Cosmetic compositions

Details Cosmetic compositions Cosmetic compositions

2000-08-02

2004-03-02

Hartley, Michael G. (Department: 1616)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S405000, C424S063000, C514S129000, C252S175000

Reexamination Certificate

active

06699485

ABSTRACT:

The present invention relates to stable, monophasic concentrated compositions containing (per)fluoropolyethers, which are diluted with carriers and excipients in order to be used in the product field for personal care, specifically cosmetic and toilet preparations.
In particular the formulations of the present invention contain functionalized (per)fluoropolyethers, capable to confer improved protective hydro/oil-repellence properties to the formulation itself. The monophasic formulations of the present invention can be used, after dilution, as cosmetic products for the skin and hair-protection towards irritating agents (acids, bases, solvents, detergents) and allergens.
It is well known in the prior art that (per)fluoropoly-ethers due, to their hydro- and oil-repellence and high filmogenic property are very good protective agents towards both hydrophilic and lipophilic irritating agents.
It is also known that it is not possible to use (per)fluoropolyethers as such for the personal care and hygiene and that said compounds must be carried in suitable formulations for topic use in order to advantageously utilize the above mentioned properties of (per)fluoropolyethers.
The (per)fluoropolyether incorporation in polyphase systems in particular under the form of thri-phase emulsions (oil/water/PFPE), used as creams and lotions for skin hydration and protection, is well known. See for example the patents in the name of the Applicant EP 196,904, EP 355,848, EP 390,206. The latter relates to the preparation of concentrated compositions of (per)fluoropolyethers in glycerine in order to facilitate their incorporation in aqueous monophasic systems.
The (per)fluoropolyethers used in these patents have per-fluoroalkyl end groups, which therefore are not reactive end groups.
The drawback of polyphase systems resides in that they require the presence of two essential components: mineral oils (vegetable, animal or synthetic) and emulsifiers (surfactants). The properties of both these components negatively affect the hydro-repellent and/or oil-repellent action of (per)fluoropolyethers having perfluoroalkyl end groups. Therefore in the thri-phase systems of the prior art the hydro- and oil-repellent properties of (per)fluoropolyethers having perfluoroalkyl end groups are reduced.
Also in (per)fluoropolyether systems with glycerine good hydro-repellence values are not obtained.
The thri-phase emulsions are the carrier by which according to the prior art, it is possible to use the above mentioned properties of (per)fluoropolyethers, other systems for formulating compositions having a topic use containing (per)fluoropolyethers, for instance monophase water-based compositions having hydro- and oil-repellent properties, being not available.
The need was felt to have available monophase systems based on perfluoropolyethers having improved hydro- and oil-repellence properties with respect to the known polyphase systems.
The Applicant has surprisingly and unexpectedly found monophase concentrated compositions containing functionalized (per)fluoropolyethers, said compositions dilutable with suitable carriers and excipients, in order to obtain products for the personal care, in particular cosmetic and toilet preparations, said cosmetic preparations having a combination of hydro- and oil-repellence properties clearly superior to those of the above described polyphase systems and even superior to those of the pure (per)fluoropolyethers.
An object of the present invention are therefore concentrated compositions comprising the following components:
A) a (per)fluoropolyether phosphate of general formula:
R
f
—[CF
2
CH
2
—O—L—P(O)(OZ
1
)(OZ
2
)]
1
  (I)
 wherein 1=1 or 2;
L is a a bivalent linking group, preferably of the (CHR
1
CHR
2
O)
n
type wherein R
1
, R
2
equal to or different from each other are selected from H, CH
3
; n is an integer in the range 1-50, preferably 1-6;
Z
1
equal to or different from Z
2
selected from H, alkaline or ammonium cation, di- or tri-alkanolammonium cation wherein alkanol comprises from 1 to 20 C atoms, preferably 1-4 C atoms, di- or tri- or tetra-alkylammonium cation wherein alkyl comprises from 1 to 20 C atoms, preferably 1-4 C atoms, or R
f
—CF
2
CH
2
—O—L—;
R
f
is a (per)fluoropolyether chain comprising repeating units selected from one or more of the following ones:
a) —(C
3
F
6
O)—;
b) —(CF
2
CF
2
O)—;
c) —(CFL
0
O)—, wherein L
0
=—F, —CF
3
;
d) —CF
2
(CF
2
)
z
,CF
2
O—, wherein z′ is an integer 1 or 2;
e) —CH
2
CF
2
CF
2
O—;
when R
f
is monofunctional (1=1), an end group is of the perfluoroalkyl type such as for example CF
3
O, C
2
F
5
O, C
3
F
7
O; optionally a fluorine atom in the perfluoroalkyl end groups can be substituted by a chlorine or hydrogen atom; examples of these end groups are Cl(C
3
F
6
)O, H(C
3
F
6
O);
B) a solvent selected from the following ones: linear or branched when possible alcohols, from 2 to 3 carbon atoms and their methyl ethers; linear or branched glycols from 2 to 6 carbon atoms or linear or branched mono alkylethers wherein the alkyl group ranges from 1 to 4 carbon atoms; dimethoxymethane, known as methyl, acetone;
C) water.
The preferred compound of general formula (I) is the one wherein Z
1
and Z
2
are different from R
f
—CF
2
CH
2
—O—L—; preferably Z
1
=Z
2
=H and in formula (I) 1=2.
In particular, R
f
is of perfluoropolyether type and it has preferably one of the following structures:
—(CF
2
O)
a
—(CF
2
CF
2
O)
b
—  1)
with b/a in the range 0.3-10, extremes included, a being an integer different from 0;
—(CF
2
—(CF
2
)
z′
—CF
2
O)b′—  2)
wherein z′ is an integer equal to 1 or 2;
—(C
3
F
6
O)
r
—(C
2
F
4
O)
b
—(CFL
0
O)
t
—,  3)
with r/b=0.5-2.0(r+b)/t=10-30, b and t being integers different from 0;
—(OC
3
F
6
)
r
—(CFL
0
O)
t
—OCF
2
—R′
f
—CF
2
O—(C
3
F
6
O)
r
—(CFL
0
O)
t
—  4)
—(CF
2
CF
2
CH
2
O)
q′
—R′
f
—O—(CH
2
CF
2
CF
2
O)
q′
—  5)
wherein:
R′
f
is a fluoroalkylene group from 1 to 4 carbon atoms;
L
0
is selected between F, CF
3
;
—(C
3
F
6
O)
r
—OCF
2
—R′
f
—CF
2
O—(C
3
F
6
O)
r
—  6)
wherein in said formulas:
—(C
3
F
6
O)— can represent units of formula:
—(CF(CF
3
)CF
2
O)— and/or —(CF
2
—CF(CF
3
)O)—
a, b, b′, q′, r, t, are integers, whose sum is such that R
f
has number average molecular weight {overscore (M)}
n
values in the range of about 300 and about 5,000, and preferably in the range 800-2,500.
The preferred (per)fluoropolyether chain R
f
is selected from the following structures:
from the bifunctional ones (1=2):
—(CF
2
O)
a
—(CF
2
CF
2
O)
b—;
—(C
3
F
6
O)
r
—(C
2
F
4
O)
b
—(CFL
0
O)
t—;
from the monofunctional ones (1=1):
(C
3
F
6
O)
r
—(CFL
0
O)
t—;
wherein L
0
and the a,b,r,t indexes have the above mentioned value, still more preferably —(CF
2
O)
a
—(CF
2
CF
2
O)
b
—.
The compounds of formula (I) preferably used according to the present invention are those having L=(CH
2
—CH
2
O)
n
with n=1-3; Z
1
equal to or different from Z
2
is selected from H, NH
4
, or an alkaline metal cation; 1=2.
The compounds of general formula (I), having the following formulas, are still more preferred:
 CF
3
—O(CF
2
CF(CF
3
)O)
r
(CF
2
O)
a
—CF
2
—CH
2
(OCH
2
CH
2
)
n
O—PO(OH)
2
  (II)
wherein r/a=0.5-2.0 and n=1-2;
—CF
2
—O(CF
2
CF
2
O)
b
(CF
2
O)
a
—CF
2
—[CH
2
—(OCH
2
CH
2
)
n
O—PO(OH)
2
]
2
  (III)
wherein b/a=0.5-3.0 and n=1-2;
wherein a, b and r have the above mentioned meaning.
The component B) is preferably selected from: ethanol, ethylene glycol, isopropanol, propanol, acetone, methoxyethanol, propylene glycol, propan-1,2-diol, dimethoxy methane, methoxy-isopropanol, diethylene glycol, butan-1,4-diol, diethylenglycol monoethylenether, pentan-1,2-diol, diethylenglycol monoethylether, dipropylenglycol, dipropylenglycol monomethylether, dipropylenglycol monoethylether; still more preferably: ethanol, isoprop

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