Composition comprising a water-insoluble solid organic UV-screening agent and a compound capable of establishing hydrogen bonds

Abstract

The present invention relates to a composition comprising, in a cosmetically acceptable medium, at least one water-insoluble solid organic UV-screening agent (A) at least one compound (B) that may be obtained by reaction between: an oil bearing at least one nucleophilic and/or electrophilic reactive function, and a junction group capable of establishing hydrogen bonds with one or more partner junction groups, each junction group pairing involving at least 3 hydrogen bonds, the said junction group bearing at least one reactive function capable of reacting with the reactive function borne by the oil, the said junction group also comprising at least one unit of formula (I) or (II): in which: R1 and R3, which may be identical or different, represent a divalent carbon-based radical; R2 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, C1-C32 carbon-based and especially hydrocarbon-based radical, which may comprise one or more heteroatoms chosen from O, N, S, F, Si and P. ##STR00001##

Claims

1. A composition comprising, in a cosmetically acceptable medium, a) a water-insoluble solid organic UV-screening agent (A) having a solubility in water of less than 0.1% at 25° C. and at an atmospheric pressure of 760 mmHg and having a solubility of at least 1% in isopropyl N-lauroyl sarcosinate, at 25° C. and at an atmospheric pressure of 760 mmHg selected from the group consisting of Butylmethoxydibenzoylmethane, compound having the following formula: ##STR00080##  and Ethylhexyl triazone, and b) at least one a compound (B) selected from the group consisting of B 1: 2-Decyltetradecanol functionalized with ureidopyrimidone having the following formula: ##STR00081##  and B2: Diisostearyl malate functionalized with a ureidopyrimidone having the following formula: ##STR00082## and c) at least one volatile or non-volatile hydrocarbon-based oil and/or at least one volatile or non-volatile silicon-based oil.

2. The composition according to claim 1, in which the amount of compound (B) present in the compositions ranges between 1% and 80% by weight.

3. The composition according to claim 1, wherein the water-insoluble solid organic UV-screening agent (A) is Butylmethoxydibenzoylmethane.

4. The composition according to claim 3, wherein the B compound has the following formula: ##STR00083##

5. The composition according to claim 3, wherein the B compound has the following formula: ##STR00084##

6. The composition according to claim 1, wherein the B compound has the following formula: ##STR00085##

7. The composition according to claim 1, wherein the B compound has the following formula: ##STR00086##

8. The composition according to claim 1, wherein the water-insoluble solid organic UV-screening agent (A) has the following formula: ##STR00087##

9. The composition according to claim 8, wherein the B compound has the following formula: ##STR00088##

10. The composition according to claim 8, wherein the B compound has the following formula: ##STR00089##

11. The composition according to claim 1, wherein the water-insoluble solid organic UV-screening agent (A) is Ethylhexyl triazone.

12. The composition according to claim 11, wherein the B compound has the following formula: ##STR00090##

13. The composition according to claim 11, wherein the B compound has the following formula: ##STR00091##

14. A process for making up for keratin materials selected from the group consisting of skin, the lips, the nails, the eyelashes and the hair, comprising the application to the said materials of a composition as defined according to claim 1.

Description

EXAMPLES

Synthesis Examples

(1) Compounds (B1) and (B2) below of the invention were used.

(2) Synthesis of Compound (B1): 2-Decyltetradecanol Functionalized with Ureidopyrimidone

(3) ##STR00068##

(4) 126 g of 2-decyltetradecanol (Jarcol I-24®, JARCHEM, CAS #[58670-89-6]) were heated at 100° C. under reduced pressure for 4 hours to dry them. Next, the oil thus dried was added, over 4 hours, at 50° C. and under argon, to a mixture of 94.7 g of isophorone diisocyanate (IPDI, CAS #[4098-71-9]) and of dibutyltin dilaurate catalyst (DBTDL, CAS #[77-58-7]). Assay of the isocyanate allowed the reaction progress to be monitored. At half-equivalence, 126 g of propylene carbonate (PC, CAS #[108-32-7]) and 53.3 g of 6-methylisocytosine (MIC, CAS #[3977-29-5]) were added. Stirring and heating were continued at 100° C. for 16 hours, and disappearance of the isocyanate was monitored by infrared spectroscopy. Disappearance of the peak at 2250 cm.sup.−1 was observed. In parallel, the disappearance of the amine originating from the isocytosine was monitored by means of an amine assay. At the end of the reaction, the temperature was reduced to 50° C., 100 ml of ethanol were added and stirring was continued for 5 hours. After filtering through Celite and stripping with isododecane, the desired product conveyed in isododecane, at a solids content of 50%, was obtained. The product was especially characterized by GPC and HPLC coupled to mass spectroscopy.

(5) ##STR00069##
Synthesis of Compound (B2): Diisostearyl Malate Functionalized with a Ureidopyrimidone

(6) ##STR00070##

(7) The same process as for the preparation of (B1) was used, replacing the Jarcol I-24® with diisostearyl malate (CAS #[67763-18-2], Lubrizol). The desired product conveyed in isododecane, in a solids content of 50%, was obtained. The product was especially characterized by GPC and HPLC coupled to mass spectroscopy.

(8) ##STR00071##
The Following Water-Insoluble Solid Organic UV-Screening Agents (A) were Used: UV-screening agent No. 1 of the dibenzoylmethane type: Butylmethoxydibenzoylmethane (Parsol 1789®)

(9) ##STR00072## UV-screening agent No. 2 of the phenylbenzotriazole type (Drometrizole Trisiloxane®):

(10) ##STR00073## UV-screening agent No. 3 of the merocyanine type:

(11) ##STR00074## UV-screening agent No. 4 of the merocyanine type:

(12) ##STR00075## UV-screening agent No. 5 of the triazine type: Ethylhexyl triazone (Uvinul T150®)

(13) ##STR00076## UV-screening agent No. 6 of the triazine type: 2,4-bis(n-butyl 4′-aminobenzoate)-6-[(3-{1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-disiloxanyl}propyl)amino]-s-triazine,

(14) ##STR00077##

(15) The synthesis of this screening agent is described in patent FR 96/13684. UV-screening agent No. 7 (outside the invention): n-butyl 4-[(4,6-bis{[4-(butoxycarbonyl)phenyl]amino}-1,3,5-triazin-2-yl)amino]benzoate)triazine:

(16) ##STR00078## UV-screening agent No. 8 of the triazine type: 2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI name: bis-Ethylhexyloxyphenol methoxyphenyl triazine sold under the trade name Tinosorb S by BASF.

(17) ##STR00079##
Solubility Test of the Screening Agents (A) in Mixtures of Compounds (B) and of Isododecane —

(18) Maximum Solubility:

(19) 300 mg of water-insoluble solid UV-screening agent (A) or of UV-screening agent outside the invention were weighed out in a 10 ml flask, and compound (B) (as a mixture at 50% by weight in isododecane) was then added in increasing amounts until dissolution of the screening agent was complete. The dissolution was performed by sonication at 45° C. for 30 minutes, followed by cooling to room temperature. The stability of the solution was checked over two months at room temperature; the solution was considered stable when no formation of precipitate was observed at the end of this period. The maximum solubility was given in w/w %, which represents the mass percentage of UV-screening agent in the (B)/isododecane/UV-screening agent mixture. The maximum solubility of the solid screening agent (A) in a solution of isododecane alone (Bo) was also measured as reference. The results are as follows:

(20) TABLE-US-00001 Maximum solubility of the UV- screening Compound agent UV-screening agent (B) (w/w %) UV-screening agent No. 1 - (B.sub.0) 1 Butylmethoxydibenzoylmethane (B1) 15 (invention) (B2) 15 UV-screening agent No. 2 - (B.sub.0) 5 Drometrizole trisiloxane (B1) 30 (invention) (B2) 30 UV-screening agent No. 3 of the (B.sub.0) insoluble merocyanine type (invention) (B1) 5 (B2) 2.5 UV-screening agent No. 4 - (B.sub.0) insoluble merocyanine type (B1) 2.5 (invention) (B2) 5 UV-screening agent No. 5: (B.sub.0) <1 Ethylhexyl triazone (Uvinul (B1) 20 T150 ®) (invention) (B2) 20 UV-screening agent No. 6 - 2,4- (B.sub.0) <3 bis(n-butyl 4′-aminobenzoate)-6- (B1) 10 [(3-{1,3,3,3-tetramethyl-1- (B2) 10 [(trimethylsilyl)oxy]disiloxanyl}propyl)amino]- s-triazine (invention) UV-screening agent No. 7 (B.sub.0) insoluble n-butyl 4-[(4,6-bis{[4- (B1) insoluble (butoxycarbonyl)phenyl]amino}- (B2) insoluble 1,3,5-triazin-2-yl)amino]benzoate)triazine (outside the invention) UV-screening agent No. 8 (B.sub.0) 1 bis-Ethylhexyloxyphenol (B1) 5 methoxyphenyl triazine (B2) 5 (Tinosorb S ®) (invention)

(21) These results show that compounds B1 and B2 make it possible to dissolve screening agents (A) Nos. 1 to 6 and 8.

(22) Gloss Tests of Films Containing Water-Insoluble Solid UV-Screening Agents (A) in Compounds (B)

(23) Preparation of the Films:

(24) The UV-screening agent/isododecane/compound (B) mixtures as prepared previously were diluted by adding the 50/50 weight/weight compound (B)/isododecane mixture such that the concentration of UV-screening agent is at 2.5% or 5% by weight in the isododecane/compound (B) mixture, and the mixture was then heated at 45° C. for 30 minutes, followed by cooling to room temperature to obtain a homogeneous mixture. The films were prepared on contrast cards, using a 100 μm film spreader, and dried (drying, i.e. removal of the isododecane by evaporation at room temperature at atmospheric pressure) for 24 hours at room temperature. Films based on a 50/50 weight/weight compound (B)/isododecane mixture, without UV-screening agent (A), were also prepared, in the same manner, to serve as controls in the gloss measurement. Isododecane does not participate in the gloss of the film. As a result of its volatility, it disappears at the time of the gloss measurement.

(25) Gloss Measurement:

(26) The gloss of the films prepared previously was measured with a glossmeter (Dr Lange Ref 03 Reflektometer glossmeter) at three angles (20, 60 and 85°); the reported values are average values (minimum of two measurements) at 20° for the films prepared at the indicated w/w % values.

(27) TABLE-US-00002 Concentration of UV- screening agent as a weight percentage in the isododecane/ Gloss of Compound compound (B) the film UV-screening agent (B) mixture obtained Reference without screening (B1) 0 69 ± 1 agent (B2) 0 72 ± 1 UV-screening agent No. 1 - (B1) 5 74 ± 1 Butylmethoxydibenzoylmethane (B2) 5 77 ± 1 (invention) UV-screening agent No. 2 - (B1) 5 81 ± 1 Drometrizole trisiloxane (B2) 5 81 ± 1 (invention) UV-screening agent No. 3 of the (B1) 2.5 79 ± 1 merocyanine type (B2) 2.5 81 ± 1 (invention) UV-screening agent No. 4 - (B1) 2.5 83 ± 1 merocyanine type (B2) 5 83 ± 1 (invention) UV-screening agent No. 5: (B1) 5 84 ± 1 Ethylhexyl triazone (Uvinul (B2) 5 84 ± 1 T150 ®) (invention) UV-screening agent No. 6 - 2,4- (B1) 5 82 ± 1 bis(n-butyl 4′-aminobenzoate)-6- (B2) 5 82 ± 1 [(3-{1,3,3,3-tetramethyl-1- [(trimethylsilyl)oxy]disiloxanyl}propyl)amino]- s-triazine (invention) UV-screening agent No. 7 (B1) insoluble N/A n-butyl 4-[(4,6-bis{[4- (B2) insoluble N/A (butoxycarbonyl)phenyl]amino}- 1,3,5-triazin-2-yl)amino]benzoate)triazine (outside the invention) UV-screening agent No. 8 (B1) 5 84 ± 1 bis-Ethylhexyloxyphenol (B2) 5 83 ± 1 methoxyphenyl triazine (Tinosorb S ®) (invention)

(28) On account of its insolubility, the films containing the UV-screening agent No. 7 (outside the invention) could not be prepared.

(29) It was observed, firstly, that compounds (B) made it possible to dissolve the screening agents (A) in accordance with the invention in the 50/50 weight/weight compound (B)/isododecane mixture and, secondly, that compounds (B) formed with the said screening agents (A) a homogeneous film with enhanced gloss relative to the film obtained without UV-screening agent.

Examples 1 and 2 of Lipsticks

(30) The following lipsticks were prepared

(31) TABLE-US-00003 Example 2 Example 1 (outside the Constituents Ingredient (invention) invention) a) Compound (B1) at a 20% 20% solids content of 11% in isododecane b) Phenyl trimethicone 40% 45% c) UV-screening agent 5% — No. 2 - Drometrizole trisiloxane (Mexoryl XL) d) Performalene 500-L 15% 15% Polyethylene e) Phenyl 20% 20% trimethicone/Red 7 (3/1)
Preparation Process The mass ratios of the components are detailed in the table; the mixtures were prepared so as to have 150 g of final mixture. Components a), b) and c) were mixed using a Rayneri blender at 100° C. until homogeneous (˜5 minutes). Next, component d) was added and the mixture thus obtained was stirred at 100° C. until homogeneous (˜5 minutes). Next, component e) was added and the mixture thus obtained was stirred at 100° C. until homogeneous (˜20 minutes). The mixture was transferred into a lipstick mould heated to 42° C., and the assembly was then allowed to cool to room temperature, before being cooled to 4° C. for 20 minutes, and then opened. The lipstick wands thus obtained were placed in hermetically sealed packaging to prevent evaporation of the isododecane.
Evaluation of the Gloss

(32) The two lipsticks of Examples 1 and 2 were evaluated on the hand in a blind test by a panel of 10 experts. 10 out of 10 people judged the film formed on the hand with Example 1 of the invention to be glossier than the film formed using Example 2 on the hand.