Cosmetic or dermatological composition comprising a merocyanine and an oily phase comprising at least one alkyl or alkylene carbonate

Abstract

A cosmetic or dermatological composition comprising: a) at least one merocyanine of formula (1) or (2) ##STR00001## b) at least one oily phase comprising at least one alkyl or alkylene carbonate is provided. Also provided is a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising applying to the surface of the keratin material, of at least one of the above compositions. Also provided is a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising applying to the surface of the keratin material, of at least one of the above compositions. In addition, provided is a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising applying to the surface of the keratin material, of at least one of the above compositions.

Claims

1. A cosmetic or dermatological composition comprising: a) at least one merocyanine corresponding to either of formulae (1) and (2) below or an E/E- or E/Z-geometrical isomer form thereof: ##STR00060## in which: R.sub.1 and R.sub.2, independently of each other, are 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, these groups possibly being substituted with at least one hydroxyl group or else interrupted with at least one —O—; or else R.sub.1 and R.sub.2 form, together with the nitrogen atom which links them, a —(CH.sub.2).sub.n— ring which may be optionally interrupted with —O— or —NH—; R.sub.3 is a —(C═O)OR.sub.6 group; or a —(CO)NHR.sub.6 group; 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, said groups possibly being substituted with one or more OH; 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 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, independently of each other, are hydrogen; 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, said groups possibly being interrupted with one or more O and/or substituted with one or more OH; a C.sub.3-C.sub.22 cycloalkyl group or a C.sub.3-C.sub.22 cycloalkenyl group, said groups possibly being interrupted with one or more —O—; or else R.sub.7 and R.sub.8 form, together with the nitrogen which links them, a —(CH.sub.2).sub.n ring which 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 potentially 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, said groups possibly being 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, said C.sub.3-C.sub.22 cycloalkyl group or C.sub.3-C.sub.22 cycloalkenyl group possibly being interrupted with one or more —O—; n is a number between 2 and 7; and, b) at least one oily phase comprising at least one alkyl or alkylene carbonate.

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 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 may be substituted with one or more hydroxyls; one of the R.sub.1 or R.sub.2 radicals is a C.sub.4-C.sub.22 alkyl group; or else R.sub.1 and R.sub.2 form, together with the nitrogen which links them, a —(CH.sub.2).sub.n— ring which may be interrupted with —O— and/or —NH—; and R.sub.4 and R.sub.5 and n have the same meanings indicated in claim 1.

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 —(CH.sub.2).sub.m—O—R.sub.12 radical, 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 bonded, 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, independently of each other, are 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 atom to which they are bonded, a piperidyl or morpholinyl radical; R.sub.3 is a —(C═O)OR.sub.6 group; or a —(CO)NHR.sub.6 group; R.sub.6 is a C.sub.1-C.sub.22 alkyl group, which may be substituted with one or more —OH; R.sub.4 and R.sub.5 are 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, independently of each other, are 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 —(C═O)OR.sub.6 group; or a —(C═O)NHR.sub.6 group; 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 bonded 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, independently of each other, are a hydrogen or a C.sub.1-C.sub.8 alkyl group, which 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 bonded 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 bonded, a morpholinyl or piperidyl radical; A is —O—; or —NH; R.sub.H is a C.sub.1-C.sub.22 alkyl group, which 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 bonded 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 —(CH.sub.2).sub.m—O—R.sub.12 radical, 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; and R.sub.7 and R.sub.8, independently of each other, are hydrogen; or a C.sub.1-C.sub.12 alkyl group, which may be interrupted with one or more O; or R.sub.7 and R.sub.8 form, together with the nitrogen atom to which they are bonded, 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-00006 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 formula (3) below and also the E/E- or E/Z-geometrical isomer forms thereof: ##STR00108## 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, said groups possibly being 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: TABLE-US-00007 14   ethyl (2Z)-cyano{3-[(3- methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate 15   (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3- [(3-methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanamide 25   2-ethoxyethyl (2Z)-cyano{3-[(3- methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate 27   2-methylpropyl (2Z)-cyano{3-[(3- methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate 29   2-butoxyethyl (2Z)-cyano{3-[(3- methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate 31   3-methoxypropyl (2Z)-cyano{3-[(3- methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate 37   3-ethoxypropyl (2Z)-cyano{3-[(3- methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate

15. The composition according to claim 14, in which the merocyanine of formula (3) is chosen from the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (25) and/or the compound ethyl (2Z)-cyano[3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene]ethanoate (14) and mixtures thereof and preferably the compound (25).

16. The composition according to claim 1, in which the merocyanine(s) are present in a concentration ranging from 0.1% to 25% by weight relative to the total weight of the composition.

17. The composition or dermatological composition according to claim 1, comprising: a) at least a merocyanine corresponding to formula (3) and also the E/E- or E/Z-geometrical isomer forms: ##STR00116## in which: A is —O— or —NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more O; b) at least one oily phase comprising at least one alkyl or alkylene carbonate, present in concentrations ranging from 0.1% to 98% by weight relative to the total weight of the composition.

18. The composition according to claim 1, in which the alkylene chain(s) of the alkylene carbonate(s) is (are) a C2-C6 alkyl radical; and/or in which the alkyl radical(s) of the alkyl carbonate(s) is (are) a C1-C6 alkyl radical.

19. The composition according to claim 1, in which the sum of the carbons of the alkylene chain(s) of alkylene carbonate(s) and/or the sum of the carbons of the alkyl radical(s) of alkyl carbonate(s) is (are) ranging from 2 to 6 carbon atoms.

20. The composition according to claim 1, in which the alkylene carbonate(s) are chosen from the alkylene carbonates of formula (4) below: ##STR00117## in which formula (4) R′ denotes a hydrogen atom, a linear or branched C.sub.1-C.sub.6 alkyl radical, a linear or branched C.sub.1-C.sub.4 hydroxyalkyl radical; R″ represents a hydrogen atom, a linear or branched C.sub.1-C.sub.6 alkyl radical, a linear or branched C.sub.1-C.sub.4 hydroxyalkyl radical; m is 1, 2 or 3.

21. The composition according to claim 1, in which the alkylene carbonate(s) are chosen from the alkylene carbonates of formula (4) below: ##STR00118## in which formula (4) the radical R′ represents a hydrogen atom, a linear or branched C.sub.1-C.sub.4 alkyl radical, a linear C.sub.1-C.sub.2 hydroxyalkyl radical; R″ represents a hydrogen atom, a linear or branched C.sub.1-C.sub.2 alkyl radical, a linear C.sub.1-C.sub.2 hydroxyalkyl radical, and m is 1.

22. The composition according to claim 1, in which the alkylene carbonate(s) are chosen from ethylene carbonate, propylene carbonate, 1,2-butylene carbonate and glyceryl carbonate.

23. The composition according to claim 1, in which the alkyl carbonate(s) are chosen from those of formula (5) below:
R′—O—CO—O—R″ in which formula (5) R′ denotes a linear or branched C.sub.1-C.sub.5 alkyl radical, a linear or branched C.sub.1-C.sub.4 hydroxyalkyl radical; R″ represents a linear or branched C.sub.1-C.sub.5 alkyl radical, a linear or branched C.sub.1-C.sub.4 hydroxyalkyl radical; the sum of the carbons of R′ and R″ ranging from 2 to 6.

24. The composition according to claim 1, in which the alkyl carbonate(s) are chosen from diethyl carbonate and dipropyl carbonate.

25. The composition according to claim 1, in which the alkyl or alkylene carbonate(s) are present in concentrations ranging from 0.1% to 98% by weight relative to the total weight of the composition.

26. The composition according to claim 1, further comprising an additional UV-screening agent.

27. The composition according to claim 1, in which the merocyanine(s) are present in a concentration ranging from 0.1% to 25% by weight relative to the total weight of the composition, the alkyl or alkylene carbonate(s) are present in concentrations ranging from 0.1% to 98% by weight relative to the total weight of the composition and the at least one oily phase is present in a concentration ranging from 5% to 98% by weight relative to the total weight of the composition.

28. The composition according to claim 1, in which the merocyanine(s) are present in a concentration ranging from 0.2% to 20% by weight relative to the total weight of the composition, the alkyl or alkylene carbonate(s) are present in concentrations ranging from 0.5% to 50% by weight relative to the total weight of the composition and the at least one oily phase is present in a concentration ranging from 10% to 80% by weight relative to the total weight of the composition.

29. The composition according to claim 1, in which the merocyanine(s) are present in a concentration ranging from 0.5% to 10% by weight relative to the total weight of the composition, the alkyl or alkylene carbonate(s) are present in concentrations ranging from 5% to 15% by weight relative to the total weight of the composition and the at least one oily phase is present in a concentration ranging from 10% to 80% by weight relative to the total weight of the composition.

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

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

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

Description

EXAMPLES

(1) Protocol for evaluating solubility

(2) The solubility of merocyanine in the oily solutions is evaluated macroscopically and microscopically. It is considered that the merocyanine is soluble if, at room temperature, the solution appears to the eye to be clear and translucent, and it does not have any visible crystals under a white-light or polarized-light microscope (objective ×20 to ×40). The solubility is evaluated at room temperature, on the day of preparation of the solution and then over time. During this time period, the solutions are stored at room temperature and/or at 4° C., away from the light.

Examples 1-6: Oily Compositions

(3) The following oily compositions were prepared according to the process below.

(4) TABLE-US-00002 Example 1 Example 2 Example 3 (according to the (outside the (outside the Ingredients invention) invention) invention) Compound (25) 10 10 10 Propylene carbonate 90 — Isopropyl lauroyl — — 90 sarcosinate (Eldew 205 from Ajinomoto) Dicaprylyl carbonate 90 (Cetiol CC from BASF) Solubility at room >2 months Insoluble 14 days temperature Solubility at 4° C. >2 months Insoluble  7 days Example 4 Example 5 Example 6 (according to the (outside the (outside the Ingredients invention) invention) invention) Compound (14) 10 10 10 Propylene carbonate 90 — Isopropyl lauroyl — — 90 sarcosinate (Eldew 205 from Ajinomoto) Dicaprylyl carbonate 90 (Cetiol CC from BASF) Solubility at room >2 months Insoluble 14 days temperature Solubility at 4° C. .sup. 1 month Insoluble  3 days

Examples 7-12: Oleo-Alcoholic Compositions

(5) The following compositions were prepared according to the above process.

(6) TABLE-US-00003 Example 7 Example 8 Example 9 (according to the (outside the (outside the Ingredients invention) invention) invention) Merocyanine 17   17 17   compound (25) Propylene carbonate 41.5 — Isopropyl lauroyl — 41.5 sarcosinate (Eldew 205 from Ajinomoto) Dicaprylyl carbonate — 41.5 — (Cetiol CC from BASF) Ethanol 41.5 41.5 41.5 Solubility at room >2 months 1 day 1 day temperature Solubility at 4° C. >2 months 1 day 1 day Example 10 Example 11 Example 12 (according to the (outside the (outside the Ingredients invention) invention) invention) Merocyanine 17   17 17   compound (14) Propylene carbonate 41.5 — Isopropyl lauroyl — 41.5 sarcosinate (Eldew 205 from Ajinomoto) Dicaprylyl carbonate — 41.5 — (Cetiol CC from BASF) Ethanol 41.5 41.5 41.5 Solubility at room >2 months >2 months >2 months temperature Solubility at 4° C. >2 months 3 days 3 days

Examples 13-15: Oleo-Alcoholic Compositions

(7) The following compositions were prepared according to the process below.

(8) TABLE-US-00004 Example 13 Example 14 Example 15 (according to the (outside the (outside the Ingredients invention) invention) invention) Merocyanine 20 20 20 compound (25) Propylene carbonate 40 — — Isopropyl lauroyl — 40 — sarcosinate (Eldew 205 from Ajinomoto) Dicaprylyl carbonate — — 40 (BASF) Ethanol 40 40 40 Solubility at room >2 months 1 day 1 day temperature Solubility at 4° C. >2 months 1 day 1 day
Process for preparing the oils:

(9) The compositions described in Examples 1 and 15 are prepared in the following manner: the screening agent and the oil are successively introduced into a container and are then stirred using a magnetic stirrer and heated at 90° C. for between 10 minutes and 1 hour, until the merocyanine has dissolved.

Examples 16-17: Reverse Emulsion Compositions

(10) The following compositions were prepared:

(11) TABLE-US-00005 Example 16 Example 17 (according to the (outside the Ingredients invention) invention) Polyglyceryl Polyricinoleate 3.75 3.75 Dioctyl oxide 7.5 7.5 Isopropyl palmitate 7.5 7.5 Isohexadecane 7.5 7.5 Isocetyl yl stearate 7.5 7.5 Octane-1,2-diol 0.5 0.5 Anisic acid 0.15 0.15 Propylene carbonate 5 — Isopropyl lauroyl sarcosinate (Eldew — 5 205 from Ajinomoto) Hectorite modified with 1 1 stearylbenzyldimethylammonium Merocyanine compound (25) 1 1 Deionized water qs 100% qs 100% Glycerol 6 6 Pentane-1,2-diol 2 2 Propane-1,3-diol 3 3 Citric acid monohydrate 0.1 0.1 Ethanol 5 5 Solubility at room temperature >1 month 14 days Solubility at 4° C. >1 month 14 days

(12) These results show that the alkyl or alkylene carbonate according to the invention make it possible to maintain the solubility of the merocyanine over time at room temperature and at low temperature.