AU654844B2 - Stable emulsions of perfluoropolyethers and fat substances and process for preparing them - Google Patents

Description

1- P/00/01i1 Regulation 3.2

AUSTRALIA

Patents Act 1 990 654844

ORIGINAL

COMPLETE SPECIFICATION STANDARD PATENT Invention Title: S TA B LE EM U L SIO NS O F PERFLUOROPOLYETHERS AND FAT SUBSTANCES AND PROCESS FOR PREPARING

THEM

e..

Cd 0.

.d The following statement is a full description of this invention, including tne best method of performing it known to us: C. C.

C C

C

C. II LC a t tale It a a GH&CO REF: P17052-DA:RPW:RK o j- T -2- The present invention relates to stable emulsions of perfluropolyethers having perfluoroalkyl end groups and of fat substances.

It is known that said perfluoropolyethers exhibit a very high hydrophobicity and lipophobicity, wherefore it was possible to prepare stable aqueous emulsions thereof only by by means of particular combinations of components of the same emulsions.

eo.

o.o U.S. patent 4,803,067 discloses stable emulsions of *4 0 perfluoropolyethers having perfluoroalkyl end groups in oil/ water emulsions or water/oil emulsions obtained by using emulsifiers. These emulsions are utilized, in particular, in lotions and creams for cosmetology and dermatology, in consideration of the excellent properties of said perfluoropolyethers in said t, applications, due to the particular formation, on the skin, of a water-repellent, oxygen-permeable and carbon dioxide-permeable protective film, which permits the normal skin respiration.

European Patent Application ,No. 390.20.6 describes stable emTsions of perfluoropolyethers having perfluoroalkyl end groups in glycerol or other polyhydtroxylated compounds, prepared by using i1k a I S-3emulsifiers. In the preparation of cosmetic or dermatological products, the abovesaid emulsions are added to basic formulations containing the other components.

So far it was not possible to obtain stable emulsions of perfluoropolyethers with fat" substances, although the need for such emulsions of anhydrous or substantially anhydrous nature was strongly felt in the cosmetic and dermatological sectors or in industrial appliances, wherein said anhydrous or substantially anhydrous emulsions would have permitted to preserve the hydrophobic nature of the anhydrous products whereinto they would have been introduced.

It has now been found that it is possible to obtain stable emulsions of perfl'uoropolyethers having perfluoroalkyl end groups (hereinafter briefly referred to as perfluoropoly- Ge C ethers) and fat substances if one or more fat substances in the liquid state is or are added, under stirring, to an emulsion of perfluoropolyether in glycerol or other polyhydroxylated compounds in the presence of a surfactant which is soluble in glycerol or in the other polyhydroxylated compounds.

The existence of said stable emulsions of perfluoro- 44 t S polyethers and fat substances in jlycerol or other polyhydroxylated compounds is very surprising since it is not possible to emulsify a fat substance in glycerol or in another polyhydroxylated compound and it is not possible to emulsify

_I-

4, 4 *e 4 44.

1 14 *i 4 4444 I I I 4( I I~ 4 a perfluoropolyether in a fat substance. It has surprisinly been found that the presence of a perfluoropolyether in emulsion in glycerol or other polyhydroxylated compounds makes it possible to emulsify the fat substance in the perfluoropolyether-glycerol system or in the perfluoropolyether-other polyhydroxylated compounds system.

Thus, embodiment(s) of the present invention may provide stable, anhydrous or substantially anhydrous emulsions of perfluoropolyethers and fat substances.

Other embodiment(s) may provide a process for preparing, such emulsions.

The present invention therefore provides stable emulsions of perfluoropolyethers having perfluoroalkyl end groups and of fat substances comprising: one or more perfluoropolyethers having perfluoroalkyl end groups: 1-50% by weight, one or more polyhydroxylated compounds selected from glycerol and other polyalcohols and the saccharides, containing at least three hydroxylic groups, said compounds being dissolved in water or in a hydrophilic solvent when they are solid: 10-95% by weight, including water and hydrophilic solvent, if any, one or more fat substances having a melting temperature not higher than 100°C: 10-80% by weight,

CZZ-N-V

one or more emulsifiers: 0.1-10% by weight.

By the term fat substance it is meant: 1) a liquid product (oil) insoluble in water and in the polyhydroxylated compounds as defined hereinabove, and 2) a prodlct which is solid'at room temperature is insoluble in water and in the polyhydroxylated compounds and has a melting temperature not exceeding 100 0

C.

The perfluoropolyethers having perfluoroalkyl end groups, i.e. free from functional groups, are well-known compounds, which are described, along with their method of preparation, in several documents, among which British patent 1,104,482, U.S. patents 3,242,218; 3,665,041; 3,715,378; t 41 4,523,039; European patent applications 148,482; 151,877 't t t and 191,490 and international patent applications WO 87/00538 Sand WO 87/02992. Several perfluoropolyethers are available on the market under the trademarks FomblinR), Galden

(R)

e Krytox and Demnum Suitable perfluoropolyethers are the ones characterized by the presence of one or more repeating perfluorooxyalkylene units: 6 I(C a) (CF -CF 2 0) b (CF 2 0) c) (C 3

F

6 simplified formula for (CF 2

-CF-O)

CF 3 d) (CF 2 -CF d) 2 2 i s- U r -i -4_.HS' 6e) (CF2-CF2-CF20) f) (CFO)

CF,

CF R 11 I 3 f g) -C C I I CF R 3 f Pf If C-0- Rf f 0 0 0000 4 *0 0 0 "9 r* 0 *000 0 09 0* 90 where the groups, like or unlike each other, are a fluorine atom or a perfluoroalkyl group preferably containing 1 to 3 carbon atoms.

Preferably the perfluoropolyethers suitable for the present invention exhibit the following individual perfluorooxyalkylene units or the following combinations of perfluorooxyalkylene units: I) (CF 2 -CF 0) and (CF20), these units being statistically distributed along the perfluoropolyether chain; or II) (CF -CFO) and (CFXO), where X is F or CF3, 32

F

3 said units being statistically distributed along t~i chain; or III) (CF 2

-CF

2 (CF2-CFO) and (CFXO),

CF

3 wherein X is F or CF 3 said units being statistically distributed along the chain; or s -7 IV) (CF-CF O2 or

CF

3 V) (CF 2

-CF

2 -CF20); or VI) (CF 2 -CF20); or VII) CF

R

-C 0 C C 0 CF R R C3 f where the groups, like or unlike each other, are a fluorine atom or a perfluoroalkyl group preferably containing 1 to 3 carbon atoms; or VIII) (CF 2 0-CF 2 S, ,Suitable are also the perfluoropolyethers containing 4 t perfluorooxyethane rings t 4, T B 0 -CF -A C- or S I I I F CF--0

CF

2

F

2

R

It tf, wherein T, A, B and R, like or different from one ant I t other, are perfluorooxyalkyl' perfluoropolyoxyalt 4 kyl or perfluoroalkyl radicals preferably containing tt 1 to 6 carbon atoms.

Examples of suitable perfluoropolyethers having repeating perfluorooxyalkylene units are the ones belonging to the following classes:

A

8 A) R f- -(C3F60)a(CF- b(CF20) -R'

CF

3 3 4 1r 1414 4 I 41 I I 1(

SI

44 I i i 44 4F1 where: Rf and R'f, like or unlike each other, are selected from the group consisting of CF 3

C

2

F

5 and C3F7; units C3F 0 (oxytrifluoromethyltrifluoroethylene), CF-0 and CF 0

CF

3 L3 are statistically distributed along the chain; a is an integer; b and c are integers or zero; a when the sum is other than zero, the ratio b+c ranges from 5 to B) CF30-(C2F40)d(CF20)e-CF 3 where units C2F 0 and CF 2 0 are statistically distributed along the chain;; d and e are integers; the d/e ratio varies from 0.3 to C) CF 0-(C F 0) (C2 F 0) -(CFXO)h-CF 3 where units C 3

F

6 0, C 2

F

4 0 and CFXO are statistically distributed along the chain; X is F or CF 3 f, g and h are integers; the ratio ranges from 1 to g+h and the ratio ranges from 1 to D) R(O-(CF CF CF 0).Rng Y 222 j where R 3 and R like or different from each other, are

-CF

3 or -C2F 5 and j is an integer.

3 2 9

S

S.

I S perfluoropolyethers suitable for use in the present invention typically have a number average molecular weight ranging from 500 to 20,000 and, preferably, from 1,000 to 10,000.

The polyhydroxylated compounds suited to the present invention are described more in detail in the cited European patent application 390,206 in the name of the saame App.li.cahnt which is incorporated in the specification of the present invention as a reference.

When the polyhydroxylated compound is solid, it is dissolved in water or in a hydrophilic solvent. It is advisable to use the minimum amount of water or of hydrophilic solvent which is necessary to dissolve the compound.

Suitable hydrophilic solvents are, for example, glycols, glycerol, lower alcohols, ethereal solvents and diglymes, also admixed with water.

However, water is usually utilized as a solvent.

Suitable are the concentrated aqueous solutions (syrups) of polyalcohols and saccharides, which are commercially available.

Usually the concentration of the solutions ranges from 50% to 80% by weight.

Best preferred polyhydroxylated compounds are glycerine, diglycerol, triglycerine and tetraglycerine.

K\

The oils and the fats according to the present invenion can be of vegetable, animal, hydrocarbon or synthetic f CII 10 nature. They are preferably fatty alcohols, acids, esters and amides, silicone oils and hydrocarbon' oils and fats.

The emulsifier shall be soluble in the polyhydroxylated compound. Among the suitable emulsifiers, the following ones can be cited as examples,: sodium laurylsulphate, sulphosuccinate (sulphosuccinic hemiester), coco amphocarboxyglycinate, potassium cetylphosphate, sodium alkyl-polyoxyethylene-ether carboxylate, benzalconium chloride, alkylamidopropylbetaine, coco amidQpropylbetaine.

S.. The emulsions according to the present invention have preferably the following composition: perfluoropolyether or perfluoropolyethers: 5-25% by weight; one or more polyhydroxylated compounds: 10-59% by weight; fat substance or substances: 35-80% by weight; .o emulsifier or emulsifiers: 0.3-3% by weight.

0 The most preferred emulsions cont i' from 10 to by weight of polyhydroxylated compound.

Commbnly, the emulsions contain only one perfluoropolyether and only one polyhydroxylated compound.

Depending on the nature and proportion of the components, the emulsions of the i-esent invention exhibit a very

JI

1 i o) O 4000 e 9 So a o 44 6 4 4 *a 4 44 0 S4 0* i*

*I

I

~qj 11 wide viscosity range, which makes them suitable for a broad applicative field. The least viscous emulsions have, for example,a viscosity of 2,000 cps (centipoises)at 25°C, while the most viscous emulsions have, for example, a viscosity of 1,000,000 cps or above.

The viscosity increases with the concentration of the fat substances and of the perfluoropolyethers and when use is made of more viscous polyhydroxylated compounds.

At equal concentration, also the nature of the fat substances influences the viscosity.

The viscosity of the emulsions can be lowered, if so desired, by addition of water or of alcohols. Suitable alcohols are, for example, alkyl alcohols having 1 to 4 carbon atoms, and ethylene glycols containing 2 to 4 carbon atoms.

The addition of water or alcohol tends to lower the stability of the emulsions, wherefore it is not advisable to add more than about 20% thereof,calculated on the total weight of the emulsion.

The minimum added amount of water or alcohol is, for example, equal to If water or alcohol is added, the per cent amount of the other components, of course, is reduced, although maintaining unaltered their reciprocal proportions.

The water- or alcohol-containing emulsions are useful in those applications in which a low or relatively low viscosity without a high hydrophobicity is desired.

12 According to the present invention, stable emulsions are considered the ones, which do not give rise to phase separation phenomena after centrifugation at 4,000 rpm for a time of 30 minutes and a subsequent treatment in oven at 50 0

C

for a week.

The emulsions according to the present invention can be prepared as follows: to an emulsion of one or more perfluoropolyethers in one or more polyhydroxylated compounds containing one or more emulsifiers which are soluble in said polyhydroxylated compounds (such emulsion will be briefly referred to as "pre-emulsion") there are added, under stirring, one or more fat substances in the liquid state.

.The pre-emulsion is at a temperature, which is not critical; in most cases it is at room temperature.

When the fat substance is solid at room temperature, it is added to the pre-emulsion in the molten state or dissolved, in particular, in a liquid fat substance conforming to the present invention, preferably a hydrocarbon oil, while 2 heating, if necessary, in order to favour the dissolution.

When the fat substance is added at a temperature above the room temperature, it is advisable to preheat the S pre-emulsion to a temperature next or equal to the temperature of the fat substance.

The preparation of the pre-emulsions is described i; in detail in Europeani patent application 390,206 already citi 1 1 .^llWll T L *U Lu GRIFFITH HACK CO S 023 0) 0 1 i, 13 ed herein.

I tt Iic rtl If I (i CC Such emulsions are preparable by adding the perfluoropolyether or perfluoropolyethers, under stirring, to a solution of one or more emulsifiers in one or more polyhydroxylated compounds.

At the end of the addition it is advisable to go on stirring at a lower speed, for example for 30-120 minutes, in order to obtain the best homogenization.

It is assumed that the outer phase of the emulsions according to the present invention consists of the polyhydroxylated compound or compounds, while the perfluoropolyether or perfluoropolyethers and the fat substance or substances conEtitute inner dispersed phases. In act, these emulsions are dilutable with glycerol and with water (without having recourse to mechanical stirring), but are not dilutable with perfluoropolyethers and fat substances (unless mechanical stirring is utilized). Also the fact that the viscosity increases as the content of perfluoropolyethers or of fat substances increases, indicates that these two types of components form the inner phases.

The emulsions of the present invention have a wide field of uses in cosmetology and dermatology and in the industrial sector.

The introduction of liposoluble substances into the oily phase (such as, for example, vitamins or solar filters) e t C ti i tl S 1 cPI I

IC

14 i3 *r s 44$r, t41 4 I P 4~tl 4 or of glycerol-soluble substances permits to functionalize the cosmetic and dermatological preparations.

Among the cosmetic applications there are to be cited for example: barrier creams, sun-preparations, lip-ointments and anhydrous cosmetics, such as lipsticks and sticks.

Among the dermatological applications there are to be cited,for example, the skin protective preparations and the medicament-slow-release preparations.

Among the industrial applications there are to be cited the lubrication and the water-repellent treatments of textiles and leather.

The anhydrous nature of the emulsions, or in any case,the presence therein of little water am 'nts, makes biologically more stable the cosmetic and dermatological products prepared with said emulsions. In fact, said products do not require, usually, the presence of preservatives. Also the anhydrous nature of the emulsions secures a higher persistence of said products on the skin. A further advantage in the same applicative fields consists in the fact that the emulsions according to the present invention require the presence of lesser amounts of surfactant than the ones which are contained in the emulsions of perfluoropolyethers in water/oil or oil/water emulsions described in the above-cited U.S. patent 4,803,067.

The following examples are given merely for illustrative purposes and should not be construed to be a limi- 4' a t C4

I

i_ i 15 ation of the scope of the present invention.

Examples I to 33 illustrate various emulsions conforming to the present invention and the modalities for preparing them. All the compositions are indicated in by weight.

The stability test is the one previously described.

The utilized perfluoropolyethers have the structure and the characteristics indicated hereinbelow: Fomblin

CF

3 -(0-CF-CF (0-CF -0CF 3 CF n m

CF,

CI

,trI ±1 tC ft n/m 20 to M.W. (number average molecular weight)= 3,200.

-Galden D03 the same formula as the preceding product n/m 20 to M.W. 870 -Fomblin HC/R the same formula as the preceding product n/m 20 to M.W. 6,600 Demnum

F(CF

2

CF

2 -CF0) nCF CF 3 M.W. 4,500 -Fomblin CF3-(OCFCF2 (OCF -OCF p/q 0.6 to q0.

p/q 0.6 to 0.7

I

16 M.W. 9,400 EXAMPLE 1 Fomblin HC/25 59% Glycerol 29% Texapon N/40* 2% Vaseline oil (density: 0.83) sodium lauryl sulphate (solution at 28%) produced by Henkel.

Into the pre-emulsion of Fomblin HC/25, glycerol and Texapon N/40, the vaseline oil was added at room temperature, while stirring by means of a Silverson L/2R turboemulsifier at 5,000-6,000 rpm.

Unless otherwise specified, the emulsions illustrated in the following ex:amples were prepared according to the same procedure.

The emulsion was stable. Its viscosity, as well as

S

the one of the emulsions of the subsequent examples, was determined by means of a Brookfield digital eight-speed viscosimeter, model RTV-II, following the manufacturer's rules.

Viscosity: 36,600 cps (centipoises) at 25 0 C (5 impel, ler 29).

EXAMPLE 2 0 0 Fomblin HC/25 29% Glycerol 59% Texapon N/40 2% Vaseline oil 17 Viscosity: 2,000 cps (5 rpm, impeller 29) at Stable emul s ion.

EXAMPLE 3 Fomblin HC/25 Glycerol 39% Texapon N/40 2% V ine M 1l 39% Viscosity: 50,000 cps (5 rpm, impeller 29) at 25 0

C.

Stable emulsion.

EXAMPLE 4 Fomblin HC/25 Glycerol 29% Thxaporn N/40 2% Vaseline oil 54% Viscosity: 950,000 cps (1rpm, impeller 29) at 25 0

C.

Stable emulsion.

EXAMPLE A Fomblin HC/25 t Glycerol 59% Texapon N/40 2% Vaseline oil 29% Viscosity: 3,100 cps (5 rpm, impeller 29) at 25 0

C.

Stable emulsion.

EXAMPLE 6 Fomblin HC/25 it Itt t t t itt.

t 1: -one or more fat substances having a melting temperature not higher than 1O 0 C: 10-80/0 by weight, -18- Glycerol 39% Texapon N/40 2% Silicone oil (350 cps) 39% Stable emulsion.

EXAMPLE 7 Fomiblin HC/25 Glycerol 39,)% Texapon N/40 2% M~ixture of 50% of silicone oil andI 50% of vaseline oil 39% Stable emulsion.

EXAMPLE 8 Fomblin FIC/25 t *Glycerol 39% Texapon N/40 2% Abil K4 (volatile silicone) 39% Stable emulsion.

EXAfIPLE 9 Foniblin HC/25 'C C, Ot Glycerol 39% Texapon N/40 2% Wheat germ oil1 39% Stable emulsion.

'EXAMPLE Fomblin IIC/25 19- Glycerol 39% Texapon N/40 2% Jojoba oil1 39% Stable emulsion.

EXAM-PLE 11 Fomblin HC/25 Glycerol 39% Texapon N/40 2% Eutans.! G (2-octyl-dodecanol) produced by Henkel 39% Stable emulsion.

EXAIAPLE 12 Fomblin HC/25 Glycerol 3 9 Texapon N/40 2% riirytol (triglyceride of the capric and caproic. acids) produced by Henkel 39% Stable emulsion.

EXAI1PLE 13 Fomblin HC/25 Glycerol 39% Texapon N/40 2% Octyl stearate (Cetiol 868 produced by Henkel) 39% 20 00 *090 00

C

*q so 8000 0 (~0 eQ 0 Co C~ C 06

C

*00060 0 0 .ii t 00 *0 0* 9 00 *0 0 a. se *Q C a h 6,

S

a

C

CCC" ~0 0 S Stable emulsion.

EXAMPLE 14 Fomblin HC/25 Glycerol 39% Texapon N/40 2% Olive-oil 39% Stable emulsion.

EXAMPLE Fomblin HC/25 Glycerol 39% Texapon N/40 2% Paraffin ClO/C13 39% Stable emulsion.

Example 16 Fomblin HC/25 Glycerol 39% Texapon N/40 2% Ropy vaseline 39% T lopy vaseline was introduced in the molten state at a temper~.Ure of about 55 0 C into the pre-emulsion pre~heatped to Stable emulsion.

EXAMPLE 17 Fomblin HC/25 Glycerol 39% Texapon N/40 2%

I

t

'U

21- Ropy vaseline 13% Paraffin CJO/C13 26% The ropy vaseline and the paraffin were premixed before being introduced into the pre-emulsion.

Stable emulsion.

EXAMPLE 18 Fomblin HC/25 Glycerol 39% Texapon N/40 2% Castor-oil 39% Stable emulsion.

EXAMPLE 19 Fomblin HC/25 Glycerol 39% Texapon N/40 2% Linseed-oil 39% Stable emulsion.

,EXAMPLE Fomblin HC/25 14% Glycerai 27% Texapon N/40 2% Vaseline oil 52% Water Water was added last.

Stable emulsion.

4 4 a I II 4 44 44 44 4 22 Viccis~ty: 37,500 cps at 25 0 C (5 rpm, impeller 21).

EXAMPLE 21 Fomblin HC/25 13% Glycerol 27% Texapon N/40 2% Vaseline oil 43% Water Stable emulsion.

Viscosity: 7,000 cps at 25 0

C

EXAMPLE 22 Fomblin HC/25 Glycerol Texapon N/40 Vaseline oil (15 rpm, impeller 21).

t 12% 23% 2% 43%

I

I

II

4 I. I it It It W at er Stable emulsion.

EXAMPLE 23 Galden 003 Glycerol Texapon N/40 Vaseline oil Stable emulsion.

EXAMPLE 24 Foniblin HC/R G I ytero0 1 39% 2% 39% 39% -23 Texapon N/40 2% Vaseline oil 39% Stable emulsion.

EXAMPLE Demnum S/65 Glycerol 39% Texapon N/40 Vaseline oil 39% Stable emulsion.

EXA1MPLE 26 Fomblin Z 25 CrGlycerol 3 9% CTexapon N/40 2% Vaseline oil 39% Stable emulsion.

EXAMPLE 27 Fomiblin HC/25 Glycerol 39% Coco amidopropylbetaine 2% Vaseline oil 39% Stable emulsion.

EXA14PLE 28 Fomnblin HC/25 Glycerol 39% j ~Benzalconium c hlIor id e 24 (solution at 50% in water) 2% Vaseline oil 39% Stable emulsion.

EXAMPLE 29 Fomblin HC/25 Diglycerol 39% Texapon N/40 2% Vaseline oil 39% Highly viscous, stable emulsion.

Viscosity: 1,000,000 cps (5 rpm, impeller 29) at 25 0

C.

EXAMPLE Fombli HC/25 Sorbitol (70% in water) 39% Texapon N/40 2% Vaseline oil 39% Stable emulsion.

EXAMPLE 31 Fomblin HC/25 8% Glycerol 27% Diglycerol 8% Vaseline oil Texapon N/40 2% Stable emulsion.

Viscosity: 180,000 cps (1 rpm, impeller 4) at t t t t t EC O E Ct fC EC rr e c t -r 25 EXAMPLE 32 Fomblin HC/25 Glycerol Amphisol K 2% Cetiol 868 53% Abil K4 potassium cetyl-phosphate produced by Givaudan octyl stearate produced by Henkel volatile silicone produced by Tego Cosmetics.

Viscosity: 340,000 cps at 20 0

C.

Stable emulsion.

EXAMPLE 33 F* Fo in HC/25 S* Glycerol Amphisol K 3% Cetiol 868 63% Abil K4 4% This preparation was effected in hot conditions by preheating S* the pre-emulsion to about 50 0 C since the viscosity increase which occurs at high oil concentrations makes it difficult to obtain it in cold conditions.

Viscosity: 500,000 cps at 20 0

C

Stable emulsion.

EXAMPLE 34 Examples 34 to 37 illustrate,for comparative purposes, com-

C

t. t t I t 0 t t t C 26 positions which are not conforming to the present invention.

Glycerol Vaseline oil 49% Texapon N/40 1% The emulsion was fully unstable, with quick separation when at rest.

EXAMPLE Fomblin HC/25 Vaseline oil 79% Texapon N/40 1% The emulsion was fully unstable, with quick separation of Fomblin HC/25 when at rest.

EXAMPLE 36 Fomblin HC/25 Vaseline oil 49% Texapon N/40 1% Stability: as in example EXAMPLE 37 Fomblin HC/25 Vaseline oil 67% Arlacel 989 3% ethoxylated fatty acid produced by I.C.I.

Stabil'ity: as:tn EXAMPLE 38 This example illustrates a barrier cream and its preparation: A) glycerine u 1 1 i

I

27 Fomblin HC/R potassium cetyl phosphate (Amphisol K produced by Givaudan 2% B) mineral oil 48% dimethicone To pre-emulsion A, preheated to about 55°C, phase B was gradually added under stirring. Stirring was then carried on less intensely until room temperature was reached.

The cream viscosity was of 290,000 cps (1 rpm, impeller 6) at 0

C.

EXAMPLE 39 This example illustrates a vitaminic hydrating cream, prepared according to the modalities of example 38: A) glycerine Fomblin HC/25 potassium cetyl phosphate 2% B) octyl dodecanol (Eutanol G produced by Henkel) 50.5% cyclomethicone (Abil K4 produced by Tego Cosmetics) tocopherol acetate 2% retinyl palmitate The cream viscosity was of 180,000 cps (1 rpm, impeller 6) at t C- C

TI(

1:T p

K

uII .vnCiy CAiImpiS re given merely TOr ii ustrative purposes and should not be construed to be a limiti 28 EXAMPLE Another vitaminic hydrating cream like the preceding one was prepared, with the exception that 1% of camomile glycolic extract was added.

The presence of this little amount of glycol was sufficient to bring the viscosity from 180,000 cps to 50,000 cps.

EXAMPLE 41 This example relates to a sun-cream p' oared as in example 38, with the only exception that phase B was preheated: A) glycerine S* Fomblin HC/R potassium cetyl phosphate 2% B) octyl stearate 46% 6 ethyl hexyl p-methoxycinnamate S 0: (Parisol MCX produced by Gavaudan) cyclomethicone 9 o "Karit6 butter" 2% oo099 1 The cream viscosity was of 480,000 cps (1 rpm, impeller 6) at 200C 9.9 9.' 9

Claims (13)

1. Stable emulsions of perfluoropolyethers having perfluoroalkyl end groups and fat substances, comprising: one or more perfluoropolyethers having perfluoroalkyl end groups: 1-50% by weight, one or more polyhydroxylated compounds selected from glycerol and other polyalcohols, and saccharides, containing at least three hydroxylic groups, said compounds being dissolved in water or in a hydrophilic solvent when they are solid: 10-95%, including water or the hydrophilic solvent, if any, one or more fat substances having a melting temperature not higher than 100 0 C: 10-80%, one or more emulsifiers which are soluble in the above said polyhydroxylated compound or compounds: 0.1-10%.

2. The stable emulsions according to claim 1, further characterised in that the perfluoropolyether or perfluoropolyethers have a number average molecular weight ranging from 500 to 20,000.

3. The stable emulsions according to claim 1 or 2, further characterised in that the polyhydroxylated compounds are selected from glycerol, diglycerol, triglycerine and tetraglycerine. 25

4. The stable emulsions according to any one of the preceding claims, further characterised in that the fat substances are selected from the group composed of fatty alcohols, acids, esters and amides, silicone oils and hydrocarbon oils and fats.

5. The stable emulsions according to any of the preceding claims, further characterised in that the emulsifiers are of the ionic type.

6. The stable emulsions according to any one of the preceding claims, consisting of: one or more perfluoropolyethers having perfluoroalkyl end groups: 5-25% by weight, one or more polyhydroxylated compounds: 10-59%, S- one or more fat substances: 35-80%, I /I 30 one or more emulsifiers: 0.3-3%.

7. The stable emulsions according to claim 6, containing from 10 to 40% by weight of one or more polyhydroxylated compounds.

8. The stable emulsions according to any one of the preceding claims, characterised in that they contain furthermore up to 20% by weight of water or of an alcohol referred to the total emulsion, the alcohol being selected from alkyl alcohols having 1 to 4 carbon atoms and ethylene glycols containing 2 to 4 carbon atoms.

9. A process for preparing the stable emulsions as claimed in any one of claims 1 to 8, characterised in that one or more fat substances in the liquid state are added under stirring to a pre-emulsion of one or more perfluoropolyethers in one or more polyhydroxylated compounds, containing one or more emulsifiers which are soluble in said compounds.

The process according to claim 9, characterised in that when the fat substance is solid at room temperature, it is added to the pre-emulsion in the molten state or dissolved in a liquid fat substance.

11. Use of the stable emulsions as claimed in any one of claims 1 to 8 in the preparation of cosmetic and dermatological products. 25

12. Stable emulsions of perfluoropolyethers having perfluoroalkyl end groups and of fat substances substantially as herein described with reference to any one of the Examples.

13. A process for preparing the stable emulsions as defined in claim 12 substantially as herein described with reference to any one of the Examples. .It *I C *CC Dated this 22nd day of February 1994 AUSIMONT S.p.A. By their Patent Attorney GRIFFITH HACK CO -I _T_ STABLE EMULSIONS OF PERFLUOROPOLYETHERS AND FAT SUBSTANCES AND PROCESS FOR PREPARING THEM. ABSTRACT 0, *0 o The invention relates to stable emulsions of perfluoropolyethers 6000 0O a having perfluoroalkyl end groups and of fat substances, consisting of: one or more perfluoropolyethers having perfluoroalkyl end groups: 1-50% by weight, one or more polyhydroxylated compounds selected from glycerol and 1o polyalcohols other than glycerol and saccharides, containing at least three hydroxylic groups, said compounds being dissolved in water or in a hydrophilic solvent when they are solid: 10-95% by weight, including water and the hydrophilic solvent, if any, one or more fat substances having a melting tempertature not higher than 100°C: 10-80% by weight, one or more emulsifiers: 0.1-10% by weight. These emulsions are utilized, in particular, in cosmetology and dermatology. i