Cosmetic or dermatological composition comprising a merocyanine and an oily phase comprising at least one polyalkylene glycol
10792234 ยท 2020-10-06
Assignee
Inventors
Cpc classification
A61Q17/04
HUMAN NECESSITIES
A61K8/4993
HUMAN NECESSITIES
International classification
Abstract
The present invention relates to an in particular cosmetic or dermatological compositions comprising, in a physiologically acceptable support: a) at least one merocyanine of formula (1) or (2) (1), (2) b) at least one oily phase comprising at least one polyalkylene glycol of formula (4): (4) and to their use for caring for and/or making up a keratin material. ##STR00001##
R.sub.1(OCH.sub.2CH.sub.2).sub.x(OCH(CH.sub.3)CH.sub.2).sub.yOR.sub.2(4)
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: ##STR00062## 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, it being possible for these groups to be substituted with at least one hydroxyl group or to be 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, it being possible for the said groups to be 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 may be substituted with a C.sub.1-C.sub.4 alkyl group and/or interrupted with one or more O or with NH; n is a number between 2 and 7; 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, it being possible for the said groups to 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, it being possible for the said groups to be 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 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 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, it being possible for the said groups to be 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, it being possible for the said C.sub.3-C.sub.22 cycloalkyl group or C.sub.3-C.sub.22 cycloalkenyl group to be interrupted with one or more O; and b) at least one oily phase comprising at least one polyalkylene glycol of formula (4) below:
R.sub.1(OCH.sub.2CH.sub.2).sub.x(OCH(CH.sub.3)CH.sub.2).sub.yOR.sub.2(4) in which 1) either R.sub.1 and R.sub.2 denote hydrogen, x and y, which may be identical or different, may range from 0 to 12, with x+y ranging from 3 to 15 or 2) R.sub.1 denotes a C.sub.1-C.sub.4 alkyl group, R.sub.2 denotes hydrogen and x is equal to zero and y ranges from 2 to 5 or 3) R.sub.1 denotes a linear or branched C8-C22 alkyl or alkenyl radical or mixture of radicals, a (C8-C9)alkylphenyl radical, a radical R3CONHCH2-CH2- with R3 denoting a linear or branched C9-C21 alkyl or alkenyl radical, x is an integer or decimal number (mean value) which ranges from 2 to 15, y is equal to zero and R2 represents the group CH.sub.2COOM with M denoting H, ammonium, Na, K, Li, Mg or a monoethanolamine or triethanolamine residue.
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: The composition according to claim 1, 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 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)n- ring which 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 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 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 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 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 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 1-47 having the structures identified in Table A below and also the E/E- or E/Z-geometrical isomer forms thereof: TABLE-US-00007 TABLE A Structure 1
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 also the E/E- or E/Z-geometrical isomer forms thereof: ##STR00110## 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, it being possible for the said groups to be 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 14, 15, 25, 27, 29, 31 and 37 having the structures identified in Table below and also the E/E- or E/Z-geometrical isomer forms thereof: ##STR00111## ##STR00112##
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: ##STR00113## and/or the E/E form having the following structure: ##STR00114##
16. The composition according to claim 1, in which the at least one merocyanine is present in a concentration ranging from 0.1% to 15% by weight relative to the total weight of the composition.
17. The composition according to claim 1, in which the polyalkylene glycols of formula (4) are chosen from tripropylene glycol methyl ether, polyethylene glycols containing from 3 to 10 ethylene oxide units and the compounds of formula (6)
R.sub.1OC.sub.2H.sub.4
.sub.xOCH.sub.2COOM in which R1 denotes a linear or branched C8-C18 alkyl radical or mixture of radicals, x is an integer or decimal number (mean value) which may range from 4 to 12, y is equal to zero and with M denoting H, ammonium, or Na.
18. The composition according to claim 1, in which the polyalkylene glycol of formula (4) is chosen from polyethylene glycol containing 6 ethylene oxide units (INCI name PEG-6) and polyethylene glycol containing 8 ethylene oxide units (INCI name PEG-8).
19. The composition according to claim 1, in which the at least one polyalkylene glycol of formula (4) is present in concentrations 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 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 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 0.2% to 10% by weight relative to the total weight of the composition and the at least one polyalkylene glycol of formula (4) is present in concentrations ranging from 0.5% to 40% by weight relative to the total weight of the composition.
24. The composition according to claim 1, in which the at least one merocyanine is present in a concentration ranging from 0.5% to 5% by weight relative to the total weight of the composition and the at least one polyalkylene glycol of formula (4) is present in concentrations ranging from 1% to 20% by weight relative to the total weight of the composition.
25. The composition according to claim 19, in which the at least one merocyanine is present in a concentration ranging from 0.1% to 15% by weight relative to the total weight of the composition.
26. The composition according to claim 1, which further comprises an additional UV-screening agent.
Description
EXAMPLE A1: PREPARATION OF COMPOUND (14)
(1) ##STR00058##
(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 dimethylacetamide (1,8-diazabicyclo[5.4.0]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. Melting point: 92.7 C.
EXAMPLE A2: PREPARATION OF COMPOUND (15)
(8) ##STR00059##
(9) 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:
(10) TABLE-US-00003 Example Base Solvent Example A2.1 DBU dimethylacetamide (1,8-diazabicyclo[5.4.0]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
(11) The crude product (15) is obtained in the form of a dark brown oil.
(12) 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.
(13) Melting point: 84.7-85.3 C.
EXAMPLE A3: PREPARATION OF COMPOUND (27)
(14) ##STR00060##
(15) 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.
(16) The following base/solvent combinations are used:
(17) TABLE-US-00004 Example Base Solvent Example A3.1 DBU dimethylacetamide (1,8-diazabicyclo[5.4.0]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
(18) 15.97 g of the crude product (27) are obtained in the form of a dark brown oil.
(19) After chromatography on a column of silica gel (eluent: toluene/acetone), 13.46 g of product are obtained in the form of yellowish crystals.
(20) Melting point: 96.3 C.
EXAMPLE A4: PREPARATION OF COMPOUND (25)
(21) ##STR00061##
(22) 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.
(23) The following base/solvent combinations are used:
(24) TABLE-US-00005 Example Base Solvent Example A4.1 DBU dimethylacetamide (1,8-diazabicyclo[5.4.0]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
(25) Solubility Evaluation Protocol
(26) 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, then over time. During this interval, the solutions are stored at room temperature and at 4 C.
(27) TABLE-US-00006 5 (outside 1 the Ingredients (invention) 2 3 4 invention) Compound (25) 5 5 5 5 5 PEG-6 95 PEG-8 95 Tripropylene 95 glycol methyl ether Carboxylic acid 95 lauryl ether (AKYPO RLM 100 from KAO Propylene 95 glycol Solubility at t.sub.0 soluble soluble soluble soluble soluble Solubility at t.sub.1M soluble soluble soluble soluble insoluble solubility at t.sub.2M soluble soluble soluble soluble insoluble