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'Compose Of Type Bis Uree, Composition Including/Understanding It, Use And Proceeded Of Cosmetic Treatment"

Abstract: The present invention relates to a cosmetic or pharmaceutical  composition  comprising,  in a physiologically acceptable medium, a fatty phase and at least one compound of general formula (I), used to texture the said fatty phase: The invention also relates to the use of such a compound for texturing the said composition, and the said compounds of general formula (I). The invention also relates to a method of cosmetic treatment using the said composition.

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Patent Information

Application #
Filing Date
08 May 2007
Publication Number
47/2007
Publication Type
INA
Invention Field
PHARMACEUTICALS
Status
Email
Parent Application

Applicants

L'OREAL
14 RUE ROYALE 75008 PARIS,FRANCE

Inventors

1. SANDRINE CHODOROWSKI-KIMMES
6, RUE DE LA FORTERELLE 60300 SENLIS, FRANCE

Specification

The present invention relates to compositions, in particular cosmetic or pharmaceutical compositions, having a liquid fatty phase textured with a bis-urea type compound.
To structure oils and give them the desired texture or viscosity, the use of organogelling agents is well known to persons skilled in the art. Organogelling agents are known as being small molecules capable of structuring an organic medium, at low concentration. They can modify the molecular interactions inside the oil and change its physical and/or chemical characteristics. However, the solubilization of these organogelling molecules in an oil or a mixture of oils requires a temperature which is often high, which can generate additional heating costs and in particular be incompatible with the presence of heat-sensitive molecules. Furthermore, the gel thus obtained does not always have the required stability over time: the organogelling agent can precipitate and/or exude over time.
Several classes of organogelling agents are well known to persons skilled in the art, including bis-urea type compounds.
The use of certain bis-ureas as organogelling agent was envisaged in particular in the documents WO 02/47628, JP 2003-064346, JP 08-237942 and JP 10-236981. These documents describe, inter alia, the use of bis-ureas for texturing cosmetic or non-cosmetic media. Many articles also exist which describe organic molecules functionalized by one or more ureas, including in particular the articles by Bouteiller et al., in New J. Chem., 2000, 24, 845-848; Langmuir, 2002, 18, 7218-7222 and J. Am. Chem. Soc. 2003, 125, 13148-13154 describing the use of certain bis-ureas in organic solvents such as toluene, carbon tetrachloride or dodecane for the purpose of gelling the latter.

There may also be mentioned Hanabusa et al. which describes the behaviour of bis-urea molecules as organogelling agent (Langmuir 2003, 19(21), 8622-8624). The article by Hamilton et al. in Tetrahedron Letters, 1998, 39, 7447-7450 describes the ability of certain bis-urea derivatives to behave as gelling agents in certain organic solvents.
However, all the bis-ureas described in these documents are not solubilized at room temperature and/or in all cosmetic oils, and in particular in silicone oils, alone or as a mixture with carbon-based oils.
In the field of texturing of compositions comprising silicone oils or solvents, there may be mentioned in particular JP 2004262856 which describes silicone derivatives of amino acids, in particular valine derivatives substituted with linear or graft PDMS chains capable of gelling the silicone oils without being limited by the other components of the formula. There may also be mentioned JP 2004182692 or JP 2004182693 which describe, as gelling agent, silicone oils, silicone-based bis-amide derivatives which may be cyclic or non-cyclic.
Still in the cosmetics field, there may also be mentioned WO 9736572 which describes a cosmetic composition formed of an oil containing at least one silicone unit and at least one gelling agent composed of a siloxane unit and a group forming hydrogen bonds. There may also be mentioned WO 03/105801 which describes a cosmetic composition comprising a fatty phase at least partially silicone-based and structured with a PDMS containing at least two groups capable of forming an H bond.
There may also be mentioned WO 2004/052963 which describes siloxane polymers comprising groups capable of forming at least 4 hydrogen bonds, and capable of gelling compositions, in particular cosmetic compositions.
Finally, WO 2005/005557 may be noted, which mentions in particular the use, as controlling agent in rheology, of an agent derived from the reaction between one or more polyisocyanates and one or more amines. The amine may contain a heteroatom.
In the non-cosmetic fields, there may be mentioned EP 0406731 which describes bis-urea molecules monofunctionalized by siloxane functional groups. This type of molecule is known in the field of adhesion, the treatment of surfaces and that of textiles, in particular.
However, none of these documents proposes a chemical family comprising compounds capable of texturing, thickening, or even gelling, a variety of cosmetic media such as media consisting solely of carbon-based or hydrocarbon-based oils and/or solvents, or alternatively consisting solely of silicone oils, or alternatively consisting of a mixture of carbon-based and silicone oils.
Thus, the applicant is searching for such compounds which are capable of texturing and/or structuring nonaqueous cosmetic media, whether they comprise silicone and/or non-silicone (carbon-based) cosmetic oils .
It is known that, in order to identify a gelling compound capable of satisfactorily texturing a particular cosmetic composition and capable of being solubilized at room temperature in the oils of the said composition, numerous tests must generally be performed beforehand.
A need therefore exists for texturing (or organogelling) compounds which could be described as universal in so far as they would be effective for texturing, at room temperature, a large number of silicone or non-silicone cosmetic oils, and a mixture thereof.

The aim of the present invention is precisely to provide novel compounds capable of texturing, thickening, or even gelling, cosmetic compositions, regardless of the nature of the oils which they comprise.
A subject of the present invention is therefore a cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, a fatty phase and at least one compound of general formula (I) as defined below, or one of its salts and/or isomers.
Another subject of the invention is the use of such a compound of formula (I) for texturing a cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, a fatty phase.
Another subject of the invention consists of compounds of general formula (la), or one of their salts and/or isomers.
Unexpectedly, it has been discovered that the bis-urea compounds as defined above, and mixtures thereof, were texturing, in particular thickening, or even gelling, agents of choice for satisfying the need for universal organogelling agents expressed above; in particular, the compounds according to the invention are solubilized at room temperature in a large range of carbon-based and/or silicone cosmetic oils and solvents, and can make it possible to modify the viscosity of these oils and solvents even at low concentrations, in particular less than 5% by weight.
The bis-urea type compounds according to the invention correspond to the following general formula (I):


in which:
- A is a group of formula (II):with Rl being a linear or branched Ci to €4 alkyl radical, and * symbolizing the points of attachment of the group A to each of the two nitrogen atoms of the rest of the compound of general formula (I), and
- R and R', which are identical or different, are
chosen from:
- i) the radicals of formula (III): which: L is a single bond or a saturated or unsaturated,
linear, branched and/or cyclic, divalent carbon, in
particular hydrocarbon (alkylene), radical, comprising
1 to 18 carbon atoms, and capable of comprising 1 to 4
a) a saturated or unsaturated, linear, branched and/or cyclic carbon, in particular hydrocarbon (alkyl), radical, comprising 1 to 18 carbon atoms, and capable
of comprising 1 to 8 heteroatoms chosen from N, 0, Si
and S; or alternatively
b) a silicone radical of formula:
(Figure Removed)
n being between 0 and 100, in particular between 1 and 50, even between 2 and 30, preferably between 3 and 20; and R2 to R6 being, independently of each other, linear or branched carbon, in particular hydrocarbon (alkyl), radicals, having 1 to 12, in particular 1 to 6, carbon atoms, and capable of comprising 1 to 4 heteroatoms, in particular 0;
- Rb and Re are, independently of each other, chosen from:
a) saturated or unsaturated, linear, branched and/or
cyclic carbon, in particular hydrocarbon (alkyl),
radicals, comprising 1 to 18 carbon atoms, and capable
of comprising 1 to 4 heteroatoms chosen from N, 0, Si
and S ;
b) the radicals of formula:
(Figure Removed)
c)
n being between 0 and 100, in particular between 1 and 50, even between 2 and 30, preferably between 3 and 20; and R'2 to R'6 being, independently of each other, linear or branched carbon, in particular hydrocarbon (alkyl), radicals, having 1 to 12, in particular 1 to 6, carbon atoms, and capable of comprising 1 to 4 heteroatoms, in particular 0,
and
- ii) saturated or unsaturated, linear, branched and/or
cyclic Ci to Cao alkyl radicals optionally comprising 1
to 3 heteroatoms chosen from 0, S, F and N;
it being understood that at least one of the radicals R
and/or R1 is of formula (III).
It has indeed been observed that this family of bis-urea compounds could allow the texturing of silicone media, in particular when the two radicals R and R' were silicone-based, that is to say of formula (III) . When one of the radicals R or R' is non-silicone-based, that is to say an alkyl radical as defined above, it is possible to texture silicone media with these compounds, but also carbon-based media and media comprising a mixture of silicone and carbon-based oils.
In particular, the group A may be of formula:

(Figure Removed)
Rl and * being as defined above.
In particular, Rl may be a methyl group, which leads to a group A of formula:

in which * are as defined above.In particular, the according to the invention
may be in the form of a mixture linked to the fact that
A may be a mixture of 2, 4-tolylene and 2, 6-tolylene, in particular in (2,4 isomer)/(2,6 isomer) ratios varying from 95/5 to 80/20.
According to the invention, at least one of the radicals R and/or R1 should be of formula (III) :
In this formula, L is preferably a saturated or unsaturated, linear, branched and/or cyclic divalent carbon, in particular hydrocarbon (alkylene) radical comprising 1 to 18 carbon atoms, and capable of comprising 1 to 4 heteroatoms chosen from N, 0 and S. In the radical L, the carbon chain may be interrupted by the heteroatom(s) and/or may comprise a substituent comprising the said heteroatom(s ) .
In particular, L may have the structure -(CH2)n- with n = 1 to 18, in particular 2 to 12, or even 3 to 8 . Preferably, L is chosen from methylene, ethylene, propylene, butylene, and in particular n-butylene or octylene radicals.
The radical L may also be branched, for example of the -CH2-CH (CH3) - type, which leads to the following radical of formula ( III ) :
(Figure Removed)

C
The radical Ra may be a saturated or unsaturated, linear, branched and/or cyclic carbon, in particular hydrocarbon (alkyl), radical comprising 1 to 18 carbon atoms, and capable of comprising 1 to 8 heteroatoms

chosen from N, 0, Si and S. The carbon chain may be interrupted by the heteroatom(s) and/or may comprise a substituent comprising the said heteroatom (s) ; the heteroatoms may in particular form one or more -SiO-(or -OSi-) groups.
Thus, the radical Ra may have the structure -(CH2)n'-CH3 with n1 = 0 to 17, in particular 1 to 12, or even 1 to 6. In particular, Ra may be methyl, ethyl, propyl or butyl.
It may also have the structure - (CH2) x-0- (CH2) z-CH3 or alternatively - (CH2) x-0- (CH2) y-0- (CH2) z-CH3, with x = 1 to 10, preferably 2; y = 1 to 10, preferably 2, and z = 0 to 10, preferably 0 or 1.
The radical Ra may also have the structure -SiR4R5R6 (case where n = 0) , in which R4, R5 and R6 are, independently of each other, preferably, alkyl radicals having 1 to 12 carbon atoms, in particular 1 to 6 carbon atoms; in particular R4 , R5 and/or R6 may be chosen from methyl, ethyl, propyl and butyl. The radical Ra may also be a silicone radical of formula
(Figure Removed)
in which R2 to R6 are, independently of each other, preferably alkyl radicals having 1 to 12 carbon atoms, in particular 1 to 6 carbon atoms; in particular R2 to R6 may be chosen from methyl, ethyl, propyl, butyl; and in particular a radical:

(Figure Removed)
with n = 1 to 100; and still more particularly a radical:
The radicals Rb and Re, which are identical or
different, may be saturated or unsaturated, linear,
branched and/or cyclic carbon, in particular
hydrocarbon (alkyl), radicals comprising 1 to 18 carbon
atoms, and capable of comprising 1 to 8 heteroatoms
chosen from N, 0, Si and S. In these radicals, the
carbon chain may be interrupted by the heteroatom(s)
and/or may comprise a substituent comprising the said
heteroatom(s); the heteroatoms may form in particular
one or more -SiO- (or -OSi-) groups.
Thus they may have the structure -(CH2)m-CH3 with m = 0
to 17, in particular 1 to 12, or even 2 to 5; in
particular Rb and/or Re may be methyl, ethyl, propyl or
butyl.
They may also have the structure -0- (CH2)m' -CHa with
m' = 0 to 5, in particular 1 to 4, and in particular
methoxy or ethoxy.
They may also have the structure -0-(CH2) x-0-(CH2) z-CH3
or -0-(CH2)x-0-(CH2)y-0-(CH2) z-CH3, with x = 1 to 10,
preferably 2; y = 1 to 10, preferably 2, and z = 0 to
10, preferably 0 or 1.
They may also have the structure:
n being between 0 and 100, in particular between 1 and 50, even between 2 and 30, preferably between 3 and 20; and R'2 to R'6 being, independently of each other, preferably alkyl radicals having 1 to 12 carbon atoms, in particular 1 to 6 carbon atoms; in particular R'2 to R'6 may be chosen from methyl, ethyl, propyl and butyl.
When they are of formula (III), the radicals R and/or R' are preferably chosen from the following radicals:
(Table Removed)
Preferably, in these formulae, L is a linear or branched C1-C8 alkylene radical, in particular methylene, ethylene, propylene, butylene, and in particular n-butylene, octylene or of formula -CH2-CH(CH3)-.
In a particular embodiment, R and R', which are identical or different, are both of formula (III).
In another embodiment, one of the radicals R or R1 represents a saturated or unsaturated, linear, branched and/or cyclic Ci to C30 alkyl radical, optionally comprising 1 to 3 heteroatoms chosen from 0, S, F and N.
This is found to be particularly advantageous for conferring a universal character on the compounds of formula (I), that is to say allowing them to texture polar or apolar carbon-based media, linear or cyclic silicone media, mixed oils, that is to say carbon-based, partially silicone-based, and mixtures thereof. The carbon chain may be interrupted by the heteroatom(s) and/or may comprise a substituent comprising the said heteroatom(s), in particular in the form of a carbonyl (-CO-) group, of one or more hydroxyl (-OH) radicals, and/or of an ester radical -COOR", with R" = a linear or branched alkyl radical having 1 to 8 carbon atoms.
Thus, the said radical R or R1 may be a group chosen from:
(Figure Removed)
* having the definition given above.
In a preferred embodiment, R or R' represents a saturated or unsaturated, branched, in particular monobranched, preferably non-cyclic alkyl radical comprising 3 to 16 carbon atoms, in particular 4 to 12, even 4 to 8 carbon atoms, and optionally comprising 1 to 3 heteroatoms chosen from 0, S, F and/or N, preferably 0 and/or N.
In particular, R or R' may be tert-butyl or 2-ethylhexyl radicals or of formula:
The fact that one of the radicals R or R1 is branched allows to obtain a good compatibility of the compounds with a broader range of solvents, as well silicone ones than carbonated ones.
When the compound of formula (I) comprises a radical R which is an alkyl radical, and therefore a radical R1 which is of formula (III), the ratio between nR and nR-is preferably between 5/95 and 95/5, for example between 10/90 and 90/10, in particular between 40/60 and 85/15, in particular between 50/50 and 80/20, or even between 60/40 and 75/25;
nR being the number of moles of amine NH2-R and nR. being the number of moles of amine NHj-R' used to prepare the compound of formula (I).
The compounds according to the invention may be provided in the form of salts and/or isomers of compounds of formula (I).
Preferably, the compounds according to the invention have a molecular mass lower than 5000, in particular lower than 3000, preferably ranging between 300 and 5000, even between 400 and 3000; this makes it possible to differentiate them from silicone polymers, specially PDMS polymers, carrying urea functions, and which can be used, in particular in mixture, in gelling systems for silicone oils. The advantage related to the use of low molecular weight molecules lies in their best compatibility and solubility, with respect to carbonated and silicone oils, in particular polar oils; together with their facility of being formulated, compared to polymers.
Preferably, the compounds of formula (I) according to the invention may be chosen, alone or as a mixture, from the following compounds, and their salts and
isomers:
(Figure Removed)
In general, the compounds of general formula (I) according to the invention may be prepared by the reaction between at least one diisocyanate of formula OCN-A-NCO, and at least one primary amine R-NH2, with A and R as defined above.

When the radicals R and R1 are different, the diisocyanate is reacted with a mixture of at least two primary amines: R-NH2 + R'-NH2.
The diisocyanate OCN-A-NCO may be provided in the form of a mixture of position isomers of the substituent RI on the group A, in particular in the ratios 95/5 or 80/20 (2,4 TDI isomer)/(2,6 TDI isomer).
Preferably, the amine(s) used are in a molar ratio of 2 to 3 equivalents, in particular 2.1 to 2.5, or even 2.2 equivalents per equivalent of diisocyanate(s). The general reaction scheme is the following:
It is obviously possible to use a mixture of primary
amines, and in particular two primary amines.
In the particular case where two primary amines are
used for the reaction, the nR/nR> molar ratio may be
between 5/95 and 95/5; this ratio obviously depends on
the chemical nature of each of the amines, and will be
easily determined by persons skilled in the art on the
basis of their knowledge.
This is particularly true when R and R1 are both of
formula (III). When R is an alkyl radical, and
therefore R' of formula (III), the said nR/nR> molar
ratio may be between 5/95 and 95/5, for example between
15/85 and 90/10, in particular between 40/60 and 85/15,
in particular between 50/50 and 80/20;
nR being the number of moles of amine NH2-R and nRi
being the number of moles of amine NH2-R' used to
prepare the compound of formula (I).
There may be mentioned in particular the mixture of
primary amines marketed by Clariant under the name
'aminopropylbis(trimethylsiloxy)silane', which corresponds
to a mixture comprising 80 to 99.5% by weight, in
particular 90 to 99% by weight of a first primary amine

of formula NH2- (CH2) 3-Si [OSi (CH3) 3] 2Me and 0.5 to 20% by
weight, in particular 1 to 10% by weight of a second
primary amine of formula
NH2-CH2-CH (CH3) -Si [OSi (CH3) 3] 2Me .
The reaction is generally carried out under an inert atmosphere, for example under argon, in an anhydrous medium with, for example, a reaction medium temperature which is maintained between 15°C and 40°C. The diisocyanate may be dissolved in an anhydrous solvent such as tetrahydrofuran, 2-methyltetrahydro-furan, N-methylpyrrolidone, butyl acetate or alternatively methyl ethyl ketone at a concentration which may range from 1 to 30% by weight, preferably from 2 to 20%, or even 4 to 10% by weight. A solution containing the amine(s) may be prepared in the same solvent as the diisocyanate, at a concentration which may range from 0.1 to 99.9% by weight. The temperature of the reaction medium should preferably not exceed 40°C and the concentration of the amine as well as the rate of addition of the solution containing the amine are preferably adjusted accordingly.
The reaction medium may be kept stirring, for example, for 30 minutes to 12 hours. The progress of the reaction may be monitored by infrared spectrometry (in particular by observing the disappearance of the NCO band between 2250 and 2280 cm"1) .
At the end of the reaction, the reaction medium may be poured into a large quantity of acidic water (in particular pH 3-4 with HC1) . A generally white precipitate is then obtained which is filtered, washed, for example, several times in particular with water, and dried under reduced pressure, in particular under vacuum or freeze-dried.
The precipitate corresponds to the expected compound of formula (I), or to the expected mixture of compounds of formula (I), and may be characterized by NMR (1H and/or 13C) spectrometry and/or by mass-coupled HPLC.

The compound may be used as it is for texturing the oily medium considered.
Indeed, the compounds of formula (I), alone or as a mixture in any proportions, may be solubilized in a wide variety of oils and are therefore found to be effective for texturing the oils or mixture of oils considered, by conferring the desired physical and/or chemical properties on them.
The compound of formula (I) is advantageously soluble at a temperature of less than or equal to 50°C, or even less than or equal to 30°C, and in particular at room temperature (25°C), in the liquid fatty phases customarily used in the cosmetics field, and therefore in the fatty phase to be textured.
The compound according to the invention therefore finds a very special application in the customary cosmetic or pharmaceutical compositions, in particular as texturing agent, thickening agent, or even gelling agent, for the liquid fatty phase contained in the said composition.
The said compound of formula (I), alone or as a mixture, may be present in the said compositions in an effective quantity, that is to say in a quantity necessary and sufficient to obtain texturing of the liquid fatty phase considered in the composition according to the invention.
The expression "textured liquid fatty phase" is understood to mean that the said fatty phase assumes the state of a gel or of a thickened liquid. It can flow under its own weight. It can undergo deformation at constant volume if a stress is exerted. This texturing results in particular in an increase in viscosity due in particular to the introduction of at least one compound of formula (I).

Thus, the compositions according to the invention may comprise from 0.01 to 20% by weight, in particular from 0.05 to 15% by weight, or even from 0.1 to 10% by weight, even better from 1 to 8% by weight, and better still from 2 to 5% by weight, of compound(s) of formula (I) relative to the total weight of the composition. The effective quantity of compound(s) of formula (I) may represent in particular from 0.01 to 20% by weight, in particular from 0.05 to 15% by weight, or even from 0.1 to 10% by weight, even better from 1 to 8% by weight, and better still from 2 to 5% by weight, relative to the weight of the said liquid fatty phase. It is clear that this effective quantity can vary significantly, inter alia, according to the nature of the bis-urea derivative compound, whether it is used in the pure state or as a mixture with other bis-urea derivatives of formula (I), and the nature of the liquid fatty phase.
The cosmetic or pharmaceutical compositions according to the invention additionally comprise a physiologically acceptable, in particular cosmetically acceptable, medium, that is to say compatible with keratin materials such as the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows, the scalp and the nails.
The composition according to the invention comprises, in a physiologically acceptable medium, at least one liquid fatty phase capable of being textured. The expression liquid fatty phase is understood to mean, for the purpose of the invention, a fatty phase that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg), composed of one or more lipophilic compounds chosen from silicone oils, carbon-based oils and carbon-based solvents, as defined below, which are liquid at room temperature. The liquid fatty phase may represent 0.1 to 90% by weight of the composition, in particular from 0.5 to 35% by weight,

in particular from 1 to 30% by weight, even from 2 to 20% by weight, better still 3 to 15% by weight, of the total weight of the composition.
The liquid fatty phase may therefore comprise an oil and/or a solvent which may be carbon-based, in particular hydrocarbon-based, and/or fluorinated; this oil or solvent may be chosen in particular from: I/ esters of monocarboxylic acids with monoalcohols and polyalcohols; advantageously, the said ester corresponds to the following formula: R13.-CO-0-R'2 where:
R'i represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylene double bonds, optionally substituted and whose hydrocarbon chain may be interrupted by one or more heteroatoms chosen from N and 0 and/or one or more carbonyl functional groups, and
R*2 represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably of 3 to 30 carbon atoms and even better of 3 to 20 carbon atoms, optionally comprising one or more ethylene double bonds, optionally substituted and whose hydrocarbon chain may be interrupted by one or more heteroatoms chosen from N and 0 and/or one or more carbonyl functional groups. The expression "optionally substituted" is understood to mean that R'i and/or R*2 may carry one or more substituents chosen, for example, from groups comprising one or more heteroatoms chosen from 0 and/or N, such as amino, amine, alkoxy, hydroxyl. Examples of R'i groups are those derived from preferably higher fatty acids chosen from the group consisting of acetic, propionic, butyric, caproic, caprylic, pelargonic, capric, undecanoic, lauric, myristic, palmitic, stearic, isostearic, arachidic, behenic, oleic, linolenic, linoleic, oleostearic, arachidonic and erucic acids, and mixtures thereof.

Preferably, R'i is an unsubstituted branched alkyl group of 4 to 14 carbon atoms, preferably of 8 to 10 carbon atoms and R2 is an unsubstituted branched alkyl group of 5 to 15 carbon atoms, preferably of 9 to 11 carbon atoms.
There may preferably be mentioned in particular Ce-C48 esters, optionally incorporating into their hydrocarbon chain one or more heteroatoms from N and 0 and/or one or more carbonyl functional groups; and more particularly purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, and heptanoates, octanoates, decanoates or ricinoleates of alcohols or polyalcohols, for example fatty alcohols, and isopropyl N-lauroylsarcosinate (in particular Eldew-205SL from Ajinomoto).
2/ fluorinated oils such as perfluoropolyethers, perfluoroalkanes such as perfluorodecalin, perfluoroadamantanes, monoesters, diesters and triesters of perfluoroalkyl phosphates and fluorinated ester oils.
3/ hydrocarbon-based vegetable oils with a high content of triglycerides consisting of fatty acid esters of glycerol in which the fatty acids may have varied chain lengths, it being possible for the latter to be saturated or unsaturated, linear or branched; these oils are in particular wheatgerm, maize, sunflower, shea, castor, sweet almond, macadamia, apricot, soybean, rapeseed, cottonseed, lucern, poppy seed, pumpkin seed, sesame, gourd, avocado, hazelnut, grape seed or blackcurrant seed, evening primrose, millet, barley, quinoa, olive, rye, safflower, candlenut, passion flower and musk rose oils; or alternatively triglycerides of caprylic/capric acids such as those sold by the company Stearinerie Dubois or

those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel,
4/ C6 to C4o ethers.
5/ Cs-C32 fatty acids, such as oleic, linoleic or linolenic acid.
6/ so-called "fatty" alcohols, and in particular C6-C32 monoalcohols such as oleyl alcohol and octyldodecanol .
If linear or branched hydrocarbons or f luorocarbons of synthetic or mineral origin, such as paraffin oils (such as Cg-Cie isoparaf f ins, isododecane, isohexadecane) and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutenes such as squalane, and mixtures thereof.
There may be mentioned in particular linear or branched, in particular volatile, Ce-Cw alkanes .
8/ bifunctional oils, comprising two functional groups chosen from esters and/or amides and comprising from 6 to 30 carbon atoms, in particular 8 to 28 carbon atoms, even better from 10 to 24 carbons, and 4 heteroatoms chosen from 0 and N; preferably the amide and ester functional groups being in the chain.
9/ and mixtures thereof.
The liquid fatty phase may also comprise one or more silicone oils, which may be volatile or non-volatile. For the purposes of the invention, the volatile oils have at room temperature (25°C) and atmospheric pressure (760 mmHg) a vapour pressure ranging from 0.02 mmHg to 300 mmHg (2.66 Pa to 40 000 Pa) and even better ranging from 0.1 to 90 mmHg (13 Pa to 12 000 Pa) . The non-volatile oils then correspond to a vapour pressure of less than 0.02 mmHg (2.66 Pa).

The silicone oil(s) may be chosen from:
- linear or cyclic volatile silicone oils such as
linear or cyclic polydimethylsiloxanes (PDMS) having
from 3 to 7 silicon atoms. By way of example of such
volatile oils, there may be mentioned compounds such as
octyltrimethicone, hexyltrimethicone, decamethylcyclo-
pentasiloxane (or D5), octamethylcyclotetrasiloxane (or
D4), dodecamethylcyclohexasiloxane (or D6), decamethyl-
tetrasiloxane (or L4), in particular KF 96 A from Shin
Etsu, volatile PDMSs (polydimethylsiloxane) and in
particular DC 200 (1.5 cSt) from Dow Corning, PDMS
DC 200 (2 cSt) from Dow Corning, PDMS DC 200 (5 cSt)
from Dow Corning, PDMS DC 200 (3 cSt) from Dow Corning,
and/or mixtures thereof.
There may also be mentioned heptamethyloctyltri-siloxane, dodecamethylpentasiloxane, polymethylcetyl-dimethylsiloxane and/or mixtures thereof. The volatile silicone oil may also be chosen from the group comprising fluorinated silicone oils such as silicones having alkyl and perfluoroalkyl groups, silicones having oxyethylenated/oxypropylenated (OE/PP) side groups and having perfluorinated groups, silicones having perfluorinated or polyfluorinated side groups and having glycerolated side groups, and perfluoroalkylmethylphenylsiloxanes.
- non-volatile silicone oils such as polydimethyl
siloxanes (PDMS), polyalkylmethylsiloxanes, dimethicone
copolyols, alkylmethicone copolyols, cetyldimethicone,
silicones having alkylglyceryl ether groups, silicones
having amine side groups and dilauroyltrimethylol
propane siloxysilicate. The alkyl groups of these oils
have in particular from 2 to 24 carbon atoms.
The non-volatile silicone oils which can be used may be in particular linear, non-volatile polydimethylsiloxanes (PDMS) which are liquid at room temperature; the polydimethylsiloxanes containing alkyl, alkoxy or phenyl groups which are pendant and/or at the silicone chain end, groups each having from 2 to 24 carbon

atoms; phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates, cetyldimethicone, silicones having alkylglyceryl ether groups, silicones having amine side groups, fluorinated silicones having pendant group(s) or groups (s) at the chain end having from 1 to 12 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, dimethiconols and/or mixtures thereof.
- and mixtures thereof.
The liquid fatty phase to be textured may comprise a mixture of carbon-based and silicone oils which may therefore be advantageously textured by the compounds of formula (I) according to the invention.
Preferably, the compositions according to the invention comprise a liquid fatty phase which comprises at least one lipophilic compound chosen from:
- C6-C32, preferably C8-C28 even better C12-C26,
monoalcohols, and preferably octyldodecanol;
- C6-C32, preferably even better, branched
alkanes, and preferably isododecane or the parleam of
formula -(CH2-CH(CH3) ) n-, n being an integer varying
from 4 to 8;
- Ci3-C48, preferably Ci8-C4o, even better C20-C32, linear
alkanes;
- bifunctional oils, comprising two functional groups
chosen from esters and/or amides and comprising from 6
to 30 carbon atoms, in particular 8 to 28 carbon atoms,
even better 10 to 24 carbon atoms, and 4 heteroatoms
chosen from 0 and N; preferably the amide and ester
functional groups being in the chain; in particular the
bifunctional oil may be the isopropyl N-
lauroylsarcosinate of the following formula:
-2.7 -

and more particularly that marketed under the name Eldew SL-205® from Ajinomoto;
- C8-C48 esters, optionally incorporating into their
hydrocarbon chain one or more heteroatoms from N and 0
and/or one or more carbonyl functional groups; and more
particularly purcellin oil (cetostearyl octanoate),
isononyl isononanoate, isopropyl myristate, 2-
ethylhexyl palmitate, 2-octyldodecyl stearate, 2-
octyldodecyl erucate, isostearyl isostearate, and
heptanoates, octanoates, decanoates or ricinoleates of
alcohols or polyalcohols, for example of fatty
alcohols;
- volatile or non-volatile silicone oils, and in
particular linear or cyclic polydimethylsiloxanes
(PDMS) having from 3 to 7 silicon atoms such as
decamethylcyclopentasiloxane, octamethylcyclotetra-
siloxane, dodecamethylcyclohexasiloxane and decamethyl-
tetrasiloxane; and phenylated silicones such as phenyl
trimethicones;
- and mixtures thereof.
These preferred lipophilic compounds may represent 20 to 100%, or even from 40 to 99%, in particular from 60 to 95% by weight of the total liquid fatty phase.
Indeed, the inventors observed that combinations of at least one bis-urea type compound of formula (I) with at least one lipophilic compound as defined above give particularly satisfactory results for the purposes of the invention.
The compositions according to the invention may additionally comprise at least one solid fatty substance which may be chosen from waxes and/or pasty

compounds. More particularly, the compositions according to the invention may comprise from 0.1% to 40% by weight, in particular from 0.1% to 30% by weight, and more particularly from 0.5% to 25% by weight of solid fatty substances relative to the total weight of the composition.
Among the pasty fatty substances, there may be mentioned silicone gums.
The expression wax for the purposes of the present invention is understood to mean a lipophilic compound which is solid at room temperature (25°C) and which has a reversible solid/liquid change of state, and which has a melting point greater than or equal to 30°C, even better greater than 45°C, and which may range up to 120°C. The waxes may be of plant, animal, mineral or synthetic origin; they may be carbon-based, in particular hydrocarbon-based, fluorinated and/or silicone-based. There may be mentioned in particular beeswax, carnauba wax, Candelilla wax, paraffin, microcrystalline waxes, ceresin, ozokerite; synthetic waxes such as polyethylene or Fischer-Tropsch waxes, silicone waxes, such as alkyl or alkoxydimethicone having from 16 to 45 carbon atoms; and mixtures thereof.
The composition may comprise an aqueous phase which may essentially consist of water or which may comprise a mixture of water and a water-miscible organic solvent, chosen in particular from monoalcohols having from 1 to 5 carbon atoms such as ethanol or isopropanol; glycols having from 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1,3-butylene glycol, dipropylene glycol, C3~C4 ketones; and C2-C4 aldehydes. The aqueous phase may be present in an amount of 1% to 95% by weight, in particular of 3% to 80% by weight, and in particular of 5% to 60% by weight, relative to the total weight of the composition.
The composition according to the invention may also be free of water (0%).

The composition according to the invention may comprise at least one organic or inorganic colourant, which may be chosen from lipophilic dyes, hydrophilic dyes, pigments, pearlescent agents, materials having a specific optical effect, and mixtures thereof. This colouring matter may be present in an amount of 0.01 to 50% by weight relative to the total weight of the composition, in particular of 0.5 to 40% and more particularly of 1 to 25%, and in particular of 5 to 20% by weight relative to the total weight of the composition.
The composition according to the invention may additionally comprise one or more fillers, in particular in an amount ranging from 0.01% to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.05% to 30% by weight.
The composition according to the invention may also comprise ingredients commonly used in the cosmetics field, such as vitamins, thickeners, gelling agents, trace elements, emollients, sequestrants, perfumes, alkalifying or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, antihair-loss agents, antidandruff agents, propellants, ceramides, polymers, cosmetic active agents, or mixtures thereof. Of course, persons skilled in the art will be careful to choose this or these optional additional compounds, and/or their quantity, such that the advantageous properties of the composition according to the invention are not, or not substantially, impaired by the addition envisaged.
The composition according to the invention may be provided in particular in the form of a suspension, a dispersion, a solution, in particular which is organic, a gel, an emulsion, in particular an oil-in-water (0/W) or water-in-oil (W/0), or a multiple (W/O/W or

polyol/0/W or 0/W/O) emulsion, in the form of a cream, a paste, a mousse, a dispersion of vesicles, in particular of ionic or non-ionic lipids, a two-phase or multiphase lotion, a spray, a powder, a stick or a baton.
Persons skilled in the art will be able to choose the appropriate galenic form, and its method of preparation, on the basis of their general knowledge, taking into account, on the one hand, the nature of the constituents used, in particular of their solubility in the carrier, and, on the other hand, thp application
envisaged for the composition. Thus, composition shows surprising results and is a synergistic composition.
The composition according to the invention may be a make-up composition, in particular a product for the complexion such as a foundation, a blusher or an eye shadow; a product for the lips such as a lipstick or a care product for the lips; a concealer product; a blusher, a mascara, an eyeliner; a make-up product for the eyebrows, a lip pencil or an eye pencil; a product for the nails such as a nail varnish or a care product for the nails; a make-up product for the body or the hair (mascara or lacquer for the hair).
The composition according to the invention may be a composition for protecting or caring for the skin of the face, the neck, the hands or the body, in particular an anti-wrinkle, anti-fatigue or anti-ageing composition, which makes it possible to make the skin radiant, a moisturizing or treatment composition; an anti-sun or after-sun or artificial tanning composition.
The composition according to the invention may also be a hair product, in particular for hair dyeing, care and hygiene, hair-styling, holding the hairstyle or shaping the hair. The hair compositions are preferably shampoos, gels, hair setting lotions, blow drying lotions, hair care or hygiene compositions or fixing and hair-styling compositions such as lacquers, gels or sprays.

The composition according to the invention finds a very special application in the field of make-up compositions, in particular in foundations, mascaras and lipsticks.
The composition according to the invention may be manufactured by known processes, generally used in the cosmetics or pharmaceutical field.
The subject of the invention is also a method of cosmetic treatment, in particular for making-up, cleansing, sun protection, shaping, dyeing and/or caring for keratin materials, in particular the skin of the body or of the face, the lips, the nails, the eyebrows, the hair and/or the eyelashes, comprising the application to the said materials of a cosmetic composition as defined above.
The invention is illustrated in greater detail in the following examples given by way of illustration.
General Method of Preparation
Various preparations of bis-urea type compounds were
made, comprising at least one silicone unit and at
least one non-silicone unit.
The various mixtures are obtained in one step, the
general synthesis scheme being represented below:

(Figure Removed)

Various mixtures are prepared according to the ratio of HI (number of moles of 2-ethylhexylamine) over r\2 (number of moles of 3-aminopropylmethylbis (trimethyl-siloxy) silane) and the percentage of toluene diisocyanate (TDI) isomer (95/5 or 80/20) .
These mixtures were prepared according to the same procedure as described below. The specific quantities selected for each starting raw material are specified in the examples .
Tolylene diisocyanate dissolved in anhydrous THF is mixed with 2.2 equivalents of amine dissolved in anhydrous THF.
The reaction is carried out under an inert atmosphere (argon) in anhydrous medium with a temperature of the reaction medium which is maintained between 15°C and 40°C.
In parallel, a solution of amine (Y) is prepared in THF. Since the temperature of the reaction medium should preferably not exceed 40°C, the amine concentration and the rate of addition of the amine solution (Y) are adjusted accordingly. The reaction medium is kept stirred while monitoring the progress of the reaction by infrared spectrometry (disappearance of the NCO band between 2250 and 2280 cm"1) . Once the diisocyanate has completely reacted, the reaction mixture is added to acidified water (pH 3) with hydrochloric acid, the precipitate obtained is filtered, washed several times with water and finally dried under vacuum or freeze-dried. A white powder is obtained and used as it is after analysis (mass-coupled HPLC).
Examples 1 and 2 (R = R' = 3-aminopropylmethylbis(trimethylsiloxy) silane)
In these examples, the mixture finally obtained is characterized by mass-coupled HPLC and by 1R NMR.
Example 1
Starting raw materials:
- TDI: 95/5 as (2,4 isomer)/(2,6 isomer); m = 5 g
(28.71 mmol)
- HI = 0
- n2 = 63.16 mmol (2.2 eq.) that is m = 17.6 g of 3-
aminopropylmethylbis(trimethylsiloxy)silane, with a
beta isomer level of less than 1%.
Example 2
Starting raw materials:
- TDI: 80/20 as (2,4 isomer)/(2,6 isomer)
- HI = 0
- n2 = 63.16 mmol (2.2 eq.) that is m = 17.6 g of 3-
aminopropylmethylbis(trimethylsiloxy)silane, with a
beta isomer level of less than 1%.
The mixture finally obtained in Examples 1 and 2 comprises the following bis-ureas:

(Figure Removed)

Examples 3 and 4 (R = 2-ethylhexyl and R' = 3-amino-propylmethylbis(trimethylsiloxy)silane)
In these examples, the mixture finally obtained is characterized by mass-coupled HPLC and 1H NMR.
Example 3
Starting raw materials:
- TDI: 95/5 as (2,4 isomer)/(2,6 isomer); m = 0.317 g
(1.82 mmol)
- HI = 2 mmol (1.1 eq.) that is m = 0.259 g of 2-ethyl-
hexylamine;

- n2 = 2 mmol (1.1 eq.) that is m = 0.560 g of 3-amino-
propylmethylbis(trimethylsiloxy)silane, with a beta
isomer level of less than 1%.
Therefore nR/n'R = 1.
Example 4
Starting raw materials:
- TDI: 95/5 as (2,4 isomer)/(2,6 isomer); m = 50 g
(0.29 mol)
- m = 0.44 mol (1.5 eq.) that is m = 56.87 g of 2-
ethylhexylamine;
- n2 = 0.19 mol (0.66 eq.) that is m = 53.13 g of 3-
aminopropylmethylbis(trimethylsiloxy) silane, with a
beta isomer level of less than 1%.
Therefore nR/n'R = 2.23 (69/31).
The mixture finally obtained in Examples 3 and 4 comprises the following bis-ureas:
(Figure Removed)

The molecular weight of the compounds having one silicone moiety is 582, and the one of compounds having two silicone moiety (one on each side) is 732.
Example 5
The mixtures prepared in Examples 1 to 4 above, and
comparative compounds A and B, are tested in an amount
of 1% by weight in 100 ml of various lipophilic
compounds, for their thickening or texturing
properties, at room temperature (25°C, 1 atm.}•
The lipophilic compounds chosen are: isododecane,
parleam, octyldodecanol, isononyl isononanoate, phenyl
trimethicone, volatile silicone D5 and volatile
silicone L4 .
The thickening/texturing properties are judged satisfactory if the mixture of compounds is solubilized at room temperature in the said lipophilic compound, and if an increase in the viscosity of the said lipophilic compound is observed. Advantageously, the solution obtained is generally clear, transparent and homogeneous.
The comparative mixtures A and B are the following:
- Comparative A:
starting raw materials:
- TDI: 95/5 as (2,4 isomer)/(2,6 isomer)
- ni = 2.2 eq. (2-ethylhexylamine) and n2 = 0
- Comparative B:
starting raw materials:
- TDI: 95/5 as (2,4 isomer)/(2,6 isomer)
- ni = 1.6 eq. of 2-ethylhexylamine
- n2 = 0
- (Table Removed)
n3 It is observed that the compounds of Examples 1 to 4, in accordance with the invention, make it possible to gel a wide range of silicone solvents (partially silicone-based such as phenyltrimethicone, purely silicone-based and cyclic such as D5 and purely silicone-based and linear such as L4) and to give clear and homogeneous solutions in most cases.
Moreover, the compounds of Examples 3 and 4, in which a radical R is carbon-based (alkyl), and more particularly the compound of Example 4, make it possible to texture/thicken a wide range of silicone solvents (linear and cyclic), but also polar or apolar carbon-based oils and solvents, while giving clear and homogeneous solutions in most cases.
This is however not the case with the compounds of Examples 1 and 2, purely silicone-based; these compounds make it possible to texture/thicken the carbon-based oils envisaged, but the solutions obtained are not always clear (problem of deposit or phase separation).
Example 6
In an identical manner to Example 1, the following
compound is prepared:
Starting raw materials:
- TDI: 95/5 as (2,4 isomer)7(2,6 isomer); m = 10 g
(57.41 mmol)
- HI = 0
- n2 = 126.3 mmol (2.2 eq.) that is m = 35.23 g of 3-
aminopropylmethylbis(trimethylsiloxy)silane, with a
beta isomer level of less than 10% (assayed at 7%) ;
that is to say a mixture of amine of formula
NH2-CH2-CH2-CH2-Si[OSi(CH3)3]2Me and of amine of formula:
NH2-CH2-CH(CH3)-Si[OSi(CH3)3]2Me (called beta isomer),
the second being present in a quantity of less than 10%
by weight.
The mixture finally obtained behaves like that of Example 1, which contained a maximum of 1% by weight of beta isomer: it is solubilized and increases the viscosity of silicone oils, and in particular of D5 and L4.
Example 7
In an identical manner to Example 1, the following
compound is prepared:
- TDI: 95/5 as (2,4 isomer)/(2,6 isomer)
- n1= 0
- n2 = 2.2 eq. of bis-trimethylsilanylmethylamine
(primary amine containing silicon).
The mixture obtained is insoluble in all the solvents mentioned in Example 5. This shows that it is not sufficient to add a silicon unit to the structure of the organogelling compound to obtain a compound capable of gelling silicone-based and/or carbon-based solvents, and even less both carbon-based and silicone-based solvents.
Example 8: Hair-styling gel
A hair-styling gel composition is prepared comprising (% by weight):

3% 5% 5%
qs 100% is obtained
- compound of Example 4
- isoeicosane
- tridecyl trimellitate
- isododecane
A very thick, crystal
gel
haircare qualities.
product with completely

which is a satisfactory



Example 9: Make-up foundation
A make-up foundation is prepared comprising
weight) :
- Compound of the example 1 1,5%
- Cyclopentasiloxane 65%
- titanium dioxide 7%
- Glycerin 3%
- Nylon-12 2,5%
- iron Oxides 2,5%
- bis-PEG/PPG-14/14 dimethicone 1,8%
- magnesium sulfate 0,7%
- Isostearyl diglyceryl succinate 0,6%
- preservatives qs
- Water qsp 100%

CLAIMS
1. Cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, a fatty phase and at least one compound of general formula (I), or one of its salts and/or isomers:
- A is a group of formula (II):with Rl being a linear or branched C4 alkyl radical, and * symbolizing the points of attachment of the group A to each of the two nitrogen atoms of the rest of the compound of general formula (I), and
- R and R', which are identical or different, are
chosen from:
- i) the radicals of formula (III):L is a single bond or a saturated or unsaturated,linear, branched and/or cyclic, divalent carbon, inparticular hydrocarbon, radical, comprising 1 to 18 carbon atoms, and capable of comprising 1 to 4 heteroatoms chosen from N, 0 and S; - Ra is:a saturated or unsaturated, linear, branched and/or
cyclic carbon, in particular hydrocarbon, radical,
comprising 1 to 18 carbon atoms, and capable of
comprising 1 to 8 heteroatoms chosen from N, 0, Si and
S; or alternativelya silicone radical of formula: n being between 0 and 100; and R2 to R6 being, independently of each other, linearor branched carbon, in particular hydrocarbon, radicals, having 1 to 12 carbon atoms, and capable ofcomprising 1 to 4 heteroatoms;- Rb and Re are, independently of each other, chosenfrom:saturated or unsaturated, linear, branched and/or
cyclic carbon, in particular hydrocarbon, radicals,
comprising 1 to 18 carbon atoms, and capable of
comprising 1 to 4 heteroatoms chosen from N, 0, Si and
S;the radicals of formula:
n being between 0 and 100;
and R'2 to R'6 being, independently of each other,
linear or branched carbon, in particular hydrocarbon,
radicals, having 1 to 12 carbon atoms, and capable of
comprising 1 to 4 heteroatoms,
and
- ii) saturated or unsaturated, linear, branched and/or
cyclic Ci to CSQ alkyl radicals optionally comprising 1
to 3 heteroatoms chosen from 0, S, F and N;
it being understood that at least one of the radicals R
and/or R1 is of formula (III) .
2. Composition according to Claim 1, in which the group A is of formula:

(Figure Removed)
Rl and * being as defined in Claim 1.
3. Composition according to one of the preceding claims, in which the group A is of formula:

(Figure Removed)
4. Composition according to one of the preceding
claims, in which L has the structure -(CH2)n- with
n = 1 to 18; or alternatively L has the structure
-CH2-CH(CH3) -.5. Composition according to one of the preceding claims, in which the radical Ra is chosen from the radicals:
- having the structure -(CH2)n'-CH3 with n1 = 0 to 17;
or alternatively
- having the structure -(CH2) x-0-(CH2) z-CH3 or
alternatively - (CH2) x-0- (CH2) y-0- (CH2) z-CH3, with x = 1
to 10,y = 1 to 10, and z = 0 to 10; or alternatively
- having the structure -SiR4R5R6, in which R4, R5 and R6
are, independently of each other, alkyl radicals having
1 to 12 carbon atoms; or alternatively
- of formula:

in which R2 to R6 are, independently of each other, alkyl radicals having 1 to 12 carbon atoms.
6. Composition according to one of the preceding claims, in which Ra has the structure:with n = 1 to 100; and still more particularly a
radical:

7. Composition according to one of the preceding claims, in which the radicals Rb and Re, which are identical or different, are chosen from the radicals:
- having the structure (CH2)m-CH3 with m = 0 to 17; or
alternatively
- having the structure -0-(CH2)m'-CH3 with m1 = 0 to 5;
or alternatively
- having the structure -0-(CH2) x-0-(CH2) z-CH3 or
-0- (CH2)x-0-(CH2)y-0-(CH2) z-CH3, with x = 1 to 10, y = 1
to 10, and z = 0 to 10; or alternatively
- having the structure: n being between 0 and 100;
and R'2 to R'6 being, independently of each other,
preferably alkyl radicals having 1 to 12 carbon atoms.
8 . Composition according to one of the preceding claims, in which at least one of the radicals R and/or R' is chosen from the following radicals:
(Table Removed)
in which x = 1 to 10 and y = 1 to 10; and L being as defined above.
9. Composition according to Claim 8, in which L is a
linear or branched alkylene radical, or of
formula -CH2-CH (CH3) - .
10. Composition according to one of the preceding
claims, in which R and R" , which are identical or
different, are both of formula (III).
11. Composition according to one of Claims 1 to 9, in which one of the radicals R or R' represents a saturated or unsaturated, linear, branched and/or cyclic Ci to Cao alkyl radical, optionally comprising 1 to 3 heteroatoms chosen from 0, S, F and N.
12. Composition according to Claim 11, in which the radical R or R' is chosen from:
(Figure Removed)
* having the definition given above.
13. Composition according to one of Claims I to 9, in
which the radical R or R1 represents a saturated or
unsaturated, branched, in particular monobranched,
preferably non-cyclic alkyl radical comprising 3 to 16
carbon atoms, and optionally comprising 1 to 3
heteroatoms chosen from 0, S, F and/or N.
14. Composition according to Claim 13, in which the radical R or R' is chosen from the radicals tert-butyl and 2-ethylhexyl or of formula:
(Figure Removed)
15. Composition according to one of the preceding claims, in which the compound of formula (I) is chosen, alone or as a mixture, from the following compounds, and their salts and isomers:
(Figure-Removed)
16. Composition according to one of the preceding
claims, comprising from 0.01 to 20% by weight, in
particular from 0.05 to 15% by weight, or even from 0.1
to 10% by weight, even better from 1 to 8% by weight,
and better still from 2 to 5% by weight, of compound(s)
of formula (I) relative to the total weight of the
composition.
17. Composition according to one of the preceding
claims, in which the liquid fatty phase comprises one
or more lipophilic compounds chosen from silicone oils,
carbon-based oils and carbon-based solvents, which are
liquid at room temperature.
18. Composition according to one of the preceding
claims, in which the liquid fatty phase comprises at
least one lipophilic compound chosen from, alone or as
a mixture:
I/ esters of monocarboxylic acids with monoalcohols and polyalcohols; in particular of formula R'l-CO-O-R^ where:
R'i represents a linear or branched alkyl radical of 1 to 40 carbon atoms, optionally comprising one or more ethylene double bonds, optionally substituted and whose hydrocarbon chain may be interrupted by one or more heteroatoms chosen from N and 0 and/or one or more carbonyl functional groups, and
R'2 represents a linear or branched alkyl radical of 1
to 40 carbon atoms, optionally comprising one or more
ethylene double bonds, optionally substituted and whose
hydrocarbon chain may be interrupted by one or more
heteroatoms chosen from N and 0 and/or one or more
carbonyl functional groups;
2/ fluorinated oils;
3/ hydrocarbon-based vegetable oils with a high
content of triglycerides consisting of fatty acid
esters of glycerol in which the fatty acids may have
varied chain lengths, it being possible for the latter
to be saturated or unsaturated, linear or branched;
4/ C6 to C40 ethers,
5/ C8-C32 fatty acids,
6/ so-called "fatty" alcohols, and in particular
C6-C32 monoalcohols;
7/ linear or branched hydrocarbons or fluorocarbons
of synthetic or mineral origin;
8/ bifunctional oils, comprising two functional
groups chosen from esters and/or amides and comprising
from 6 to 30 carbon atoms, in particular 8 to 28 carbon
atoms, even better from 10 to 24 carbons, and 4
heteroatoms chosen from 0 and N; preferably the amide
and ester functional groups being in the chain;
9/ linear or cyclic, optionally fluorinated, volatile
or non-volatile silicone oils.
19. Composition according to one of the preceding claims, in which the liquid fatty phase comprises at least one lipophilic compound chosen from, alone or as a mixture:
- C8-C48 esters, optionally incorporating into their hydrocarbon chain one or more heteroatoms from N and 0 and/or one or more carbonyl functional groups; and more particularly purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, and heptanoates, octanoates, decanoates or ricinoleates of
alcohols or polyalcohols, for example fatty alcohols, and isopropyl N-lauroylsarcosinate;
- perfluoropolyethers, perfluoroalkanes such as
perfluorodecalin, perfluorodamantanes, monoesters,
diesters and triesters of perfluoroalkyl phosphates and
fluorinated ester oils;
- wheatgerm, maize, sunflower, shea, castor, sweet
almond, macadamia, apricot, soybean, rapeseed,
cottonseed, lucern, poppy seed, pumpkin seed, sesame,
gourd, avocado, hazelnut, grape seed or blackcurrant
seed, evening primrose, millet, barley, quinoa, olive,
rye, safflower, candlenut, passion flower and musk rose
oils; or alternatively triglycerides of caprylic/capric
acids;
- oleic, linoleic or linolenic acids;
- oleyl alcohol and octyldodecanol;
- paraffin oils (such as C8-Ci6 isoparaffins,
isododecane, isohexadecane) and derivatives thereof,
petroleum jelly, polydecenes, hydrogenated
polyisobutenes such as squalane, and mixtures thereof;
- linear or branched, in particular volatile, C^-C^s
alkanes;
- linear or cyclic volatile polydimethylsiloxanes
(PDMS) having from 3 to 7 silicon atoms, and in
particular octyltrimethicone, hexyltrimethicone,
decamethylcyclopentasiloxane (or D5) , octamethylcyclo-
tetrasiloxane (or D4), dodecamethylcyclohexasiloxane
(or D6), decamethyltetrasiloxane (or L4) , heptamethyl-
octyltrisiloxane, dodecamethylpentasiloxane, poly-
methylcetyldimethylsiloxane; fluorinated silicone oils
such as silicones having alkyl and perfluoroalkyl
groups, silicones having oxyethylenated/oxypropylenated
(OE/PP) side groups and having perfluorinated groups,
silicones having perfluorinated or polyfluorinated side
groups and having glycerolated side groups, and
perfluoroalkylmethylphenylsiloxanes;
- non-volatile silicone oils such as polydimethyl
siloxanes (PDMS), polyalkylmethylsiloxanes, dimethicone
copolyols, alkylmethicone copolyols, cetyldimethicone,
silicones having alkylglyceryl ether groups, silicones having amine side groups and dilauroyltrimethylol propane siloxysilicate; the polydimethylsiloxanes containing alkyl, alkoxy or phenyl groups which are pendant and/or at the silicone chain end, groups each having from 2 to 24 carbon atoms; phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates, cetyldimethicone, silicones having alkylglyceryl ether groups, silicones having amine side groups, fluorinated silicones having pendant group(s) or group(s) at the chain end having from 1 to 12 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, dimethiconols and/or mixtures thereof.
20. Composition according to one of the preceding claims, in which the liquid fatty phase comprises at least one lipophilic compound chosen from:
- C6-C32, preferably C8-C28, even better C12-C26,
monoalcohols, and preferably octyldodecanol;
- C6-C32, preferably even better Ci2-C2e, branched
alkanes, and preferably isododecane or the parleam of
formula - (CH2-CH(CH3) ) n being an integer varying
from 4 to 8;
- preferably even better C20-C32, linear
alkanes;
- bifunctional oils, comprising two functional groups
chosen from esters and/or amides and comprising from 6
to 30 carbon atoms, in particular 8 to 28 carbon atoms,
even better from 10 to 24 carbon atoms, and 4
heteroatoms chosen from 0 and N; preferably the amide
and ester functional groups being in the chain; in
particular the bifunctional oil may be the isopropyl N-
lauroylsarcosinate of the following formula:
esters, optionally incorporating into their hydrocarbon chain one or more heteroatoms from N and 0 and/or one or more carbonyl functional groups; and more particularly purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, and heptanoates, octanoates, decanoates or ricinoleates of alcohols or polyalcohols, for example of fatty alcohols;
- volatile or non-volatile silicone oils, and in
particular linear or cyclic polydimethylsiloxanes
(PDMS) having from 3 to 7 silicon atoms such as decamethylcyclopentasiloxane, octamethyIcyclotetra-siloxane, dodecamethylcyclohexasiloxane and decamethyl-tetrasiloxane; and phenylated silicones such as phenyl trimethicones;
- and mixtures thereof.
21. Composition according to one of Claims 17 to 20,
in which the lipophilic compounds represent 20 to 100%,
or even from 40 to 99%, in particular from 60 to 95% by
weight of the total liquid fatty phase.
22. Composition according to one of the preceding
claims, additionally comprising at least one
constituent chosen from waxes, pasty compounds, water,
water-miscible organic solvents; organic or inorganic
colourants; fillers, vitamins, thickeners, gelling
agents, trace elements, emollients, sequestrants,
perfumes, alkalifying or acidifying agents,
preservatives, sunscreens, surfactants, antioxidants,
antihair-loss agents, antidandruff agents, propellants,
ceramides, polymers, cosmetic active agents, and mixtures thereof.
23. Composition according to one of the preceding
claims, provided in the form of a make-up composition,
in particular a product for the complexion such as a
foundation, a blusher or an eye shadow; a product for
the lips such as a lipstick or a care product for the
lips; a concealer product; a blusher, a mascara, an
eyeliner; a make-up product for the eyebrows, a lip
pencil or an eye pencil; a product for the nails such
as a nail varnish or a care product for the nails; a
make-up product for the body or the hair (mascara or
lacquer for the hair); of a composition for protecting
or caring for the skin of the face, the neck, the hands
or the body, in particular an anti-wrinkle, anti-
fatigue or anti-ageing composition, which makes it
possible to make the skin radiant, a moisturizing or
treatment composition; an anti-sun or after-sun or
artificial tanning composition; of a hair composition,
in particular for hair dyeing, care and hygiene, hair-
styling, holding the hairstyle or shaping the hair.
24. Method of cosmetic treatment, in particular for
making-up, cleansing, sun protection, shaping, dyeing
and/or caring for keratin materials, in particular the
skin of the body or of the face, the lips, the nails,
the eyebrows, the hair and/or the eyelashes, comprising
the application to the said materials of a cosmetic
composition as defined in one of the preceding claims.
25. Use of a compound of formula (I) as defined in one
of Claims 1 to 15, for texturing a cosmetic or
pharmaceutical composition comprising, in a
physiologically acceptable medium, a fatty phase.
26. Compound of general formula (la), or one of its
salts and/or isomers:

in which: - A is a group of formula (II):

with Rl being a linear or branched Ci to C$ alkyl radical, and * symbolizing the points of attachment of the group A to each of the two nitrogen atoms of the rest of the compound of general formula (I), and
- R and R', which are identical or different, are
chosen from:
- i) the radicals of formula (III):in which:
- L is a single bond or a saturated or unsaturated,
linear, branched and/or cyclic, divalent carbon, in
particular hydrocarbon, radical, comprising 1 to 18
carbon atoms, and capable of comprising 1 to 4
heteroatoms chosen from N, 0 and S;
- Ra is :
a) a saturated or unsaturated, linear, branched and/or cyclic carbon, in particular hydrocarbon, radical, comprising 1 to 18 carbon atoms, and capable of comprising 1 to 8 heteroatoms chosen from N, 0, Si and S; or alternatively

b) a silicone radical of formula:
(Figure Removed)

n being between 0 and 100;
and R2 to R6 being, independently of each other, linear
or branched carbon, in particular hydrocarbon,
radicals, having 1 to 12 carbon atoms, and capable of
comprising 1 to 4 heteroatoms;
- Rb and Re are, independently of each other, chosen
from:
a) saturated or unsaturated, linear, branched and/or
cyclic carbon, in particular hydrocarbon, radicals,
comprising 1 to 18 carbon atoms, and capable of
comprising 1 to 4 heteroatoms chosen from N, 0, Si and
S;
b) the radicals of formula:
n being between 0 and 100;
and R'2 to R'6 being, independently of each other,
linear or branched carbon, in particular hydrocarbon,
radicals, having 1 to 12 carbon atoms, and capable of
comprising 1 to 4 heteroatoms,
and
- ii) saturated or unsaturated, branched C3 to Cie alkyl
radicals optionally comprising 1 to 3 heteroatoms
chosen from 0, S, F and N;
it being understood that at least one of the radicals R
and/or R' is of formula (III).
27. Compound according to Claim 26, in which the radical R or R' is chosen from the radicals tert-butyl and 2-ethylhexyl or of formula:
(Figure Removed)
28. Compound according to claims 26 or 27, chosen, alone or as a mixture, from the following compounds, and their salts and isomers:
(Figure Removed)
29. Cosmetic or pharmaceutical composition, method of cosmetic treatment substantially as herein described with reference to the foregoing examples.

Documents

Application Documents

# Name Date
1 1004-DEL-2007-Form-18-(07-05-2010).pdf 2010-05-07
2 1004-DEL-2007-Correspondence-Others-(07-05-2010).pdf 2010-05-07
3 abstract.jpg 2011-08-21
4 1004-del-2007-form-5.pdf 2011-08-21
5 1004-del-2007-form-3.pdf 2011-08-21
6 1004-del-2007-form-2.pdf 2011-08-21
7 1004-del-2007-form-1.pdf 2011-08-21
8 1004-del-2007-description (complete).pdf 2011-08-21
9 1004-del-2007-correspondence-others.pdf 2011-08-21
10 1004-del-2007-claims.pdf 2011-08-21
11 1004-del-2007-abstract.pdf 2011-08-21
12 1004-del-2007-Form-13-(16-12-2013).pdf 2013-12-16
13 1004-del-2007-Correspondence Others-(16-12-2013).pdf 2013-12-16
14 1004-DEL-2007-FER.pdf 2016-08-05
15 Other Patent Document [16-08-2016(online)].pdf 2016-08-16
16 Form 26 [20-01-2017(online)].pdf 2017-01-20
17 1004-DEL-2007-Power of Attorney-250117.pdf 2017-01-30
18 1004-DEL-2007-Correspondence-250117.pdf 2017-01-30
19 1004-DEL-2007-AbandonedLetter.pdf 2017-04-22