Cosmetic or dermatological composition comprising alkyl polypentoside vesicles, and method for preparing the same
09730880 · 2017-08-15
Assignee
Inventors
- Angelique Pichot (Saint Jean de Braye, FR)
- Valerie Alard (Orleans, FR)
- Thierry Pouget (Saint Cyr en Val, FR)
- Dominique Scattarelli (Orleans, FR)
- Cedric Ernenwein (Nouvion le Vineux, FR)
- Boris Estrine (Nanteuil la Foret, FR)
Cpc classification
A61K8/604
HUMAN NECESSITIES
International classification
Abstract
The present invention relates to a cosmetic or dermatological composition containing a continuous aqueous phase in which are dispersed vesicles based on at least one alkyl polypentoside, and also comprising at least one alcohol and at least one surfactant. More precisely, the cosmetic or dermatological composition comprises at least one cosmetic or dermatological active agent and at least one continuous aqueous phase in which are dispersed vesicles, said vesicles comprising at least one alkyl polypentoside obtained by reaction of a pentose and of at least a first and a second fatty alcohol comprising a different number of carbon atoms ranging from 10 to 12, said polypentoside having an average polymerization degree of less than or equal to 2, and said composition also comprising at least one surfactant having a HLB of less than 10, and at least one alcohol containing from 1 to 5 carbon atoms. The present invention also relates to a process for preparing the composition, which consists in placing a mixture comprising alkyl polypentoside, the surfactant and the alcohol in contact with an aqueous phase with stirring.
Claims
1. A cosmetic or dermatological composition comprising at least one cosmetic or dermatological active agent, at least one continuous aqueous phase, and at least one alkyl polypentoside that is obtained by reaction of a pentose with a first saturated or unsaturated, and linear or branched fatty alcohol comprising 10 carbon atoms, and a second fatty alcohol, saturated or unsaturated, and linear or branched comprising 8 carbon atoms, wherein the composition further comprises at least one surfactant having a HLB of less than 10 and ethanol, the surfactant and ethanol being in a sufficient amount for the alkyl polypentoside to form vesicles from 0.1 to 10 μm that are dispersed in the continuous aqueous phase, wherein the vesicles each have a shell that is made of at least one double layer of alkyl polypentosides, have a substantially constant average size during storage of the composition at a temperature of between 4° C. and 50° C. for a duration of at least 30 days, and comprise said cosmetic or dermatological active agent.
2. The composition of claim 1, wherein the pentose is D-xylose.
3. The composition of claim 1, wherein the average polymerization degree of the polypentoside is between 1 and 1.8.
4. The composition of claim 1, wherein the first fatty alcohol is 1-decanol and/or the second fatty alcohol is 1-octanol.
5. The composition of claim 1, wherein the mass ratio between the first and the second fatty alcohol is between 80/20 and 99/1.
6. The composition of claim 1, wherein said composition comprises from 0.01% to 20% by weight of the alkyl polypentoside.
7. The composition of claim 1, wherein the surfactant having a HLB of less than 10 is a nonionic surfactant selected from the group consisting of sorbitan esters of a non-hydroxylated aliphatic fatty acid and weakly ethoxylated sorbitan esters.
8. The composition of claim 1, wherein the surfactant having a HLB of less than 10 is selected from the group consisting of sorbitan monolaurate, sorbitan monooleate, sorbitan monostearate, sorbitan trioleate, sorbitan tristearate, sorbitan sesquioleate and sorbitan POE(2) stearate.
9. The composition of claim 1, wherein said composition comprises sorbitan monolaurate, ethanol and an alkyl polypentoside obtained by reaction of D-xylose, 1-decanol and 1-octanol, said polypentoside having an average polymerization degree ranging from 1.4 to 1.6.
10. The composition of claim 1, wherein said composition is in the form of an aqueous solution, an aqueous-alcoholic solution, an aqueous dispersion, an aqueous gel, an aqueous-alcoholic gel, or an oil-in-water (O/W) emulsion.
11. The composition of claim 1, wherein said composition comprises at least one gelling agent for the aqueous phase selected from the group consisting of crosslinked copolymers of acrylic acid and of ethyl acrylate, and cellulose derivatives.
12. A cosmetic or dermatological composition comprising at least one cosmetic or dermatological active agent, at least one continuous aqueous phase, and at least one alkyl polypentoside that is obtained by reaction of a pentose and of at least a first and a second fatty alcohol comprising, independently of each other, a number of carbon atoms ranging from 8 to 12, each of these fatty alcohols being eventually saturated or unsaturated, and linear or branched, said polypentoside having an average polymerization degree of less than or equal to 2, wherein the composition further comprises at least one surfactant having a HLB of less than 10 and at least one monoalcohol containing from 1 to 5 carbon atoms, the surfactant and monoalcohol being in a sufficient amount for the alkyl polypentoside to form vesicles from 0.1 to 10 μm that are dispersed in the continuous aqueous phase, wherein the vesicles each have a shell that is made of at least one double layer of alkyl polypentosides, have a substantially constant average size during storage of the composition at a temperature of between 4° C. and 50° C. for a duration of at least 30 days, and comprise said cosmetic or dermatological active agent.
13. The composition of claim 12, wherein said composition comprises from 0.01% to 5% by weight of said monoalcohol.
14. The composition of claim 12, wherein said composition comprises from 0.1% to 1% by weight of said monoalcohol.
15. The composition of claim 12, wherein said composition comprises from 0.01% to 6% by weight of said surfactant.
16. The composition of claim 12, wherein said composition comprises from 0.1% to 2% by weight of said surfactant.
17. The composition of claim 12, wherein said surfactant is sorbitan monolaurate.
18. The composition of claim 12, wherein said composition comprises an alkyl polypentoside/surfactant mass ratio ranging between 1 and 9.
19. The composition of claim 12, wherein the active agent is selected from the group consisting of compounds having antiaging activity, for preventing or retarding the appearance of the signs of aging of the skin or for slowing down or attenuating the effects thereof, or alternatively for promoting cellular or tissue longevity; active agents with skin depigmenting, bleaching or lightening activity; active agents with slimming activity; active agents with moisturizing activity; active agents with calmative, soothing, relaxing or anti-inflammatory activity; active agents with stimulatory activity on cutaneous microcirculation to improve the radiance of the complexion, in particular of the face; active agents with seboregulatory activity for caring for greasy skin; active agents for cleansing or purifying the skin; active agents with free-radical-scavenging activity, and any mixture thereof.
20. The composition of claim 12, further comprising from 0.1 to 5% by weight of at least one gelling agent for the aqueous phase.
21. A cosmetic or dermatological composition comprising at least one cosmetic or dermatological active agent, at least one continuous aqueous phase, and from 0.01% to 20% of at least one alkyl polypentoside that is obtained by reaction of D-xylose with 1-decanol, and 1-octanol, wherein the mass ratio between the 1-decanol and the 1-octanol ranges between 80/20 and 99/1; wherein the composition further comprises from 0.01% to 6% by weight of at least one surfactant comprising sorbitan monooleate and from 0.01% to 5% by weight of ethanol, thereby having the surfactant and ethanol providing the alkyl polypentoside in the form of vesicles from 0.1 to 10 μm that are dispersed in the continuous aqueous phase, wherein the vesicles each have a shell that is made of at least one double layer of alkyl polypentosides, have a substantially constant average size during storage of the composition at a temperature of between 4° C. and 50° C. for a duration of at least 30 days, and comprise said cosmetic or dermatological active agent.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
(1)
(2)
(3) The invention is illustrated in greater detail in the examples that follow.
EXAMPLE 1: AQUEOUS COMPOSITION ACCORDING TO THE INVENTION
(4) Preparation
(5) An octyl decyl polyxylose was prepared using D-xylose and a fatty alcohol mixture in excess according to a process known to those skilled in the art, such as the process described in examples 1 and 2 of patent application EP 1750834 (AGRO INDUSTRIE RECHERCHES ET DEVELOPPEMENTS).
(6) D-Xylose and a mixture of fatty alcohols comprising 1-decanol (first fatty alcohol, C10) and 1-octanol (second fatty alcohol, C8), in a[C10/C8] mass ratio of 90/10, were placed in contact in acidic medium.
(7) The polyxylose obtained—noted (C8/C10) alkyl polyxylose—is used in the composition of the present example and also in comparative examples 2.1 to 2.3.
(8) The preparation conditions were adapted so that the octyl decyl polyxylose has a degree of polymerization of about 1.5.
(9) A composition in the form of an aqueous gel having the composition below was prepared (the percentages are given on a weight basis).
(10) Phase A
(11) TABLE-US-00001 Caffeine 1.0 Phenoxyethanol 1.0 Purified water qs 100
(12) Phase B
(13) TABLE-US-00002 Sodium acrylates copolymer 1.0 Hydrogenated polyisobutene 0.75 Phospholipids 0.25 Polyglyceryl-10 stearate 0.25 Sunflower seed oil (Helianthus annuus) 0.25 Tocopheryl acetate <0.01
(14) Phase C
(15) TABLE-US-00003 (C8/C10) Alkyl polyxylose 3.5 Sorbitan monolaurate 1.0 Ethanol 0.5
(16) Phase A and phase B were prepared by mixing the ingredients of which they are composed. Phases A and B were mixed together to obtain a homogeneous mixture. The compounds of phase C were then added to this mixture, and a shear was applied using a stand-supported Rayneri® mixer equipped with a deflocculating paddle at a speed of 500 rpm for 15 minutes allowing the formation of multilamellar vesicles. After homogenization, the vesicles formed are dispersed in the continuous phase of the composition thus prepared.
(17) Characterization of the Vesicles
(18) Just after preparation of the composition, the presence of vesicles was observed by electron microscopy after freezing and cryofracture of a sample of the composition.
(19) The method that was used is cryostripping, which makes it possible to prepare a replica of the structure observable by transmission electron microscopy. This technique comprises four essential steps:
(20) 1. freezing;
(21) 2. fracture and etching;
(22) 3. shading and formation of the replica;
(23) 4. cleaning of the replica.
(24) Finally, visualization of the replica using a transmission electron microscope and visual analysis of the images.
(25) The images show a homogeneous dispersion of spherical or virtually spherical objects in positive and negative and having, in the case of the multilamellar vesicles, several spherical striations at the periphery reflecting the rolling-up of several layers.
(26)
(27) Study of Stability Over Time
(28) Samples of each of the composition of the invention were subjected to various lighting and temperature conditions so as to test its stability.
(29) TABLE-US-00004 Stability of the composition of example 1 (table 1) Darkness 4° C. 45° C. (room temperature) T0 Pale yellow gel, characteristic odor 1 month Stable gel Stable gel Stable gel 1.5 months Presence of vesicles in the gel (FIG. 1) 15 months Stable creamy- Yellowish color, fluid Stable gel white gel with slight release of water at the surface
(30) The composition was stored at 4° C., 25° C. and 45° C. for fifteen months and was then observed visually and on an optical microscope (magnification ×10).
(31) Replicas of cryofractures were prepared and observed by transmission electron microscopy on samples that had not been stored and on samples that were considered stable at room temperature and in the dark after 45 days (1.5 months), according to the method described previously.
(32) The observation under an optical microscope made it possible to confirm the presence of vesicles in the composition stored after 15 months of storage under these conditions.
(33) Under the test conditions, the composition of the invention is as stable as the control formula free of phase C forming the vesicles (comparative example 2.4, table 2). The addition of phase C forming the vesicles in the composition does not induce any unfavorable phenomenon with regard to the stability.
(34) In the final analysis, it is observed that the preparation of a composition that is stable over time, which comprises vesicles based on alkyl polypentoside, is possible only in the presence in the formula of an alcohol (ethanol in the present example) and of a surfactant having a HLB of less than 10 (sorbitan monolaurate in the present example).
(35) Stability of the Control Without Vesicles
(36) The composition having the formula below was prepared, which differs from the preceding composition in that it does not comprise the compounds of phase C, and which is thus free of vesicles (the percentages are expressed on a weight basis).
(37) Phase A
(38) TABLE-US-00005 Caffeine 1.0 Phenoxyethanol 1.0 Water qs 100
(39) Phase B
(40) TABLE-US-00006 Sodium acrylates copolymer 1.0 Hydrogenated polyisobutene 0.75 Phospholipids 0.25 Polyglyceryl-10 stearate 0.25 Sunflower seed oil (Helianthus annuus) 0.25 Tocopheryl acetate <0.01
(41) Samples of the control formula were subjected to various lighting and temperature conditions so as to evaluate their stability.
(42) TABLE-US-00007 Stability of the control formula without vesicles (table 2) Darkness 4° C. 45° C. (room temperature) T0 Pale yellow gel, characteristic odor 14 months Stable white gel Creamy-white gel, Stable pale yellow gel very slight release at the surface, stable
(43) After 14 months under the conditions described in the table, the control formula does not show any significant change in its texture. The composition is stable.
EXAMPLE 2: STABILITY STUDY
Comparative Example 2.1
(44) An aqueous composition having the formula below was prepared. The percentages are given on a weight basis.
(45) Phase A
(46) TABLE-US-00008 Caffeine 1.0 Water qs 100
(47) Phase B
(48) TABLE-US-00009 C8/C10 alkyl polyxylose of example 1 15.0
(49) The alkyl polyxylose prepared according to the process described in example 1 was dispersed in the caffeine solution prepared previously.
(50) The presence of vesicles was confirmed by optical microscopy.
(51) The composition was placed, on the one hand, in darkness at room temperature, and, on the other hand, in an oven at 4° C.
(52) The result obtained is as follows: After 1 month at 4° C.: appearance of crystals in the composition. After 3 months at room temperature: appearance of crystals in the composition.
(53) The composition prepared in this comparative example, which does not contain any alcohol or any surfactant having a HLB of less than 10 is unstable under the study conditions.
Comparative Example 2.2
(54) An aqueous composition having the formula below was prepared, which is distinguished from that of the invention in that it does not contain any alcohol. The percentages are given on a weight basis.
(55) Phase A
(56) TABLE-US-00010 Caffeine 1.0 Water qs 100
(57) Phase B
(58) TABLE-US-00011 C8/C10 alkyl polyxylose of example 1 15.0 Sorbitan monolaurate 1.0
(59) The compounds of phase B were dispersed in the caffeine solution (phase A) prepared previously.
(60) The presence of vesicles in the cosmetic composition was confirmed by optical microscopy.
(61) The composition was stored, on the one hand, in darkness at room temperature, and, on the other hand, in an oven at 4° C.
(62) The result obtained is as follows: After 1 month at 4° C.: appearance of crystals in the composition. After 3 months at room temperature: appearance of crystals in the composition.
(63) In the absence of an alcohol, the composition prepared in this comparative example is unstable under the study conditions.
(64) According to one variant of this comparative example, the sorbitan monolaurate was replaced with sorbitan sesquioleate (HLB=3.7).
(65) The appearance of crystals in the composition in the course of the stability study was also observed.
Comparative Example 2.3
(66) An aqueous composition having the formula below was prepared, which, unlike that of the invention, does not comprise any surfactant having a HLB of less than 10.
(67) Phase A
(68) TABLE-US-00012 Caffeine 1.0 Water qs 100 Acrylates/C10-30 alkyl acrylate crosspolymer 0.4
(69) Phase B
(70) TABLE-US-00013 C8/C10 alkyl polyxylose of example 1 4.75 Ethanol 0.25
(71) Phase A was prepared by dispersing the polymers in water.
(72) Phase B was added, and the aqueous composition was then homogenized by gentle shear.
(73) The presence of non-vesicular lamellar phases was observed.
(74) In the absence of cosurfactant having a HLB of less than 10, no formed vesicle is observed in the aqueous phase, unlike what is observed for the composition of the invention.
(75) The results are collated in the table below.
(76) TABLE-US-00014 Com- Com- Com- parative parative parative Example example example example INGREDIENTS 1 2.1 2.2 2.3 Caffeine 1.0 Water qs 100 Acrylates/C10-30 alkyl 0.4 — — 0.4 acrylate crosspolymer C8/C10 Alkyl polyxylose 14.75 15.0 15.0 14.75 of example 1 Sorbitan monolaurate 1.0 — 1.0 — Ethanol 0.25 — — 0.25 STABILITY After 1 month at 4° C. stable crystals crystals no vesicles After 3 months at 20° C. stable crystals crystals no vesicles
EXAMPLE 3: STUDY OF CUTANEOUS PENETRATION
(77) Aim of the Study
(78) Hydrophilic active agents have difficulty in crossing the stratum corneum, the skin's more lipophilic barrier, whence the interest in vectorizing them in order to promote their penetration.
(79) The aim of the study, performed in vitro on frozen total pig ear skin, was to evaluate the efficacy of vesicles based on alkyl polypentosides, for improving the penetration into and distribution in the surface layers of the skin of active agents that are unequally distributed, especially on account of their hydrophilicity/amphiphilicity.
(80) Principle
(81) The diffusion of a tracer, caffeine, across the thawed pig ear skin, mounted on a Franz diffusion cell, was measured, under occlusive conditions.
(82) Caffeine was chosen as a tracer on account of its hydrophilicity which makes it sparingly capable of crossing the skin barrier.
(83) A Franz diffusion cell comprises two superposed compartments communicating via the membrane used for the study.
(84) The skin, used as membrane, is placed stratum corneum facing upwards, between these two compartments. The aqueous solution or the galenical composition to be tested containing caffeine is introduced into the upper compartment in contact with the skin. A certain amount of caffeine, dissolved in the solution or the composition, crosses the membrane constituted by the skin, and is then collected in the lower compartment in a “receiving” solution. The withdrawal apparatus collects a sample of receiving solution at regular time intervals. The samples are assayed by HPLC in order to determine the amount of caffeine that has crossed the skin. Processing of the data makes it possible to calculate the flow of caffeine, the penetration kinetics over 40 hours and also the absorption yields in 24 hours.
(85) Implementation Conditions Amount and mode of application:
(86) After thawing and selection of the skins, deposition zones were determined and limited on each of these skins so that they had an area of 9 cm.sup.2. Next, each composition was deposited, at a rate of 2 mg/cm.sup.2, using a micropipette and applied using a finger stall presaturated with the galenicals.
(87) The penetration kinetics were established by withdrawals of 0.2 ml of the receiving liquid at 4 hours, 8 hours, 24 hours, 28 hours, 32 hours and 46 hours, using a manual withdrawal pipette. The withdrawn samples were assayed by HPLC.
(88) The cutaneous penetration of the active agents was, in the context of this study, mainly used for comparative purposes. Various formulations were evaluated via this technique for the purpose of demonstrating those that promote or limit the penetration of various active agents. Formulations tested: composition of example 1 and control formulation without vesicles in accordance with comparative example 2.3. Study parameters:
“Lara Spiral” Franz Cell: Exposure area of 3.8 cm.sup.2 Receiving volume of 6.5 ml
Receiving Solution: 10 mmol phosphate buffer 120 mmol NaCl 2.7 mmol KCl 0.1% sodium azide Surfactant: Tween 80® at 0.5%
Quality of the Skins: Pig ear skins that are not boiled, or tattooed, or stamped, cut into 3 cm by 3 cm pieces and extended tautly at the surface of the lower compartment of the Franz cells.
Application Conditions Randomized deposition on each explant of 18 mg of formulation, i.e. 0.18 mg of active principle (dose corresponding to an application under the real conditions of use of a cosmetic product). Study performed under occlusive conditions on whole skin.
Number of Replicas: 3 Franz cells for each formulation tested
Temperature and Stirring: Mean temperature of the bath thermostatically maintained at 34° C. Mean stirring of 200 rpm
Rainin® Withdrawal Apparatus Rainin® manual withdrawal pipette
HPLC Assay Conditions: Assay apparatus: Agilent®, CD 017070 Column: End capped C18 grafted RP18 HPLC column, end capped Lichrospher® 100 RP reverse-phase apolar column (125×4) mm, 5 μm Eluent: A=H.sub.2O+0.1% HClO.sub.4 B=Acetonitrile Gradient: Isocratic 15% of B Injection: 20 μl every 20 min Detection: λ.sub.caffeine=270 nm Flow rate: 1 ml/min
Calibration range: dissolution of the standards from 0.5 to 500 ppm in a water/ethanol mixture (50/50).
Caffeine Concentration In order to avoid underestimating the cutaneous absorption, the caffeine concentration in the receiving liquid needed to be less than 10% of the limit solubility concentration. The limit solubility concentration of caffeine in the receiving liquid was 16 mg/ml. The maximum concentration of caffeine collected during the study was less than 9.9 μg/ml.
(89) Results
(90) The kinetic transmembrane diffusion results were expressed in the form of histograms showing this yield at 4 hours, 24 hours, 32 hours and 46 hours for the two formulations in
(91) At each withdrawal, larger transcutaneous passage of caffeine was observed in the case where the composition applied to the skin comprises vesicles based on alkyl polypentosides as defined previously.