 1% to about 15 % by weight of alcoholic solvent, and
wherein the composition comprises anti-acne active in an amount
exceeding its solubility in an equivalent mixture of water and solvent.

24
9. An anti-acne cosmetic composition according to any of Claims 1 to 8
wherein the anti-acne active is selected from salicylic acid, retinoic
acid, azelaic acid, lactic acid, glycolic acid, pyruvic acid,
flavonoids, and derivatives and mixtures thereof.
10. An anti-acne cosmetic composition according to Claims 1 or 9
comprising from about 0.1% to about 10% by weight of the
anti-acne active.
11. An anti-acne cosmetic composition according to any of Claims 1 to
10 comprising from about 1% to about 50% by weight of silicone oil
selected from volatile silicones, non-volatile silicones and mixtures
thereof.
12. An anti-acne cosmetic composition according to Claim 11 wherein
the volatile silicone oil is selected from cyclic polyorganicsiloxanes
having viscosities less than about 10 centistokes and linear
polyorganosiloxanes having viscosities of less than about 5
centistokes at 25°C, and mixtures thereof.
13. An anti-acne cosmetic composition according to Claim 12 wherein
the volatile silicone oil is selected from cyclic polydimethylsiloxanes
containing from about 3 to about 9 silicon atoms, preferably
containing from about 4 to about 5 silicon atoms and linear
polydimethylsiloxanes containing from about 3 to about 9 silicon
atoms.
14. An anti-acne cosmetic compositions according to Claim 13 wherein
the non-volatile silicone oil comprises a polydiorganosiloxane-
polyoxyalkylene copolymer containing at least one
polydiorganosiloxane segment and at least one polyoxyalkylene
segment.
15. An anti-acne cosmetic composition according to Claim 14 wherein
the polydiorganosiloxane-polyoxyalkylene copolymer is dimethicone
copolyol.

16. An anti-acne cosmetic composition according to any of Claims 1 to
15 additionally comprising from about 0.1% to about 30% by weight
of humectant.
17. An anti-acne cosmetic composition according to Claim 16 wherein
the humectant is glycerin.
18. An anti-acne cosmetic composition according to any of Claims 1 to
17 comprising from about 0.01% to about 10% by weight of
pigment or mixture of pigments.
19. An anti-acne cosmetic composition according to any of Claims 1 to
18 wherein the anti-acne active is salicylic acid.
20. An anti-acne cosmetic composition according to any of Claims 1 to
19 additionally comprising from about 0.1% to about 10% by weight
of polyvinylpyrrolidone complexing agent.
21. An anti-acne cosmetic composition according to any of Claims 1 to
20 additionally comprising from about 0.01% to about 5% by weight
of citric acid or salt thereof.
22. An anti-acne cosmetic composition according to Claim 21 wherein
the silicone oil comprises from about 2% to about 25%, preferably
from about 5 % to about 15 % by weight of compositions of
non-volatile silicones.
23. An anti-acne cosmetic composition according to any of Claims 1 to
22 additionally comprising from about 1% to about 15% by weight of
an emollient which is a natural or synthetic oil selected from
mineral, vegetable and animal oils, fats and waxes, fatty acid esters,
fatty alcohols. alkylene glycol and polyalkylene glycol ethers and
esters, fatty acids and mixtures thereof.
24. An anti-acne cosmetic composition according to Claim 23 wherein
the emollient is selected from isopropylpalmitate, isopropyl

26
isostearate, dioctyl maleate, propylene glycol dicaprylate/propylene
glycol dicaprate, caprylic triglyceride/capric triglyceride, squalane,
mineral oil, cetearylisononanoate and lanolin alcohol, and mixtures
thereof.
25. An anti-acne cosmetic composition according to any of Claims 1 to
24 wherein the aqueous/alcoholic solution of anti-acne active has a
pH of from about 1 to about 7, preferably from about 2 to about 5,
more preferably from about 2 to about 4.
26. Process for preparing an anti-acne composition according to any of Claims
1 to 25, the process comprising the steps of:
(a) preparing the first aqueous phase by dissolving the anti-acne active
in an aqueous/alcoholic solution;
(b) admixing the first aqueous phase with the oil phase; and
(c) subsequently adding one or more additional aqueous phase or
phases to the resulting mixture to form the multiple phase
water-in-oil emulsion, the first and/or additional aqueous phase or
phases having dissolved therein the coalescence inhibitor.

Description

Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.


~ WO 96104894 PCr~US95~10134~
21 q6q82
Anti-Acne Cosmetic Compositions
T~rhni~l Field
~ The present invention relates to cosmetic compositions. In particular it
relates to tinted cosmetic cu~ ions which provide excellent
m~ tnri~tinn together with improved anti-acne activity and skin anti-
ageing benefits and formulation and colour stability.
Back~round of the Invention
Skin is made up of several layers of cells which coat and protect the
keratin and collagen fibrous proteins that form the skeleton of its structure.
The outermost of these layers, referred to as the stratum corneum, is
known to be co~ osed of 250 A protein bundles surrounded by 80 A thick
layers. Anionic surfactants and organic solvents typically penetrate the
stratum corneum membrane and, by delipidization (i.e. removal of the
lipids from the stratum corneum), destroy its integrity. This destruction of
the skin surface topography leads to a rough feel and may eventually
permit the snrf~~t~nt or solvent to interact with the keratin, creating
irritation.
It is now recognised that ~ g the proper water gradient across the
statum corneum is hlll~u~ L to its l;mction~lity Most of this water, which
is sometimes considered to be the stratum corneum's plasticizer, comes
from inside the body. If the humidity is too low, such as in a cold climate,
incnffi~i.ont water remains in the outer layers of the stratum corneum to
properly plasticize the tissue; and the skin begins to scale and becomes
itchy. Skin permeability is also decreased somewhat when there is
in~(1eql~te water across the stratum corneum. On the other hand, too
much water on the outside of the skin causes the stratum corneum to
ultimately sorb three to five times its own weight of bound water. This
swells and puckers the skin and results in a~ uAilllal~ly a two to three fold
increase in the permeability of the skin to water and other polar m~lec~ 5
Thus, a need exists for compositions which will assist the stratum corneum
in ~ hlillg its barrier and water retention functions at optimum
p~,.ru-lllance in spite of deleterious interactions which the skin may
encuu~ in washing, work, and recreation.

~ WO 96/04894 PCT/US9S11013S~
2~ 96~2
Conventional cosmetic cream and lotion compositions as described, for
example, in Sagarin, Cosmetics Science and Technology, 2nd Edition,
Vol.l, Wiley Interscience (1972) and Encyclopaedia of Chemical
Technology, Third Edition, Volume 7 are known to provide varying
degrees of emolliency, barrier and water-retention (l"..~ ",g) benefits.
However, they can also suffer serious negatives in terms of skin feel (i.e.
they often feel very greasy on the skin) as well as having poor rub-in,
absorption and residue characteristics.
It would also be desirable to provide a cosmetic composition which
delivered pigments to the skin of the user at the same time as providing
excellent ll-oi~lulis~lion. A pigmented cosmetic composition can serve to
even skin tone and texture and to hide pores, imperfections, fine lines and
the like.
At the same time, it would be desirable to provide a moisturising
composition having topical anti-acne activity. There are many co--.~uul.ds
which are known to exhibit anti-acne properties when applied topically to
the skin. A commonly used keratolytic agent having anti-acne activity is
salicylic acid. As salicylic acid is virtually insoluble in water however, it
is difficult to incorporate into the aqueous phase of an emulsion
ct~mpr citi-ln Delivery of salicylic acid from the pigment-cc "l~;"i.~g oil
phase of an emulsion composition can, on the other hand, lead to
discolouration of the composition due to interaction between the salicylic
acid and pigments, especially of the iron oxide type. Furthermore, in
compositions requiring high water levels, such as skin moisturising
compositions, salicylic acid tends to ple~i~iL~Le out of solution. It would
therefore be desirable to deliver salicylic acid in soluble form from the
aqueous phase but without the salicylic acid ~ iL~Lil.g out of solution.
It is acco.di..~,ly one object of the present invention to provide a cosmetic
composition which exhibits anti-acne activity together with moi~LulisaLiu..
benefits.

~ WO g6104894 PCr/US95J101~
23l 969~32
r ~
It is a further object of the invention to provide a cosmetic composition in
the form of a multiple phase emulsion having improved product and colour
stability.
~ Sl~mm~-y of the Invention
According to one aspect of the present invention there is provided an anti-
acne cosmetic composition in the form of a multiple phase water-in-oil
emulsion, wherein the composition C~ i5C~.
(a) two or more aqueous phases; and
(b) a co~ cc~nce inhibitor for preventing co~l~sc~n- e of the aqueous
phases;
and wherein at least a first aqueous phase co-"~ es an anti-acne active in
the form of an aqueous/alcoholic solution.
According to the present invention there is also provided a process for
preparing an anti-acne composition, the process colll~lish~g the steps of:
(a) plep~lillg the first aqueous phase by dissolving the anti-acne active
in an aqueous/alcoholic solution;
(~h~ admixing the first aqueous phase with the oil phase; and
(c) suhseqll~nfly adding one or more S~ itinn~l aqueous phase or
phases to the resulting mixture to form the multiple phase
water-in-oil emulsion, the first and/or aMitif~n~l aqueous phase or
phases having dissolved therein the co~l~sr~nre inhibitor.
The compositions of the present invention provide anti-acne activity and
skin anti-ageing benefits, together with improved product and colour
stability and superior moisturisation, skin feel and a~pcdl~lncc.
All levels and ratios are by weight of total composition, unless otherwise
in~ te~
De.t~ Description of the Invention
The compositions of the present invention are multiple phase water-in-oil
~mnlci~gn~ which comprise two or more aqueous phases. At least a first

~ WO 96/04894 2 ~r~q98'l~l35
aqueous phase comprises an anti-acne active in the form of an
aqueous/alcoholic solution. Suitable anti-acne actives for use herein
include salicylic acid, retinoic acid, azelaic acid, lactic acid, glycolic acid,pyruvic acid, flavonoids, and dcliv~lives and salts thereof, and mixtures
thereof.
The anti-acne active used in the composition herein is preferably selected
from salicylic acid and azelaic acid, and mixtures thereof, more preferably
salicylic acid. The anti-acne active is present at a level of from about
0.1% to about 10%, preferably from about 0.1% to about 5%, more
preferably from about 0.5% to about 3%, by weight of composition.
The anti-acne active is solubilized in water or an alcoholic solution, for
example, solutions based upon C2-C6 alcohols, diols and polyols,
preferred alcohols being selected from ethanol, dipropylene glycol,
butylene glycol, hexylene glycol, and mixtures thereof. Alcohol is
preferably present in the compositions herein at a level of from about l ~o
to about 20%. The final aqueous/alcoholic anti-acne active solution
preferably has a pH at ambient le~ clalule (25~C) of less than about PKa
+ I, where pKa is the logarithmic acidity constant for the fully plolollat~ d
anti-acne active. In preferred embodiments, the pH of the final solution is
less than about pKa.
The logarithmic acidity constant is thus defined by reference to the
equilibrium
H+ + Hn-lA = HnA
where HnA is the fully protonated acid, n is the number of protons in the
fully protonated acid and Hn 1 A is the conjugate base of the acid
Cu~ ull.lhlg to loss of one proton.
The acidity constant (Kn) for this equilibrium is therefore
[HnA]
[H+] [Hn-lA]

~ WO 96104894 2 1 9 6 9 8 2 PCT/US9S/1013--
and PKa = logloKn
For the purposes of this cpecific~ion, acidity constants are defined at 25~C
~ and at zero ionic strength. Literature values are taken where possible (see
Stability Constants of Metal-Ion Complexes, Special Publication No. 25,
The Chemical Society, London); where doubt arises they are d.,t~ .ed
by pofp~n~ mptric titration using a glass electrode.
The pKa of the acidic anti-acne active used herein is preferably in the
range of from about 1 to about 6, more preferably from about 1 to about
4.5, especially from about 1.5 to about 4Ø
The pH of the final aqueous/alcoholic anti-acne active solution is
preferably in the range of from about 1 to about 7, more preferably from
about 2 to about 5, especially from about 2 to about 4. At pH values of
less than about 5 the aqueous phase is preferably free of acid labile species
such as acrylic acid/ethyl acrylate copolymers and
polygly~,el~/lmethacrylate.
Another essential CVlll~ull~illt of the compositions herein is a coSIlPccPn~e
inhibitor for preventing co~lpscpnre of the aqueous phases. Preferably the
co~lPccen~e inhibitor is an electrolyte or mixture of electrolytes, preferably
sodium chloride. The co~lPscPn~e inhibitor is present at a level of from
about 0.05~0 to about 5%, preferably from about 0.01% to about 2~o by
weight of composition.
The compositions of the invention are in the form of a multiple phase
water-in-oil emulsion comprising two or more aqueous phases As
mPn~inmPd hereinabove the compositions of the invention comprise at least
a first aqueous phase which comprises an anti-acne active in the form of an
aqueous/alcoholic solution. This first aqueous phase preferably colllL,lises
no more than about 20% by weight of water. The compositions of the
invention also comprise a second aqueous phase which preferably
comprises at least about 15 % by weight of composition of water.
Preferably the compositions of the invention comprise in total from about
309'o to about 50% by weight of water and about 1% to about 15% by

~ WO 96/04894 PCT111S95/1~1135~
2 1 96982
weight of alcoholic solvent. The compositions herein will generally
comprise anti-acne active in an amount eYcee~ing its solubility in an
equivalent mixture of water and solvent measured under ambient
c~n~itirlnc (25~C). It is a feature of the invention however that by virtue
of the multiple phase form of the comrn~iti~n and the use of a co~l~sc.onre
inhibitor as described herein, the anti-acne material can be formulated in
soluble form at levels eY~ee~ling its normal solubility in a single phase
water/alcohol system.
Preferably the compositions of the invention comprise a pyrrolidone-based
complexing agent. The pyrrolidone-based complexing agent is useful
herein from the viewpoint of aiding solubilization of the anti-acne active
and also an interfacial film former for the aqueous phases for preventing
co~lr.scrnce of the aqueous phases. The pyrrolidone-based complexing
agent used herein is preferably selected from polyvinylpyrrolidone
comrlrYing agents or Cl-C4 alkyl polyvi--yl~yi-~Jlidone complexing agents
having a molecular weight (viscosity average) in the range from about
1500 to about 1,500,000, preferably from about 3000 to about 700,000,
more preferably from about 5000 to about 100,0Q0. Suitable examples of
pyrrolidone-based complexing agents are polyvinylpyrrolidone (PVP) (or
povidone) and butylated polyvinylpyrrolidone. The most preferred
pyrrolidone-based complexing agent herein is a polyvinylpyrrolidone
complexing agent. PVP is col-----el.,idlly available under the trade name
Luviskol (RTM) from BASF. A preferred PVP complexing agent herein is
Luviskol K17 which has a viscosity-average molec~ r weight of about
9,000. Other pyrrolidone-based complexing agents for use herein include
C1-C1g alkyl or hydroxyalkyl pyrrolidones such as lauryl pyrrolidone.
The pyrrolidone-based complexing agent is present in the comro~ition
herein in a level of from about 0.1 ~o to about 10%, preferably from about
0.1% to about 5 % by weight of composition. The weight ratio of anti-acne
active: pyrrolidone-based complexing agent is in the range from about
10:1 to about 1:10, preferably from about 5:1 to about 1:5.
Preferred el..bodil--~ ls of the invention ~ lition~lly comprise from about
0.01% to about 5%, preferably from about 0.1% to about 1%, especially
from about 0.170 to about 0.57c by weight of an acid or salt thereof which

~ WO 96104894 2 1 9 6 9 8 2 PCT/1159~11013~
is soluble in water at pH values of less than or equal to the pKa of the
co~ dillg acid, for example, an acid selected from citric acid, boric
acid, and salts, and mixtures thereof. These materials are valuable herein
in c.""l,i"~ion with the pyrrolidone-based comrlt ~ing agent from the
viewpoint of aiding solubilization of the anti-acne active. Particularly
preferred herein from this viewpoint is a sodium salt of citric acid. In
preferred embodiments, the acid or salt thereof is soluble to a level of at
least 5% w/w at 25~C.
The composition of the invention is in the form of a multiple phase water-
in-oil emulsion containing two or more, preferably two discrete internal
aqueous phases. In preferred embodiments the oil phase co~ ,-ises a
mixture of volatile silicones and non-volatile silicones. The silicone oil is
present in an amount of from about 1 % to about 50% by weight. Suitable
volatile silicone oils include cyclic and linear volatile polyo,~ ;ln~nlos
(as used herein, "volatile" refers to those materials which have a
measurable vapour pressure at ambient con~itinn~).
A description of various volatile silicones is found in Todd, et al..
"Volatile Silicone Fluids for Cosmetics", 91 Cosmetics and Toiletries 27-
32 (1976).
Preferred cyclic silicones include polydimethylsiloxanes cullL~ ih.g from
about 3 to about 9 silicon atoms, preferably containing from about 4 to
about 5 silicon atoms. Preferred linear silicone oils include the
polydi-..~lllyl~ilrlY~n~s c--nt:linin~ from about 3 to about 9 silicon atoms.
The linear volatile silicones generally have viscosities of less than about 5
c.onfictnk~ at 25~C, while the cyclic materials have viscosities of less than
about 10 crnti~tf~krs Examples of silicone oils useful in the present
invention include: Dow Corning 344, Dow Corning 21330, Dow Corning
345, and Dow Corning 200 (m~mlf~rhlred by the Dow Corning
Corporation): Silicone 7207 and Silicone 7158 (m~mlf~rtllred by the
Union Carbide Corporation). SF:202 (m~mlf~rtllred by General Electric)
and SWS-03314 (m~mlf~rlllred by Stauffer Chemical).
Suitable non-volatile silicones preferably have an average viscosity of from
about 1,000 to about 2,000,000 mm2.s~1 at 25~C. more preferably from

21 9~98~
~ WO 96/04894 PCT/US95/1013--
about 10,000 to about 1,800,000 mm2.s~1, even more preferably from
about 100,000 to about 1,500,000 mm2.s~1. Lower viscosity non-volatile
silicone cnnrlitioning agents, however, can also be used. 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 non-
volatile silicone fluids for use herein include polyalkyl siloxanes, polyaryl
siloxanes, polyalkylaryl siloxanes, polysiloxanes with amino fimrtinn:ll
substitutions, polyether siloxane copolymers, and mixtures thereof. The
siloxanes usefiul in the present invention may be endcapped with any
number of moieties, inr~ ling, for example, methyl, hydroxyl, ethylene
oxide, propylene oxide, amino and carboxyl. However, other silicone
fluids having skin contlitioning properties may be used. The non-volatile
polyalkyl siloxane fluids that may be used include, for example,
polydimethylciloY~nrc These siloxanes are available, for example, from
the General Electric Company as a Viscasil (RTM) series and from Dow
Corning as the Dow Corning 200 series. Preferably, the viscosity ranges
from about 10 mm2.s~1 to about 100,000 mm2.s~1 at 25~C. The
polyalkylaryl siloxane fluids that may be used, also include, for example,
poly.l.~Ll.yl~hcl.yl~iloxanes. These siloxanes are available, for example,
from the General Electric Company as SF 1075 methyl phenyl fluid or
from Dow Corning as 556 Cosmetic Grade Fluid. The polyether siloxane
copolymer that may be used includes, for example, a polypropylene oxide
modified dimethylpolysiloxane (e.g., Dow Corning DC-1248) although
ethylene oxide or mixtures of ethylene oxide and propylene oxide may also
be used.
References (licrlr,~in~ suitable silicone fluids include US-A-2,826,551,
Green; US-A-3,964,500, Drakoff, issued June 22nd, 1976; US-A-
4,364,837, Pader; and GB-A-849,433, Woolston. In addition, Silicone
Compounds distributed by Petrarch Systems Inc., 1984 provides an
extensive (though not exclusive) listing of suitable silicone fluids.
Preferred non-volatile silicones for use herein include
polydiorg:~nn~ Yz~n~-polyoxyalkylene copolymers cnnt~ining at least one
polydior~nncilnY~np segment and at least one polyoxyalkylene segment,
said polydiorganosiloxane segment consisting essentially of

~ WO 96104894 2 1 9 6 q 8 2 PCT/US95/10~3~!
~ :,
RbSiO(4-b)/2
.
siloxane units wherein b has a value of from about O to about 3, inclusive,
there being an average value of approximately 2 R radicals per silicon for
all siloxane units in the copolymer, and R denotes a radical selected from
methyl, ethyl, vinyl, phenyl and a divalent radical bonding said
polyoxyalkylene segment to the polydiorgs3n(~ t)Y~n~ segment, at least
about 95% of all R radicals being methyl; and said polyoxyalkylene
segment having an average molecular weight of at least about 1000 and
consisting of from about O to about 50 mol percent polyoxypropylene units
and from about 50 to about 100 mol percent polyoxyethylene units, at least
one terminal portion of said polyoxyalkylene segment being bonded to said
polydiorg:~nt~ Y~n~ segment, any terminal portion of said
polyoxyalkylene segment not bonded to said polydiorg~n~ ilnY~n~ segment
being satisfied by a ~f,. ~ g radical; the weight ratio of
polydiorganosiloxane segments to polyoxyalkylene segments in said
copolymer having a value of from about 2 to about 8. Such polymers are
described in US-A-4,268,499.
More preferred for use herein are polydiorganosiloxane-polyoxyalkylene
copolymers having the general formula:
IH3 IH3 IH3 IH3
H3C-- si --o--(si--~)x (si--o)y--si--~CH3
CH3 CH3 13H6 CH3
o - ==(C2H40)a(C3H60)bR

~ WO 96/04894 2 1 9 6 9 8 2 PCT/USgS/10135--
~o
wherein x and y are selected such that the weight ratio of
polydiorg~nociloY~nP segments to polyoxalkylene segments is from about 2
to about 8, the mol ratio of a:(a+b) is from about 0.5 to about 1, and R is
a chain t~ . ,.,i"-ll"g group, especially selected from hydrogen; hydroxyl;
alkyl, such as methyl, ethyl, propyl, butyl, benzyl; aryl, such as phenyl;
alkoxy such as methoxy, ethoxy, propoxy, butoxy; benzyloxy; aryloxy,
such as phenoxy; alkenyloxy, such as vinyloxy and allyloxy; acyloxy, such
as acetoxy, acryloxy and propionoxy and amino, such as dim~tllyla-llillo.
The number of and average molecular weights of the segments in the
copolymer are such that the weight ratio of polydiorganosiloxane segments
to polyoxyalkylene segments in the copolymer is preferably from about 2.5
to about 4Ø
Suitable copolymers are available CO~ ially under the tradenames
Belsil (RTM) from Wacker-Chemie GmbH, GPcrh~ftcbereich S, Postfach
D-8000 Munich 22 and Abil (RTM) from Th. Grllrlc( hmi~l Ltd,. Tego
House, Victoria Road, Ruislip, Mirl~llPsP~, HA4 OYL. Particularly
preferred for use herein are Belsil (RTM) 6031, Abil (RTM) B88183 and
DC3225C. A preferred silicone herein is known by its CTFA ~IPcign~tir)n
as flimPthirrmP copolyol.
The silicone oil phase preferably culllL~Iises from about 2% to about 25%,
more preferably from about 5% to about 15% by weight of composition of
non-volatile silicones.
A highly preferred colll~o~ t of the compositions herein is a hnmPct~nt or
mixture of l,.l~,.r~ . The hllml~ct~nt or mixture of I, ".r~t;. 1~ herein is
present in an amount of from about 0.1 % to about 30% preferably from
about 5% to about 25%, and more preferably from about 10% to about
20% by weight of composition. The hnmPct~nt or mixture of hnmPct:~ntc
is preferably present in one or more of the aqueous phases.
The hnm~pct~nt can be hlcOl~Ola~d at least partly into the oil phase of the
water-in-oil emulsion so as to form a mllltiph~ce hllmPct:lnt-in-oil-in-water
dispersion. The oil phase can comprise from about 0.1% to about 10%,
more preferably from about 0.1% to about 3% by weight of l..""P.IZ~nt on
.

~ WO 96104894 2 1 9 6 9 8 2 PC'r/US95~101~
a composition basis. The humectant can be introduced into the oil phase in
the form of a mixture with or incorporated within a particulate lipophilic or
hydrophobic carrier material.
Suitable hllll.f.. t~ include sorbitol, panthenols, propylene glycol,
butylene glycol, hexylene glycol, alkoxylated glucose d~livaLi~.,a, such as
Glucam (RTM) E-20, hexanetriol, and glucose ethers, and mixtures
thereof. Urea is also suitably added as a hlllll~ in one or more of the
internal aqueous phases.
The panthenol moisturiser can be selected from D-panthenol ([R]-2,~
dihydroxy-N-[3-hydroxypropyl)]-3,3-dhllclllyll,.ltdl~ide), DL-p~nthPnnl,
calcium pantothenate, royal jelly, p~nthPtinf, p~ntothPinP, palllll.,llyl ethyl
ether, pangamic acid, pyridoxin, pantoyl lactose and Vitamin B complex.
The preferred hlllllfcli."l herein is glycerine. Chemically, glycerine is
1,2,3-propanetriol and is a product of commerce.
Preferred embodiments herein comprise a pigment or mixture of pigments.
Suitable pigments for use herein can be inorganic and/or organic. Also
included within the term pigment are materials having a low colour or
lustre such as matte finishing agents, and also light scattering agents.
Examples of suitable pigments are iron oxides, acylglnt~m~te iron oxides,
ultramarine blue, D&C dyes, carmine, and mixtures thereof.
The composition of the invention can also include at least one matte
finishing agent. The function of the matte finishing agent is to hide skin
defects and reduce shine. Such cosmPti~lly acceptable inorganic agents,
i.e., those included in the CTFA Cosmetic Ingl~dicl~t Dictionary, Third
Ed., as silica, hydrated silica, silicone-treated silica beads, mica, talc,
polyethylene, titanium dioxide, bentonite, hectorite, kaolin, chalk,
diatomaceous earth, zinc oxide (USP or ultrafine) and the like may be
utilized. Of particular usefulness as a matte finishing agent is low lustre
pigment such as titanated mica (mica coated with titanium dioxide) coated
with barium sulfate. Of the inorganic components useful as a matte
finishing agent low lustre pigment, talc, polyethylene, hydrated silica,
kaolin, titanium dioxide and mixtures thereof are particularly preferred.

21 q~982
WO 96104894 PCTIUS95/1013
12
Materials suitable for use herein as light-scattering agents can be generally
described as spherical shaped inorganic materials having a particle size of
up to about 100 microns, preferably from about 5 to about 50 microns, for
example spherical silica particles.
The total conc~ nllalion of the pigment may be from about 0.1 to about
25% by weight and is preferably from about 1 to about 10% by weight of
the total ct mpo~iti~-n, the exact concGIlL~dLion being dep~n-l~nt to some
extent upon the specific mixture of pigments selected to achieve the desired
shades. The preferred compositions contain from about 2% to about 20%
by weight of titanium dioxide and most preferably from about 5 % to about
10% by weight of titanium dioxide.
The preferred pigments for use herein from the viewpoint of
moisturisation, skin feel, skin appearance and emulsion compatibility are
treated pigments. The pigments can be treated with colllL,vunds such as
amino acids such as Iysine, silicones, lauroyl, collagen, polyt;Lllyl~lle,
lecithin and ester oils. The more preferred pigments are the silicone
(polysiloxane) treated pigments.
In preferred embodiments of the invention the water is present in two
discrete internal aqueous phases, the anti-acne active only being present in
one of the aqueous phases. This is particularly beneficial from the
viewpoint of being able to provide a stable composition having a high
water level withoul pl~ iLdtion of the anti-acne active out of solution.
The compositions of the present invention can also comprise a particulate
cross-linked hydrophobic acrylate or methacrylate copolymer. This
copolymer is particularly valuable for reducing shine and controlling oil
while helping to provide effective moisturization benefits. The cross-
linked hydrophobic polymer is preferably in the form of a copolymer
lattice with at least one active ingredient dispersed uniformly throughout
and entrapped within the copolymer lattice. Alternatively, the hydrophobic
polymer can take the form of a porous particle having a surface area (N2-
BET) in the range from about 50 to 500, preferably 100 to 300m2/g and
having the active ingredient absorbed therein.

2 1 96982
~ WO 96/04894 PCT/US95/1013
13
The cross-linked hydrophobic polymer when used herein is in an amount
of from about 0.1% to about 10% by weight and is preferably incorporated
in the external silicone-containing oil phase. The active ingredient can be
one or more or a mixture of skin compatible oils, skin compatible
l~ emollients, lllvi~luliGhlg agents and ~UIl~Cl~ s. The polymer
material is in the form of a powder, the powder being a combined system
of particles. The system of powder particles forms a lattice which includes
unit particles of less than about one micron in average diameter,
agglomerates of fused unit particles of sized in the range of about 20 to 100
microns in average diameter and aggregates of clusters of fused
agglomerates of sizes in the range of about 200 to 1,200 microns in
average diameter.
The powder material of the present invention which can be employed as
the carrier for the active ingredient can be broadly described as a cross-
linked "post absorbed" hydrophobic polymer lattice. The powder
preferably has entrapped and dispersed therein, an active which may be in
the form of a solid, liquid or gas. The lattice is in particulate form and
cl),,~lillllrs free flowing discrete solid particles when loaded with the activematerial. The lattice may contain a prefletermin~d quantity of the active
material. The polymer has the structural formula:
ICH3 - ICH3
--CH2--lC lC--CH2--
IC=O IC=O
~l O
1~ - R" - Y
o
C=O
--CH2--C
CH3 ~ X
where the ratio of x to y is 80:20, R' is -CH2CH2- and R" is -
(CH2)1 1CH3-

~ WO 96/04894 2 1 9 6 9 8 2 PCT/I~S95/10135
14
The hydrophobic polymer is a highly crosslinked polymer, more
particularly a highly cross-linked polymethacrylate copolymer. The
material is m~mlf~r.hlred by the Dow Corning Corporation, Midland.
Mirhig~n, USA, and sold under the trademark POLYTRAP (RTM) . It is
an ultralight free-flowing white powder and the particles are capable of
absorbing high levels of lipophilic liquids and some hydrophilic liquids
while at the same time l"~;"~ i"g a free-flowing powder character. The
powder structure consists of a lattice of unit particles less than one micron
that are fused into agglomerates of 20 to 100 microns and the agglomerates
are loosely clustered into macro-particles or aggregates of about 200 to
about 1200 micron size. The polymer powder is capable of cc ~ hling as
much as four times its weight of fluids, PmnlciQn~, dispersions or melted
solids.
Adsorption of actives onto the polymer powder can be accomplished using
a stainless steel mixing bowl and a spoon, wherein the active is added to
the powder and the spoon is used to gently fold the active into the polymer
powder. Low viscosity fluids may be adsorbed by addition of the fluids to
a sealable vessel cnnt:lining the polymer and then tumbling the materials
until a consistency is achieved. More elaborate blending c~lui~ such
as ribbon or twin cone blenders can also be ernployed. The preferred
active ingredient for use herein is glycerine. Preferably, the weight ratio
of hnmPc.t~nt carrier is from about 1:4 to about 3:1.
Also suitable as a highly cross-linked polymethacrylate copolymer is
Microsponges SQ47. This takes the form of generally spherical particles of
cross-linked hydrophobic polymer having a pore size of from about 0.01 to
about 0.05,um and a surface area of 200-300m2/g. Again, it is preferably
loaded with hnmPc~nt in the levels described above.
The compositions of the invention can also contain a hydrophilic
gelling agent at a level preferably from about 0.01% to about 10%,
more preferably from about 0.02% to about 2%, and especially from
about 0.02% to about 0.5%. The gelling agent preferably has a
viscosity (1~0 aqueous solution, 20~C, Brookfield RVT) of at least
about 4000 mPa.s, more preferably at least about 10,000 mPa.s and
especially at least 50,000 mPa.s.

~ W096104894 2 1 q6982 ~ 3~
Suitab!e hydrophilic gelling agents can generally be described as
water-soluble or colloidally water-soluble polymers, and include
cellulose ethers (e.g. hydroxyethyl cellulose, methyl cellulose,
hydro~y~lul,ylL.ethyl cellulose), polyvinylalcohol, poly4u 1~ "i"."
10, guar gum, hydroxypropyl guar gum and xanthan gum.
Other suitable gelling agents suitable for use herein are oleogels such
as trihydroxystearin and :~lnmininm m~gn~cillm hydroxy stearate.
The gelling agents herein are particularly valuable for providing
excellent stability characteristics over both normal and elevated
temperatures.
The compositions herein can ~rlitir~n~lly comprise an emollient.
Emollients suitable for the compositions of the present invention include
natural and synthetic oils selected from mineral, vegetable, and animal
oils, fats and waxes, fatty acid esters, fatty alcohols, alkylene glycol and
polyalkylene glycol ethers and esters, fatty acids and mixtures thereof.
Suitable emollients for use herein include, for example, optionally
hydroxy-substituted Cg-Cso unsaturated fatty acids and esters thereof, C1-
C24 esters of Cg-C30 saturated fatty acids such as isopropyl myristate,
cetyl palmitate and octyldodecylmyristate (Wickenol 142), beeswax,
saturated and u~ tuldlcd fatty alcohols such as behenyl alcohol and cetyl
alcohol, hydlucdllJulls such as mineral oils, petrolatum and squalane, fatty
sorbitan esters (see US-A-3988255, Seiden, issued October 26 1976),
lanolin and lanolin dclivdlives, such as lanolin alcohol ethoxylated,
hydroxylated and acetylated lanolins, cholesterol and derivatives thereof,
animal and vegetable triglycerides such as almond oil, peanut 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, gla~esccd oil, and sunflower seed oil
and Cl C24 esters of dimer and trimer acids such as diisu~lo~yl dimerate,
diiso~L~alyllllalate, diisostearyldimerate and lliiso~l~alylllilllcldl~.
:

2 1 90982
~ WO 96/04894 PCTIUS95/1013
16
Preferred emollients are selected from hydlo~,dlbulls such as
icohP~ t1Pr~n~, mineral oils, petrolatum and squalane, lanolin alcohol, and
stearyl alcohol. These emollients may be used in~lepPn~lpnfly or in
mixtures and may be present in the composition of the present invention in
an amount from about 1% to about 307c by weight, and preferably are
present in an amount from about 5% to about 15% by weight of the total
composition.
The composition may also contain a~ iti~n~l materials such as, for
example, fragrances, fillers such as nylon, sun-screens, pl~selvdli~,s,
proteins, ~ntiox~ ntc~ chelating agents and water-in-oiMPmlllcifPrc as
a,uul U~)l idl~ .
Another optional COIIIIJOIIelll of the make-up composition is one or more
ultraviolet absorbing agents. Ultraviolet absorbing agents, often described
as sunscreening agents, can be present in a concentration in the range of
between about 1% and about 12% by weight, based on the total weight of
composition. Preferably, the UV absorbing agents constitute between
about 2% and 8% by weight. More preferably, the UV absorbing agents
can be present in the composition in a concentration range of between
about 4% and about 6% by weight. Of the ultraviolet absorbing agents
suitable for use herein, bell~u~,hellone-3, octyl dimethyl PABA (Padimate
O) and mixtures thereof are particularly preferred.
Another optional but preferred colllpol~ ll herein is one or more ~ itil)n~
chelating agents, preferably in the range of from about 0.02% to abûut
0.10% by weight, based on the total weight of the composition.
Preferably, the chelating agent is present in a concentration in the range of
between about 0.03% and about 0.07% by weight, based on the total
weight of the composition. Among the chelating agents that may be
included in the composition is tetrasodium EDTA.
Another optional but preferred colllpon~nl of the cosmetic composition is
one or more pl~ sel v~livcs. The ~ l v~tive conc~,.llldlion in the
foundation composition, based on the total weight of that composition, is in
the range of between about 0.05% and about 0.8~o by weight, preferably
between about 0.1% and about 0.3% by weight. Suitable pl~S~I~ativeS for

~ WO 96104N94 2 1 9 6 ~ 8 2 PCT/US9~1013~
use herein include sodium benzoate and propyl paraben, and mixtures
thereof.
The cosmetic compositions of the present invention can be in the form of
uloi~lu~i~iulg creams, lotions or gels, and pigmented compositions such as
tinted moisturisers, foundation and liquid concealers.

~ WO 96/04894 2 ~ 9 6 9 8 2 PCT/I~S95/10135~
18
The following Table is provided to illustrate compositions of the present
invention:
Example I II III IV V VI VII
Wt Wt Wt Wt Wt Wt Wt
% % % % % % %
A.
Cetyloctanoate 1.00 0.0 0.0 0.0 0.0 0.0 2.0
Cyclomethicone 8.57 8.0 8.3 9.0 12.0 8.57 8.57
Cyclomethicone/
~lim~thicon~
copolyol (90:10) 12.00 12.5 11.5 12.1 12.3 11.00 12.1
Pluluyl~ldben 0.75 0.75 0.0 0.75 0.0 0.75 0.75
(33%) in laureth-7
Dimethicone Fluid 0.0 0.0 2.0 0.0 0.0 0.0 0.0
Benzophenene-3 0.0 0.0 0.0 0.0 0.0 2.0 0.0
Propylene glycol
Dicaprylate/
Dicaprate 0.0 0.0 0.0 4.0 0.0 5.0 0.0
Isûpropyl Palmitate 3.0 0.0 3.0 0.0 4.0 0.0 0.0
B.
Titanium Dioxide
(silicone treated) 2.0 2.0 2.5 2.0 3.0 3.5 2.6
Titanium Dioxide
treated (Alnminillm
hydrate, stearic
acid) 2.0 2.0 1.0 1.5 1.8 2.1 1.0
Titanated Micas 0.1 0.0 0.0 0.0 0.0 0.0 0.1
Talc 3.38 4.5 5.0 0.7 0.7 0.7 3.38
Silica 0.6 0.0 0.0 0.0 0.6 0.0 0.0
Nylon 0.0 0.0 0.0 0.0 0.5 0.0 0.0
Zinc Oxide 2.0 2.0 1.0 2.0 2.0 2.0 2.0
(Microfine)

~ WO 96104894 2 1 9 6 9 8 2 PCTIUS95/1013~
19
Example I II m IV V VI VII
Wt Wt Wt Wt Wt Wt Wt
% % % % % % %
C.
Cy~lom~hi~n~/ 0.5 0.5 05 0 5 0 5 0 5 0 5
D.
Yellow Iron Oxide 0.5 0.6 0~2 0.53 0.61 0.54 0.5
Red I}on Oxide 0.2~ 0.3 0.31 0.25 0.27 0.2 0.3
Black Iron Oxide 0.05 0.1 0.07 0.05 0.06 0.07 0.1
E.
Synthetic Wax 0.1 0.5 0.5 0.1 0.0 0.0 0.0
Arachidyl behenate 0.3 0.0 0.0 0.3 0.5 0.3 0.3
Stearic Acid 0.0 0.0 0.0 0.0 0.0 0.0 2.5
Palmitic Acid 0.0 0.0 0.0 0.0 0.0 2.5 0.0
Silica 0.1 0.0 0.1 0.0 0.1 0.0 0.1
(Spheron P1500)
Trihydroxy-stearin 0.3 0.3 0.5 0.6 0.0 0.0 0.0
Cyclomethicone 1.0 1.0 0.0 0.0 1.0 1.0 1.0
Beeswax 1.5 1.2 0.0 0.0 1.3 0.0 0.0
AbilWED9 0.0 3.0 0.0 0.0 0.0 0.0 0.0

~ WO 96/04894 2 1 q 6 9 8 2 . PCINS95/10135
E~xample I II III IV V VI VII
Wt Wt Wt Wt Wt Wt Wt
% % % % % % %
G.
Ethylene brassylate 0.05 0.0 0.0 0.0 0.0 0.05 0.05
BHT 0.05 ~-~ ~-~ ~ ~ ~ ~ 0-05 0.05
Deionized water 7.55 7.6 7.7 7.65 7.6 7.4 7.63
Ethanol 4.0 5.5 4.0 8.0 4.5 5.0 4.0
Salicylic acid 1 1 1 2 2 2 0.0
Azeleic acid 0.0 0.0 0.0 0.0 0.0 0.0 5
Dipropylene glycol 6.0 5.0 6.5 7.00 8.0 6.0 5.0
Polyvinylpyrrolid-
one (Luviskol K17) 1 2 1.5 1 1 1 2
Sodium citrate 0.3 0.3 0.3 0.2 0.4 0.3 0.4
I.
Deionized water 12.0 12.2 11.5 11.8 12.0 12.1 12.2
Sodium chloride 0.2 0.2 0.2 0.2 0.1 0.2 0.1
Tetrasodium EDTA 0.04 0.04 0.04 0.04 0.04 0.04 0.04
Glycerin 4 4 4 4 4 4 4
Deionized water to 100
Sodium chloride 0.2 0.3 0.2 0.3 0.3 0.3 0.4
Polyvinylpyrrolid-
one (Luviskol K17) 0.5 0.0 0.0 0.6 1.0 0.8 0.0
Tetrasodium EDTA 0.06 0.06 0.06 0.06 0.06 0.06 0.06
Glycerin 6.0 6.0 6.0 6.0 6.0 6.0 6.0
Sodium Citrate 0.1 0.0 0.1 0.2 0.0 0.0 0.0
K.
Deionized Water 0.0 0.0 0.0 0.0 10.0 0.0 0.0

~ WO 96/04894 2 1 9 6 9 8 2 PCT/lIS95/1~113~
Example I Il III IV V VI VII
Wt Wt Wt Wt Wt Wt Wt
% % % % % % %
L.
Propylene Glycol 0.0 0.0 0.0 2.0 0.0 0.0 0.0
Xanthan Gum 0.0 0.0 0.0 0.08 0.0 0.0 0.0
M.
Essential Oils 0.0 0.0 0.0 0.20 0.0 0.0 0.0
Perfume Oil 0.0 0.25 0.0 0.20 0.0 0.0 0.0
Vitamin A
Palmitate 0.0 0.05 0.0 0.0 0.0 0.0 0.0
N.
AloeVera Gel 0.0 0.0 3.0 0.0 0.0 0.0 0.0
Chamomile Extract 0.0 0.0 0.1 0.0 0.0 0.0 0.0
* Contains about 1% propylene glycol.
The various culllpullc~ listed in the Table have been sc~ tt~d into
groups, the c~n~tihlpnt~ of each group being mixed together before being
added to members of the remaining groups in accùldallcc with the
procedures set forth below.
In the first step, the mixbure of components of phase A is stirred for
d~lulullldk;ly S minutes with sheer mixing until homogPnPous. With high
speed sheer mixing, the materials of phase B are added gradually to A and
the batch is mixed for 20 minutes until dispersed.
The components of phase C and then phase D are slowly added to the
mixture of phases A and B with high shear mixing until dispersed. Silica
is added at this pohlt and dispersed through the mixture.

~ WO 96/04894 2 l q 6 9 8 2 PCT/US95/1013~
The resulting batch heated to 90~C before the addition of the c~ ollelll~i
of phase E. The vessel is cooled to 55~C and the premixed phase F is
added. The batch is mixed until homogeneous. The mixture is cooled to
30~C and phase G is added.
Phase H is prepared by first dissolving the polyvhlyl~y,,ulidone
~ olll~le~-illg agent in alcoholic solvent and then dissolving the anti-acne
active followed by the remaining components, ending with adding a
solution of citric acid or salt. Phase I is then added to phase H and the
resulting mixture is added to the oil phase. Premixed phase J is then also
added to the oil phase.
Finally phases K, L, M and N are added as diluent.
The resulting composition is ready for p~rk~gjng
The compositions of the Examples exhibit moisturisation, anti-acne
activity, skin anti-ageing benefits, together with improved formulation and
colour stability, skin feel and appearance.

Dessin représentatif

Désolé, le dessin représentatif concernant le document de brevet no 2196982 est introuvable.

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Demande publiée (accessible au public) 1996-02-22

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THE PROCTER & GAMBLE COMPANY
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GILLIAN SCOTT BRIGGS
GRAEME DOUGLAS TELFER SMITH
TERESA BARBARA CROOK
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Date
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Nombre de pages   Taille de l'image (Ko) 
Page couverture 1997-05-20 1 16
Description 1996-02-22 22 989
Abrégé 1996-02-22 1 42
Revendications 1996-02-22 4 159
Revendications 1997-03-11 3 151
Page couverture 1998-06-04 1 16
Courtoisie - Lettre d'abandon (R30(2)) 2000-02-03 1 171
Courtoisie - Lettre d'abandon (taxe de maintien en état) 2000-09-05 1 184
PCT 1997-02-06 6 202
Taxes 1997-02-06 1 45