SUNSCREEN COMPOSITIONS COMPRISING BUTYL METHOXYDIBENZOYLMETHANE, TRIAZINE DERIVATIVES AND PHOTOSTABILIZER

Abstract

The present invention relates to sunscreen or daily care compositions comprising butyl methoxydibenzoylmethane, at least one UV filter selected from triazine derivatives, at least one photostabilizer selected from butyl octyl salicylate, benzotriazolyl dodecyl p cresol, ethyl hexyl methoxycrylene, polyester-8, diethyl hexyl syringylidenemalonate, trimethoxybenzylidene pentanedione, diethylhexyl 2,6-naphthalate, a fused ring cyanoacrylate derivative and polyester-25, wherein the composition does not comprise octocrylene and ethyl hexyl methoxy cinnamate.

Claims

1.-12. (canceled)

13. A sunscreen or daily care composition comprising (i) 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane); and (ii) at least one UV filter selected from triazine derivatives; and (iii) at least one photo stabilizer selected from the group consisting of butyloctyl salicylate, benzotriazolyl dodecyl p cresol, ethylhexyl methoxycrylene, polyester-8, diethylhexyl syringylidenemalonate, trimethoxybenzylidene pentanedione, diethylhexyl 2,6-naphthalate, a fused ring cyanoacrylate derivative, polyester-25 and combinations thereof; wherein the composition does not comprise 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 at least one UV filter selected from triazine derivatives is selected from the group consisting of soluble triazine derivatives, particulate triazine derivatives and combinations thereof.

15. The sunscreen or daily care composition according to claim 14, wherein the soluble triazine derivative is selected from the group consisting of 4,4′,4″-(1,3,5-triazine-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), 4,4′-[[6-[[4-[[(1,1-dimethylethyl)amino]carbonyl]phenyl]amino]-1,3,5-triazin-2,4-diyl]diimino]bis-benzoic acid-bis(2-ethylhexyl)ester (INCI diethylhexyl-butamidotriazone), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5 triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine) and combinations thereof.

16. The sunscreen or daily care composition according to claim 14, wherein the particulate triazine derivative is selected from the group consisting of 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI trisbiphenyl triazine), 5,6,5′,6′-tetraphenyl-3-3′-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine) and combinations thereof.

17. The sunscreen or daily care composition according to claim 13, wherein the composition is free of any cinnamic acid derivatives.

18. The sunscreen or daily care composition according to claim 13, wherein the composition comprises 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane) in an amount of from 1% to 5% by weight, based on the total weight of the composition.

19. The sunscreen or daily care composition according to claim 13, wherein the composition comprises the at least one UV filter selected from triazine derivatives in an amount of from 0.5% 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 photostabilizer in an amount of from 0.5% to 5% 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 parabens.

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

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

24. Use of a sunscreen or daily care composition as defined in claim 13 for enhancing the photo stability of the at least one UV filter selected from triazine derivatives.

25. The sunscreen or daily care composition according to claim 13, wherein the composition comprises the at least one UV filter selected from triazine derivatives in an amount of from 0.5% to 5% by weight based on the total weight of the composition.

Description

EXAMPLES

Process of Manufacture of Sunscreen Compositions

[0416] The ingredients of part A, as well as the ingredients of part B as provided below in Tables 1.1, 1.2, 1.3 and 1.4 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. Subsequently, the sunscreen composition was cooled down to room temperature under stirring and the pH of each composition was adjusted to 6.5-7.00 with NaOH (30%).

[0417] All amounts referred to in the following tables refer to the respective amounts in % by weight, based on the total weight of the composition.

Sunscreen Compositions

[0418]

TABLE-US-00001 TABLE 1.1 Recovery of EHT Ingredient Comparative Comparative Comp. Comp. Comp. Comp. Comp. Comp. Comp. Comp. Comp. (Trade Name) Comp. 1a Comp. 1b 2a 2b 2c 2d 2e 2f 2g 2h 2i Part A Dibutyl adipate 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 (Cetiol B) C.sub.12-C.sub.15 alkyl benzoate 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 (Cetiol AB) Stearyl alcohol (Lanette  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50 18) Polyester-8 — —  3.00 — — — — — — — — (Polycrylene) Diethylhexyl 2,6-naph- — — —  3.00 — — — — — — — thalate (Corapan TQ) Ethylhexyl methoxy- — — — —  3.00 — — — — — — crylene (SolaStay S1) Trimethoxybenzylidene — — — — —  2.00 — — — — — pentanedione (Synoxyl HSS) Polyester-25 — — — — — —  3.00 — — — — (Bis-Methoxycrylene/ octyldodecyl adipic acid/methylpropane-diol copolymer) Micah (=fused ring — — — — — — —  3.00 — — — cyanoacrylate derivative) Butyloctyl Salicylate — — — — — — — —  3.00 — — Benzotriazolyl Dodecyl — — — — — — — — —  1.00 — p Cresol Diethylhexyl — — — — — — — — — —  1.00 Syringylidenemalonate BMDBM —  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00 EHT (Uvinul T150)  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00 BEMT (Tinosorb S) — — — — — — — — — — — Part B Water qsp qsp qsp qsp qsp qsp qsp qsp qsp qsp qsp 100% 100% 100% 100% 100% 100% 100% 100% 100% 100% 100% Glycerin  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00 Disodium EDTA  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20 (EDTA BD) Acrylates/Beheneth-25  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00 methacrylate copolymer (Tinovis GTC UP) Xanthan Gum  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50 (Rheocare XGN)

TABLE-US-00002 TABLE 1.2 Recovery of BEMT Ingredient Comparative Comparative Comp. Comp. Comp. Comp. Comp. Comp. Comp. Comp. (Trade Name) Comp. 1c Comp. 1d 3a 3b 3c 3d 3e 3f 3g 3h Part A Dibutyl adipate 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 (Cetiol B) C.sub.12-C.sub.15 alkyl benzoate 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 (Cetiol AB) Stearyl alcohol  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50  2.50 (Lanette 18) Polyester-8 — —  3.00 — — — — — — — (Polycrylene) Diethylhexyl 2,6-naph- — — —  3.00 — — — — — — thalate (Corapan TQ) Ethylhexyl methoxy- — — — —  3.00 — — — — — crylene (SolaStay Si) Trimethoxybenzylidene — — — — —  3.00 — — — — pentanedione (Synoxyl HSS) Polyester-25 — — — — — — —  3.00 — (Bis-Methoxycrylene/ octyldodecyl adipic acid/methylpropane-diol copolymer) Micah (=fused ring — — — — — — —  3.00 — — cyanoacrylate derivative) Benzotriazolyl Dodecyl — — — — — — — — —  1.00 p Cresol BMDBM —  3.00  3.00  3.00  3.00  3.00  3.00  3.00  3.00  3.00 EHT (Uvinul T150) — — — — — — — — — — BEMT (Tinosorb S)  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00  1.00 Part B Water qsp qsp qsp qsp qsp qsp qsp qsp qsp qsp 100% 100% 100% 100% 100% 100% 100% 100% 100% 100% Glycerin  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00 Disodium EDTA  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20  0.20 (EDTA BD) Acrylates/Beheneth-25  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00  2.00 methacrylate copolymer (Tinovis GTC UP) Xanthan Gum  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50  0.50 (Rheocare XGN)

TABLE-US-00003 TABLE 1.3 Recovery of DBT Ingredient Comparative Comparative Comp. Comp. Comp. (Trade Name) Comp. 1e Comp. 1f 4a 4b 4c Part A Dibutyl adipate 15.00 15.00 15.00 15.00 15.00 (Cetiol B) C.sub.12-C.sub.15 alkyl benzoate 10.00 10.00 10.00 10.00 10.00 (Cetiol AB) Stearyl alcohol 2.50 2.50 2.50 2.50 2.50 (Lanette 18) Polyester-8 — — 3.00 — — (Polycrylene) Diethylhexyl 2,6-naph- — — — 3.00 — thalate (Corapan TQ) Butyloctyl Salicylate — — — — 3.00 BMDBM — 2.00 2.00 2.00 2.00 DBT (Uvasorb H EB) 1.00 1.00 1.00 1.00 1.00 Part B Water qsp qsp qsp qsp qsp Glycerin 100% 100% 100% 100% 100% Disodium EDTA 2.00 2.00 2.00 2.00 2.00 (EDTA BD) 0.20 0.20 0.20 0.20 0.20 Acrylates/Beheneth-25 2.00 2.00 2.00 2.00 2.00 methacrylate copolymer (Tinovis GTC UP) Xanthan Gum 0.50 0.50 0.50 0.50 0.50 (Rheocare XGN)

TABLE-US-00004 TABLE 1.4 Recovery of BEMT + EHT Ingredient Comparative Comparative Comp. Comp. Comp. Comp. (Trade Name) Comp. 1g Comp. 1h 5a 5b 5c 5d Part A Dibutyl adipate 15.00  15.00  15.00  15.00  15.00  15.00  (Cetiol B) C.sub.12-C.sub.15 alkyl benzoate 10.00  10.00  10.00  10.00  10.00  10.00  (Cetiol AB) Stearyl alcohol 2.50 2.50 2.50 2.50 2.50 2.50 (Lanette 18) Polyester-8 — — — — — — (Polycrylene) Diethylhexyl 2,6-naph- — — — 3.00 thalate (Corapan TQ) Ethylhexyl 3.00 methoxycrylene (SolaStay Si) Trimethoxybenzyli- — — — 3.00 dene pentanedione (Synoxyl HSS) Butyloctyl Salicylate 3.00 BMDBM — 3.00 3.00 3.00 3.00 3.00 EHT (Uvinul T150) 1.00 1.00 1.00 1.00 1.00 1.00 BEMT (Tinosorb S) 1.00 1.00 1.00 1.00 1.00 1.00 Part B Water qsp qsp qsp qsp qsp qsp 100% 100% 100% 100% 100% 100% Glycerin 2.00 2.00 2.00 2.00 2.00 2.00 Disodium EDTA 0.20 0.20 0.20 0.20 0.20 0.20 (EDTA BD) Acrylates/Beheneth-25 2.00 2.00 2.00 2.00 2.00 2.00 methacrylate copolymer (Tinovis GTC UP) Xanthan Gum 0.50 0.50 0.50 0.50 0.50 0.50 (Rheocare XGN)

[0419] Recovery Measurements on Photo Stability of EHT

[0420] The UV filter compositions as defined in Tables 1.1 to 1.4 are applied on roughened quartz plates (2 ml/cm.sup.2). Plates are irradiated using Atlas CPS device at different duration times (MED=Minimal Erythema Dose): [0421] 0 h (0 MED, no irradiation) [0422] 1 h (5 MED), [0423] 2 h (10 MED), [0424] 4 h (20 MED).

[0425] 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 EHT.

TABLE-US-00005 TABLE 2.1 Comparative Comparative Comp. Comp. Comp. Comp. 1a Comp. 1b 2a 2b 2c 0 MED 100% 100% 100% 100%  100% 5 MED  97%  92%  97% 94% 102% 10 MED  94%  79% 100% 87% 101% 20 MED  90%  31%  88% 79% 100% Comp. 2d Comp. 2e Comp. 2f Comp. 2g Comp. 2h Comp. 2i 0 MED 100% 100% 100% 100%  100% 100%  5 MED  99% 106% 102% 92% 101% 99% 10 MED 102% 100% 102% 87%  96% 85% 20 MED  96%  96%  98% 68%  85% 49% A person skilled in the art is aware that data above 100% after irradiation are due to common measurement fluctuations.

[0426] Recovery Measurements on Photo Stability of BEMT

[0427] The UV filter compositions as defined in Table 1.2 are applied on roughened quartz plates (2 ml/cm.sup.2). Plates are irradiated using Atlas CPS device at different duration times (MED=Minimal Erythema Dose): [0428] 0 h (0 MED, no irradiation) [0429] 1 h (5 MED), [0430] 2 h (10 MED), [0431] 4 h (20 MED).

[0432] 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 BEMT.

TABLE-US-00006 TABLE 2.2 Comparative Comparative Comp. Comp. Comp. Comp. Comp. Comp. Comp. Comp. Comp. 1c Comp. 1d 3a 3b 3c 3d 3e 3f 3g 3h  0 MED 100% 100% 100% 100% 100% 100% 100% 100% 100% 100%  5 MED 96%  93% 104%  94% 106%  94%  96%  98% 102% 102% 10 MED 99%  84%  99%  93% 104%  94%  92%  99%  98%  98% 20 MED 98%  78%  96%  86% 100%  92%  86%  95%  90%  90% A person skilled in the art is aware that data above 100 % after irradiation are due to common measurement fluctuations.

[0433] Recovery Measurements on Photo Stability of DBT

[0434] The UV filter compositions as defined in Table 1.3 are applied on roughened quartz plates (2 ml/cm.sup.2). Plates are irradiated using Atlas CPS device at different duration times (MED=Minimal Erythema Dose): [0435] 0 h (0 MED, no irradiation) [0436] 1 h (5 MED), [0437] 2 h (10 MED), [0438] 4 h (20 MED).

[0439] 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 DBT.

TABLE-US-00007 TABLE 2.3 Comparative Comparative Comp. Comp. Comp. Comp. 1e Comp. if 4a 4b 4c 0 MED 100% 100% 100% 100% 100% 5 MED  92%  85% 101%  95%  91% 10 MED  84%  60% 101%  82%  83% 20 MED  62%  30%  85%  68%  71% A person skilled in the art is aware that data above 100 % after irradiation are due to common measurement fluctuations.

[0440] Recovery Measurements on Photo Stability of BEMT+EHT

[0441] The UV filter compositions as defined in Table 1.4 are applied on roughened quartz plates (2 ml/cm.sup.2). Plates are irradiated using Atlas CPS device at different duration times (MED=Minimal Erythema Dose): [0442] 0 h (0 MED, no irradiation) [0443] 1 h (5 MED), [0444] 2 h (10 MED), [0445] 4 h (20 MED), [0446] 10 h (50 MED).

[0447] 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 BEMT+EHT.

TABLE-US-00008 TABLE 2.4 Comparative Comparative Comp. 1g Comp. 1h Comp. 5a BEMT EHT BEMT EHT BEMT EHT 0 MED 100% 100% 100%  100%  100%  100%  5 MED 102% 103% 93% 95% 97% 97% 10 MED  99%  99% 87% 89% 99% 99% 20 MED 100% 100% 74% 76% 97% 98% 50 MED  99%  99% 53% 47% 92% 95% Comp. 5b Comp. Sc Comp. 5d BEMT EHT BEMT EHT BEMT EHT 0 MED 100% 100% 100%  100%  100%  100%  5 MED 103% 103% 97% 98% 97% 98% 10 MED 104% 103% 89% 94% 95% 98% 20 MED 101% 100% 85% 90% 90% 95% 50 MED  95%  89% 69% 68% 70% 73% A person skilled in the art is aware that data above 100% after irradiation are due to common measurement fluctuations.