Oily phase in an aqueous phase dispersion stabilized by cubic gel particles and method of making

Composition in the form of a stable dispersion. This composition comprises: (a) from 60 to 98% by weight of an aqueous phase, and (b) from 2 to 40% by weight of an oily phase, said oily phase being dispersed in said aqueous phase and stabilized using cubic gel particles, said particles being essentially formed of: (i) 0.1 to 15% by weight, relative to the total weight of the composition, of at least one component selected from the group consisting of 3,7,11,15-tetramethyl-1,2,3-hexadecanetriol or phytanetriol, N-2-alkoxycarbonyl derivatives of N-methylglucamine and unsaturated fatty acid monoglycerides, and (ii) 0.05 to 3% by weight, relative to the total weight of the composition, of a dispersing and stabilizing agent, said agent being selected from the group consisting of surface-active agents which are water-soluble at room temperature, containing a linear or branched, saturated or unsaturated fatty chain having from 8 to 22 carbon atoms. Use in particular in the cosmetic, dermatological and pharmaceutical fields.

The present invention relates to a composition in the form of a dispersion 
of an oily phase in an aqueous phase, the oily phase being stabilized by 
using cubic gel particles formed by using a water-soluble surface-active 
agent containing a fatty chain, and to a process for its preparation. 
A large variety of products are in the form of a dispersion of an oily 
phase in an aqueous phase, such as in the form of an emulsion. Such is the 
case most particularly for cosmetic, dermatological or pharmaceutical 
products, these dispersions imparting good sensory properties to the skin 
and being easy to apply. 
However, it is well known that dispersions, and in particular emulsions, 
lack stability over time, in particular on account of variations in 
temperature; these emulsions "break" giving rise to two separate phases, 
rendering them unusable. 
The nature and the concentration of the emulsifying agent used may have a 
significant influence on the stability of such compositions. 
However, it is well known that the choice and concentration of a suitable 
emulsifying agent will depend on various factors and, in particular, on 
the oil or oils constituting the oily phase of the dispersion or of the 
emulsion. 
Moreover, it should be noted that certain surfactants are not free of 
drawbacks, in particular when they are employed at high concentration for 
the purpose of improving the stability. 
Indeed, they may lead to certain irritation phenomena on sensitive skin. 
It has now been observed, surprisingly and unexpectedly, that it is 
possible to obtain dispersions of an oily phase in an aqueous phase, which 
are particularly stable and non-irritant, using a very large variety of 
oils, by using cubic gel particles containing a low proportion of a 
water-soluble surface-active agent containing a fatty chain. The 
dispersions thus obtained moreover have particularly satisfactory sensory 
qualities. 
The term cubic gel used according to the present invention denotes 
transparent gels which are isotropic in polarized light, in the form of a 
cubic liquid crystal phase. The cubic phases are organized in a bipolar 
manner into separate hydrophilic and lipophilic domains, in close contact 
and forming a thermodynamically stable three-dimensional network. Such an 
organization has been described in particular in "La Recherche", Vol. 23, 
pp. 306-315, March 1992 and in "Lipid Technology", Vol. 2, No. 2, pp. 
42-45, April 1990. Depending on the arrangement of the hydrophilic and 
lipophilic domains, the cubic phase is said to be of normal or reverse 
type. The term "cubic gel" used in the present invention obviously groups 
together the gels having the various types of cubic phases. 
The subject of the present invention is thus a composition in the form of a 
dispersion comprising: 
(a) from 60 to 98% by weight of an aqueous phase, and 
(b) from 2 to 40% by weight of an oily phase, said oily phase being 
dispersed in said aqueous phase and stabilized by using cubic gel 
particles, said particles being essentially formed of: 
(i) 0.1 to 15% by weight, relative to the total weight of the composition, 
of at least one component selected from the group consisting of 
3,7,11,15-tetramethyl-1,2,3-hexadecanetriol or phytanetriol, 
N-2-alkoxycarbonyl derivatives of N-methylglucamine and unsaturated fatty 
acid monoglycerides, and 
(ii) 0.05 to 3% by weight, relative to the total weight of the composition, 
of a dispersing and stabilizing agent, said agent being selected from the 
group consisting of surface-active agents which are water-soluble at room 
temperature, containing a linear or branched, saturated or unsaturated 
fatty chain having from 8 to 22 carbon atoms. 
According to a specific embodiment of the compositions according to the 
invention, the relative weight proportion of component (i) to the weight 
of the oily phase is between 0.02/1 and 1/1, and preferably between 0.05/1 
and 0.5/1. 
According to a specific embodiment of the compositions according to the 
invention, the relative weight proportion of component (i) to the weight 
of said dispersing and stabilizing agent is between 2 and 200, and 
preferably less than or equal to 50. 
The phytanetriol of the cubic gel particles is a known compound, which is 
marketed in particular under the name "Phytanetriol-63926".RTM. by the 
company Roche. 
Among the N-2-alkoxycarbonyl derivatives of N-methylglucamine which may be 
mentioned in particular are those corresponding to the following formula 
(I): 
##STR1## 
in which: 
R represents a branched C.sub.6 -C.sub.18 alkyl radical. 
Among these derivatives, there may in particular be mentioned 
N-2-hexyldecyloxycarbonyl-N-methylglucamine, 
N-2-ethyl-hexyloxycarbonyl-N-methylglucamine and 
N-2-butyloctyloxycarbonyl-N-methylglucamine. 
The compounds of formula (I) as defined above are novel and may be prepared 
according to a process comprising the steps consisting: 
(a) in dissolving N-methylglucamine in a mixture of water and an organic 
solvent, 
(b) in dispersing sodium bicarbonate in the mixture obtained above, at a 
suitable proportion corresponding approximately to four times the molar 
proportion of N-methylglucamine, 
(c) in then introducing an alkyl chloroformate into the reaction mixture 
obtained, the alkyl radical being C.sub.6 -C.sub.18, in a suitable 
proportion, generally in an equimolar proportion relative to that of 
N-methylglucamine, and then in allowing the mixture to react, and 
(d) in recovering the N-2-alkoxycarbonyl derivative of N-methylglucamine 
formed. 
The organic solvent used in step (a) is generally tetrahydrofuran. 
Step (d) consists in filtering the reaction mixture obtained after step 
(c), in collecting the pasty residue by filtration and then in dissolving 
it in acetone so as to crystallize it at a temperature of the order of 
5.degree. C. After filtration, the crystals are drained and dried under 
vacuum. Examples of the preparation of certain N-2-alkoxycarbonyl 
derivatives of N-methylglucamine will be given below in the experimental 
section. 
According to a specific embodiment of the compositions according to the 
invention, the cubic gel particles contain, as component (i), a mixture of 
phytanetriol in a proportion of from 1 to 40% by weight relative to the 
weight of the mixture, and of at least one N-2-alkoxycarbonyl derivative 
of N-methylglucamine of formula (I) in a proportion of from 60 to 99% by 
weight relative to the weight of the mixture. 
According to a preferred form of this embodiment, the proportion of 
phytanetriol is from 10 to 30% by weight relative to the weight of the 
mixture, and that of the N-2-alkoxycarbonyl derivative of 
N-methylglucamine is from 70 to 90% by weight relative to the weight of 
the mixture. 
The unsaturated fatty acid monoglycerides are preferably those having a 
C.sub.16 -C.sub.22 unsaturated fatty chain. 
Among these monoglycerides, there may in particular be mentioned glyceryl 
monooleate or monoolein and glyceryl monolinoleate or monolinolein. 
It is, of course, possible to use, in the compositions according to the 
invention, a mixture of monoglycerides as defined above as well as a 
mixture of unsaturated fatty acid monoglycerides and saturated fatty acid 
monoglycerides, the proportion of saturated fatty acid monoglycerides 
preferably being, however, less than that of unsaturated fatty acid 
monoglycerides. 
According to another embodiment of the compositions according to the 
invention, the cubic gel particles contain, as component (i), a mixture of 
phytanetriol in a proportion of from 1 to 50% by weight relative to the 
total weight of the mixture, and at least one unsaturated fatty acid 
monoglyceride in a proportion of from 50 to 99% by weight relative to the 
total weight of the mixture. 
According to a preferred form of this embodiment, the proportion of 
phytanetriol is from 10 to 30% by weight relative to the weight of the 
mixture, and that of unsaturated fatty acid monoglyceride is from 70 to 
90% by weight relative to the weight of the mixture. 
The dispersing and stabilizing agent (ii) is preferably selected from the 
group consisting of: 
(1) polyol alkyl or alkenyl ethers or esters, 
(2) N-acylated amino acids and derivatives thereof and peptides N-acylated 
with an alkyl or alkenyl radical, and salts thereof, 
(3) alkyl or alkenyl ether or ester sulphates, and the derivatives and 
salts thereof, 
(4) polyoxyethylenated alkyl or alkenyl fatty ethers or esters, 
(5) polyoxyethylenated alkyl or alkenyl carboxylic acids and salts thereof, 
(6) N-alkyl or N-alkenyl betaines, 
(7) alkyltrimethylammonium or alkenyltrimethyl-ammonium and salts thereof, 
and 
(8) mixtures thereof. 
In the compounds listed above, the alkyl and alkenyl radicals have from 8 
to 22 carbon atoms and may be in the form of mixtures. 
1--Polyol alkyl or alkenyl ethers or esters 
Among these, there may in particular be mentioned: 
(a) sorbitan alkyl or alkenyl esters polyoxyethylenated with at least 20 
units of ethylene oxide, such as sorbitan palmitate 20 EO or Polysorbate 
40 marketed under the name "Montanox 40 DF".RTM. by the company Seppic, 
and sorbitan laurate 20 EO or Polysorbate 20 marketed under the name 
"Tween 20".RTM. by the company ICI, 
(b) polyglyceryl alkyl or alkenyl esters containing at least 10 units 
derived from glycerol, which may or may not be oxyethylenated, such as 
polyglyceryl-10 laurate marketed under the name "Decaglyn 1-L".RTM. by the 
company Nikko Chemicals, 
(c) polyglyceryl alkyl or alkenyl ethers, such as polyglyceryl-3 
hydroxylauryl ether marketed under the name "Chimexane NF".RTM. by the 
company Chimex, and 
(d) alkyl or alkenyl ethers or esters of mono- or polysaccharides such as 
those derived from glucose, fructose, galactose, maltose or lactose and 
especially the monoesters in positions -1 and -6 of D-fructose, of 
decylglucose and of decylpolyglucose. 
2--N-Acylated amino acids and derivatives thereof and peptides N-acylated 
with an alkyl or alkenyl radical and salts thereof 
Among these, those for which the alkyl or alkenyl radical has at least 12 
carbon atoms are preferably used. 
According to the invention, the term amino acids refers to .alpha., .beta. 
or .gamma.-amino acids. As N-acylated amino acid salts, there may for 
example be mentioned those of N-acylated glutamate such as monosodium 
cocoyl glutamate, monosodium lauroyl glutamate, disodium C.sub.14 
-C.sub.20 alkoyl glutamate (the C.sub.14 -C.sub.20 alkoyl radical being 
derived from hydrogenated tallow), respectively marketed under the names 
"Acylglutamate CS-11".RTM., "Acylglutamate LS-11".RTM. and "Acylglutamate 
HS-21".RTM. by the company Ajinomoto. 
There may also be mentioned N-acylated lysines such as lauroyllysine 
marketed under the name "Amihope LL".RTM. by the company Ajinomoto. 
The N-acylated amino acid derivatives and salts thereof are preferably 
N-acylated sarcosinates, such as sodium lauroyl sarcosinate marketed under 
the name "Oramix L30".RTM. by the company Seppic, sodium myristoyl 
sarcosinate and sodium palmitoyl sarcosinate respectively marketed under 
the names "Nikkol Sarcosinate MN".RTM. and "Nikkol Sarcosinate PN".RTM., 
by the company Nikko Chemicals. 
Among the N-acylated peptides, there may be mentioned those derived from 
all or part of collagen or keratin, such as sodium lauroyl collagen and 
palmitoyl keratin marketed under the names "Proteol B 30".RTM. and 
"Lipacide PK".RTM. by the company Seppic. 
3--Alkyl or alkenyl ether or ester sulphates, and the derivatives and salts 
thereof 
Among these, those for which the alkyl or alkenyl radical has at least 12 
carbon atoms are preferably used. 
Among the alkyl or alkenyl ether sulphates, the alkyl ether sulphate salts, 
and in particular sodium lauryl ether sulphate, are preferably used. 
Among the alkyl or alkenyl ester sulphates, there may for example be 
mentioned the esters of isethionic acid and the salts thereof, and in 
particular sodium cocoyl isethionate marketed under the name "Geropon AC 
78".RTM. by the company Rhone Poulenc. 
4--Polyoxyethylenated alkyl or alkenyl fatty ethers or esters 
Among these, those for which the alkyl or alkenyl radical has at least 12 
carbon atoms are preferably used. Those particularly preferred have at 
least 20 units of ethylene oxide, for example such as PEG-20 stearate, 
laureth-23, oleth-20 and PEG-25 phytosterol. 
5--Polyoxyethylenated alkyl or alkenyl carboxylic acids and salts thereof 
Among these, those containing at least 10 ethylene oxide units are 
preferably used, for example such as laureth-10 carboxylic acid and 
oleth-10 carboxylic acid. 
6--N-alkyl or N-alkenylbetaines 
Among these, those for which the alkyl or alkenyl radical has at least 12 
carbon atoms are preferably used, for example such as laurylamidopropyl 
betaine and oleylamidopropyl betaine. 
7--Alkyltrimethylammonium or alkenyltrimethylammonium and salts thereof 
Among these, those for which the alkyl or alkenyl radical has at least 12 
carbon atoms are preferably used. The bromides and chlorides, such as 
cocoyltrimethyl-ammonium chloride and cetyltrimethylammonium bromide, are 
preferably used as salts. 
When the component (i) is an N-2-alkoxycarbonyl derivative of 
N-methylglucamine of formula (I), polyglyceryl-3 hydroxylauryl ether, 
sodium lauryl ether sulphate or cetyltrimethylammonium bromide is 
preferably used as dispersing and stabilizing agent (ii). 
According to a specific embodiment of the compositions according to the 
invention, the cubic gel particles additionally comprise from 0.0005% to 
5% by weight and preferably from 0.001% to 2% by weight of a 
water-insoluble ionic amphiphilic lipid. 
Among these, there may in particular be mentioned: 
(i) phospholipids such as natural phospholipids, for instance soya or egg 
lecithin, chemically or enzymatically modified phospholipids, for instance 
hydrogenated lecithin or phosphatidic acid sodium salt, and synthetic 
phospholipids such as dipalmitoylphosphatidylcholine, 
(ii) fatty acid phosphonic esters such as monocetyl phosphate and the 
sodium and potassium salts thereof, marketed under the name "Monafax 
160".RTM. by the company Mona, and dimyristyl phosphate and the sodium and 
potassium salts thereof, marketed under the name "Mexoryl SY".RTM. by the 
company Chimex, 
(iii) N-acylated derivatives of glutamic acid, such as monosodium stearoyl 
glutamate marketed under the name "Acylglutamate HS 11".RTM. by the 
company Ajinomoto and the monosodium cocoyl-(C.sub.14 -C.sub.20) alkoyl 
glutamate mixture, the C.sub.14 -C.sub.20 alkoyl radical being derived 
from hydrogenated tallow, marketed under the name "Acylglutamate GS 
11".RTM. by the company Ajinomoto, 
(iv) sodium cetyl sulphate marketed under the name "Nikkol SCS".RTM. by the 
company Nikko Chemicals, 
(v) sodium cocoyl monoglyceride sulphate marketed under the name "Nikkol 
SGC 80 N".RTM. by the company Nikko Chemicals, and 
(vi) quaternary ammonium derivatives such as behenyltrimethylammonium 
chloride, dilauryldimethylammonium chloride, distearyldimethylammonium 
chloride and 4,5-dihydro-1-methyl-2-(C.sub.14 -C.sub.20) 
alkoyl-1-(2-(C.sub.14 -C.sub.20) alkoyl-aminoethyl) imidazolium methyl 
sulphate, the C.sub.14 -C.sub.20 alkoyl radicals being derived from 
hydrogenated tallow, marketed under the name "Rewoquat W75H".RTM. by the 
company Rewo Chemische, and dialkylhydroxyethylmethylanmonium methyl 
sulphate in which the alkyl radicals are derived from tallow, which may or 
may not be hydrogenated, marketed under the name "Stepanquat VP 85".RTM. 
by the company Stepan and "Quaternium-82" marketed by the company Seppic 
under the name "Amonyl DM".RTM.. 
The incorporation of these water-insoluble ionic amphiphilic lipids imparts 
a surface charge to the cubic gel particles which causes mutual 
electrostatic repulsion of the particles. 
The cubic gel particles as defined above generally have a mean size, 
measured using a BI 90 laser granulometer from the company Brookhaven 
Instruments Corporation, of approximately 0.05 .mu.m to approximately 1 
.mu.m, and preferably of less than or equal to 0.5 .mu.m. 
It is also possible to incorporate into the cubic gel particles, various 
types of active compounds. In particular, the said particles may contain a 
hydrophilic active substance or a lipophilic active substance. 
Obviously, by virtue of the specific structure of the cubic gel particles, 
it is possible to incorporate into the latter both hydrophilic active 
substances and lipophilic active substances even if there is a certain 
incompatibility between these active substances. 
Among the various active substances which may be incorporated, there may in 
particular be mentioned: 
1) antioxidants or anti-free-radical agents such as proteins and enzymes, 
for example superoxide dismutase (SOD), lactoperoxidase and lactoferrin; 
peptides and derivatives thereof such as taurine and carnosine; 
sequestering agents such as phytic acid and polyphosphonic derivatives; 
flavonoids such as rutin and .alpha.-glycosylrutin; chlorophylline; 
ethoxyquine; guanosine; tocopherols, in particular .alpha.-, .beta.- or 
.gamma.-tocopherols and in particular d-.alpha.-tocopherol marketed under 
the name "Copherol 1300".RTM. by the company Henkel, as well as tocopherol 
acetate, di-t-butylhydroxybenzylidenecamphor marketed under the name 
"Mexoryl SAD".RTM. by the company Chimex and t-butylhydroquinone marketed 
under the name "Embanox".RTM. by the company Rhone-Poulenc; ascorbyl 
palmitate and .beta.-carotene, 
2) hydrating agents or humectants such as hyaluronic acid and the sodium 
salt thereof; .beta.-glycerophosphate; glycerol and sorbitol, 
3) UV screening agents such as the products marketed under the names 
"Eusolex 232".RTM. by the company Merck, "Parsol 1789".RTM. and "Parsol 
MCX".RTM. by the company Givaudan-Roure, "Mexoryl SX".RTM. by the company 
Chimex and "Uvinul T150".RTM. by the company BASF, 
4) keratolytic agents such as proteolytic enzymes and, in particular, 
subtilisin, trypsin, .alpha.-chymotrypsin and papain; retinoic acid and 
.alpha.-hydroxy acids, these being aromatic in particular, such as 
salicylic acid and derivatives thereof, in particular 
5-n-dodecanoylsalicylic acid, 
5) tanning accelerators such as caffeine, and tyrosine derivatives such as 
glucose tyrosinate and the N-L-malyltyrosine disodium salt, 
6) depigmenting agents such as kojic acid, glycolic acid, vitamin C and 
especially magnesium ascorbyl phosphate, and arbutin and derivatives 
thereof, 
7) natural dyes such as dyestuffs extracted from plants, such as 
chlorophyllin and .beta.-carotene, or extracted from animals, such as 
cochineal carmine, and caramel, 
8) tanning agents such as dihydroxyacetone, and indoles, 
9) lipid regulators such as .gamma.-orizanol, extract of Centella asiatica 
containing genin and asiatic acid, caffeine, and theophylline, 
10) anti-ageing and anti-wrinkle agents such as hydroxy acids and, in 
particular, .alpha.-hydroxy acids such as glycolic acid, salicylic acid 
and derivatives thereof, such as n-octanoyl salicylic acid marketed under 
the name "Mexoryl SAB".RTM. by the company Chimex, lactic acid and 
derivatives thereof such as glyceryl lactate stearate and glyceryl lactate 
palmitate which are marketed by the company Grinsted under the respective 
names "Lactodan B 30".RTM. and "Lactodan F 15".RTM., and octyldodecyl 
lactate marketed under the name "Cosmol 13".RTM. by the company Nisshin 
Oil Mills; retinol and derivatives thereof, such as retinol acetate, 
palmitate and propionate, and retinoids, 
11) anti-inflammatory and cicatrizing agents such as 
18-.beta.-glycyrrhetinic acid and salts thereof, in particular such as the 
ammonium salt thereof, .alpha.-bisabolol, corticoids, and extract of 
Centella asiatica, 
12) Antibacterial and antifungal agents such as benzalkonium chloride, 
chlorhexidine, hexetidine, and hexamidine, 
13) insect repellents such as diethyl and dimethyl toluamides, 
14) deodorants such as hexachlorophene, and triclosan, the product marketed 
under the name "Irgasan DP 300".RTM. by the company Ciba-Geigy, 
15) anti-dandruff agents such as octopirox, andpyridinethione derivatives 
such as those marketed under the names "Omadine".RTM. by the company Olin, 
16) agents for combating hair loss such as methyl or hexyl nicotinate, and 
minoxidil, 
17) hair dyes such as oxidation couplers and bases, direct dyes, and 
auto-oxidizable dyes, 
18) permanent-waving reducing agents such as thio-glycolic acid, cysteine, 
cysteamine, N-acetylcysteine, N-acetylcysteamine, and glyceryl 
thioglycolate, 
19) conditioners for skin and hair such as cationic polymers and cations, 
and 
20) essential oils such as oil of bergamot. 
In the compositions according to the invention, it is possible to use 
either cubic gel particles containing no active substances, or particles 
containing hydrophilic or lipophilic active substances, or alternatively, 
particles containing both hydrophilic and lipophilic active substances. 
In the compositions according to the invention, the oily phase is dispersed 
in the aqueous phase and is generally in the form of droplets with a mean 
size of between 0.1 .mu.m and 10 .mu.m. 
The oily phase of the compositions according to the invention consists 
essentially of at least one oil of plant, animal, mineral or synthetic 
origin, which is preferably cosmetically, dermatologically or 
pharmaceutically acceptable. 
Among the plant oils which may be mentioned in particular are sunflower 
oil, corn oil, soya oil, marrow oil, grapeseed oil, blackcurrant seed oil, 
jojoba oil, sweet almond oil, safflower oil, sesame oil, borage oil, 
hazelnut oil, macadamia oil and the liquid fraction of karite butter. 
Plant oils which may also be used are essential oils such as oil of 
eucalyptus, oil of hybrid lavender, oil of lavender, oil of vetiver, oil 
of Litsea cubeba, oil of lemon, oil of sandalwood, oil of rosemary, oil of 
camomile, oil of savory, oil of nutmeg, oil of cinnamon, oil of hyssop, 
oil of caraway, oil of orange, oil of geraniol, oil of prickly juniper and 
oil of bergamot. 
Among the animal oils which may be mentioned in particular are fish oils, 
turtle oil, mink oil and hydrogenated squalene (or perhydrosqualene). 
Mineral oils which may be mentioned in particular are liquid paraffin and 
isoparaffins. 
Among the synthetic oils which may be mentioned in particular are 
hydrocarbons such as isohexadecane, polydecene and polyisobutene, fatty 
alcohols such as octyldodecanol, isostearyl alcohol and oleyl alcohol, 
esters such as essential fatty acid glycerides, triglycerides of capric 
and caprylic acids and mixtures thereof, and linear or branched fatty acid 
esters with fatty alcohols, such as purcellin oil (stearyl octanoate). 
Synthetic oils which may also be used in the compositions according to the 
invention are silicone oils of linear type such as polydimethylsiloxane, 
of cyclic type such as cyclopentadimethylsiloxane, and of organically 
modified type such as polyphenyltrimethylsiloxane and 
polydimethylsiloxane, oxyethylenated or oxypropylenated. 
There may also be mentioned fluoro oils such as 
perfluorodecahydronaphthalenes, for instance perfluorodecalin, as well as 
oils of polymeric type such as perfluoropolymethyl isopropyl ethers. 
According to one embodiment of the compositions according to the invention, 
it is also possible to incorporate at least one active substance into the 
oily phase and/or into the aqueous phase. This active substance may be 
chosen in particular among the active substances as defined above. 
The aqueous phase of the composition according to the invention may also 
contain various conventional additives. Among these, preserving agents, 
fragrances, pigments (TiO.sub.2), dyestuffs, fillers and gelling agents 
may be mentioned in particular. 
Among the gelling agents which may be used in the compositions according to 
the invention, there may be mentioned in particular cellulose derivatives 
such as hydroxyethyl cellulose and alkylhydroxyethyl celluloses, algae 
derivatives such as satia gum, natural gums such as tragacanth, synthetic 
polymers such as mixtures of polycarboxyvinyl acids and in particular 
those marketed under the names "Carbopol".RTM. by the company Goodrich or 
"Synthalen".RTM. by the company 3V SA. 
The proportion of gelling agent is generally between 0.1 and 2% by weight 
relative to the total weight of the composition. 
The subject of the present invention is also a process for the preparation 
of a composition in the form of a dispersion, this process consisting of 
at least two steps. 
The first step consists in preparing an aqueous dispersion of cubic gel 
particles as defined above, by fragmentation, with a homogenizer, of a 
cubic gel formed by using at least one component (i) as defined above, 
water, optionally in the presence of water-insoluble ionic amphiphilic 
lipids and/or hydrophilic and/or lipophilic active substances and at least 
one dispersing and stabilizing agent (ii) as defined above. The 
homogenizer may be of the rotor-stator type with a high shear gradient, 
such as "Virtis".RTM. or "Heidolph Diax 600".RTM. or a high-pressure 
homogenizer operating between approximately 200 and 1800 bar (20 to 180 
MPa). 
The size of the cubic gel particles may be modified by the nature and 
concentration of the dispersing and stabilizing agent (ii) used. 
It is, of course, possible to introduce various additives and/or active 
substances into the aqueous phase at this stage in the preparation of the 
aqueous dispersion of the cubic gel particles. 
After formation of the cubic gel particles, the dispersing and stabilizing 
agent is generally outside the said particles. 
The second step consists in then adding to the obtained dispersion an oily 
phase optionally containing certain lipophilic additives and/or active 
substances and in subjecting the mixture to mechanical stirring which may 
be performed in particular using a homogenizer of the same type as those 
defined above. 
Various additives and/or active substances may also be introduced at this 
stage of the preparation. 
In particular, when it is desired to prepare a gelled dispersion, an 
aqueous solution containing a gelling agent is generally added to the 
mixture obtained after the second step. 
The compositions according to the invention in dispersion form are more 
particularly intended for cosmetic, dermatological or pharmaceutical use 
and are in various forms such as, in particular, a milk, a cream or a 
serum. 
Examples of the preparation of N-2-alkoxycarbonyl derivatives of 
N-methylglucamine will now be given by way of illustration, along with 
several examples of compositions in dispersion form according to the 
invention.

EXAMPLES 
Preparation of N-2-alkoxycarbonyl derivatives of N-methylglucamine 
Example A 
Preparation of N-2-hexyldecyloxycarbonyl-N methylglucamine 
In a reactor, 70.2 g of N-methylglucamine (0.36 mol) are dissolved in a 
mixture consisting of 60 ml of water and 80 ml of tetrahydrofuran, and 
120.96 g of sodium bicarbonate (1.44 mol) are then dispersed therein. 
While maintaining the temperature of the reaction mixture at 8.degree. C., 
109.62 g of 2-hexyldecanoyl chloroformate (0.36 mol) are added dropwise 
and the mixture is left to react for 3 hours with stirring at 5.degree. C. 
After the mixture has been left to stand overnight at room temperature, it 
is filtered and concentrated. The pasty residue is then dissolved in 1 
liter of acetone. After crystallization by cooling, the product is 
filtered off and then recrystallized from 0.5 liter of acetone. The 
crystallized product is then filtered off and dried. 100 g of 
N-2-hexyldecyloxycarbonyl-N-methylglucamine are thus obtained (yield: 60%) 
with a melting point of: 70.6.degree. C. 
According to the same procedure as that described above, 
N-2-ethylhexyloxycarbonyl-N-methylglucamine (melting point: 74.2.degree. 
C.) and N-2-butyloctyloxycarbonyl-N-methylglucamine (melting point: 
77.degree. C.) were also prepared. 
EXAMPLES OF COMPOSITIONS 
Example 1 
An aqueous dispersion of cubic gel particles is obtained by mixing together 
3 g of phytanetriol and 1.28 g of water, to which are added 75.7 g of an 
aqueous solution containing 0.95 g of Polysorbate 40 marketed under the 
name "Montanox 40 DF".RTM. by the company Seppic. The mixture is then 
predispersed and homogenized, at room temperature, using a homogenizer of 
"Virtis".RTM. type at 35,000 rpm for 5 minutes, this stirring being 
repeated 4 times. 
To the aqueous dispersion of cubic gel particles obtained is then added 
0.02 g of preserving agents, followed by an oily phase consisting of 10 g 
of apricot almond oil and 10 g of volatile silicone oil marketed under the 
name "Dow Corning Fluid 345".RTM. by the company Dow Corning. After 
stirring at room temperature using a homogenizer of "Virtis".RTM. type at 
35,000 rpm for 5 minutes, this stirring being repeated 5 times, a stable 
dispersion of good consistency which is pleasant to apply is obtained. 
The mean size of the droplets of the oily phase is approximately 0.51 .mu.m 
(polydispersity factor: 0.6). 
Example 2 
An aqueous dispersion of cubic gel particles is obtained by mixing together 
2.97 g of phytanetriol and 0.03 g of monosodium stearoylglutamate marketed 
under the name "Acylglutamate HS-11".RTM. by the company Ajinomoto and 
1.28 g of water, to which are added 75.7 g of an aqueous solution 
containing 0.95 g of Polysorbate 40. The mixture is then predispersed and 
homogenized, at room temperature, using a homogenizer of "Virtis".RTM. 
type at 35,000 rpm for 5 minutes, this stirring being repeated 4 times. 
To the aqueous dispersion of cubic gel particles obtained is then added 
0.02 g of preserving agents, followed by an oily phase consisting of 10 g 
of apricot almond oil and 10 g of volatile silicone oil marketed under the 
name "Dow Corning Fluid 345".RTM. by the company Dow Corning. After 
stirring at room temperature using a homogenizer of "Virtis".RTM. type at 
35,000 rpm for 5 minutes, this stirring being repeated 5 times, a stable 
and homogeneous dispersion is obtained. 
The mean size of the droplets of the oily phase is approximately 0.37 .mu.m 
(polydispersity factor: 0.05). 
Examples 3, 4, 5 and 6 (Comparative) 
The compositions below were prepared, taking the composition of Example 1 
as reference and according to the same procedure: 
______________________________________ 
Example 3: 
Polysorbate 40 0.95 g 
Preserving agents 0.02 g 
Apricot almond oil 10 g 
Volatile silicone oil marketed under the name 
10 g 
"Dow Corning Fluid 345" .RTM. by the company Dow Corning 
Water, qs 100 g 
Example 4: 
Polysorbate 40 0.95 g 
Monosodium stearoylglutamate 
0.03 g 
Preserving agents 0.02 g 
Apricot almond oil 10 g 
Volatile silicone oil marketed under the name 
10 g 
"Dow Corning Fluid 345" .RTM. by the company Dow Corning 
Water, qs 100 g 
Example 5: 
Monosodium stearoylglutamate 
0.03 g 
Preserving agents 0.02 g 
Apricot almond oil 10 g 
Volatile silicone oil marketed under the name 
10 g 
"Dow Corning Fluid 345" .RTM. by the company Dow Corning 
Water, qs 100 g 
______________________________________ 
The mean size of the lipid droplets in the dispersions obtained was then 
calculated by measurement using a BI90 laser granulometer from the company 
Brookhaven Instruments Corporation. 
The stability of the dispersions obtained was also evaluated by macroscopic 
observation after 1 month at room temperature. A composition is considered 
to be stable when no separation of the aqueous and oily phases is observed 
after standing for 1 month. 
The following results were obtained: 
______________________________________ 
Size of the lipid 
Stability after 1 
Examples droplets month 
______________________________________ 
Example 1 
0.51 .mu.m Stable 
Example 3 
&gt;1 .mu.m Unstable 
Example 4 
&gt;1 .mu.m Unstable 
Example 5 
&gt;2 .mu.m Unstable 
______________________________________ 
The dispersion of Example 3, which is unstable, differs from that of 
Example 1 only in the absence of cubic gel particles. This shows the 
importance of the latter for the good stability of the dispersion. 
The dispersion of Example 4 is identical to that of Example 3 but contains 
a water-insoluble ionic amphiphilic lipid, namely monosodium 
stearoylglutamate. The presence of the latter has no effect on the 
stability, and this example again shows the importance of the cubic gel 
particles on the stability. 
The dispersion of Example 5 is identical to that of Example 4 but contains 
no dispersing and stabilizing agent, namely Polysorbate 40. Here also, the 
lone presence of a water-insoluble ionic amphiphilic lipid does not make 
it possible to obtain a stable dispersion. 
The result of this comparative study is that only the presence of cubic gel 
particles leads to dispersions having good stability. 
Example 6:Day Cream 
An aqueous dispersion of cubic gel particles is obtained by mixing 
together, at room temperature, 2.97 g of phytanetriol, 0.03 g of 
monosodium stearoylglutamate marketed under the name "Acylglutamate 
HS-11".RTM. by the company Ajinomoto, 0.1 g of tocopherol acetate and 1.3 
g of demineralized water, to which are added, at room temperature, 51 g of 
an aqueous solution containing 3 g of glycerol, 0.01 g of guanosine and 1 
g of polysorbate 40. 
The mixture is then dispersed and homogenized at room temperature using a 
homogenizer of "Heidolph Diax 600".RTM. type fitted with an 18 G 
dispersion head, at 25000 rpm for 15 minutes, followed by 4 passages at 
600 bar through a high-pressure homogenizer of "Soavi".RTM. type. 
To the aqueous dispersion of cubic gel particles obtained (referred to as 
dispersion A) is added a solution B obtained by mixing together the 
following ingredients: 
______________________________________ 
Solution B: 
Apricot almond oil 12 g 
Sunscreen 1 g 
Volatile silicone oil marketed under the name 
12 g 
"Dow Corning Fluid 345" .RTM. by the company Dow Corning 
Fragrance 0.3 g 
______________________________________ 
The mixture is then homogenized to room temperature using a high-pressure 
homogenizer of "Soavi".RTM. type, by 4 passages at 600 bar. 
A solution C is then added thereto, this solution being obtained by mixing 
together the following ingredients: 
______________________________________ 
Solution C: 
Cetylhydroxyethyl cellulose marketed under the name 
1 g 
"Natrosol Plus Grade 330 CS" .RTM. by the company Aqualon 
Preserving agents 0.3 g 
Demineralized water 18 g 
______________________________________ 
The mixture is then homogenized at room temperature using a paddle stirrer 
of "Heidolph RZR 50".RTM. type, at 50 rpm for 30 minutes. 
The dispersion obtained in the form of a cream is stable and homogeneous. 
It is easy to apply to the skin, is not sticky, and does not feel tacky, 
and protects the skin against the harmful effects of free radicals. 
Example 7:Anti-ageing Day Cream 
According to the same procedure as described in Example 6, a day cream was 
prepared in the form of a dispersion by mixing together the following 
parts: 
______________________________________ 
Dispersion A 
Phytanetriol 2.97 g 
Monosodium stearoylglutamate marketed under the name 
0.03 g 
"Acylglutamate HS-11" .RTM. by the company Ajinomoto 
Vitamin E 0.1 g 
Glycerol 3 g 
Polysorbate 40 marketed under the name "Montanox 40 
1 g 
DF" .RTM. by the company Seppic 
Polyphosphonate marketed under the name "Dequest 2046" .RTM. 
0.1 g 
by the company Monsanto 
Superoxide dismutase marketed under the name 
0.0005 g 
"CU-ZN SOD" .RTM. by the company Bio-Technology 
Demineralized water 44.4995 g 
Solution B 
Blackcurrant seed oil 10 g 
Jojoba oil 7 g 
Vitamin E 1 g 
Volatile silicone oil marketed under the name 
4 g 
"Dow Corning Fluid 345" .RTM. by the company Dow Corning 
Sunscreen 1 g 
Fragrance 0.3 g 
Solution C 
Cetylhydroxyethyl cellulose marketed under the name 
1 g 
"Natrosol Plus Grade 330 CS" .RTM. by the company Aqualon 
Preserving agent 0.3 g 
Demineralized water 23.7 g 
______________________________________ 
Example 8:Hydrating Milk 
According to the same procedure as described in Example 6, a hydrating milk 
was prepared in the form of a dispersion by mixing together the following 
parts: 
______________________________________ 
Dispersion A 
Phytanetriol 1.96 g 
Cetyl phosphate marketed under the name "Monofax 160" .RTM. 
0.04 g 
by the company Mona 
Synthetic ceramide marketed under the name "Mexanyl GZ" .RTM. 
0.2 g 
by the company Chimex 
Glycerol 2 g 
L-Hydroxyproline 1 g 
Polysorbate 40 marketed under the name "Montanox 40 DF" .RTM. 
0.75 g 
by the company Seppic 
Polyethylene oxide containing 8 mol of ethylene 
1 g 
oxide (PEG-8) 
Triethanolamine 0.02 g 
Demineralized water, qs 61.58 g 
Solution B 
Sweet almond oil 5 g 
Volatile silicone oil 5 g 
Fragrance 0.3 g 
Solution C 
Sodium hyaluronate 0.05 g 
Demineralized water 10 g 
______________________________________ 
After homogenization of dispersion A and solutions B and C, solution D 
below was finally added: 
______________________________________ 
Solution D 
Mixture of polycarboxyvinyl acids marketed under the name 
0.3 g 
"Carbopol 980" .RTM. by the company Goodrich 
Preserving agents 0.3 g 
Triethanolamine qs pH 6.5 
Demineralized water 10.5 g 
______________________________________ 
Example 9:Day Fluid 
______________________________________ 
Dispersion A 
Phytanetriol 0.27 g 
N-2-hexyldecyloxycarbonyl-N-methylglucamine such as that 
2.43 g 
obtained in Example A 
Lecithin marketed under the name "Epikuron 145 V" .RTM. by 
0.3 g 
the company Lucas Meyer 
Guanosine 0.01 g 
Glycerol 3 g 
Polyglyceryl-3 hydroxylauryl ether marketed under the name 
0.5 g 
"Chimexane NF" .RTM. by the company Chimex 
Demineralized water 69.09 g 
Solution B 
Apricot almond oil 5 g 
Sunscreen 1 g 
Volatile silicone oil 5 g 
Fragrance 0.3 g 
Solution C 
Mixture of polycarboxyvinyl acids marketed under the name 
0.2 g 
"Carbopol 980" .RTM. by the company Goodrich 
Preserving agents 0.3 g 
Triethanolamine qs pH 6.5 
Demineralized water 12.6 g 
______________________________________ 
Example 10:Day Cream 
According to the procedure described in Example 6, a day cream is prepared 
in the form of a dispersion by mixing together the following parts: 
______________________________________ 
Dispersion A 
Phytanetriol 0.3 g 
Mixture of unsaturated fatty acid mono-glycerides 
2.55 g 
marketed under the name "Myverol 18-99" .RTM. by the 
company Eastman-Kodak 
Lecithin marketed under the name "Epikuron 200" .RTM. by 
0.15 g 
company Lucas Meyer 
Glycerol 3 g 
L-Hydroxyproline 1 g 
D-Panthenol 0.5 g 
Polyphosphonate marketed under the name "Dequest 2046" .RTM. 
0.1 g 
by the company Monsanto 
Monosodium lauroylglutamate marketed under the name 
0.1 g 
"Acylglutamate LS-11" .RTM. by the company Ajinomoto 
Demineralized water 56.85 g 
Solution B 
Jojoba oil 10 g 
Di-t-butylhydroxybenzylidenecamphor marketed under the name 
0.05 g 
"Mexoryl SAD" .RTM. by the company Chimex 
Volatile silicone oil 10 g 
Fragrance 0.3 g 
Solution C 
Mixture of polycarboxyvinyl acids marketed under the name 
0.4 g 
"Carbopol 980" .RTM. by the company Goodrich 
Preserving agents 0.3 g 
Lysine, qs pH 6.5 
Demineralized water 14.4 g 
______________________________________