COSMETIC COMPOSITION COMPRISING A POLYHYDROXYALKANOATE IN AN OILY MEDIUM

Abstract

The invention relates to a composition comprising: a) a polyhydroxyalkanoate copolymer comprising the following polymeric units A, B and C: —[—O—CH(R1)-CH.sub.2—CO—]-unit A —[—O—CH(R2)-CH.sub.2—CO—]-unit B —[—O—CH(R3)-CH.sub.2—CO—]-unit C in which: R1 denotes a linear alkyl radical having from 5 to 9 carbon atoms; R2 denotes a linear alkyl radical having a carbon number corresponding to the number of carbon atoms of the R1 radical −2; R3 denotes a linear alkyl radical having a carbon number corresponding to the number of carbon atoms of the R1 radical −4; b) an oily medium comprising a non-silicone oil chosen from ester oils, carbonate oils and nonpolar hydrocarbon oils having from 8 to 14 carbon atoms.

Claims

1. A composition comprising: a) a polyhydroxyalkanoate copolymer comprising the following polymeric units A, B and C:
—[—O—CH(R1)-CH2-CO—]— unit A
—[—O—CH(R2)-CH2-CO—]— unit B
—[—O—CH(R3)-CH2-CO—]— unit C in which: R1 denotes a linear alkyl radical having from 5 to 9 carbon atoms; R2 denotes a linear alkyl radical having a carbon number corresponding to the number of carbon atoms of the R1 radical −2; R3 denotes a linear alkyl radical having a carbon number corresponding to the number of carbon atoms of the R1 radical −4; the molar percentage of unit A being greater than the molar percentage of unit B and greater than the molar percentage of unit C; b) an oily medium comprising a non-silicone oil chosen from: ester oils, carbonate oils, branched nonpolar hydrocarbon oils having from 8 to 14 carbon atoms, as a mixture with a monoalcohol having from 2 to 6 carbon atoms according to a monoalcohol/branched nonpolar hydrocarbon oil ratio by weight ranging from 1/99 to 10/90; and when the polymer is such that the R1 alkyl group has from 6 to 9 carbon atoms, the non-silicone oil is also chosen from nonpolar hydrocarbon oils having from 8 to 14 carbon atoms in the absence of monoalcohol having from 2 to 6 carbon atoms; when the polymer is such that the R1 alkyl group comprises 9 carbon atoms, the non-silicone oil is also chosen from hydrogenated polyisobutylenes.

2. The composition as claimed in claim 1, wherein, for the copolymer, the unit A is present in a molar percentage ranging from 40% to 97.5%, the unit B is present in a molar percentage ranging from 2% to 40% and the unit C is present in a molar percentage ranging from 0.5% to 20%, with respect to all of the units A, B and C.

3. The composition as claimed in claim 1, wherein the copolymer comprises units A having an R1 alkyl radical having 5 carbon atoms, units B having an alkyl radical having 3 carbon atoms and units C having an alkyl radical having 1 carbon atom.

4. The composition as claimed in claim 1, wherein the copolymer comprises from 85 mol % to 97.5 mol % of unit A, from 2 mol % to 10 mol % of unit B and from 0.5 mol % to 7 mol % of unit C.

5. The composition as claimed in claim 1, wherein the copolymer comprises units A having an R1 alkyl radical having 6 carbon atoms, units B having an alkyl radical having 4 carbon atoms and units C having an alkyl radical having 2 carbon atoms.

6. The composition as claimed in claim 1, wherein the copolymer comprises from 60 mol % to 94.5 mol % of unit A, from 5 mol % to 35 mol % of unit B and from 0.5 mol % to 7 mol % of unit C.

7. The composition as claimed in claim 1, wherein the copolymer comprises units A having an R1 alkyl radical comprising 9 carbon atoms, units B having an alkyl radical having 7 carbon atoms and units C having an alkyl radical having 5 carbon atoms.

8. The composition as claimed in claim 1, wherein the copolymer comprises from 40 mol % to 50 mol % of unit A, from 30 mol % to 40 mol % of unit B and from 10 mol % to 20 mol % of unit C.

9. The composition as claimed in claim 1, wherein the copolymer has a number-average molecular weight ranging from 50 000 to 150 000.

10. The composition as claimed in claim 1, wherein the copolymer is present in a content ranging from 0.1% to 30% by weight, with respect to the total weight of the composition.

11. The composition as claimed in claim 1, wherein the nonpolar hydrocarbon oil having from 8 to 16 carbon atoms is chosen from branched C.sub.8-C.sub.16 alkanes and linear C.sub.8-C.sub.16 alkanes.

12. The composition as claimed in claim 1, wherein the ester oil is chosen from triglycerides consisting of C.sub.4-C.sub.24 fatty acid esters of glycerol; monoester oils of formula R.sub.4COOR.sub.5 in which R.sub.4 represents a hydrocarbon chain comprising from 5 to 19 carbon atoms and R5 represents a hydrocarbon chain provided that R.sub.4+R.sub.5 is ≥9 carbon atoms; esters of lactic acid and of C.sub.10-20 alcohol; diesters of malic acid and of C.sub.10-C.sub.20 alcohol; esters of pentaerythritol and of C.sub.8-C.sub.22 carboxylic acid; diesters of formula (II) R6-O—C(═O)—R′6-C(═O)—O—R″6, with R6 and R″6, which are identical or different, represent a saturated or unsaturated and linear or branched C.sub.4 to C.sub.12 alkyl chain optionally exhibiting at least one saturated or unsaturated ring, and R′6 represents a saturated or unsaturated C.sub.1 to C.sub.4 alkylene chain; diesters of formula (III) R7-C(═O)—O—R′7-O—C(═O)—R″7, with R7 and R″7, which are identical or different, represent a C.sub.4 to C.sub.12 alkyl chain represent a saturated or unsaturated and linear or branched C.sub.4 to C.sub.12 alkyl chain, and R′7 represents a saturated or unsaturated C.sub.1 to C.sub.4 alkylene chain.

13. The composition as claimed in claim 1, wherein the carbonate oils are chosen from the carbonates of formula R8-O—CO—O—R9, with R8 and R9, which are identical or different, represent a C.sub.4 to C.sub.12 alkyl chain.

14. The composition as claimed in claim 1, which comprises a monoalcohol of 2 to 6 carbon atoms.

15. The composition as claimed in claim 1, wherein it comprises a physiologically acceptable medium.

16. A nontherapeutic cosmetic method for the treatment of keratinous substances, comprising the application, to the keratinous substances, of a composition as claimed in claim 1.

17. The composition as claimed in claim 1 wherein the polyhydroxyalkanoate copolymer consists of the polymeric units A, B and C.

18. The composition as claimed in claim 14 wherein the monoalcohol is chosen from ethanol or 1-butanol.

19. The composition as claimed in claim 14 wherein the monoalcohol is ethanol.

20. The composition as claimed in claim 2, wherein the copolymer comprises units A having an R1 alkyl radical having 5 carbon atoms, units B having an alkyl radical having 3 carbon atoms and units C having an alkyl radical having 1 carbon atom.

Description

EXAMPLES

Example 1

[0057] A polymer was prepared using the Pseudomonas putida KT2440 ATCC® 47054™ microorganism and octanoic acid.

[0058] The culturing method was carried out under batch axenic conditions in 5 l Fernbach flasks (Corning® ref. 431685) containing 2 l of culture medium, shaken at 110 rev/min at 30° C. in an orbital incubator (diameter of the orbit of 2.5 cm).

[0059] The synthesis process was carried out using two distinct culture media. The first culture medium, defined CM1 “inoculum”, was used for the preparation of the inoculum. The second culture medium, defined CM2 “batch”, was used for unfed batch growth of the microorganism with octanoic acid in the Fernbach flasks.

[0060] The composition in grams per liter of the two media is described in the table below:

TABLE-US-00001 CM1 CM2 “inoculum” “batch” (NH.sub.4).sub.2SO.sub.4 4.7 5.02 Na.sub.2HPO.sub.4•7H.sub.2O 12 2.24 KH.sub.2PO.sub.4 2.7 0.5 Glucose 9 3.9 MgSO.sub.4•7H.sub.2O 0.8 1.03 Citric acid 1.6 1.03 Nutrient Broth (1) 1 / Octanoic acid / 3.8 Solution Microelements (2) / 1.4 2N NaOH q.s. for pH = 6.8 Water q.s. for 1000 g (1) The composition of the Nutrient Broth, as percentage by weight, is 37.5% beef extract and 62.5% peptone. Reference 233000 DIFCO ™. (2) The composition of the solution of microelements in grams per liter is described in the table below:

TABLE-US-00002 FeSO.sub.4•7H.sub.2O 10.0 g CaCl.sub.2•2H.sub.2O 3.0 g ZnSO.sub.4•7H.sub.2O 2.2 g MnSO.sub.4•4H.sub.2O 0.5 g H.sub.3BO.sub.3 0 3 g CoCl.sub.2•6H.sub.2O 0.2 g Na.sub.2MoO.sub.4•2H.sub.2O 0.15 g NiCl.sub.2•6H.sub.2O 0.02 g CuSO.sub.4•5H.sub.2O 1.00 g 0.5N HCl q.s. for 1000 g

[0061] 100 ml of inoculum were prepared by suspending a cryotube containing 1 ml of the strain with 100 ml of “inoculum” culture medium at a pH adjusted to 6.8 with 2N NaOH in a 250 ml Fernbach flask and then incubated at 30° C. at 150 rev/min for 24 h. 1.9 l of CM2 culture medium “BATCH” placed in a presterilized 5 l Fernbach flask were inoculated at OD=0.1 with 100 ml of inoculum. After 70 hours at 30° C. at 110 rev/min, the biomass was dried by lyophilization before being extracted with dichloromethane for 24 h. The suspension was clarified by filtration on a GF/A filter (Whatman®). The filtrate, containing the copolymer in solution in the dichloromethane, was concentrated by evaporation and then dried under high vacuum at 40° C. to constant weight. The crude polyhydroxyalkanoate was purified by precipitation of a solution of the latter in solution in 10 times its weight of dichloromethane from 10 volumes of the solution of cold methanol. The solid obtained was dried under high vacuum at 40° C. to constant weight.

[0062] The molecular weight of the polyhydroxyalkanoate obtained was characterized by size exclusion chromatography, refractive index detection. [0063] Eluent: THF [0064] Analytical flow: 1 ml/min [0065] Injection: 100 μl [0066] Columns: 1 Agilent PLGel Mixed-D column 5 μm; 300×7.5 mm; 1 Agilent PLGel Mixed-C column 5 μm; 300×7.5 mm; 1 Agilent Oligopore column; 300×7.5 mm [0067] at ambient temperature (25° C.) [0068] Detection: Waters 2487 Dual I Absorbance Detector, Waters 2414 Refractive Index Detector [0069] Integrator: refractive index at 45° C. and 64 mV [0070] Empower (GPC Module Relative/conventional molar mass) [0071] Injection time Empower 40 min [0072] Standards: High-weight polystyrene/EasiVial PS-H 4 ml from Agilent Technology Part No. PL2010-0200

[0073] The analysis makes it possible to measure the weight-average molecular weight (Mw in g/mol), the number-average molecular weight (Mn in g/mol), the polydispersity index PI (Mw/Mn) and the degree of polymerization DPn.

[0074] The monomeric composition of the polyhydroxyalkanoate obtained was defined by gas chromatography equipped with a flame ionization detector.

[0075] The identification is carried out via the injection of commercial standards and the monomeric composition was determined by methanolysis and silylation treatment.

[0076] In order to determine the monomeric composition, 7 mg of the polyhydroxyalkanoate polymer were dissolved in 1.5 ml of chloroform and were methanolyzed in the presence of 1.5 ml of a MeOH/HCl (17/2, v/v) solution at 100° C. for 4 h. The organic phase was subsequently washed with 1 ml of water and then dried over MgSO.sub.4. The silylation of the methyl esters formed was carried out by adding 100 μl of BSTFA (N,O-bis(trimethylsilyl)trifluoroacetamide) and 100 μl of pyridine to the methylated sample. The solution was heated at 70° C. for 1 h and then evaporated to dryness. The sample was then dissolved in 600 μl of dichloromethane and analyzed by chromatography under the following conditions: [0077] Hewlett Packard 6890 Series appliance [0078] Stationary phase column ZB-5 HT from Phenomenex (length: 30 m, diameter: 0.25 mm) [0079] Temperature: isothermal 60° C. to 300° C. in 6 min (heating rate: 10° C./min) [0080] Gas: Helium; flow rate: 0.8 ml/min [0081] Injector: Temperature: 250° C.; 50 ml/min [0082] Flame ionization detector; Temperature: 300° C. [0083] Injection: Volume 1 μl

[0084] A copolymer containing 91% by weight of poly(3-hydroxyoctanoate), 6% by weight of poly(3-hydroxyhexanoate) and 3% by weight of poly(3-hydroxybutanoate) was thus obtained. [0085] Mn=68 100 g/mol [0086] Mw=149 100 g/mol [0087] PI=2.2 [0088] DPn=531

Example 2

[0089] A polymer was prepared using the Pseudomonas putida KT2440 ATCC® 47054™ microorganism, octanoic acid and acrylic acid.

[0090] The culturing method was carried out under continuous axenic conditions at a dilution of D=0.25 h.sup.−1 in a 3 l chemostat containing 1.1 l of culture medium. The system was aerated with air at a flow rate of 3 vvm (vvm=volume of air per volume of fermentation medium per minute) for a dissolved oxygen (DO) setpoint at 30% saturation.

[0091] The procurement process was carried out using three distinct culture media. The first undefined culture medium (CM1) was used for the preparation of the inoculum. The second defined culture medium (CM2) was used for the unfed batch growth of the microorganism in the fermenter. The third defined culture medium (CM3) was used for the feeding, or maintenance, of the continuous fermentation containing octanoic acid and acrylic acid (inhibitor of the β-oxidation pathway).

[0092] The CM1 and CM2 media are identical to those described in example 1. The composition in grams per liter of the CM3 medium is described in the table below:

TABLE-US-00003 CM3“cotinuous” (NH.sub.4).sub.2SO.sub.4 5.02 Na.sub.2HPO.sub.4•7H.sub.2O 2.24 KH.sub.2PO.sub.4 0.5 Glucose 3 MgSO.sub.4•7H.sub.2O 1.03 Citric acid 1.03 Nutrient Broth (1) / Octanoic acid 3.8 Solution Microelements (2) 1.4 Acrylic acid 0.2 2N NaOH q.s. for pH = 6.8 Water q.s. for 1000 g

[0093] 100 ml of inoculum were prepared by suspending a cryotube containing 1 ml of the strain with 100 ml of Nutrient Broth at a pH adjusted to 7.0 with 2N NaOH in a 250 ml Fernbach flask and were then incubated at 30° C. at 150 rev/min for 24 h.

[0094] The fermenter containing 1 liter of CM2 culture medium at 30° C. was inoculated at an optical density of 0.1 at 630 nm (OD.sub.630=0.1). The system was maintained at 30° C. with stirring of 700+/−200 rev/min and adjusted in cascade with oxygenation for approximately 16 h and/or the time that the microorganism can reach its growth plateau.

[0095] Feeding the fermenter with the CM3 medium was initiated when the microorganism reached its growth plateau and withdrawal was carried out in order to retain the initial weight of fermentation medium. Once the equilibrium state was reached in continuous culture, a fraction of the withdrawn material was centrifuged in order to separate the biomass from the fermentation medium. The biomass was dried by lyophilization and then extracted with dichloromethane for 24 h. The suspension obtained was clarified by filtration on a GF/A filter (Whatman®). The filtrate obtained, comprising the copolymer in solution in the dichloromethane, was concentrated by evaporation and then dried under high vacuum at 40° C. to constant weight. The crude polyhydroxyalkanoate was purified by precipitation of a solution of the latter in solution in 10 times its weight of dichloromethane from 10 volumes of the solution of cold methanol. The solid obtained was dried under high vacuum at 40° C. to constant weight.

[0096] A copolymer comprising 96% by weight of poly(3-hydroxyoctanoate), 3% by weight of poly(3-hydroxyhexanoate) and 1% by weight of poly(3-hydroxybutanoate) was thus obtained. [0097] Mn=67 900 g/mol [0098] Mw=142 000 g/mol [0099] PI=2.1 [0100] DPn=611

Example 3

[0101] A polymer was prepared according to the procedure of example 2 using nonanoic acid (instead of octanoic acid).

[0102] A copolymer comprising 86% by weight of poly(3-hydroxynonanoate), 9% by weight of poly(3-hydroxyheptanoate) and 5% by weight of poly(3-hydroxypentanoate) was thus obtained. [0103] Mn=65 900 g/mol [0104] Mw=143 600 g/mol [0105] PI=2.2 [0106] DPn=531

Example 4

[0107] A polymer was prepared according to the procedure of example 2 using nonanoic acid (instead of octanoic acid) and without acrylic acid.

[0108] A copolymer comprising 68% by weight of poly(3-hydroxynonanoate), 27% by weight of poly(3-hydroxyheptanoate) and 5% by weight of poly(3-hydroxypentanoate) was thus obtained. [0109] Mn=55 800 g/mol [0110] Mw=124 500 g/mol [0111] PI=2.2 [0112] DPn=469

Example 5

[0113] A polymer was prepared according to the procedure of example 2 using dodecanoic acid (instead of octanoic acid).

[0114] A copolymer comprising 44% by weight of poly(3-hydroxydodecanoate), 38% by weight of poly(3-hydroxydecanoate) and 18% by weight of poly(3-hydroxyoctanoate) was obtained. [0115] Mn=67 400 g/mol [0116] Mw=129 800 g/mol [0117] PI=1.9 [0118] DPn=484

Example 6 (Outside the Invention)

[0119] A copolymer was prepared using the Pseudomonas resinovorans ATCC® 14235™ microorganism, hexanoic acid and acrylic acid according to the procedure of example 2.

[0120] The composition of the solution of microelements which is used, in grams per liter, is described in the table below:

TABLE-US-00004 ZnSO.sub.4•7H.sub.2O 0.1 g MnCl.sub.2•H.sub.2O 0.03 g H.sub.3BO.sub.3 0.3 g CoCl.sub.2•6H.sub.2O 0.2 g Na.sub.2MoO.sub.4•2H.sub.2O 0.03 g NiCl.sub.2•6H.sub.2O 0.02 g CuSO.sub.4•5H.sub.2O 0.01 g 0.5N HCl q.s. for 1000 g

[0121] A copolymer comprising 95% by weight of poly(3-hydroxyhexanoate) and 5% by weight of poly(3-hydroxyoctanoate) was thus obtained. [0122] Mn=107 200 g/mol [0123] Mw=219 100 g/mol [0124] PI=2 [0125] DPn=1227

Example 7 (Outside the Invention)

[0126] A polymer was prepared according to the procedure of example 2 using heptanoic acid (instead of octanoic acid).

[0127] A copolymer comprising 96% by weight of poly(3-hydroxyheptanoate) and 4% by weight of poly(3-hydroxypentanoate) was thus obtained. [0128] Mn=83 600 g/mol [0129] Mw=184 200 g/mol [0130] PI=2.2 [0131] DPn=845

Example 8: Test of Solubility in Oils

[0132] The solubility in various oils, which are described in the table below, of the polymers of examples 1 to 7, as well as 3 commercial polymers A to C described below, was evaluated.

[0133] 1 g of polymer was introduced into 9 g of oil in a flask, the mixture was heated at 70° C. with stirring for 1 h, the flask was then placed at ambient temperature for 24 h and the solubility of the polymer in the mixture was observed with the naked eye.

[0134] The test was also carried out with 3 commercial polymers outside the invention:

[0135] Polymer A: poly(3-hydroxybutanoate), sold under the reference 363502 Aldrich by Sigma-Aldrich

[0136] Polymer B: poly(3-hydroxybutanoate)-co-(3-hydroxyvalerate), the 3-hydroxyvalerate unit being present at 12 mol %, sold under the reference 403121 Aldrich by Sigma-Aldrich

[0137] Polymer C: poly(3-hydroxybutanoate)-co-(3-hydroxyvalerate), the 3-hydroxyvalerate unit being present at 8 mol %, sold under the reference 403105 Aldrich by Sigma-Aldrich

[0138] The following results were obtained:

TABLE-US-00005 Ex 1 Ex 2 Ex 3 Ex 4 Ex 5 Ex 6 Ex 7 A B C Isododecane − − + + + − − − − − Isododecane/ + + + + + − − − − − ethanol 97/3 Cetiol UT − − + + Dodecane − + + Parleam − − − − + − − − − − Parleam/ − − − − + − − − − − ethanol 97/3 isononyl + + + + + − − − − − isononanoate Olive oil + + + + + − − − − − Camelina oil + Dicaprylyl + carbonate Silicone L5 − − − − − − − − − − Cetiol UT: undecane/tridecane mixture from BASF Parleam: hydrogenated polyisobutene from NOF Corporation Silicone L5: dodecamethylpentasiloxane + means that the polymer is soluble in the oil tested: the mixture is homogeneous, clear and stable for one month at ambient temperature − means that the polymer is not soluble in the oil tested: the mixture is not homogeneous and the polymer precipitates or else the mixture is cloudy

[0139] The solubility test for the polymer of example 2 was supplemented with other oils described in the table below. The following results were obtained:

TABLE-US-00006 Ex 2 squalane − C.sub.15-C.sub.19 Alkane − Octyldodecanol − Isododecane/butan-1-ol + 97/3

Example 11: Evaluation of the Film-Forming and Cosmetic Properties

[0140] A solution of polymer (polymer of the examples at 10% by weight in isododecane) to be evaluated was deposited on a contrast chart (for example that sold under the reference byko-charts by BYK-Gardner) with a film drawer (speed: 50 mm/s-wet deposit 100 μm thick) and the deposited film was dried for 24 hours at ambient temperature (25° C.). The dry film has a thickness of approximately 10 μm.

[0141] The gloss of the film was measured using a glossmeter (three angles Refo 3/Refo 3D from De Lange, Labomat distributor) on the black part of the contrast chart at an angle of 20°.

[0142] The resistance of the film obtained was evaluated by separately depositing, on the dry film, two drops (one drop=10 μl) of olive oil and two drops of sebum on the black part of the contrast chart. The drops were left in contact with the dry film for 5 minutes and 30 minutes respectively and subsequently the drop of oil was wiped off and the appearance of the region of the film which was in contact with the oil was observed. If the film was damaged by the drop deposited, the polymer film is regarded is being non-resistant to olive oil and/or to sebum.

[0143] The tacky aspect of the polymer film was evaluated by touching the dry film with a finger. The following results were obtained:

TABLE-US-00007 Polymer Polymer Polymer Polymer Polymer Property Example 1 Example 2 Example 3 Example 4 Example 5 Resistance to Good Good Good Good Good Olive oil resistance resistance resistance resistance resistance Resistance Good Good Good Good Good to sebum resistance resistance resistance resistance resistance Gloss Matt film Matt film Matt film Matt film Matt film Tacky Non-tacky Non-tacky Non-tacky Non-tacky Non-tacky

[0144] The results obtained show that the five polymers according to the invention are film-forming and the film obtained is non-tacky, is matt in appearance and exhibits good resistance to oil and to sebum.

Example 12: Cosmetic Evaluation of Makeup Compositions

[0145] A makeup composition (lipstick) described below was prepared:

TABLE-US-00008 Polymer of the invention 20%  Pigment paste comprising 40% by weight 5% of pigment DC Red 7 in isododecane Isododecane q.s. for 100%

[0146] The composition was prepared with each polymer of examples 1 to 5.

[0147] Each composition was applied on a skin equivalent support made of elastomer by producing a deposited layer with a wet thickness of 100 μm, which was left to dry at ambient temperature (25° C.) for 24 hours.

[0148] The resistance of the film obtained was evaluated by separately applying 0.5 ml of olive oil and 0.5 ml of sebum; after 5 minutes of contact, the surface of the film was rubbed with a cotton swab, 25 passes of the cotton swab over the surface being carried out, and then the state of the film was observed (degraded or undegraded appearance of the film).

[0149] The resistance of the film to Scotch tape was also evaluated:

[0150] A piece of Scotch tape (Scotch® Magic™ 810 from 3M; w=19 mm, l=5 cm) was applied to the dry film. A weight of approximately 1070 g (with a surface area of 65*55 mm) was placed on the piece of Scotch tape for 30 seconds. The Scotch tape was subsequently removed and subsequently deposited on a microscope slide in order to observe the adherent surface of the Scotch tape applied and to see if it contains traces of the dry polymer film. The following results were obtained:

TABLE-US-00009 Polymer Polymer Polymer Polymer Polymer Property Example 1 Example 2 Example 3 Example 4 Example 5 Resistance to Good Good Good Good Good olive oil resistance resistance resistance resistance resistance Resistance to Good Good Good Good Good sebum resistance resistance resistance resistance resistance Scotch tape Good Good Good Good Good test resistance resistance resistance resistance resistance

[0151] The results obtained show that the compositions according to the invention exhibit good resistance to oil and to sebum and a good persistence (resistance to Scotch tape).

[0152] The lipstick composition applied to the lips thus makes it possible to obtain makeup which is resistant to oil and to sebum, thus exhibiting a good persistence.