USE OF DIETHANOLAMMONIUM DERIVATIVES AS SKIN MOISTURIZER
20180235860 ยท 2018-08-23
Inventors
Cpc classification
C07C229/38
CHEMISTRY; METALLURGY
A61K2800/40
HUMAN NECESSITIES
International classification
Abstract
The present invention relates to the cosmetic use as moisturizer for keratin materials, preferably the skin, of one or more diethanolammonium derivatives corresponding to formula (I) below, and also the optical isomers and/or geometrical isomers thereof: (I)
##STR00001##
Claims
1. A cosmetic process for moisturizing keratin materials which comprises applying to the keratin materials one or more diethanolammonium derivatives corresponding to formula (I) below, optical isomers and/or geometrical isomers thereof: ##STR00080## in which R1 and R2 independently denote: (i) a linear or branched C1-C12 alkyl radical which is saturated or unsaturated with one or more ethylenic double bond(s); said radical being optionally substituted with a group COR; or (ii) an aralkyl radical C.sub.mH.sub.2mAr such that m denotes an integer ranging from 1 to 6 and Ar denotes an aryl radical optionally substituted with a group COR; R denotes a group OR or NRR where R and R independently denote hydrogen or a linear or branched C1-C6 alkyl radical which is saturated or unsaturated with an ethylenic double bond; n is equal to 0 or 1; the electrical neutrality of said compounds being provided by an organic or inorganic external anion X (n=1) or internally (n=0) when a single COOH radical is present and forms a CO.sub.2- radical; it being understood that when R1 denotes a methyl radical and R2 denotes a methyl radical substituted with a COOH group, then n=1.
2. The process according to claim 1, in which X.sup. is chosen from the anionic forms of organic compounds bearing one or more acid functions, such as the anionic forms of amino acids, methanesulfonate, para-toluenesulfonate, camphorsulfonate, tartrate, citrate, acetate, levulinate, or methosulfate, halides, sulfates, phosphates, hydrogen phosphates, dihydrogen phosphates, carbonate or hydrogen carbonate.
3. The process according to claim 1, in which X.sup. is chosen from the anionic forms of organic compounds bearing one or more carboxylic acid functions such as among compounds of formula A or B or C: ##STR00081## With Ra1 means a hydrogen atom or an a linear or branched alkyl radical C1-C18 Ra2 means a hydrogen atom or an a linear or branched alkyl radical C1-C18 or an a linear or branched alkylcarbonyl radical C1-C18 Ra1 and Ra2 can together form a five to eight membered ring with the N atom bearing them. Ra2 and Ra3 can together form a five membered ring of formula A1 or A2 with the N atom bearing them ##STR00082## Ra3 is chosen among the radicals described below ##STR00083##
4. The process according to claim 1, in which the one or more diethanolammonium derivatives of formula (I) are chosen from the following compounds: TABLE-US-00008 Compounds Structure a
5. The process according to claim 1, in which the one or more diethanolammonium derivatives of formula (I) are chosen from the following compounds: TABLE-US-00009 Compound Structure 1
6. The process according to claim 1, in which the one or more diethanolammonium derivatives of formula (I) are such that R1 and R2 independently denote a linear or branched C.sub.1-C.sub.8 alkyl radical which is saturated or unsaturated with one or more ethylenic double bond(s), and which is optionally substituted with a group COR.
7. The process according to claim 6, in which the one or more diethanolammonium derivatives of formula (I) are such that R1 and R2 independently denote a linear or branched, saturated C.sub.1-C.sub.8 alkyl radical which is optionally substituted with a group COR where R denotes a radical chosen from OR and NRR, with R and R independently denoting hydrogen or a linear or branched, saturated C.sub.1-C.sub.6 alkyl radical.
8. The process according to claim 6, in which the one or more diethanolammonium derivatives of formula (I) are chosen from compounds (a), (b), (d) and (f).
9. A compound of formula (II) below, optical isomers and/or geometrical isomers thereof: ##STR00115## in which: R21 denotes a linear or branched C.sub.1-C.sub.12 alkyl radical which is saturated or unsaturated with an ethylenic double bond; R22 denotes a C.sub.mH.sub.2mAr aralkyl radical, where m is an integer ranging from 1 to 6 and Ar is an aryl radical substituted with a COR group, in particular a phenyl radical substituted with a COR group; R denotes an OR or NRR group where R and R independently denote hydrogen or a linear or branched C.sub.1-C.sub.6 alkyl radical which is saturated or unsaturated with an ethylenic double bond; n is equal to 0 or 1; the electrical neutrality of said compound being ensured by an organic or inorganic external anion X.sup. (n=1) or in the form of an internal salt (n=0) when a single COOH radical is present and forms a CO.sub.2.sup. radical; it being understood that when R1 denotes a methyl radical and R2 denotes a methyl radical substituted with a COOH group, then n=1; and said compounds being other than the compounds having the following formulas: ##STR00116##
10. The compound according to claim 9, wherein R22 denotes a C.sub.mH.sub.2mAr aralkyl radical, where m is an integer ranging from 1 to 6 and Ar is an aryl radical substituted with a COR group chosen among phenyl naphtyl or furyl.
11. The compound according to claim 9, which is chosen from the compounds of formula (IIA) below, optical isomers and/or geometrical isomers thereof: ##STR00117## in which: R21 denotes a linear or branched, saturated C.sub.1-C.sub.12 alkyl radical, such as methyl; R22 denotes a (CH.sub.2).sub.p-Ph radical substituted with a COR group with Ph denoting phenyl and p is an integer ranging from 1 to 4; R denotes a radical chosen from OR and NRR in which R and R independently denote hydrogen or a linear or branched, saturated C.sub.1-C.sub.6 alkyl radical; n is 0 or 1.
12. The compound according to claim 9 wherein which is chosen from compounds (c) of formula: ##STR00118## ##STR00119##
13. A compound of formula (III) below, optical isomers and/or geometrical isomers thereof: ##STR00120## in which: R31 and R32, chosen independently, denote: (i) a linear or branched C.sub.1-C.sub.12 alkyl radical which is saturated or unsaturated (ethylenic double bond) and which is substituted with a COR group; (ii) a C.sub.mH.sub.2mAr aralkyl radical, where m is an integer ranging from 1 to 6 and Ar is an aryl radical; R denotes a group OR or NRR where R and R independently denote hydrogen or a linear or branched C1-C6 alkyl radical which is saturated or unsaturated with an ethylenic double bond; n is equal to 0 or 1; the electrical neutrality of said compound being ensured by an organic or inorganic external anion X.sup. (n=1) or in the form of an internal salt (n=0) when a single COOH radical is present and forms a CO.sub.2.sup. radical; it being understood that when R1 denotes a methyl radical and R2 denotes a methyl radical substituted with a COOH group, then n=1; and said compound being other than the compounds having the following formula: ##STR00121##
14. The compound according to claim 13, which is chosen from the compounds of formula (IIIA), optical isomers and/or geometrical isomers thereof: ##STR00122## in which: R31 and R32, independently, denote a linear or branched, saturated C.sub.1-C.sub.12 alkyl radical which is substituted with a COR group; R denotes a radical chosen from OR and NRR where R and R independently denote a linear or branched, saturated C.sub.1-C.sub.6 alkyl radical.
15. The compound according to claim 13, which is chosen from compounds (b) of formula: ##STR00123## and most particularly compound (5) of formula: ##STR00124##
16. A composition comprising one or more compounds of formula (I) as defined below: optical isomers and/or geometrical isomers thereof: ##STR00125## in which R1 and R2 independently denote: (i) a linear or branched C1-C12 alkyl radical which is saturated or unsaturated with one or more ethylenic double bond(s); said radical being optionally substituted with a group COR; or (ii) an aralkyl radical C.sub.mH.sub.2mAr such that m denotes an integer ranging from 1 to 6 and Ar denotes an aryl radical optionally substituted with a group COR; R denotes a group OR or NRR where R and R independently denote hydrogen or a linear or branched C1-C6 alkyl radical which is saturated or unsaturated with an ethylenic double bond; n is equal to 0 or 1; the electrical neutrality of said compounds being provided by an organic or inorganic external anion X (n=1) or internally (n=0) when a single COOH radical is present and forms a CO.sub.2- radical; it being understood that when R1 denotes a methyl radical and R2 denotes a methyl radical substituted with a COOH group, then n=1; and one or more additional moisturizing active agents other than the compounds of formula (I).
17. The composition according to claim 16, in which the compound(s) of formula (I) are present in amounts ranging from 0.01% to 10% by weight relative to the total weight of the composition.
18. Composition comprising, in a physiologically acceptable medium, in particular a cosmetically acceptable medium, one or more compounds chosen from: TABLE-US-00010 Compounds Structure d
19. A composition comprising, in a physiologically acceptable medium one or more compounds chosen from the following compounds: TABLE-US-00011 Compound Structure 1
20. A composition, which comprises, in a physiologically acceptable medium, one or more compounds of formula (II) as defined in claim 9, optical isomers and/or geometrical isomers thereof and/or one or more compounds of formula (III) as defined below: optical isomers and/or geometrical isomers thereof: ##STR00141## in which: R31 and R32, chosen independently, denote: (i) a linear or branched C.sub.1-C.sub.12 alkyl radical which is saturated or unsaturated (ethylenic double bond) and which is substituted with a COR group; (ii) a C.sub.mH.sub.2mAr aralkyl radical, where m is an integer ranging from 1 to 6 and Ar is an aryl radical; R denotes a group OR or NRR where R and R independently denote hydrogen or a linear or branched C1-C6 alkyl radical which is saturated or unsaturated with an ethylenic double bond; n is equal to 0 or 1; the electrical neutrality of said compound being ensured by an organic or inorganic external anion X.sup. (n=1) or in the form of an internal salt (n=0) when a single COOH radical is present and forms a CO.sub.2.sup. radical; it being understood that when R1 denotes a methyl radical and R2 denotes a methyl radical substituted with a COOH group, then n=1; and said compound being other than the compounds having the following formula: ##STR00142##
21. A cosmetic process for moisturizing keratin materials, which comprises applying to said keratin materials a composition as defined in claim 16.
22. The cosmetic process according to claim 21, for promoting the persistence of a moisturizing treatment.
23. The cosmetic process according to claim 21, wherein said composition is applied to dry skin and/or to a cutaneous region chosen from: the hands, the face, the neck, the feet, the legs, the arms and forearms.
Description
EXAMPLES
A) Synthesis Examples
Example 1: Synthesis of Compound (4)
[0210] ##STR00059##
[0211] The synthesis of compound (4) is described in the following article: El-Sayed, A. A., Kantouch, F. A. and Kantouch, A. (2011), Preparation of cationic polyurethane and its application to acrylic fabrics. J. Appl. Polym. Sci., 121: 777-783
Example 2: Synthesis of Compound (12)
[0212] ##STR00060##
Synthesis of Intermediate A:
[0213] Potassium carbonate (60 g, 435 mmol) was suspended in acetone (500 ml). Diethanolamine (21 g, 200 mmol) and benzyl bromide (34.4 g, 200 mmol) were successively added. The reaction mixture was refluxed for 8 hours, cooled to room temperature and filtered. The filtrate was concentrated to dryness and then the residue was purified by silica gel column chromatography (dichloromethane/methanol: 10/1) to isolate product A in the form of a colourless oil (37.5 g, 75% yield).
Synthesis of Intermediate B:
[0214] Product A (37.2 g, 190 mmol) was dissolved in dichloromethane (300 ml). Acetic anhydride (46.5 g, 456 mmol) and triethylamine (164 ml, 1.3 mol) were successively added. The reaction mixture was stirred at room temperature for 3 hours and filtered. The filtrate was concentrated to dryness and the residue was then purified by silica gel column chromatography (hexane/ethyl acetate: 20/1) to isolate product B in the form of a yellow oil (24 g, 45% yield).
Synthesis of Intermediate C:
[0215] A solution of product B (24 g, 86 mmol) and of benzyl bromide (88 g, 514 mmol) in acetonitrile (500 ml) was refluxed for 16 hours. The reaction mixture was then concentrated under reduced pressure and the residue was purified by silica gel column chromatography (dichloromethane/methanol: 30/1) to isolate product C in the form of a colourless oil (2.7 g, 7% yield).
Synthesis of Compound (12)
[0216] A mixture of the intermediate C (2.7 g, 6 mmol) and of potassium carbonate (1.2 g, 8.7 mmol) in methanol was stirred at room temperature for 15 hours. IR-120 ion exchange resin (12 g), pre-rinsed with absolute methanol, was added. The suspension was stirred for 30 minutes and then filtered. The filtrate was concentrated under reduced pressure so as to produce a white solid. Since the Br.sup./Cl.sup. interconversion was not complete, the product was again dissolved in methanol and treated with Dowex 1x2-200 ion exchange resin (5 g). The suspension was stirred at room temperature for 15 hours and then filtered to remove the resin. Dowex 1x2-200 resin (5 g) was again added and the suspension was stirred at room temperature for 15 hours. The Dowex resin treatment cycle was repeated a further 5 times. After the final filtration, the solvent was evaporated off and the expected product was isolated in the form of a white solid (1.2 g, 61% yield).
Example 3: Synthesis of Compound (7)
[0217] ##STR00061##
[0218] N,N-Diethanolamine (2.38 g, 20 mmol) was dissolved in methanol (100 ml). 2-Bromoethane (21.6 g, 200 mmol, 10 equivalents) was added dropwise. The reaction mixture was stirred at room temperature for 15 hours and then concentrated to dryness. The residue was purified by recrystallization from a methanol/acetone mixture and compound (7) was obtained in the form of a white solid (3.2 g, 70% yield).
Example 4: Synthesis of Compound (8)
[0219] ##STR00062##
[0220] Compound (7) (3 g, 13.2 mmol) was dissolved in 50 ml of a methanol/water mixture (5/1). An ion exchange resin (ref. Dowex 1x2-200, 10 g) was suspended, the mixture was stirred at room temperature for 5 hours and the resin was then filtered off. The process was repeated until the Br.sup. ion content reached 0.5%. The solvent was then evaporated off under vacuum and compound (8) was isolated in the form of a white solid (2.1 g, 70% yield). The .sup.1H NMR spectrum (DMSO-d6) and the mass spectrum confirmed the structure of the expected product (8).
Example 5: Synthesis of Compound (9)
[0221] ##STR00063##
[0222] N-Methyl-N,N-diethanolamine (1.78 g, 15 mmol) was dissolved in methanol (60 ml). Benzyl chloride (9.5 g, 75 mmol, 5 equivalents) was added dropwise and the reaction mixture was refluxed for 15 hours. The solvent was then evaporated off under reduced pressure and the residue was purified by silica gel column chromatography (dichloromethane/methanol: 10/1) to obtain compound (9) in the form of a white solid (1.6 g, 44% yield). The .sup.1H NMR spectrum (DMSO-d6) and the mass spectrum confirmed the structure of the expected product (9).
Example 6: Synthesis of Compound (10)
[0223] ##STR00064##
[0224] N-Methyl-N,N-diethanolamine (2 g, 17 mmol) was dissolved in methanol (20 ml). 1-Bromohexane (13.9 g, 84 mmol, 5 equivalents) was added dropwise and the reaction mixture was refluxed for 8 hours. The solvent was then evaporated off under reduced pressure and the residue was purified by silica gel column chromatography (dichloromethane/methanol: 20/1) to obtain compound (10) in the form of a colourless oil (2.3 g, 48% yield).
Example 7: Synthesis of Compound (11)
[0225] ##STR00065##
[0226] Compound (10) (2.3 g, 8.1 mmol) was dissolved in 20 ml of methanol. An ion exchange resin (ref. Dowex 1x2-200, 5 g) was suspended, the mixture was stirred at room temperature for 0.15 hours and the resin was then filtered off. The process was repeated 5 times. The solvent was then evaporated off under vacuum and compound (11) was isolated in the form of a slightly yellow oil (1.6 g, 82% yield). The .sup.1H NMR spectrum (DMSO-d6) and the mass spectrum confirmed the structure of the expected product (11).
Example 8: X Interchange
[0227] The different salts are prepared the following way starting for example from the XCl or X=MeSO3 using resins Interchange as described in the figure below.
[0228] Empty cartridge was filled with hydrogenocarbonate resin (commercially available from Agilent Technology under reference PL3540-4603). Once the cartridge packed, resin was washed with demineralized water (100 ml water for 20 g of resin).
[0229] Compound 4 X=MeSO3- was solubilized in water at the concentration of 0.5 mol/L and adsorbed onto the column by gravity. Resin was then washed with water 3 times dead volume with pH control to desorb the intermediate into a stock solution.
[0230] The desired new carboxylate anion is then introduced under its acidic form (RCOOH) into the stock solution and CO2 is gently bubbling showing interchange. If the carboxylic acid is not soluble in water, tetrahydrofuran can be added to solubilize it.
[0231] The solution is then concentrated and freeze dried.
[0232] Compounds according to the invention is then characterized by NMR (disappearance of MeSO3-), MS and elemental analysis.
TABLE-US-00003 Compounds as listed in QC: the table RMN 1H/ Acid below Yield Aspect MS
Compounds:
[0233] ##STR00078## ##STR00079##
B): Evaluation of the Moisturizing Potential on Isolated Stratum Corneum by Measurement with a Corneometer
[0234] A test was performed to evaluate the moisturizing potential of the compounds of the invention formulated in an aqueous solution to an amount of 5% by weight relative to the total weight of the composition.
[0235] The technique makes it possible to measure the dielectric capacitance of stratum corneum (SC), which depends on the mean dielectric permittivity value of the tissue. The dielectric permittivity varies greatly with the amount of water contained in the SC.
[0236] The SC samples are conditioned at 75% relative humidity and at 25 C. before/during the measurements and the treatment. The capacitance measurement is performed using a Corneometer (Courage & Khazaka, Germany).
[0237] The test compound, compound 2 according to the invention or a moisturizing active agent such as glycerol, is dissolved in a water/n-propanol mixture (80/20) and the solution is deposited onto the SC at a rate of 10 l/cm.sup.2 followed by air-drying for a total duration of 1 hour 30 minutes.
[0238] Measurement is taken at T0, before the treatment, and a measurement Ttreat is taken after total drying of the treatment.
[0239] Each treatment is systematically compared with its control (vehicle) and with its T0.
[0240] Using at least two different batches of SC, four to five SC samples are measured per treatment.
[0241] The variation in the corneometer signal (HCM) after treatment is calculated first for each SC sample: DHCMi=HCMi(Ttreat)HCMi(T0). The mean of the DHCMi(vehicle) variations is then calculated for the control samples (treated with the vehicle); this mean value is subtracted from all the DHCMi(active agent) variations to correct the systematic bias.
[0242] The following is measured for each sample i: [0243] For the vehicle (control): DHCMi(veh)=HCMi.sub.veh(Ttreat)HCMi.sub.veh(T0) [0244] For the active agent: DHCMi.sub.active agent=HCMi.sub.active agent(Ttreat)HCMi.sub.active agent(T0)
[0245] To correct the systematic bias associated with the vehicle, the corrected value DHCMi.sub.corr. active agent is considered for the active agent according to: DHCMi.sub.corr. active agentDHCMi.sub.active agentM
[0246] in which M corresponds to the mean of the DHCMi(veh) variations observed on the n control samples:
[0247] The mean DHCMi corr. active agent values, and also the associated standard deviations that were obtained, are reported in the table below for compound 2 tested at 5%, in comparison with glycerol at 5%:
TABLE-US-00004 Compound 2 Glycerol according to Products tested in a at 5% the invention water/n-propanol mixture by weight at 5% by weight Mean DHCMi corr. active agent 13.8 25.9 Standard deviation 5.1 6.6
[0248] The above results are obtained from two measurement runs (more than 4 samples)
[0249] The results presented above were obtained over two measurement runs on two batches of stratum corneum. The response of the products is analysed in each run relative to the vehicle.
[0250] It emerges that this test shows that the dielectric capacitance of the stratum corneum (SC) is much better with compound 2 used according to the invention in comparison with that obtained with glycerol at the same concentration.
[0251] Unexpectedly, compound 2 used according to the invention allows good moisturization of the stratum corneum and thus of the skin. This moisturizing effect proves to be greater than that of glycerol.
[0252] The mean DHCMi corr. active agent values, and also the associated standard deviations that were obtained, are reported in the table below for two salts of compound a, compound 13 and compound 14 tested at 5%, in comparison with glycerol at 5%:
TABLE-US-00005 Products tested Compound 13 Compound 14 in a Glycerol according to according to water/n-propanol at 5% the invention the invention mixture by weight at 5% by weight at 5% by weight Mean DHCMi corr. 11 14 13 active agent
[0253] The results presented above were obtained over two measurement runs on two batches of stratum corneum. The response of the products is analysed in each run relative to the vehicle.
[0254] It emerges that this test shows that the dielectric capacitance of the stratum corneum (SC) is better with the compounds 13 and 14 used according to the invention in comparison with that obtained with glycerol at the same concentration.
[0255] Unexpectedly, these 2 compound 13 and 14 used according to the invention allows good moisturization of the stratum corneum and thus of the skin.
C): Evaluation of the Pleasant Feel of the Compositions, i.e Having No Discomfort Sensations Such as Tautness by Measurement with Internal Stresses Test
[0256] The aim of this study is to compare the properties of the deposit formed when applying aqueous solutions of raw material HYBRIDUR 875 available from AIR PRODUCTS AND CHEMICALS (which is a an aqueous 40% dispersion of an interpenetrated networks of polyurethane polymers and polyacrylic). This raw material is currently used in skincare products present on the market. It is well known for its tightening properties but also for the discomfort generated Hybridur 875 solution forms a deposit which develops high values of internal stresses, as already well-known.
[0257] The principle of internal stress test is representative of generated tightness.
[0258] The solutions of polymer are deposited on a nitrile substrate cut in 12 specimens (see below). A given volume is applied on each specimen, with 4 replicates by solution.
[0259] For standard test, a volume of 26 l of a solution of 7% of active material is applied. It corresponds to a quantity of 0.64 mg.Math.cm.sup.2 of active material on the substrate after drying. The volume or concentration of solutions may vary with or without variations of the final quantity per cm.sup.2 after drying. In such case this will be specified.
[0260] Measurements are realized, in standard conditions, after 3 and/or 24 hours of drying at 25 C. at 45% Relative Humidity (RH). These conditions may vary (times and rate of RH) and this is specified in such case.
[0261] The tightening effect is measured by image analysis. The surface of the specimen is determined before and after the deposit formation.
[0262] The % of internal stresses (contraintes internes in French CI) is calculated as:
CI=(1S.sub.int/S.sub.tot)100
Where:
[0263] S.sub.int: internal surface of the specimen, comprised inside the retracted edges of the specimen.
[0264] S.sub.tot: total surface of the specimen before deposit of the solution
[0265] Two compositions has been prepared and tested:
[0266] Composition Y:Solution of Hybridur 87 5 at 16.8% by weight of raw material (7% of active material MA)+water 83.2% by weight compared to the total weight of the composition
[0267] Composition Z:Solution of Hybridur 875 at 16.8% by weight+5% by weight of compound 2 (5% of active material MA) according to the invention+water 78.2%
[0268] Deposits for completion of the internal stress test were prepared on nitrile substrates. 26 L solution (dispersion) are deposited and left to dry 3 hours before measurements. Deposits represent 0.6 mg.Math.cm-2 after drying at 25 C. and 45% RH.
[0269] The measurements were performed after 3 hours of drying. Each measurement is repeated 4 times. In the case of the solution Hybridur 875 two sets of 4 measurements were performed.
[0270] The internal stress values obtained for deposits made from each of the two solutions measured after drying 3H are and reported in Table below.
TABLE-US-00006 internal stresses (%) internal stresses (%) Compositions drying 3H drying3H Composition Y 32 3 35 3 Composition Z 0.5 0.7 0.9 0.6
[0271] The Hybridur 875 solution, composition Y, forms a high deposition of internal stresses
[0272] The solution Hybridur 875+5% of compound 2 according to the invention, composition Z, form a deposit that no longer develops internal stresses in the experimental accuracy close. Therefore, this deposit will not generate any sensation of tightness.
[0273] The addition of the compound 2 according to the invention allows to remove the feeling of discomfort generated by Hybridur 875 at high concentrations.
[0274] The composition comprises compounds according to the invention, such as compound 2, when applied on the keratin materials such as the skin have a pleasant feel for the consumers, i.e have no discomfort sensations such as tautness.
D) Example 9: Skin Care Cream
[0275]
TABLE-US-00007 Weight % Compound 2 .sup.4% Glyceryl monostearate 0.8% Cetyl alcohol 2.0% Stearyl alcohol 5.0% Polyoxyethylene (20 OE) stearate 3.0% Crosslinked acrylic acid (Carbopol 941) 0.3% Caprylic/capric triglycerides 12.0% Preserving agents qs Water qs 100.0%
[0276] When applied to the skin, the illustrated cosmetic formulation shows a good moisturizing effect on the skin.