Cosmetic or dermatological composition comprising a merocyanine and an oily phase comprising at least one isosorbide ether

Abstract

The present invention relates to an in particular cosmetic or dermatological composition comprising, in a physiologically acceptable support: a) at least one merocyanine of formula (1) or (2), b) at least one oily phase comprising at least one isosorbide ether. The present invention also relates to a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of the said keratin material, of at least one composition as defined above. The invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously. The invention also relates to a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously. ##STR00001##

Claims

1. A cosmetic or dermatological composition comprising, in a physiologically acceptable medium: a) at least one merocyanine corresponding to one of the following formulae (1) and (2) or one of the E/E- or E/Z-geometrical isomer forms thereof: ##STR00061## in which: R.sub.1 and R.sub.2 are, independently of each other, hydrogen; a C.sub.1-C.sub.22 alkyl group, a C.sub.2-C.sub.22 alkenyl group or a C.sub.2-C.sub.22 alkynyl group, optionally these groups are substituted with at least one hydroxyl group or optionally interrupted with at least one O; or alternatively R.sub.1 and R.sub.2 form, together with the nitrogen atom which connects them, a (CH.sub.2).sub.n ring which may optionally be interrupted with O or NH; R.sub.3 is a group (CO)OR.sub.6 or a group (CO)NHR.sub.6; R.sub.6 is a C.sub.1-C.sub.22 alkyl group, a C.sub.2-C.sub.22 alkenyl group, a C.sub.2-C.sub.22 alkynyl group, a C.sub.3-C.sub.22 cycloalkyl group or a C.sub.3-C.sub.22 cycloalkenyl group, optionally the said groups are substituted with one or more OH groups; R.sub.4 and R.sub.5 are hydrogens; or R.sub.4 and R.sub.5 form a (CH.sub.2).sub.n ring which optionally may be substituted with a C.sub.1-C.sub.4 alkyl group and/or interrupted with one or more O or with NH; R.sub.7 and R.sub.8 are, independently of each other, hydrogen; a C.sub.1-C.sub.22 alkyl group, a C.sub.2-C.sub.22 alkenyl group or a C.sub.2-C.sub.22 alkynyl group, optionally the said groups be interrupted with one or more O and/or substituted with one or more OH groups; a C.sub.3-C.sub.22 cycloalkyl group or a C.sub.3-C.sub.22 cycloalkenyl group, optionally the said groups are interrupted with one or more O; or alternatively R.sub.7 and R.sub.8 form, together with the nitrogen which connects them, a (CH.sub.2).sub.n ring which optionally may be interrupted with one or more O; R.sub.9 and R.sub.10 are hydrogen; or R.sub.9 and R.sub.10 form a (CH.sub.2).sub.n ring which optionally may be substituted with a C.sub.1-C.sub.4 alkyl and/or interrupted with an O or NH; A is O or NH; R.sub.11 is a C.sub.1-C.sub.22 alkyl group; a C.sub.2-C.sub.22 alkenyl group; a C.sub.2-C.sub.22 alkynyl group; a C.sub.3-C.sub.22 cycloalkyl group or a C.sub.3-C.sub.22 cycloalkenyl group, optionally the said groups are interrupted with one or more O; or a C.sub.1-C.sub.22 alkyl group or a C.sub.2-C.sub.22 alkenyl group which is substituted with a C.sub.3-C.sub.22 cycloalkyl group or a C.sub.3-C.sub.22 cycloalkenyl group, optionally the said C.sub.3-C.sub.22 cycloalkyl group or C.sub.3-C.sub.22 cycloalkenyl group is interrupted with one or more O; and n is a number between 2 and 7; and b) at least one oily phase comprising at least one isosorbide ether.

2. The composition according to claim 1, in which the compounds of formula (1) are chosen from those for which: R.sub.6 is a C.sub.1-C.sub.12 alkyl group which optionally may be substituted with one or more hydroxyls.

3. The composition according to claim 1, in which the compounds of formula (1) are chosen from those for which: R.sub.6 is a C.sub.1-C.sub.12 alkyl group which optionally may be substituted with one or more hydroxyls; one of the radicals R.sub.1 or R.sub.2 is a C.sub.4-C.sub.22 alkyl group; or alternatively R.sub.1 and R.sub.2 form, together with the nitrogen which connects them, a (CH.sub.2).sub.n ring which optionally may be interrupted with O and/or NH.

4. The composition according to claim 1, in which the compounds of formula (2) are chosen from those for which: R.sub.11 is a radical (CH.sub.2).sub.mOR.sub.12, in which R.sub.12 is a C.sub.1-C.sub.12 alkyl group or a C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl group; m is a number from 1 to 5.

5. The composition according to claim 1, in which the compounds of formula (1) or (2) are chosen from those for which: R.sub.1 and R.sub.2, on the one hand, and R.sub.7 and R.sub.8, on the other hand, respectively form, together with the nitrogen atom to which they are respectively attached, a piperidyl radical or a morpholinyl radical.

6. The composition according to claim 1, in which the compounds of formula (1) or (2) are chosen from those for which: R.sub.4 and R.sub.5 and R.sub.9 and R.sub.10 respectively form a carbon-based ring which contains 6 carbon atoms.

7. The composition according to claim 1, in which the compounds of formula (1) are chosen from those for which: R.sub.1 and R.sub.2 are, independently of each other, a hydrogen; or a C.sub.1-C.sub.22 alkyl group; or a C.sub.1-C.sub.22 hydroxyalkyl group; or R.sub.1 and R.sub.2 form, together with the nitrogen to which they are attached, a piperidyl or morpholinyl radical; R.sub.3 is a group (CO)OR.sub.6 or a group (CO)NHR.sub.6; R.sub.6 is a C.sub.1-C.sub.22 alkyl group which optionally may be substituted with one or more OH groups; R.sub.4 and R.sub.5 are a hydrogen; or R.sub.4 and R.sub.5 are linked together to form a carbon-based ring which contains 6 carbon atoms.

8. The composition according to claim 1, in which the compounds of formula (1) are chosen from those for which: R.sub.1 and R.sub.2 are, independently of each other, a hydrogen; or a C.sub.1-C.sub.22 hydroxyalkyl group; in which at least one of the R.sub.1 and R.sub.2 radicals is a C.sub.1-C.sub.22 hydroxyalkyl group; R.sub.3 is a group (CO)OR.sub.6 or a group (CO)NHR.sub.6; R.sub.6 is a C.sub.1-C.sub.12 alkyl group; R.sub.4 and R.sub.5 are hydrogens; or R.sub.4 and R.sub.5 are linked together to form a carbon-based ring which contains 6 carbon atoms.

9. The composition according to claim 1, in which the compounds of formula (2) are chosen from those for which: R.sub.7 and R.sub.8 are, independently of each other, a hydrogen or a C.sub.1-C.sub.8 alkyl group which optionally may be interrupted with one or more O; A is O or NH; R.sub.11 is a C.sub.1-C.sub.22 alkyl; and R.sub.9 and R.sub.10 are a hydrogen; or R.sub.9 and R.sub.10 are linked together to form a carbon-based ring which contains 6 carbon atoms.

10. The composition according to claim 1, in which the compounds of formula (2) are chosen from those for which: R.sub.7 and R.sub.8 form, together with the nitrogen atom to which they are attached, a morpholinyl or piperidyl radical; A is O or NH; R.sub.11 is a C.sub.1-C.sub.22 alkyl group which optionally may be interrupted with one or more O; and R.sub.9 and R.sub.10 are hydrogens; or R.sub.9 and R.sub.10 are linked together to form a carbon-based ring which contains 6 carbon atoms.

11. The composition according to claim 1, in which the compounds of formula (2) are chosen from those for which: R.sub.11 is a radical (CH.sub.2).sub.mOR.sub.12, in which R.sub.12 is a C.sub.1-C.sub.4 alkyl group or a C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl group; m is a number from 1 to 3; R.sub.7 and R.sub.8 are, independently of each other, a hydrogen; a C.sub.1-C.sub.12 alkyl group which optionally may be interrupted with one or more 0; or R.sub.7 and R.sub.8 form, together with the nitrogen atom to which they are attached, a morpholinyl or piperidyl radical; R.sub.9 and R.sub.10 are hydrogens or together form a carbon-based ring which contains 6 carbon atoms; and A is O or NH.

12. The composition according to claim 1, in which the compounds of formula (1) or (2) are chosen from the following compounds and also the E/E- or E/Z-geometrical isomer forms thereof: TABLE-US-00008 TABLE A Compound Structure 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47

13. The composition according to claim 1, in which the compounds of formula (1) or (2) are chosen from those corresponding to the following formula (3) and the E/E- or E/Z-geometrical isomer forms thereof: ##STR00109## in which: A is O or NH; R is a C.sub.1-C.sub.22 alkyl group, a C.sub.2-C.sub.22 alkenyl group, a C.sub.2-C.sub.22 alkynyl group, a C.sub.3-C.sub.22 cycloalkyl group or a C.sub.3-C.sub.22 cycloalkenyl group, the said groups optionally are interrupted with one or more O.

14. The composition according to claim 13, in which the merocyanines of formula (3) are chosen from the following compounds and also the E/E- or E/Z-geometrical isomer forms thereof: ##STR00110##

15. The composition according to claim 14, in which the merocyanine of formula (3) is the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (25) in its E/Z geometrical configuration having the following structure: ##STR00111## and/or the E/E form having the following structure: ##STR00112##

16. The composition according to claim 1, in which the at least one merocyanine is present in a concentration ranging from 0.1% to 10% by weight relative to the total weight of the composition.

17. The composition according to claim 1, in which the isosorbide ether is chosen from isosorbide (C1-C4) alkyls.

18. The composition according to claim 1, in which the isosorbide ether is dimethyl isosorbide.

19. The composition according to claim 1, in which the at least one isosorbide ether is present in a concentration ranging from 0.1% to 98% by weight relative to the total weight of the composition.

20. A non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of the said keratin material, of at least one composition as defined in claim 1.

21. A non-therapeutic cosmetic process for improving the colour and/or uniformity of the complexion, comprising the application, to the surface of a keratin material, of at least one composition as defined in claim 1.

22. A non-therapeutic cosmetic process for treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined in claim 1.

23. The composition according to claim 1, in which the at least one merocyanine is present in a concentration ranging from 0.1% to 10% by weight relative to the total weight of the composition and at least one isosorbide ether is present in a concentration ranging from 1% to 20% by weight relative to the total weight of the composition.

24. The composition according to claim 1, in which the isosorbide ether is chosen from isosorbide di(C1-C4) alkyls.

25. The composition according to claim 1, which further comprises at least one additional UV-screening agent.

Description

EXAMPLE A1: PREPARATION OF COMPOUND (14)

(1) ##STR00057##

(2) 122.23 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 g of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally of a solvent.

(3) The following base/solvent combinations are used:

(4) TABLE-US-00002 Example Base Solvent Example A1.1 DBU (1,8-diazabicyclo[5.4.0] dimethylacetamide undec-7-ene) Example A1.2 triethylamine isopropanol Example A1.3 3-methoxypropylamine isopropanol Example A1.4 3-methoxypropylamine tert-amyl alcohol Example A1.5 3-methoxypropylamine toluene Example A1.6 3-methoxypropylamine dimethylformamide Example A1.7 3-methoxypropylamine no solvent Example A1.8 N-morpholine isopropanol

(5) The completion of the alkylation reaction can be monitored, for example, via methods such as TLC, GC or HPLC.

(6) 162.30 g of compound (14) are obtained in the form of a brown oil.

(7) After crystallization, the product is obtained in the form of yellowish crystals.

(8) Melting point: 92.7 C.

EXAMPLE A2: PREPARATION OF COMPOUND (15)

(9) ##STR00058##

(10) 101.00 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 g of 2-cyano-N-(3-methoxypropyl)acetamide in approximately equimolar proportions in the presence of a base and optionally of a solvent. The following base/solvent combinations are used:

(11) TABLE-US-00003 Example Base Solvent Example A2.1 DBU (1,8-diazabicyclo[5.4.0] dimethylacetamide undec-7-ene) Example A2.2 triethylamine isopropanol Example A2.3 3-methoxypropylamine isopropanol Example A2.4 3-methoxypropylamine tert-amyl alcohol Example A2.5 3-methoxypropylamine toluene Example A2.6 3-methoxypropylamine dimethylformamide Example A2.7 3-methoxypropylamine no solvent

(12) The crude product (15) is obtained in the form of a dark brown oil.

(13) After chromatography on a column of silica gel (eluent: 99/1 toluene/methanol), 81.8 g of product are obtained in the form of yellowish crystals.

(14) Melting point: 84.7-85.3 C.

EXAMPLE A3: PREPARATION OF COMPOUND (27)

(15) ##STR00059##

(16) 13.09 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 10.12 g of isobutyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally of a solvent.

(17) The following base/solvent combinations are used:

(18) TABLE-US-00004 Example Base Solvent Example A3.1 DBU (1,8-diazabicyclo[5.4.0] dimethylacetamide undec-7-ene) Example A3.2 triethylamine isopropanol Example A3.3 3-methoxypropylamine isopropanol Example A3.4 N-methylmorpholine tert-amyl alcohol Example A3.5 3-methoxypropylamine toluene Example A3.6 3-methoxypropylamine dimethylformamide Example A3.7 3-methoxypropylamine no solvent

(19) 15.97 g of the crude product (27) are obtained in the form of a dark brown oil.

(20) After chromatography on a column of silica gel (eluent: toluene/acetone), 13.46 g of product are obtained in the form of yellowish crystals.

(21) Melting point: 96.3 C.

EXAMPLE A4: PREPARATION OF COMPOUND (25)

(22) ##STR00060##

(23) 148.4 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 g of 2-ethoxyethyl cyanoacetate in the presence of a base and a solvent.

(24) The following base/solvent combinations are used:

(25) TABLE-US-00005 Example Base Solvent Example A4.1 DBU (1,8-diazabicyclo[5.4.0] dimethylacetamide undec-7-ene) Example A4.2 triethylamine isopropanol Example A4.3 3-methoxypropylamine isopropanol Example A4.4 N-methylmorpholine tert-amyl alcohol Example A4.5 3-methoxypropylamine toluene Example A4.6 3-methoxypropylamine dimethylformamide Example A4.7 3-methoxypropylamine no solvent

FORMULATION EXAMPLES

Examples 1 to 3: Oily Solutions

(26) The following oily solutions were prepared according to the processes described below.

(27) TABLE-US-00006 Formula 1 Formula 2 Formula 3 (outside Ingredients (invention) (invention) the invention) Compound (25) 10 5 5 Dimethyl isosorbide 90 95 C12-15 alkyl benzoate 95 (Finsolv TN) Solubility at t.sub.0 Soluble Soluble Insoluble Solubility at t.sub.3M Soluble Soluble Insoluble
Oil Preparation Method:

(28) The compositions described in Examples 1 and 3 are prepared in the following manner: the screening agents and the oil are introduced successively into a container, followed by stirring using a magnetic stirrer and heating to 90 C. for between 10 minutes and 1 hour, until the merocyanine has dissolved.

(29) Solubility Evaluation Protocol

(30) The solubility of the merocyanine in the oily solutions is evaluated macroscopically and microscopically. It is estimated that the merocyanine is soluble if, at room temperature, the solution appears clear and translucent to the eye, and if it does not have any visible crystals under a microscope in white or polarized light (20 to 40 objective lens). The solubility is evaluated at room temperature, on the day of the preparation of the solution (solubility at to), and 3 months after its preparation (solubility at t.sub.3m). During this interval, the solutions are stored at room temperature.

Examples 4 and 5

(31) The following two compositions were prepared:

(32) TABLE-US-00007 Example 4 (outside Example 5 Ingredients the invention) (invention) Compound (25) 8.36 8.36 Uvinul A Plus 5.57 5.57 Uvinul T 150 11.14 11.14 Silatrizole 22.28 22.28 Tinosorb S 8.36 8.36 Preserving agent 1.67 1.67 Preserving agent 0.84 0.84 Dimethyl isosorbide 41.78 Isopropyl lauroyl sarcosinate 41.78 (Eldew SL 205) Stability at room temperature (no 2 days >2 months recrystallization)
Protocol for Evaluating the Maintenance of Solubility of the Formulation

(33) The maintenance of solubility of merocyanine is evaluated by observing the emulsions using a polarized-light microscope with a 20 objective lens. The solubility is considered to be maintained if no crystals are seen under the polarized light after storage of the formulation for 2 months at room temperature.

(34) These results show that dimethyl isosorbide makes it possible to maintain the solubility of merocyanine even in the presence of additional UV-screening agents.