Methylene bis-benzotriazolyl tetramethylbutylphenol for fabric staining reduction

Abstract

The present invention relates to the use of methylene bis-benzotriazolyl tetramethylbutylphenol, optionally in combination with tris-biphenyl triazine, to reduce fabric staining of a sunscreen or daily care composition, wherein the sunscreen or daily care composition comprises (i) at least one particulate UV-f liter; and/or (ii) at least one oil soluble UV-A filter, wherein the at least one oil soluble UV-A filter is present in an amount of at most 3% by weight, based on the total weight of the sunscreen or daily care composition; and/or (iii) at least one water soluble UV filter. Furthermore, the present invention relates to the use of methylene bis-benzotriazolyl tetramethylbutylphenol, optionally in combination with tris-biphenyl triazine, to facilitate the washability of such sunscreen or daily care compositions from textiles.

Claims

1. A method for reducing fabric staining of a sunscreen or daily care composition comprising incorporating 2,2′-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), optionally in combination with 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine) into the sunscreen or daily care composition, wherein the sunscreen or daily care composition further comprises (i) at least one particulate UV-filter; and/or (ii) at least one oil soluble UV-A filter, wherein the at least one oil soluble UV-A filter is present in an amount of at most 3% by weight, based on the total weight of the sunscreen or daily care composition; and/or (iii) at least one water soluble UV filter.

2. A method for facilitating washability of a sunscreen or daily care composition from textiles, comprising incorporating 2,2′-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), optionally 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), into the sunscreen or daily care composition, wherein the sunscreen or daily care composition further comprises (i) at least one particulate UV filter; and/or (ii) at least one oil soluble UV-A filter, wherein the at least one oil soluble UV-A filter is present in an amount of at most 3% by weight, based on the total weight of the sunscreen or daily care composition; and/or (iii) at least one water soluble UV filter.

3. The method according to claim 1, wherein the at least one particulate UV filter is an organic particulate UV filter, an inorganic particulate UV filter, or a combination thereof.

4. The method according to claim 1, wherein the at least one organic particulate UV-filter is selected from the group consisting of 1,1′-(1,4-piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methanone (INCI bis-(diethylaminohydroxybenzoyl benzoyl) piperazine), 5,6,5′,6′-tetraphenyl-3-3′-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine), and combinations thereof.

5. The method according to claim 1, wherein the at least one inorganic particulate UV-filter is selected from the group consisting of titanium dioxide, zinc oxide, and combinations thereof.

6. The method according to claim 1, wherein the sunscreen or daily care composition comprises the at least one particulate UV filter in an amount of from 0.1 to 10% by weight, based on the total weight of the sunscreen or daily care composition.

7. The method according to claim 1, wherein the sunscreen or daily care composition comprises 2,2′-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), optionally in combination with 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), and at least one further particulate UV filter, but no further oil soluble or water soluble UV filter.

8. The method according to claim 7, wherein the sunscreen or daily care composition comprises an overall amount of from 2 to 30% by weight, based on the total weight of the sunscreen or daily care composition, of particulate UV filters.

9. The method according to claim 1, wherein the at least one oil soluble UV-A filter is selected from the group consisting of hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate), 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane), 2-(2H-benzotriazol-2-yl)-6-[(2-ethylhexyloxy)methyl]-4-methylphenol, 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), and combinations thereof.

10. The method according to claim 1, wherein the at least one water soluble UV 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), 2-phenyl-1H-benzimidazole-5-sulfonic acid (INCI phenylbenzimidazole sulfonic acid), disodium phenyl dibenzimidazole tetrasulfonate, and combinations thereof.

11. The method according to claim 1, wherein the sunscreen or daily care composition comprises the at least one water soluble UV filter in an amount of from 0.1 to 6% by weight, based on the total weight of the sunscreen or daily care composition.

12. The method according to claim 1, wherein the sunscreen or daily care composition comprises the 2,2′-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol) in an amount of from 0.1 to 10% by weight, based on the total weight of the sunscreen or daily care composition, and wherein the sunscreen or daily care composition optionally comprises the 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), if present, in an amount of from 0.1 to 10% by weight, based on the total weight of the sunscreen composition or daily care composition.

13. The method according to claim 1, wherein the sunscreen or daily care composition further comprises at least one UV-B filter, wherein the at least one further UV-B filter 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), (RS)-2-ethylhexyl-2-hydroxybenzoate (INCI ethylhexyl salicylate), 3,3,5-trimethyl-cyclohexyl salicylate (homosalate), 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate (INCI octocrylene), (RS)-2-ethylhexyl-(2E)-3-(4-methoxyphenyl)prop-2-enoate (INCI ethylhexyl methoxycinnamate), malonate derivatives such as dimethicone diethyl benzalmalonate, diethylhexyl butamido triazone, and combinations thereof.

14. The method according to claim 1, wherein the sunscreen or daily care composition further comprises at least one oil soluble broad spectrum UV filter, wherein the at least one oil soluble broad spectrum UV filer is 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine).

15. A method for reducing fabric staining of a sunscreen or daily care composition and/or facilitating washability of the sunscreen or daily care composition from textiles, comprising incorporating 2,2′-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), optionally in combination with 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), into the sunscreen or daily care composition, wherein the sunscreen or daily care composition further comprises at least one UV-B filter, which is diethylhexyl butamido triazone; and at least one oil soluble broad spectrum UV filter, which is 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine).

16. The method according to claim 1, wherein the sunscreen or daily care composition comprises the at least one particulate UV filter in an amount of from 0.5 to 7% by weight, based on the total weight of the sunscreen or daily care composition.

17. The method according to claim 7, wherein the sunscreen or daily care composition comprises an overall amount of from 5 to 20% by weight, based on the total weight of the sunscreen or daily care composition, of particulate UV filters.

18. The method according to claim 1, wherein the at least one oil soluble UV-A filter is hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate) or 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane).

19. The method according to claim 1, wherein the sunscreen or daily care composition comprises the at least one water soluble UV filter in an amount of from 0.5 to 3% by weight, based on the total weight of the sunscreen or daily care composition.

20. The method according to claim 1, wherein the sunscreen or daily care composition comprises the 2,2′-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol) in an amount of from 0.5 to 5% by weight, based on the total weight of the sunscreen or daily care composition, and wherein the sunscreen or daily care composition optionally comprises the 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), if present, in an amount of from 0.5 to 7% by weight, based on the total weight of the sunscreen composition or daily care composition.

Description

EXAMPLES

(1) Process of Manufacture of Sunscreen Compositions

(2) The ingredients of part A as well as the ingredients of part B as provided in Tables 1.1, 1.2, 1.3, and 1.4 below for each tested sunscreen composition were combined and heated to 80° C., wherein part A was added to part B under stirring and was further homogenized. Subsequently, the composition was cooled down to room temperature under stirring. Then, part C and part D were added at room temperature.

(3) Sunscreen Compositions

(4) The sunscreen compositions compared with each other in each case provide comparable UV-A and SPF protection.

(5) TABLE-US-00001 TABLE 1.1 Comparative Ingredient (Trade Name) Composition 1a Composition 1b Part A Sucrose Polystearate, 3.00 3.00 Hydrogenated Polyisobutene (Emulgade Sucro plus) Disodium Cetearyl Sulfosuccinate 1.00 1.00 (Eumulgin Prisma) Cetearyl Alcohol (Lanette O) 2.00 2.00 Propylheptyl Caprylate (Cetiol 5.00 5.00 Sensoft) Dicaprylyl Carbonate (Cetiol CC) 5.00 5.00 Dibutyl Adipate (Cetiol B) 5.00 5.00 Phenoxyethanol and 1.00 1.00 Ethylhexylglycerin (Euxyl PE 9010) EHT (Uvinul T150) 2.00 2.00 EHS (Neo Heliopan OS) 5.00 5.00 BEMT (Tinosorb S) — 2.00 Part B Water Qsp 100 Qsp 100 Glycerine 6.00 6.00 Xanthan Gum (Rheocare XGN) 0.20 0.20 Part C MBBT in the form of a dispersion 7.00 — of 50% by weight MBBT in water (Tinosorb M) TBPT in the form of a dispersion 4.00 4.00 of 50% by weight TBPT in water (Tinosorb A2B) Part D Undecane, Tridecane (Cetiol 3.00 3.00 Ultimate) Total 100.00  100.00 

(6) TABLE-US-00002 TABLE 1.2 Comparative Composi- Composi- Composi- Ingredient (Trade Name) tion 2a tion 2b tion 2c Part A Sucrose Polystearate, 3.00 3.00 3.00 Hydroenated Polyisobutene (Emulgade Sucro plus) Disodium Cetearyl Sulfosuccinate 1.00 1.00 3.00 (Eumulgin Prisma) Cetearyl Alcohol (Lanette O) 2.00 2.00 1.00 Propylheptyl Caprylate (Cetiol 5.00 5.00 5.00 Sensoft) Cetiol OE 3.00 Dicaprylyl Carbonate (Cetiol CC) 5.00 5.00 Dibutyl Adipate (Cetiol B) 5.00 5.00 10.00  Phenoxyethanol and 1.00 1.00 1.00 Ethylhexylglycerin (Euxyl PE 9010) EHT (Uvinul T150) 2.00 2.00 1.50 EHS (Neo Heliopan OS) 5.00 5.00 5.00 DHHB (Uvinul A Plus) 2.00 3.00 3.00 BEMT (Tinosorb S) — — 1.00 Part B Water Qsp 100 Qsp 100 Gsp 100 Glycerine 6.00 6.00 2.00 Xanthan Gum (Rheocare XGN) 0.20 0.20 0.20 PartC MBBT in the form of a dispersion 6.00 6.00 — of 50% by weight MBBT in water (Tinosorb M) TBPT in the form of a dispersion 2.00 2.00 4.40 of 50% by weight TBPT in water (Tinosorb A2B) Part D Undecane, Tridecane (Cetiol 3.00 3.00 2.00 Ultimate) Total 100.00  100.00  100.00 

(7) TABLE-US-00003 TABLE 1.3 Comparative Ingredient (Trade Name) Composition 3a Composition 3b Part A Sucrose Polystearate, 3.00 3.00 Hydrogenated Polyisobutene (Emulgade Sucro plus) Disodium Cetearyl Sulfosuccinate 1.00 1.00 (Eumulgin Prisma) Cetearyl Alcohol (Lanette O) 2.00 2.00 Propylheptyl Caprylate (Cetiol 5.00 5.00 Sensoft) Dicaprylyl Carbonate (Cetiol CC) 5.00 5.00 Dibutyl Adipate (Cetiol B) 5.00 5.00 Phenoxyethanol and 1.00 1.00 Ethylhexylglycerin (Euxyl PE 9010) EHT (Uvinul T150) — 2.00 EHS (Neo Heliopan OS) — 5.00 DHHB (Uvinul A Plus) — 5.00 BEMT (Tinosorb S) — 1.50 TiO.sub.2 powder comprising 80% by 3.15 — weight of TiO.sub.2 and 20% by weight coating material comprising Al(OH).sub.3 and Stearic Acid (MT-100Z) Part B Water Qsp 100 Qsp 100 Glycerine 6.00 6.00 Xanthan Gum (Rheocare XGN) 0.20 0.20 Part C Phenylbenzimidazol sulfonic acid — 2.00 (Eusolex 232) 2-Amino-2-hydroxymethyl-1,3- — 0.90 propanediol (Tris-amino) Water — 10.00  MBBT in the form of a dispersion 9.00 — of 50% by weight MBBT in water (Tinosorb M) TBPT in the form of a dispersion 8.00 — of 50% by weight TBPT in water (Tinosorb A2B) Part D Undecane, Tridecane (Cetiol 3.00 3.00 Ultimate) Total 100.00  100.00 

(8) TABLE-US-00004 TABLE 1.4 Comparative Composi- Composi- Composi- Ingredient (Trade Name) tion 4a tion 4b tion 4c Part A Glyceryl Stearate (Cutina GMS V) 1.00 1.00 1.00 Sodium Stearyl Glutamate 0.30 0.30 0.30 (Emulgin ® SG) Stearyl Alcohol (Lanette 18) 1.00 1.00 1.00 Butylene Glycol Dicaprylate/ 4.00 4.00 4.00 Dicaprate (Dermofeel BCG) Dibutyl Adipate (Cetiol B) 3.00 3.00 3.00 C12-15 Alkyl Benzoate (Cetiol 5.00 5.00 5.00 AB) Phenoxyethanol (Protectol PE) 1.00 1.00 1.00 VP/Hexadecene Copolymer 0.50 0.50 0.50 (Antaron VP216) Silica Dimethyl Silylate (Aerosil 1.00 1.00 1.00 R972) BMDBM (Parsol 1789) 4.75 4.75 4.75 EHS (Neoheliopan OS) 4.75 4.75 4.75 EHT (Uvinul T150) 3.00 3.00 3.00 BEMT (Tinosorb S) 4.00 4.00 4.00 DHHB (Uvinul A Plus) 1.00 0.25 — Part B Water Qsp 100% Qsp 100% Qsp 100% Glycerin 7.50 7.50 7.50 Acrylates/C10-30 Alkyl Acrylate 0.10 0.10 0.10 Crosspolymer (Pemulen TR2) Xanthan Gum (Rheocare XGN) 0.40 0.40 0.40 Disodium EDTA (EDTA BD) 0.20 0.20 0.20 Part C PBSA (Eusolex 232) 1.00 1.00 1.00 Water 5.00 5.00 5.00 NaOH 30% 0.25 0.30 0.22 Part D MBBT* nano, Aqua, Decyl — 1.50 2.00 Glucoside (Tinosorb M) Ethanol 3.00 3.00 3.00 Total 100.00  100.00  100.00  SPF** 35.9  37.8  38.5  UVA-PF** (using a SPF of 30) 12.2  12.6  12.6  *Tinosorb M is a 50% active dispersion, i.e. 2% Tinosorb M correspond to 1% active UV filter amount. **calculated values.

(9) Measurement of Fabric Staining

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

(11) The difference between the color of a sunscreen 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.

(12) Further, the difference between the color of a sunscreen 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.

(13) For applying the sunscreen compositions in order to make a stain on a white textile, the sunscreen 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 was applied on a white textile (whiteness adjusted to: WG 170±10, after washing WG 190±10) in order to obtain a stain.

(14) 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.

(15) The results of sunscreen compositions 1a, 1 b, 2a, 2b, 2c, 3a, 3b, 4a, 4b and 4c are shown in Tables 2.1, 2.2, 2.3, and 2.4 as well as in FIGS. 1, 2, 3, and 4.

BRIEF DESCRIPTION OF THE DRAWINGS

(16) FIG. 1, FIG. 2, FIG. 3, and FIG. 4 show the results of sunscreen compositions 1a, 1b, 2a, 2b, 2c, 3a, 3b, 4a, 4b, and 4c.

(17) TABLE-US-00005 TABLE 2.1 Comparative Composition 1a Composition 1b Δb* (before washing) 6.63 7.22 SD (before washing) 0.11 0.16 Δb* (after 1 cycle) 1.65 4.49 SD (after 1 cycle) 0.11 0.06 Δb* (after 3 cycles) 0.89 2.82 SD (after 3 cycles) 0.07 0

(18) TABLE-US-00006 TABLE 2.2 Comparative Composi- Composi- Composi- tion 2a tion 2b tion 2c Δb* (before washing) 9.71 10.21 10.21 SD (before washing) 0.21 0.03 0.06 Δb* (after 1 cycle) 7.76 8.73 10.68 SD (after 1 cycle) 0.11 0.18 0.04 Δb* (after 3 cycles) 1.64 1.86 4.08 SD (after 3 cycles) 0.13 0.08 0.25

(19) TABLE-US-00007 TABLE 2.3 Comparative Composition 3a Composition 3b Δb* (before washing) 7.73 11.7 SD (before washing) 0.08 0.16 Δb* (after 1 cycle) 1.85 10.91 SD (after 1 cycle) 0.16 0.42 Δb* (after 3 cycles) 0.96 3.8 SD (after 3 cycles) 0 0.03

(20) TABLE-US-00008 TABLE 2.4 Comparative Composi- Composi- Composi- tion 4a tion 4b tion 4c Δb* (before washing) 10.99 10.38 10.50 SD (before washing) 0.26 0.12 0.05 Δb* (after 1 cycle) 8.54 7.73 7.89 SD (after 1 cycle) 0.25 0.27 0.28 Δb* (after 3 cycles) 5.38 4.75 4.91 SD (after 3 cycles) 0.33 0.12 0.07