EFFICIENT SUNSCREEN COMPOSITIONS WITH DIETHYLAMINO HYDROXYBENZOYL HEXYL BENZOATE AND WATER SOLUBLE UVA FILTER

Abstract

The present invention relates to sunscreen or daily care compositions comprising hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate) and at least one water soluble UVA filter, wherein the composition does not comprise 2-hydroxy-4-methoxybenzophenone (INCI oxybenzone) and ethylhexyl-2-cyano-3,3-diphenyl-acrylate (INCI octocrylene). Furthermore, the present invention relates to the use of said composition to reduce fabric staining and to facilitate the washability of a sunscreen or daily care composition.

Claims

1.-12. (canceled)

13. A sunscreen or daily care composition comprising (i) hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate); and (ii) at least one water soluble UVA filter selected from disodium phenyl dibenzimidazole tetrasulfonate in an amount of from 1% to 10% by weight based on the total weight of the composition; wherein the composition does not comprise 2-hydroxy-4-methoxybenzophenone (INCI oxybenzone), ethylhexyl-2-cyano-3,3-diphenyl-acrylate (INCI octocrylene) and 2-ethylhexyl-(2E)-3-(4-methoxyphenyl)acrylate (INCI ethylhexyl methoxy cinnamate).

14. The sunscreen or daily care composition according to claim 13, wherein the composition is free of parabens.

15. The sunscreen or daily care composition according to claim 13, wherein the composition comprises at least one further UVA filter selected from the group consisting of triazine derivatives, dibenzoylmethane derivatives, benzotriazole derivatives and combinations thereof.

16. The sunscreen or daily care composition according to claim 15, wherein the at least one further UVA filter is selected from the group consisting of 4-(tert.-butyl)-4′-methoxydibenzoylmethane (INCI butyl methoxydibenzoylmethane), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5 triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizole trisiloxane), 2-(2H-benzotriazol-2-yl)-6-(2-ethylhexyloxymethyl)-4-methyl-phenol and combinations thereof.

17. The sunscreen or daily care composition according to claim 13, wherein the composition further comprises at least one UVB filter selected from the group consisting of 4,4′,4″-(1,3,5-triazin-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), malonate derivatives such as dimethicone diethyl benzalmalonate, diethylhexyl butamido triazone, and combinations thereof.

18. The sunscreen or daily care composition according to claim 13, wherein the composition is free of phenoxyethanol.

19. The sunscreen or daily care composition according to claim 13, wherein the composition comprises hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate) in an amount of from 1% to 10% by weight, based on the total weight of the composition.

20. The sunscreen or daily care composition according to claim 13, wherein the composition comprises the at least one water soluble UVA filter in an amount of from 1% to 8% by weight based on the total weight of the composition.

21. The sunscreen or daily care composition according to claim 13, wherein the composition is free of (RS)-2-ethylhexyl-2-hydroxybenzoate (INCI ethylhexyl salicylate) and 3,3,5-trimethyl-cyclohexyl salicylate (homosalate).

22. The sunscreen or daily care composition according to claim 13, wherein the composition comprises at least one perfume.

23. Use of a sunscreen or daily care composition comprising (i) hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate); and (ii) at least one water soluble UVA filter; wherein the composition does not comprise 2-hydroxy-4-methoxybenzophenone (INCI oxybenzone) and ethylhexyl-2-cyano-3,3-diphenyl-acrylate (INCI octocrylene) to reduce fabric staining.

24. Use of a sunscreen or daily care composition comprising (i) hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate); and (ii) at least one water soluble UVA filter; wherein the composition does not comprise 2-hydroxy-4-methoxybenzophenone (INCI oxybenzone) and ethylhexyl-2-cyano-3,3-diphenyl-acrylate (INCI octocrylene) to facilitate the washability from textiles.

25. The sunscreen or daily care composition according to claim 13, wherein the composition comprises the at least one water soluble UVA filter in an amount of from 1% to 7% by weight based on the total weight of the composition.

26. The sunscreen or daily care composition according to claim 13, wherein the composition comprises the at least one water soluble UVA filter in an amount of from 1% to 6% by weight, based on the total weight of the composition.

Description

EXAMPLES

[0235] Process of Manufacture of Sunscreen Compositions

[0236] The ingredients of part A, as well as the ingredients of part B as provided below in Table 1, for each tested sunscreen composition were combined and heated to 80° C. respectively, wherein part A was added to part B under stirring and was further homogenized. If present, phase C was premixed in an ultra turrax device and added to phase A and B. Subsequently, the sunscreen composition was cooled down to room temperature under stirring and the pH of each composition was adjusted to >7.00.

[0237] All amounts referred to in the following tables refer to the respective amounts in % by weight, based on the total weight of the composition.

[0238] Sunscreen Compositions

TABLE-US-00001 TABLE 1 Comparative Ingredient (Trade Name) composition 1 Composition 1 Part A Dibutyl adipate (Cetiol B) 10.00  10.00  C.sub.12-C.sub.15 alkyl benzoate (Cetiol AB) 10.00  10.00  Stearyl alcohol (Lanette 18) 2.50 2.50 DHHB (Uvinul A Plus) 5.00 2.50 EHT (Uvinul T 150) 3.00 3.00 Part B Water qsp 100% qsp 100% Glycerin 2.00 2.00 Disodium EDTA (EDTA BD) 0.20 0.20 Acrylates/Beheneth-25 2.00 2.00 methacrylate copolymer (Tinovis GTC UP) Xanthan Gum (Rheocare XGN) 0.50 0.50 Part C Water — 5.00 Tromethamine (Tris Amino) — qs DPDT (Neoheliopan AP) — 2.5 

[0239] The calculated SPF for the comparative composition is 12.

[0240] The calculated SPF for composition 1 is 17.

[0241] Sunscreen Compositions

[0242] The ingredients of part A, as well as the ingredients of part B as provided below in Table 2, for each tested sunscreen composition were combined and heated to 80° C. respectively, wherein part A was added to part B under stirring and was further homogenized. If present, phase C was premixed in an ultra turrax device and added to phase A and B. Subsequently, the sunscreen composition was cooled down to room temperature, then add part D under stirring, finally add part E when present under stirring and adjust the pH of each composition to >7.00.

TABLE-US-00002 TABLE 2 Comparative Comparative INCI Composition 2 Composition 2 Composition 3 Composition 3 Part A Glyceryl stearate 1.00 1.00 1.00 1.00 Sodium Stearyl 0.30 0.30 0.30 0.30 Glutamate Stearyl Alcohol 1.00 1.00 1.00 1.00 Butylene Glycol Di- 4.00 4.00 4.00 4.00 caprylate/Dicaprate Dibutyl adipate 3.00 3.00 3.00 3.00 C12-15 Alkyl 5.00 5.00 5.00 5.00 Benzoate Phenoxyethanol 1.00 1.00 1.00 1.00 VP/Hexadecene Co- 0.50 0.50 0.50 0.50 polymer Silica Dimethyl 1.00 1.00 1.00 1.00 Silylate Butyl Methoxy 4.75 4.75 4.75 Diben-zoylmethane Ethylhexyl Salicylate 4.75 4.75 4.75 4.75 Ethylhexyl Triazone 3.00 1.50 1.50 1.00 Bis- 4.00 4.00 ethylhexyloxyphe-nol Methoxyphenyl Triazine Diethylamino Hydro- 1.00 1.00 1.00 1.00 xybenzoyl Hexyl Ben-zoate Part B Aqua qsp 100 qsp 100 qsp 100 qsp 100 Glycerin 7.50 7.50 7.50 7.50 Acrylates/C10-30 0.10 0.10 0.10 0.10 Alkyl Acrylate Cross- polymer Xanthan gum 0.40 0.40 0.40 0.40 Dissodium EDTA 0.20 0.20 0.20 0.20 Part C Phenylbenzimidazole 1.00 1.00 1.00 Sulfonic Acid Disodium Phenyl Di- 4.75 7.00 benzimidazole Tetra- sulfonate Water 5.00 5.00 5.00 5.00 Sodium Hydroxide qsp qsp qsp qsp Part D Ethanol 3.00 3.00 3.00 3.00 Part E Bis-ethylhexyloxy- 20.00  phenol Methoxyphenyl Triazine (Tinosorb S Lite Aqua)* *Tinosorb S Lite Aqua is a 20% aqueous dispersion of Bis-ethylhexylphenol Methoxyphenyl Triazine; 20% Tinosorb S Lite Aqua corresponds to 4% Bis-ethylhexyloxyphenol Methoxyphenyl Triazine

[0243] Measurement of Fabric Staining

[0244] Fabric staining of UV filter compositions was measured by the L*a*b as described above. The measurement was performed with a spectrophotometer using the following instrument: Remission Spectrometer Datacolor SF 400 (light D65, observer 10°).

[0245] The difference between the color of a UV filter composition stain on a white textile and the color of the white textile alone was determined following the assumption that ΔE*=Δb* in order to determine fabric staining. The lower the color difference, the lower is the fabric staining.

[0246] Further, the difference between the color of a UV filter composition stain on a white textile after 1 or 3 washing cycles and the color of the white textile alone was determined following the assumption that ΔE*=Δb* in order to determine the washability. The lower the color difference in comparison to the value obtained before washing, the more has fabric staining been reduced, i.e. the better the washability of the sunscreen composition from textiles.

[0247] For applying the UV filter compositions in order to make a stain on a white textile, the UV filter composition was diluted in water or ethanol at a concentration of 10% by weight based on the total weight of the diluted mixture. 300 mg (15 mg/cm.sup.2) of the diluted mixture is applied on a white textile (whiteness adjusted to WG 170±10, after washing WG 190±10) in order to obtain a stain.

[0248] For determining the washability, 1 or 3 washing cycles were performed in a washing machine using a temperature of 40° C. for 20 minutes and Persil Universal Gel obtained from Henkel (3 g on stain). Each textile was washed separately.

[0249] The results for the comparative composition 1 and composition 1 are shown in Table 3 and FIG. 1.

[0250] The results of comparative compositions 2, 3 and compositions 2, 3 are shown in Table 4.

TABLE-US-00003 TABLE 3 Comparative composition 1 Composition 1 Δb* (before washing) 12.25 7.06 SD (before washing) 0.22 0.17 Δb* (after 3 cycles) 6.99 4.61 SD (after 3 cycles) 0.01 0.09

TABLE-US-00004 TABLE 4 Comparative Comparative Composition 2 Composition 2 Composition 3 Composition 3 Δb* (before washing) 10.91 4.94 11.29 6.15 SD (before washing) 0.04 0.28 0.05 0.22 Δb* (after 3 cycles) 3.90 2.93 4.06 2.23 SD (after 3 cycles) 0.09 0.26 0.08 0.34

[0251] As can be seen from the results above, comparative Composition 2 containing only oil soluble UVA filters exhibits a strong fabric staining. Composition 2 containing DPDT instead of BMBDM shows a significant fabric staining reduction. Comparative Composition 3 containing Tinosorb S Lite Aqua as a water dispersed UV filter instead of DPDT shows that this UVA filter present in the water phase is not appropriate for fabric staining reduction. Composition 3 containing both DHHB and BMBDM and DPDT shows fabric staining reduction.

[0252] In a further step, the following filter combinations have been tested to show that not every UV filter present in the water phase is suitable to contribute to reduction of fabric staining. Table 5 shows a test series with various UV filters present in the water and oil phase incorporated in emulsions and their performance in reducing fabric staining.

TABLE-US-00005 TABLE 5 Test Test Test Test Test Emulsion emulsion 1 emulsion 2 emulsion 3 emulsion 4 Part A Dibutyl Adipate 10.00 10.00 10.00 10.00 C12-15 Alkyl 10.00 10.00 10.00 10.00 Benzoate Stearyl Alcohol 2.50 2.50 2.50 2.50 Diethylamino 3.00 1.50 1.50 Hydroxybenzoyl Hexyl Benzoate Ethylhexyl Triazone 3.50 1.20 2.30 2.30 Part B Aqua qsp 100 qsp 100 qsp 100 qsp 100 Glycerin 2.00 2.00 2.00 2.00 Disodium EDTA 0.20 0.20 0.20 0.20 Acrylates/Beheneth- 2.00 2.00 2.00 2.00 25 Methacrylate Co- polymer (Tinovis GTC)* Xanthan Gum 0.50 0.50 0.50 0.50 Part C Aqua 5.00 5.00 Neutralizing agent qs qs Disodium Phenyl 5.00 1.80 Dibenzimidazole Tetrasulfate Part D Bis-ethylhexyloxy- 7.50 phenol Methoxy- phenyl Triazine (Tinosorb S Lite Aqua) ** SPF calculated 15.5 15.3 14.9 15.0 UVA-PF 5.7 5.7 5.8 6.2 calculated (SPF15) UVA-PF 5.0 3.7 4.7 5 measured (SPF 15) *Tinovis GTC is a 30% polymer dispersion in water. ** Tinosorb S Lite Aqua is a 20% aqueous dispersion of Bis-ethylhexyloxyphenol Methoxyphenyl Triazine; 7.5% Tinosorb S Lite Aqua corresponds to 1.5% Bis-ethylhexyloxyphenol Methoxy-phenyl Triazine.

[0253] The test emulsions are prepared as follows: Part A and B are heated to 80° C. under stirring. Part A is added into B under stirring and homogenized. When present phase C premixed under ultra turrax device is added. It is cooled down to room temperature. When present phase D is added. The pH is checked to be >7.

[0254] The results obtained from fabric staining tests are shown in Table 6.

TABLE-US-00006 TABLE 6 Fabric staining results Test Test Test Test emulsion 1 emulsion 2 emulsion 3 emulsion 4 Δb* (before washing) 9.5 −0.85 5.29 8.60 SD (before washing) 0.05 0.06 0.23 0.13 Δb* (after 3 cycles) 3.31 0.38 2.06 2.68 SD (after 3 cycles) 0.06 0.02 0.07 0.01

[0255] Test emulsion 1 contains an oil soluble UVA filter resulting in fabric staining, which is not appreciated by the consumers. Conversely, Test emulsion 2 contains only UVA water soluble filter showing no fabric staining but lower UVA protection than required (UVA-PF measured was equal to 3.7 instead of expected 5.7 (Table 5). The inventive UV filter combination DHHB and DPDT (oil soluble and water soluble) brings about a reduction in fabric staining in test emulsion 3 by simultaneously keeping the UVA performance. In test emulsion 4 DPDT is replaced by Tinosorb S Lite Aqua which is a water dispersed UVA filter. There is no positive effect on fabric staining and washability.

[0256] Recovery Measurements on Photo Stability of TDSA

[0257] Process of Manufacture of Sunscreen Compositions

[0258] The ingredients of part A, as well as the ingredients of part B as provided below in Table 7, for each tested sunscreen composition were combined and heated to 80° C. respectively, wherein part A was added to part B under stirring and was further homogenized. If present, phase C was premixed in an ultra turrax device and added to phase A and B. Subsequently, the sunscreen composition was cooled down to room temperature under stirring and the pH of each composition was adjusted to >7.00.

[0259] Sunscreen Compositions

TABLE-US-00007 TABLE 7 Comparative Ingredient (Trade Name) composition 4 Composition 4 Part A Sucrose polystearate (and) 3 3 hydrogenated polyisobutene (Emulgade Sucro) Disodium cetearyl sulfosuccinate 1 1 (Emulgin Prisma) Dibutyl adipate (Cetiol B) 10 10 Diisopropyl sebacate 4 4 Cetearyl alcohol (Lanette O) 1 1 DHHB (Uvinul A Plus) — 6.00 Part B Water qsp 100% qsp 100% Glycerin 3.00 3.00 Disodium EDTA (EDTA BD) 0.20 0.20 Xanthan Gum (Rheocare XGN) 0.50 0.50 Part C Tromethamine (Tris Amino) qs qs TDSA* 2.00 2.00 *Pre-dispersion in water, 2% corresponds to the active amount.

[0260] The sunscreen compositions as defined above are applied on roughened quartz plates (2 μl/cm.sup.2). Plates are irradiated using Atlas CPS device at different duration times (MED=Minimal Erythema Dose): [0261] 0 h (0 MED, no irradiation) [0262] 2 h (10 MED), [0263] 10 h (50 MED).

[0264] In total, four plates are prepared for each irradiation condition. After irradiation, each plate is rinsed off with tetrahydrofuran. The rinsing solution is further analyzed via HPLC to determine the recovery of TDSA.

TABLE-US-00008 TABLE 8 Comparative composition 4 Composition 4  0 MED 100%  100%  10 MED 88% 93% 50 MED 60% 77%

[0265] In a particularly preferred embodiment, the present invention relates to the following further items.

[0266] 1. A sunscreen or daily care composition comprising [0267] (i) hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate); and [0268] (ii) at least one water soluble UVA filter;
wherein the composition does not comprise 2-hydroxy-4-methoxybenzophenone (INCI oxybenzone) and ethylhexyl-2-cyano-3,3-diphenyl-acrylate (INCI octocrylene).

[0269] 2. The sunscreen or daily care composition according to item 1, wherein the composition is free of parabens.

[0270] 3. The sunscreen or daily care composition according to item 1 or 2, wherein the at least one water soluble UVA filter is selected from the group consisting of [(3Z)-3-[[4-[(Z)-[7,7-dimethyl-2-oxo-1-(sulfomethyl)-3-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid (INCI terephthalylidene dicamphor sulfonic acid), disodium phenyl dibenzimidazole tetrasulfonate, and the combination thereof.

[0271] 4. The sunscreen or daily care composition according to any one of items 1 to 3, wherein the composition comprises at least one further UVA filter selected from the group consisting of triazine derivatives, dibenzoylmethane derivatives, benzotriazole derivatives and combinations thereof.

[0272] 5. The sunscreen or daily care composition according to item 4, wherein the at least one further UVA filter is selected from the group consisting of 4-(tert.-butyl)-4′-methoxydibenzoylmethane (INCI butyl methoxydibenzoylmethane), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5 triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizole trisiloxane), 2-(2H-benzotriazol-2-yl)-6-(2-ethylhexyloxymethyl)-4-methyl-phenol and combinations thereof.

[0273] 6. The sunscreen or daily care composition according to any one of items 1 to 5, wherein the composition further comprises at least one UVB filter selected from the group consisting of 4,4′,4″-(1,3,5-triazin-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), malonate derivatives such as dimethicone diethyl benzalmalonate, diethylhexyl butamido triazone, and combinations thereof.

[0274] 7. The sunscreen or daily care composition according to any one of items 1 to 6, wherein the composition does not comprise 2-ethylhexyl-(2E)-3-(4-methoxyphenyl)acrylate (INCI ethylhexyl methoxy cinnamate).

[0275] 8. The sunscreen or daily care composition according to any one of items 1 to 7, wherein the composition is free of phenoxyethanol.

[0276] 9. The sunscreen or daily care composition according to any one of items 1 to 8, wherein the composition comprises hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate) in an amount of from 1% to 10% by weight, based on the total weight of the composition.

[0277] 10. The sunscreen or daily care composition according to any one of items 1 to 9, wherein the composition comprises the at least one water soluble UVA filter in an amount of from 0.1% to 10% by weight, preferably in an amount of from 0.3% to 5% by weight, more preferably in an amount of from 0.5% to 3% by weight, based on the total weight of the composition.

[0278] 11. The sunscreen or daily care composition according to any one of items 1 to 10 comprising [0279] (i) hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate); and [0280] (ii) at least one water soluble UVA filter, which is [(3Z)-3-[[4-[(Z)-[7,7-dimethyl-2-oxo-1-(sulfomethyl)-3-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid (INCI terephthalylidene dicamphor sulfonic acid) and/or disodium phenyl dibenzimidazole tetrasulfonate;
wherein the composition does not comprise 2-hydroxy-4-methoxybenzophenone (INCI oxybenzone) and ethylhexyl-2-cyano-3,3-diphenyl-acrylate (INCI octocrylene); and
wherein the composition is free of parabens.

[0281] 12. The sunscreen or daily care composition according to any one of items 1 to 11, wherein the composition is free of (RS)-2-ethylhexyl-2-hydroxybenzoate (INCI ethylhexyl salicylate) and 3,3,5-trimethyl-cyclohexyl salicylate (homosalate).

[0282] 13. Use of a sunscreen or daily care composition according to any one of items 1 to 12 to reduce fabric staining.

[0283] 14. Use of a sunscreen or daily care composition according to any one of items 1 to 12 to facilitate the washability from textiles.